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CHRONOLOGICAL HISTORY OF |
1669
The alchemist Brandt Hennig is credited to have prepared phosphorus (phosphoro mirabile), the first element isolated in a quite pure state.
1673
Tachenius Otto suggested for the first time that an acid compound is hidden in fats since the strength of the alkali disappears when making soap (Hippocrates Chymicus, Paris 1673).
1719
Hensing JT published at Giessen the first monograph on the chemical examination of the brain in which he isolated phosphorus (Cerebri examen chemicum ex eodemque Phosphorus singularem omnia inflammabilia accendentem..., Giessen, Vulpius, 1719). This work was considered as a cornerstone of modern neurochemistry.
1758
First study by Poulletier de la Salle FP of a lipid (cholesterol) isolated from bile stones.
1779
Discovery by the Swedish scientist Scheele CW of glycerol obtained by heating several oils and fats with lead oxide.
1783
Fourcroy AF introduced alcohol to extract brain lipids.
1786
Chevreul M E was born the 31st of August in Angers, the capital of the central French province of Anjou.
1804
De Saussure NT described experiments showing that linseed oil was able to condense with oxygen (Recherches chimiques sur la végétation, Paris, 1804).
1811
First description by Vauquelin LN of the presence of phosphorus bound to fat in the brain (Analyse de la matière cérébrale de l'homme et de quelques animaux, Ann Mus Hist Nat 1811, 18, 212).
1813
Chevreul ME published his first paper on the composition of animal fats. Description of the concept of fatty acids.
1814
First report by Chevreul ME of the participation of water during the saponification process.
1816
Magendie F in Paris found that olive oil alone did not permit dogs to survive more then one month.
1818
First characterization by Chevreul ME of "cholesterine" in bile stones (Memoires Muséum 1818, 11, 308).
French patent (29 July) by the chemist Braconnot
for the manufacture of candles made of a mixture of bee wax and a purified
fraction from beef tallow ("absolute tallow").
Pelletier PJ et al. used for the first time the word "chlorophyll" to
name the purified green pigment of plant leaves (Ann Chim Phys 1818, 9, 194).
1819
The elaidisation reaction was obtained by a French pharmacist, Poutet JJE (Ann Chim Phys 1819, 12, 58) who observed that trioleine could be converted to the consistency of pork lard when treated with nitrogen oxides
1823
Chevreul ME published his masterly work on the chemistry of lipids "Recherches chimiques sur les corps gras d'origine animale" where he described for the first time several fatty acids (margaric, oleic, stearic, butyric and caproic acids), including isovaleric acid (he named it "acide phocénique"), the first branched-chain fatty acid to be isolated from the head oil of dolphin and from porpoise oil.
1825
MH Chevreul and JL Gay-Lussac took a patent for the manufacture of the stearic acid candle. 1825 may be considered as the beginning of oleochemistry.
1827
Prout W, English physician, recognized fat as an important nutrient in the diet along with protein and carbohydrate.
1829
Lecanu LR showed the presence of cholesterol in an extract of hen egg yolk (J de Pharm 1829, 15,1).
1831
Wackenroder HWF named carotene the hydrocarbon pigment isolated from carrots, as ruby red crystals (Giegers Magazin Pharm 1831, 33, 144).
1832
Boudet demonstrated that only olive oil was able to increase its viscosity under the action of nitrogen peroxyde which generates a new compound, elaidic acid isolated from "elaïdin" (Ann Chim 1832, 50, 391). The elaidisation reaction was discovered by Poutet (1819).
1834
Dumas MJ named "chloroform" the product obtained by
distillation of a mixture of alcohol and calcium chloride in water. Its
structure was erroneously given (C4H2Cl6) (Ann
Chim Phys 1834, 56, 113).
Couerbe J-P introduced diethyl ether to extract
brain lipids. He reported the first composition of the brain lipids including a
saponifiable fraction (céphalote) soluble in ether and containing 5.8% of
phosphorus and a non-saponifiable fraction (cérébrote) containing 2.3% of
phosphorus (Ann Chim Phys 1834, 56, 160). Couerbe made the hypothesis
that phosphorus may play an important role in the animal brain.
1837
Berzelius JJ named the yellow pigments from autumn leaves xanthophylls (Annalen 1837, 21, 257).
1838
Pelouze and Boudet made for the first time the
hypothesis that oleic acid and "margaric acid" (a mixture of palmitic
and stearic acids) could both be combined in compounds present in vegetal oils (J
de Pharm 1838, 24, 385).
Lecanu LR showed that cholesterol was present in human blood
1841
Fremy E isolated a lipidic substance from the
brain and named it oleophosphoric acid (Ann Chim Phys 1841, 2, 463).
Myristic acid (14:0) is discovered in seeds of the family Myristicaceae
by Playfair L (Ann 1841, 37, 152).
1843
Gobley NT described the first instrument devoted to lipids, the "élaïdomètre", he invented to test the purity of oils by determining their density (J Pharm Chim 1843, 4, 285).
1844
First isolation of linoleic acid
("Leinol") prepared from linseed oil by Sacc F (Ann 1844, 51, 213).
Pelouze TJ et al. described for the first time the synthesis of a natural
neutral lipid, tributyrin, by the direct esterification of glycerol and butyric
acid (Ann Chim Phys 1844, 10, 434).
1846
Claude Bernard demonstrated a lipase activity in the pancreas.
1847
Gobley NT described in egg yolk as in brain the presence of a phosphorus-containing fraction which gave by hydrolysis "oleic acid, margaric acid and phosphoglyceric acid" (J Pharm Chim 1847, 12, 5).
1848
Behenic acid (22:0) is discovered in
bean oil (seeds of Moringa oleifera) by Voelcker A (Ann 1848, 64, 342).
Saalmüller L isolated the first known hydroxy fatty acid, ricinoleic acid (12-hydroxyoleic acid), from castor oil in which it is the principal compound (Saalmüller
L, Ann 1848, 64, 108).
1849
First description by Darby S of erucic acid (22:1
n-9) in rapeseed oil (Ann 1849, 69, 1).
Lauric acid (12:0) is discovered in Lauraceae seeds (Laurus nobilis)
by Marsson T (Ann 1842, 41, 429).
1850
Gobley NT isolated from egg-yolk a phosphorus-containing lipid which was named "Lecithin" from the greek lekithos, egg yolk (J Pharm Chim, Paris, 1850, 17, 401).
Chevreul ME showed that paint drying (oxidation
of unsaturated fatty acids) is accompanied by oxygen fixation detected by a
weight increase (Mem Acad Sci 1850, 22, 685-732).
Inositol (hexahydroxycyclohexane) was first isolated from muscle by Scherer. He
coined the name 'inositol" from the Greek inos (muscle).
1852
Duffy PJ described the first reaction of lipid interesterification (tristearin with ethanol) (J Chem Soc 1852, 5, 303).
1853
Gerhardt Charles used for the first time the word "glyceride" for the simple compounds forming fats and oils (Traité de Chimie organique, 1853, t.1, 768).
First study of triglyceride
crystallization with the description of three melting points for tristearin (Duffy
PJ, J Chem Soc 1853, 5, 197).
Erucic acid (13-docosenoic acid) was first isolated from rapeseed oil (Websky
F, J Prakt Chem 1853, 58, 449).
1854
Description by Berthelot M of the first synthesis of neutral lipids in combining glycerol with fatty acids (synthesis of mono- di- and triglycerides) (Ann Chim Phys 1854, 41, 216).
1855
Heintz WH showed that "margaric acid" discovered by Chevreul was an indefinite mixture of palmitic and stearic acids.
The famous French chemist Würtz Charles proposed the right formula of glycerol (Ann Chim et Phys 1855, 43, 492).
1856
Demonstration by Bernard C of the importance of pancreatic juice and of bile for the digestion and absorption of fats in the duodenum: "Leçons de physiologie expérimentale appliquées à la médecine", Ballière, Paris.
1860
Greville Williams C named "isoprene" the liquid product obtained by distillation from Hevea rubber and determined erroneously its empirical formula as C10H8 (Williams WC, Philos Trans Roy Soc London 1860, 150, 241).
1861
Strecker characterized a nitrogen-containing
substance in bile and named it choline.
Töpler demonstrated the existence of phospholipids in plant seeds (Landw Vers
Sta 1861, 3, 85).
1862
Isolation by Beneke GM for the first time in a plant extract (pea seeds) of a compound he believed to be cholesterol (Ann Chem Pharm 1862, 122, 249).
1869
French patent by Mège-Mouriès H for the production of "margarine".
1871
The existence of lipases in plant seeds was noted by Muntz MA (Ann Chem Liebigs 1871, 22, 472).
1877
Bokay A gave the first indication of the existence of enzymes (phospholipases) in pancreatic juice hydrolyzing lecithin into glycerophosphoric acid, fatty acids and choline (Z physiol Chem 1877, 1, 157).
1878
Hesse O isolated from a vegetal extract a compound slightly different from cholesterol (cholesterin) by its composition and melting temperature, he named that new compound "phytosterine" (Ann Chem und Pharm 1878, 192, 175).
1879
Soxhlet Franz, a German chemist, pioneered extraction technology by developing a solid-liquid extraction apparatus that carries his name.
This apparatus was used first to separate fats from food (Dingler's
Polytechnisches J 1879, 232, 461).
Köttstorfer proposed to characterize fats by the saponification index (amount
of KOH needed to saponify 1 g of fat) (Z anal Chem 1879, 18, 199).
Bouchardat G obtained isoprene from natural rubber
and found that heating isoprene with HCl produced a rubber-like polymer. This was the first production of artificial
rubber (Bouchardat G, C R Acad Sci 1879, 89, 1117).
1881
Characterization of an hydroxylated fatty acid, hydroxymyristic acid, extracted from Angelica archangelica oil (Müller R, Ber 1881, 14, 2476).
1884
Publication in London of the masterly work of
Thudichum JLW "A treatise on the chemical constitution of the brain".
Description by Thudichum JLW of the presence of sphingosine in brain lipids
after alkaline hydrolysis. He isolated and named sphingomyelin a phospholipid
without glycerol but containing choline and sphingosine. He described also the
presence of cerebrosides and of a sulfated lipid (sulfatides) in brain extracts. He individualized cephalin (phosphatidylethanolamine) as a
phospholipid distinct from lecithin (phosphatidylcholine).
Description by Baron A von Hübl of the iodine index as a measure of fat
unsaturation (Dingler's Polytech J 1884, 253, 281).
1886
First description by Peters K of the diene structure of linoleic acid (Monatsch 1886, 7, 522).
Wooldridge LC proposed for the first time that the prothrombin activator is a protein/phospholipid complex.
1887
Salkowski described the presence of
cholesterol in cod liver oil and concluded that animal fats and oils contain
cholesterol while vegetal fats and oils contain phytosterols (Z anal Chem
1887, 26, 557).
First description of the triene fatty acid, linolenic acid, in hempseed oil (Hazura
K, Monatsch 1887, 8, 147)
Wallach O described for the first time the chemical structure of terpene
compounds (Zur Kenntnis der Terpene und ätherischen Oele, Justus Lieb Ann
Chem 1887, 238, 78).
1889
Chevreul Michel Eugene died the 19th of April in Paris at the age of 103.
1890
Description by Tanret C of ergosterol in "seigle" (rye) (Ann Chim Phys 1890, 20, 289).
1892
Arnaud A discovered an acetylenic fatty acid (6-octadecynoic acid or tariric acid) in seed oil of Picramnia, Simarubaceae (Bull Soc Chim 1892, 7, 233).
Schmidt A. discovered that lipid extracts of various tissues contained a lecithin-rich factor (zymoplastic agent) which was able to activate blood coagulation.
1894
Goldsobel AG established the right structure of ricinoleic acid (Ber 1894, 27, 3121).
1895
Diesel R developed the first engine to run on peanut oil, as he demonstrated later at the World Exhibition in Paris in 1900.
Overton C observed that liposoluble molecules were able to enter easily into the cells. He proposed that the cell membranes were made of lipids.
1897
Sabatier P et al. described the
hydrogenation of olefinic molecules in the presence of metallic catalyst (C R Acad Sci 1897, 124, 1358).
Thoms H proposed the denomination "phytosterol" for all sterols of
vegetal origin.
Heise R demonstrated for the first time the presence of mixed glycerides,
oleodistearin, in the fat from the kernel of Allanblackia (Guttiferae) (Tropenpflanzer
1897, 1, 10).
1898
Description by Edmed FG of the structure of oleic acid (J Chem Soc 1898, 73, 627).
1899
Altman R et al. introduced acetone in the preparation of phospholipids (separation from fats and cholesterol).
1900
At the Paris exposition, a Diesel engine, built by the French Otto Company, has been run wholly on a vegetal oil (peanut oil) (Nitske WR et al., Rudolf Diesel, pioneer of the age of power, Univ. Oklahoma Press, 1965).
1901
First use of the term "phosphatide"
by Thudichum JLW to designate phosphorus-containing lipids.
Thudichum discovered cerebronic acid (3-hydroxy 24:0) in brain lipids (Die
chemische Konstitution des Gehirns der Menschen und der Tiere, Tübingen, 1901)
1903
First description by Tswett M of a separation
procedure by column chromatography on calcium carbonate of plant pigments with
petroleum ether as eluent (Proc Warsaw Soc Nat Sci 1903, 14).
Patent in England by Normann W for the "conversion of unsaturated fatty
acids or their glycerides into saturated compounds" by hydrogenation (Patent N° 1515 A.D.
1903).
First use by Molinari E of the ozonisation method to determine the position of
double bonds in fatty chains (Ann Soc Chim Milano 1903, 9, 507).
Kyes P et al. showed that the reaction of lecithin with cobra poison produced a
new product they named "cobra-lecithide" which had the property of
hemolyzing red blood cells (Berlin klin Wochschr 1903, 40, 57).
1904
Knoop F first proposed that fatty acids were
oxidized at the b-carbon
position (Knoop F, Beitr Chem Physiol Path 1904, 6, 150).
The first cyclopentenyl fatty acid to be isolated from chaulmoogra oil was
hydnocarpic acid (from Hydnocarpus Kurzii) by Power FB et al. (J Chem
Soc 1904, 85, 838)
1906
An antiphospholipid antibody was first described by Wassermann A in his studies to develop a test for syphilis (Wassermann A et al., Dtsch Med Wochenschr 1906, 32, 745).
Tsujimoto M discovered a hydrocarbon in oils from shark liver he named "squalene" (J Soc Chem Ind Jpn, 1906, 9, 953)
1909
First description by Erdmann E et al. of the
structure of linolenic acid (Ber 1909, 42, 1334).
First isolation of arachidonic acid from liver lipids (Hartley P, J Physiol
1907, 36, 17).
H MacLean introduced cadmium chloride to improve lecithin purification (Z
Physiol Chem 1909, 59, 223).
1910
Wallach GO, Professor at Göttingen University, received the Nobel Prize "for the services which he has rendered in the development of organic chemistry and the chemical industry by his pioneering work in the field of alicyclic compounds" (Nobel Lecture, December 12, 1910). He proposed that these alicyclic lipids (terpenes) can be regarded as oligomers of isoprene.
1911
First isolation of a ketoalkanoic acid (lactarinic
acid or 6-ketostearic acid) from the mushroom Lactarius refus (Bougault
J et al., C R Acad Sci Paris 1911, 153, 572).
Willstatter R et al. discovered and named "phytol" the alcohol which
esterifies the tetrapyrrole nucleus (Ann Chem 1911, 387, 317), it was
synthesized in 1928.
Tswett M named carotenoids the group of various pigments he has separated from
plants (Ber Dtsch Bot Ges 1911, 29, 630)
1912
Howell WH presented the evidence that the
thromboplastic action of tissue juices is a property of the unsaturated
phospholipid cephalin extracted by diethyl ether from dried brain or thymus (Am
J Physiol 1912, 31, 1).
Sabatier P received the Nobel Prize for
chemistry (with Grignard V) "for his method of hydrogenating organic compounds in the presence of finely disintegrated metals
whereby the progress of organic chemistry has been greatly advanced in recent
years".
1913
McCollum EV and Davis M showed that certain
lipids must be present in the diet during growth.
Baumann A and Renall MH demonstrated independently that cephalin
(phosphatidylethanolamine) from human brain contained an aminoethyl alcohol (Biochem
Z 54, 30 and Biochem Z 1913, 55, 296).
Bordet J et al. described a lecithin-rich activator (cytozyme) in an alcohol extract of blood platelets (Ann Inst Pasteur 1913, 27, 341).
1914
First step by Bloor WR after Chevreul to the
complete recovery of polar lipids from living matter : the use of an
ethanol/ether (3/1) mixture for lipid extraction from blood plasma (J Biol Chem 1914, 17, 377).
Levene PA obtained for the first time and in pure
form sphingomyelin and elucidated its composition (J Biol Chem 1914, 18, 453).
Delezenne C et al. showed that the hemolytic "cobra-lecithide" of Kyes
(1903) was lecithin from which one unsaturated fatty acid has been
removed, they named it "lysocithin" (now lysophosphatidylcholine)(Bull soc chim 1914, 15, 421).
Schmidt E measured for the first time high serum cholesterol levels in patients
with xanthomatosis thus recognized as an essential hypercholesterolemia (Dermat Z 1914, 21, 137).
1915
Willstätter RM received the Nobel Prize for chemistry "for his researches on plant pigments, especially chlorophyll".
1916
Tsujimoto first assigned the correct empirical formula C30H50 to squalene, an unsaturated hydrocarbon he discovered in 1906 in a non-saponifiable fraction of shark liver oil.
1917
Langmuir I discovered the structure of oil-water films and proposed that fatty acids form a monolayer by orienting themselves vertically with the carboxyl groups in contact with the surface of the water (Langmuir I, J. Am Chem Soc 1917, 39, 1848).
1920
Cyanolipids, fatty acid esters of branched hydroxy C5 nitriles, were first reported in 1920 to occur in Sapindaceae seed oil ( ). They were shown to be cyanogenic, thus possibly providing a protective function for the plant.
1921
First separation by Twitchell E of unsaturated and saturated fatty acids by lead precipitation (Ind Eng Chem 1921, 13, 806).
1922
Funk C invented the term "Vitamins".
After showing that the antirachitic principle and
vitamin A were distinct substances, the group of McCollum EV
named the new substance vitamin D (J Biol Chem 1922, 53, 293).
Moureu C et al. named "antioxygene" several phenolic substances which
prevent the oxidation of various compounds, including butter and vegetal oils
(linseed, wallnut) (C R Acad Sci Paris 1922, 174, 258).
1924
Patent in England by Van Loon C for the
interesterification process of industrial fats (Patent N° 249,916).
Sure B proposed the name vitamin E for a factor which, when absent in diets, was
responsible of reproductive failure (J Biol Chem 1924, 58, 693).
Lieb H identified cerebrosides as the stored material in cells from patients
with Gaucher's disease (Hoppe-Seylers Z physiol Chem 1924, 140, 305).
The chemical structure of isovaleric acid (3-methylbutanoic acid) from marine
origin was proposed (André E, Bull Soc Chim Fr 1924, 35, 857) after
comparison with isovaleric acid from valerian root and a synthetic specimen.
1925
First classification of lipids by Bloor WR (Chem
Rev 1925-26, 2, 243).
Gorter et al. demonstrated that red blood cells are covered by a layer of fatty substances
(glycerophospholipids) that is two molecules thick
(a bilayer) (Gorter E et al., Physiol Rev 1925, 51, 66).
Hess AF et al. demonstrated that the factor active in preventing rickets in rats
was present in the non-saponifiable moiety of a vegetal oil exposed to UV
radiations (Hess AF et al., J Biol Chem 1925, 63, 297). Soon after, they
demonstrated that irradiated "phytosterol" or cholesterol was able to
confer rickets protection. They hypothesized that UV exposure of the skin is the
physiological protection against rickets in animals (Hess AF et al., J Biol
Chem 1925, 63, 305).
1926
Car FH and Price EA discovered the
well known color test of vitamin A with antimony trichloride (Biochem J
1926, 20, 497).
The word "Lipid" first appeared in a paper by Sperry WM (J Biol
Chem 1926, 68, 357), term including fats and all substances associated with
them.
Klenk E discovered and described hydroxynervonic (2-hydroxy 24:1n-9) in brain
cerebrosides (Z physiol Chem 1926, 157, 291).
1927
First isolation by Chibnall AC et al. of
phosphatidic acid from cabbage leaves (Biochem J 1927, 21, 233).
Wieland HO received the Nobel Prize in chemistry for studies "on the constitution of the
bile acids and related substances".
Hilditch TP proposed a new chemical method based on potassium permanganate
oxidation to appreciate the importance of trisaturated triglycerides in a
natural mixture (J Chem Soc 1927, 3106).
1928
Windaus AOR received the Nobel Prize in
chemistry for studies
"on the constitution of sterols and their connection with the
vitamins". The vitamin in question was vitamin D and Windaus was the first
person to receive an award mentioning vitamins.
First demonstration of the presence of "trans" isomers of fatty acids
in ruminant depot fats by Bertram SH (Biochem Z 1928, 197, 433).
The structure of phytol was elucidated (Fisher FG et al., Ann Chem 1928, 464,
69).
Introduction of a mixture of diethyl ether/ethanol (1/3) for lipid extraction (Bloor
WR, J Biol Chem 1928, 77, 53).
1929
Isolation by Macheboeuf M et al. of pure
lipoproteins (Disc Faraday Soc 1929, 6, 62).
Klenk E established that sphingosine contained a straight chain of 18 carbon
atoms (Z physiol Chem 1929, 185, 169).
Isolation from tubercle bacilli of the first branched-chain acid (tuberculostearic
acid or 10-methylstearic acid) higher than isovaleric acid (Anderson RJ et
al., J Biol Chem 1929, 85, 77).
Burr GO et al. reported that fat or rather certain fatty acid components
of fat have special nutrient qualities in rats (J Biol Chem 1929, 82, 345).
Moore T proved the in vivo conversion of carotene to vitamin A (Lancet
1929, ii, 217).
Hilditch TP et al. showed that the catalytic hydrogenation of oleate generated
new fatty acids which resulted from both geometrical and positional
isomerization (Proc Roy Soc London 1929, 552, 563).
Bloor WR established that phospholipids and sphingolipids are efficiently
extracted using a mixture of ethanol and ether (3/1) (J Biol Chem 1929, 82, 273).
1930
Burr GO et al. discovered the essentiality of the
long-chain polyunsaturated fatty acids (linoleic and linolenic acids) (J Biol Chem 1930, 86, 587).
Anderson RJ reported the presence of inositol in lipids of tubercle bacilli (J
Am Chem Soc 52, 1607).
First demonstration of the biosynthesis of vitamin A from b-carotene
in rat, by means of nutritional experiments (Moore
T, Biochem J, 1930, 24, 692).
1931
Kuhn R et al. rediscovered the technique of Tswett
(1931) and revived column chromatography in the course of studies on carotenoids
(Z Physiol Chem 1931, 197, 141).
Kuhn R et al. separated for the first time carotene into three isomers, a-carotene,
b-carotene,
and g-carotene
(Chem Ber 1931, 64, 1354).
First use of chloroform replacing ether in the Bloor's mixture (1914) to improve
polar lipid extraction (Bornmann JH, J Assoc Off Agric Chem 1931, 14, 489).
The group of Karrer P gave the correct structure of vitamin A (Helv Chim Acta
1931, 14, 1036).
Cummings MJ et al. suggested that vitamin E has specific anti-oxidant capacities
(J Nutr 1931, 3, 421).
1932
Windaus A described the right structure of
cholesterol (Ann Rev Biochem 1932, 1, 109).
Description of a fatty acid oxidase activity ("lipoxydase") in soja
seeds (André E et al., C R Acad Sci Paris 1932, 194, 645).
1933
Blix G isolated sulfatide from human brain after Thudichum (1884) and determined its structure, a sulfated galactosylceramide (Z Physiol Chem 1933, 219, 82). Its complete structure was elucidated in 1962.
1934
Description by Noller CR et al. of the synthesis
of oleic acid (J Am Chem Soc 1934, 56, 1563).
Klenk E identified sphingomyelin as the stored phospholipid in cells from
patients with Niemann-Pick disease (Hoppe-Seylers Z physiol Chem
1934, 229, 161).
1935
Klenk E characterized a new type of acidic glycolipid, named substance X (named in 1942 gangliosides), from the brain of patients suffering from amaurotic familial idiocy (Hoppe-Seyler's Z Physiol Chem 1935, 235, 24).
Howell discovered that the platelet factor
described by Bordet in 1913 (cytozyme) was a cephalin (phosphatidylethanolamine)
rather than a lecithin (Physiol Rev 1935, 15, 435).
Toyama Y et al. reported the isolation of an eicosapentaenoic acid from sardine
oil which they named timnodonic acid (EPA) (Bull Chem Soc Jap
1935, 10, 192).
Danielli JF et al. described a basic model for the structure of cellular membrane
which was accepted by biologists for many years : a "sandwich" of lipids (arranged in a bilayer)
covered on both sides with proteins (Danielli J F et al. J Cell Comp Physiol
1935, 5, 495).
1936
Isolation by Evans HM et al. of a and
b-tocopherols
from plant oils (J Biol Chem 1936, 113, 319).
First use by Schoenheimer R et al. of radioactive isotope (Deuterium) to study
the in vivo conversion of stearic acid into oleic acid (J Biol Chem 1936, 114,
381).
First description by Thannhauser SJ et al. of a chromatographic method for
phospholipids using an aluminum oxide column (J Biol Chem 1936, 116, 527).
Thannhauser SJ et al. described that a
mixture of chloroform and methanol (2/1) is the most efficient for the
extraction of phospholipids (J Biol Chem 1936, 116, 533).
Klenk E et al. constructed the first microdistillation device which was capable
fractionating a mixture of fatty acid methyl esters (C16 and C18) (Klenk E et al., Physiol
Chem 1936, 242, 250). Later on, an improvement of that device was reported
(Klenk E et al., Z Physiol Chem 1941, 267, 260).
Quick AJ found that lipid solvents greatly reduce
the coagulant activity of tissue extract (thromboplastin) suggesting that the
active substance is a lipoprotein (Am J Physiol 1936, 114, 282).
An important component of Mycobacterium tuberculosis wax, phthiocerol, is
isolated and its global formula determined (Stodola
FH et al., J Biol Chem 1936, 114, 467)
The term "steroids" was coined by Callow
RK et al. (Proc Royal Soc London series A 1936, 157, 194) "for
the group of compounds comprising the sterols, bile acids, heart poisons,
saponins, and sex hormones".
1937
Moore T first postulated the formation of
conjugated double bonds when linolenic acid was treated with alkali (
Biochem J 1937, 31, 138).
Discovery by Olcott HS et al. of the antioxidant properties of tocopherols (J Am
Chem Soc 1937, 59, 1008).
First synthesis of linoleic acid (Noller CR et al., J Am Chem Soc 1937, 59,
522)
1938
First description of thin-layer chromatography on
a microscope slide coated with aluminum oxide (Izmailov NA et al. Farmatsiya (Mosk.) 1938, 3,
1).
Kuhn R received the Nobel Prize for chemistry "for his work on carotenoids and vitamins.
The correct structure of
a-tocopherol
is proposed by Fernholz E (J Am Chem Soc 1938, 60, 700).
The group of Karrer P prepared chemically
a-tocopherol
(vitamin E) (Helv Chim Acta 1938, 21, 520).
Mycolic acids were isolated and named from a waxy extract of human tubercle bacillus (Mycobacterium
tuberculosis) (Stodola FH et al., J Biol Chem
1938, 126, 506).
1939
Feulgen R et al. showed that phospholipid
fractions from heart and brain containing an acetal phosphatide (now
plasmalogen) release fatty aldehydes on acid hydrolysis (Hoppe-Seyler's Z
Physiol Chem 1939, 260, 217).
First detection of inositol and inositol monophosphate in the phospholipid fraction of soybean lipids (Klenk
E et al., Z physiol Chem 1939, 258, 33).
1940
Hilditch TP published his most important work
"The chemical constitution of natural fats".
The first description of the urea-fatty acid complexes by Bengen F which revolutionized fat chemistry for
about 20 years (German Patent Appl. OZ 12438, march 18, 1940).
Dolby DE et al. discuss the possibility that linoleic acid would represent the
physiological precursor of arachidonic acid (Biochem J 1940, 34, 1422).
Lipids containing trehalose were recognized in studies on the lipid composition
of Mycobacterium tuberculosis (Anderson RJ, The Harvey Lectures 1940,
35, 271).
1941
Burr GO and Miller used the alkali conjugation as
a rapid analytical method for determining linoleic acid content of vegetable
fats.
Trappe W showed that lipids can be eluted in fractions from an alumina column by
applying consecutively various solvents of different polarities. Thus, he
defined a "eluotropic series of solvents" (Biochem Z 1940, 305, 150).
Pangborn MC gives the name "cardiolipin" to a lipid isolated from beef
heart, and with antigenic properties in the complement-fixation test for
syphilis (Proc Soc Exptl Biol Med 1941, 48, 484).
MacFarlane MG et al. demonstrated the presence of a "lecithinase C"
(now phospholipase C) in the Clostridium welchii toxin which cleaved
phosphorylcholine from lecithin (and sphingomyelin) (Biochem J 1941, 35, 884).
Klenk E isolated a product from a cerebroside fraction for which he introduced
the name "neuraminic acid" (Z physiol Chem 1941, 268, 50).
Brückner J described a micro method for the determination of cerebrosides based
on the colorimetric determination of galactose by means of orcinol and sulfuric
acid (Z physiol Chem 1941, 268, 163).
1942
First description by Klenk E of
"gangliosides", formerly named in 1935 "substance X",
phosphorus-free glycosphingolipids containing sialic acid and present in brain gray
matter and ganglia cells (Hoppe-Seylers Z Physiol Chem
1942, 273, 76).
First description of the correct formula of sphingosine (Carter HE et al., J
Biol Chem 1942, 142, 449).
First description by Folch J of a phospholipid containing inositol in the brain
(J Biol Chem 1942, 142, 963).
First isolation by Folch J of phosphatidylserine
and phosphatidylethanolamine
from brain cephalin fraction (J
Biol Chem 1942, 146, 35).
Cardiolipin was discovered in
beef heart tissue (Pangborn MC, J Biol Chem 1942, 143, 247) but, later, it was
recognized to be not specific to the heart.
First liquid chromatography separations of fatty acids concerning
short-chain acids by Smith EL (Biochem J 1942, 36, 22).
Farmer EH et al. suggested for the first time that the primary autoxidation
product of unconjugated fatty chains is a hydroperoxide formed by the addition
of an oxygen molecule to a carbon atom adjacent to the double bond (J Chem Soc
1942, 119).
Von Mikusch JD reported the isolation, from alkali-isomerized acids of castor
oil, of the first conjugated linoleic acid (10,12-linoleic acid) (J Am Chem Soc 1942, 64, 1580).
Matsuda S reported the isolation of docosahexaenoic acid (DHA) from fish oil (J Soc Chem Ind Jap 1942, 45, 49).
1943
Description by Arens CL et al. of the right
structures of linoleic and arachidonic acids (Biochem J 1943, 37, 1).
Dam H and Doisy EA received the Nobel prize in Physiology or Medicine for the
discovery of vitamin K, its pure preparation, the determination of its chemical
structure and the synthetic production of that vitamin.
Cramer DL et al. developed the fractional crystallization of fatty acids or
their methyl esters for their isolation from organic solvents at very low
temperature, thus avoiding degradation of unsaturated molecules (J biol Chem
1943, 151, 427).
Farmer EH developed the hydroperoxide hypothesis of lipid peroxidation from
studies on oleic acid (J Chem Soc 1943 p119 and 541).
The existence of a direct metabolic relationship between cholesterol and bile
acids was first established by Bloch K et al. (J Biol Chem 1943, 149, 511).
1944
First description by Craig LC of the countercurrent distribution of organic compounds (J Biol Chem 1944, 155, 519).
1945
The formation of mono- and diglycerides
("lower glycerides") was demonstrated to occur during pancreatic
lipolysis both in vitro and in vivo, no free glycerol appearing
during the first 5 hr of the reaction (Frazer AC et al., Biochem J 1945, 39,
122).
Ginger LG et al. isolated a levorotatory fatty acid, mycocerosic acid, from the
‘‘purified waxes’’ of Mycobacterium tuberculosis (Ginger LG et
al., J Biol Chem 1945, 157, 203).
Gortner WA established that phospholipids are better quantified by phosphorus
determination than with any other methods (Gortner WA, J Biol Chem 1945, 159,
97).
1946
Rhamnolipids were found for the first time in Pseudomonas pyocyanea growth on glucose (Bergstrom S et al., Ark Kem Mineral Geol 1946, 23A, 1).
1947
First synthesis by Rose WG of a phospholipid,
dipalmitoyl glycerophosphoethanolamine (J Am Chem Soc 1947, 69, 1384).
Carter HE et al. proposed the term "sphingolipide" as a convenient
designation for lipids containing sphingosine (cerebrosides, sphingomyelin,
gangliosides...) (J Biol Chem 1947, 169, 77).
Carter HE et al. proposed the correct structure of sphingosine, previously
discovered by Thudichum JL in 1884 (J Biol Chem 1947, 170, 285).
Hanahan DJ et al. suggested the presence in vegetal tissues of an enzyme (now
phospholipase D) producing phosphatidic acid from various phospholipids (J Biol
Chem 1947, 168, 233).
Hildtitch TP et al. showed that low temperature crystallization gives more
precise data for the analysis of unsaturated fatty acids than the old lead salt
separation procedure (J Soc Chem Ind 1947, 66, 284).
The first issue of the journal "Lipids" appeared that year.
1948
Holman RT et al. studied fatty acids by
spectrophotometry after alkaline isomerization at high temperature inducing
conjugation of double bonds (Holman RT et al., Arch Biochem Biophys 1948, 19,
474). By this means, it was possible to measure the content of dienoic,
trienoic, tetraenoic, pentaenoic and hexaenoic acids in lipid extracts.
Separation by Swain LA of unsaponifiable lipids into three fractions on an
alumina column (Can Chem 1948, 32, 533).
Successful separation by Boldingh J of methyl esters of long-chain fatty acids
by reversed-phase chromatography on filter paper impregnated with vulcanized
rubber latex (Experientia 1948, 4, 270).
The process of fatty acid oxidation was discovered to be localized in
mitochondria (Grafflin AL et al., J Biol Chem 1948, 176, 95; Knox WE et al.,
J Biol Chem 1948, 176, 117).
1949
Folch J purified and characterized from the brain
cephalin fraction a diphosphoinositide preparation (J Biol Chem 1949, 177,
505).
Bolland established that the primary autoxidation products of linoleic
acid are hydroperoxides containing conjugated dienes
(Q Rev 1949, 3, 1).
1950
Widmer C and Holman RT discovered that linoleic
acid fed to essential fatty acid-deficient rats, was the precursor of
arachidonic acid and that a-linolenic acid was the precursor of pentaene and
hexaene acids.
First separation by Howard GA and Martin AJP of C12-C18 fatty acids by
reversed-phase partition chromatography on kieselguhr impregnated with liquid
paraffin and aqueous methanol as eluent (Biochem J 1950, 46, 532).
Baer E et al. achieved the synthesis of phosphatidylcholine via the
phosphorylation of a diacylglycerol (J Am Chem Soc 1950, 72, 942).
Raphael RA et al. described the first synthesis of linoleic acid (Nature 1950,
165, 235) and linolenic acid (J Chem Soc 1950, 2100).
Reiser R demonstrated that the high levels of saturated fatty acids in ruminant
animal fat are due to the hydrogenation of the dietary unsaturated fatty acids
in the rumen (J Nutr 1950, 42, 319).
Asselineau J elucidated the structure of mycolic acids (C R Acad Sci Paris 1950, 230, 1620).
Craig LC gave the first description of a rotary evaporator as a versatile
laboratory concentration device enabling the rapid quantitative recovery of
solute from large volume of solvents (Craig LC et al., Anal Chem 1950, 22,
1462).
1951
Kirchner JG applied for the first time thin layer
chromatography on silica to lipidic compounds
(terpenes from citrus juices) (Anal Chem 1951, 23, 420).
Hanahan DJ et al. purified a phospholipid (phosphatidylcholine) from egg yolk on
an alumina column (J Biol Chem 1951, 192, 623).
Baer E described the synthesis of phosphatidic acid by treatment of
diacylglycerol with diphenylchlorophosphate and removal of the phenyl group by
catalytic reduction (J Biol Chem 1951, 189, 235).
Hofman K et al. discovered cyclopropane (lactobacillic acid) fatty acids in gram-negative bacteria (J
Biol Chem 1951, 195, 473).
Yamakawa T et al prepared a ganglioside from horse erythrocytes which contained
galactose and neuraminic acid but not hexosamine which they named hematoside
(now GM3) (J Biochem 1951, 38, 199).
Zilch KT et al. reported an analysis of fat oxidation product (fatty acids,
mono- and diglycerides) by countercurrent distribution methods (Anal Chem
1951, 23, 775).
Discovery of branched-chain fatty acids (odd- and even-numbered carbon from C13
through to C18) in natural fats (butter) (Shorland FB, Biochem J 1951, 51,
207).
Nichols PL et al. reported that alkali-isomerization of linoleic acid gave a
mixture of cis-9,trans-11- and trans-10,cis-12-octadecadienoic acid, now known
as conjugated linoleic acids (CLA) (Nichols PL et al., J Am Chem Soc 1951,
73, 247).
Folch J et al. described a type of membrane lipoproteins, proteolipids, which
are soluble in a mixture of chloroform and methanol (Folch J et al., J Biol
Chem 1951, 191, 807).
First description of the countercurrent separation of "the higher normal
fatty acids" (C5-C18) (Barry GT et al., J Biol Chem 1951, 188, 299).
Galactosamine was identifies in brain gangliosides (Klenk E, Hoppe-Seyler Z
Physiol Chem 1951, 288, 216).
1952
Borgström B proposed silicic acid as
adsorbent for column chromatography separating neutral lipids and phospholipids
(Acta
Physiol Scand 1952, 25, 101).
First separation by James AT and Martin AJP of fatty acids up to 12 carbon atoms
by "Gas-liquid partition
chromatography" (Biochem J 1952, 50, 679).
Martin AJP and Synge RLM received the Nobel Prize for chemistry in part for
laying down the basis for partition chromatography.
Mattson FH et al. reported for the first time the presence of 2-monoacylglycerol
in the rat intestinal tract as the result of lipolytic action (J Nutr 1952, 48,
335).
For the first time, trans
fatty acids were demonstrated by infrared analysis to be present in substantial
quantities in a natural product, beef fat (Swern D et al., JAOCS 1952, 29, 44).
Yamakawa T et al. purified from human erythrocytes a ceramide-based glycolipid
containing galactosamine but not neuraminic acid which they named globoside (J
Biochem 1952, 39, 393).
The first issue of the journal "Progress in the Chemistry of Fats and other Lipids"
appeared that year.
1953
First isolation by Faure M et al. of
phosphatidylinositol from wheat germ and heart (C R Acad Sci Paris 1953, 236,
1104).
Fillerup DL et al. used a silicic acid column and a stepwise development with
diethyl ether-petroleum ether mixtures to fractionate plasma lipid classes (Proc
Soc exp Biol 1953, 83, 574).
Lipoic acid (or thioctic acid) is isolated in pure form from beef liver by Reed
LJ et al (J Am Chem Soc 1953, 75, 1767).
Yamakawa T et al. found that glycolipid fractions of human erythrocytes
inhibited haemagglutination of erythrocytes by ABO blood group antiserum (Jpn
J Exp Med 1953, 23, 327).
Discovery of the "phospholipid effect" which results in the generation
of diacylglycerol from the hydrolysis of membrane phosphoinositides through the
action of a neuromediator, acetylcholine (Hokin MR et al., J Biol Chem 1953, 203, 967).
The long-chain thiokinase which catalyzes the ATP-requiring conversion of fatty
acids (C8 to C18) to the corresponding acyl CoA esters was discovered (Kornberg
A et al., J Biol Chem 1953, 204, 329).
Lynen F and his group recognize the nature of the b-oxidation
cycle of fatty acids (Lynen F et al., Biochim Biophys Acta 1953, 12, 299).
Ruzicka L formulated the "biogenetic isoprene rule" as follows: “…the
carbon skeleton of terpenes is composed by isoprene units linked in regular or
irregular arrangement.” (Ruzicka L, Experientia 1953, 9, 357).
Woodward RB et al. explained the correct origin of all the carbon atoms of
cholesterol (Woodward RB et al., J Amer Chem Soc 1953, 75, 2023).
24-Hydroxycholesterol was detected in human brain and named cerebrosterol (Ercoli
IA et al., J Am Chem Soc 1953, 75, 3284). This oxysterol seems to play a
role as a physiological regulator of cholesterol homeostasis and as atherogenic
factor.
1954
First suggestion by Klenk E et al. of the right
structure of plasmalogens (Hoppe-Seyler's Z Physiol Chem 1954, 296, 179).
Tappel AL proposed a unified theory for vitamin E action as a lipid antioxidant (Tappel
AL, Arch Biochim Biophys 1954, 473-485).
Bloch K and Lynen F received the Nobel Prize for medicine "for their discoveries concerning the mechanism and regulation of the
cholesterol and fatty acid metabolism".
Dawson RMC made an important advance in phospholipid methodology in describing
the separation of the individual water-soluble products of methanolysis of the
total phospholipid fraction (Biochim Biophys Acta 1954, 14, 374).
Carter HE et al. described for the first time the presence of phosphoinositol
containing sphingolipids in plant extracts (named in 1958 "phytoglycolipids"). They described
also the presence of a new long-chain base, phytosphingosine (Carter HE et
al. J Biol Chem 1954, 206, 613).
1955
First application by Lea CH et al. of paper chromatography
on cellulose treated with silicic acid for
phospholipid separation (Biochem J 1955, 60, 353).
The first lipoamino acid to be isolated was serratamic acid (hydroxydecanoyl
serine) from a strain of Serratia (Cartwright NJ, Biochem J 1955, 60,
238).
Demonstration by Mattson and Beck of a high specificity of pancreatic lipase for
triglyceride primary esters (J Biol Chem 1955, 214, 115).
Jensen RG et al. described for the first time the synthesis of mixed acid
triglycerides (J Dairy Sci 1964, 47, 1012).
Description of the specific presence of trans fatty acids in the depot fats of
ruminants in contrast to their absence in non-ruminants (Shorland FB, Biochem
J 1955, 61, 603).
The "phospholipid effect" discovered in 1953 is now attributed to a
phosphoinositide in connection with phosphatidic acid metabolism
(phosphatidylinositol cycle) (Hokin LE et al.,Biochim Biophys Acta 1955, 18, 102).
1956
Svennerholm L showed for the first time that the
ganglioside isolated by Klenk in 1942 was formed at least of two fractions
separated by cellulose column chromatography (Nature 1956, 177, 524).
First separation by Marinetti GV et al. of individual phospholipids by TLC (Biochim
Biophys Acta 1956, 21, 168).
First demonstration of the occurrence of different molecular species of
phospholipids by Rhodes DN et al. in effecting a partial separation by silicic
acid chromatography (Biochem Probl Lipids 1956, Proc 2nd
intern conf Ghent, 1955, p 73).
First evidence for the occurrence of glycosylated glycerides by Carter HE, isolating
two "lipocarbohydrate" fractions from wheat flour (J Amer
Chem Soc 1956, 78, 3735). They were correctly identified in 1961.
Discovery that mevalonic acid is incorporated quantitatively into cholesterol in
cell-free systems with loss of carbon dioxide (Tavormina PA et al., J Am Chem
Soc 1956, 78, 4498).
The chemical structure of the cord factor of Mycobacterium tuberculosis
was established as trehalose dimycolate (Noll H et al., Biochim Biohys Acta
1956, 20, 299).
Discovery of the first polyisoprenoid alcohol, solanesol, in tobacco leaves
(Rowland RL et al., J Am Chem Soc 1956, 78, 4680).
First demonstration of the formation of hydroxylated derivatives of cholesterol
by mouse liver mitochondria (Fredrickson
et al., Biochim Biophys Acta 1956, 22, 183-187).
1957
First isolation by Bergström S of prostaglandins
(Acta Chem Scand 1957, 11, 1086).
Description by Folch J et al. of the most universal method of lipid extraction
using a mixture of chloroform/methanol (2/1) (J Biol Chem 1957, 226,
497).
Biggs R et al. demonstrated that all phospholipid
fractions showed coagulant activity but none of them was as active as the crude
cephalin (Brit J Haematol 1957, 3, 387).
The first bioactive fatty acid amide, N-acylethanolamine, was reported as a constituent of soy lecithin and
peanut meal and as a potent anti-inflammatory compound (Kuehl FF et al., J Am Chem Soc 1957, 79, 5577).
1958
First isolation by Carter HE et al. of an ether
phospholipid from egg-yolk (J Biol Chem 1958, 232, 681).
The structure of phosphatidylglycerol was first described (Benson AA et al.,
Biochim Biophys Acta 1958, 27, 189).
Carter HE et al. described in plant seed extracts
new complex sphingolipids with a polar head
group containing phosphoinositol, hexosamine and other sugar units, which were named
"phytoglycolipide" (JAOCS 1958, 35, 335; J Biol Chem 1958, 233, 1309).
These phytosphingosine-containing lipids were the first sphingolipids to be
described with structural features of a glycolipid and of a phospholipid.
Morton RA discovered and named ubiquinone (coenzyme Q) in the unsaponifiable
fraction of liver lipids (Nature 1958, 182, 1764)
Bernhard K et al. demonstrated that stearic acid could be desaturated
aerobically to oleic acid by a mitochondria-free cellular supernatant (Helv
1959, 42, 152).
1959
Description by Weicker H (Klin Wsch 1959, 37,
763) and by Mangold HK (Fette Seifen, Anstrichm 1959, 61, 877) of separations of
various lipids by TLC on silica gel .
Bremer J et al. discovered that phosphatidylethanolamine may generate
phosphatidylcholine via three successive methylation steps (using in vivo labeled
methionine) (Biochim Biophys Acta 1959, 35, 287).
First description of the exact structure of phosphatidylinositol (Pizer FL et
al., J Am Chem Soc 1959, 81, 915).
The first major compositional analysis of the lipids of a virus (Influenza
virus) was performed by Frommhagen LH et al. (Virology 1959, 8, 176).
First identification by the Nobel laureate Butenandt A. of a pheromone,
10,12-hexadecadien-1-ol (bombycol), secreted by the female butterfly, Bombyx
mori (Butenandt A et al., Z Naturforsch 1959, 14, 283-4).
Benson AA et al. discovered a sulfolipid (sulfoquinovosyl diacylglycerol) in a
microalgae Chlorella (Benson
AA et al., Proc Natl Acad Sci USA 1959, 45, 1582).
The first issue of the "Journal of Lipid Research" appeared that year.
1960
Sjovall J isolated prostaglandin E from sheep
prostate glands and showed that it was a 20-carbon fatty acid with blood
pressure-lowering activity.
Myelin was shown to be rich in ethanolamine plasmalogen.
Hawthorne JN proposed a classification of phospholipids, yet adopted (J Lipid
Res 1960, 1, 255).
Holman RT et al. showed that, in a few cases, it is possible to fractionate the
esters of cis and trans isomeric fatty acids by TLC on silica gel (J Am Oil Chem
Soc 1960, 37, 323).
Holman RT described the presence of high amounts of 20:3(n-9) (Mead acid) in
animals deprived of essential fatty acids and proposed the triene/tetraene ratio
as an indicator of essential fatty acid deficiency (J Nutr 1960, 70, 405).
Kaufmann HP et al. reported the separation of fatty acids by TLC using silica
gel layers impregnated with undecane (Fette, Seifen, Anstrichm 1960, 62, 1014).
Pennock JF et al. discovered in human kidney lipids a C100 isoprenoid alcohol
which was named dolichol (from Greek dolichos, long) (Pennock
RA et al. Nature, 1960, 186, 470).
Roine PE et al. described pathological effects (necrosis and fibrosis) on
cardiac tissue of a diet rich in rapeseed oil (rich in erucic acid) (Z
Ernährungswiss 1960, 1, 118).
Carter HE et al. identified cerebrosides in wheat flour (Biochim Biophys Acta
1960, 45, 402).
Mycosides are defined as specific glycolipids of Mycobacterial origin. They have
the structure of phthiocerol dimycocerosate (Smith DW et al., Nature 1960,
186, 887).
After the report of inositol phospholipids in brain by Folch in 1942, Grado C et
al. demonstrated that mono-, di-, and triphosphoinositides were present in
bovine brain (Grado C et al., J Biol Chem 1960, 235, PC23).
1961
The International Union of Biochemists has defined
the nomenclature of phospholipase
activities.
Carter HE et al. identified two important glycoglycerolipids in wheat flour,
mono- and digalactosyl-diacylglycerol (J Lipid Res 1961, 2, 215 and 223).
Glycoglycerolipids, identified as mannosyldiacylglycerol, were detected for the
first time in bacteria (Micrococcus lysodeikticus) (Macfarlane MG,
Biochem J 1961, 80, 45).
Dutton HJ et al. described the separation of cis-octadecenoate (oleate) and
trans-octadecenoate (elaidate) by countercurrent distribution (Chem Ind 1961,
1874).
Osbond JM et al. made the first total synthesis of arachidonic acid (J Chem
Soc 1961, 2779-87).
Imai J demonstrated that the oxidative desaturation of a saturated fatty acid
(palmitic acid) is depressed in diabetic rats (J Biochem Tokyo 1961, 49, 642).
Kennedy EP described the general pathways of the glycerolipid biosynthesis in
animal cells (Fed Proc 1961, 20, 934).
Bremer J et al. characterized a membrane-bound enzyme (PEMT) which converted
phosphatidylethanolamine to phosphatidylcholine (Biochim Biophys Acta 1961,
46, 205).
The first total synthesis of a cerebroside is reported (Shapiro D et al., J
Am Chem Soc 1961, 83, 3327).
Farnesol (a sesquiterpene) and its derivative farnesal were identified as
juvenile hormones in insects (Schmialek PZ, Z Naturforsch 1961, 16b, 461 and
Wigglesworth VB, J Insect Physiol 1961, 7, 73).
1962
First separation of glycerides by TLC on silver nitrate impregnated plates
by De Vries B (Chem Ind, London, 1962,
1049) and Barret CB et al. (Chem Ind, London, 1962, 1050) .
Edition by Stahl E of the first book on TLC, "Dünnschicht-Chromatographie,
Springer-Verlag, Berlin".
Kaufmann HP et al. reported the reversed-phase separation of fatty acids by a
complex two-dimensional TLC employing a catalytic hydrogenation
on the plate (Fette, Seifen, Anstrichm 1962, 64, 81).
First description of a direct titration method for analytical hydrogenation to
determine precisely the unsaturation of lipids (Brown HC et al., J Am Chem
Soc 1962, 84, 1493).
Discovery of O-amino acid (alanyl and lysyl) esters of phosphatidylglycerol in a
gram-positive bacteria Clostridium welchii (MacFarlane MG, Nature
1962, 196, 136).
The first GLC analysis of natural triglycerides from milk fat was reported (Kuksis
A et al., Can J Med Sci 1962, 40, 679).
Hematoside, the ganglioside of horse erythrocytes, is the first ganglioside
(GM3) whose structure was elucidated (Klenk E et al., Z Physiol Chem 1962, 327, 249).
The complete structure of sulfatide (sulfated galactosylceramide) was elucidated
including the position of the sulfate group attached to the C3 of galactose (Yamakawa
T et al., J Biochem 1962, 52, 226).
Methyl jasmonate was discovered in flowers of jasmine and was shown to be a
fragrant component in the essential oil from these flowers (Demole E et al.,
Helv Chim Acta 1962, 45, 675).
Discovery of diether-type phospholipids in a an extremely halophilic bacteria (Halobacterium
cutrirubrum) (Sehgal SN et al., Can J Biochem Physiol 1962, 40, 69).
First demonstration of the presence of 2-aminoethylphosphonic acid and its
glycerol ester in lipid extracts
of the sea anemone, Anthopleura elegantissima (Kittredge JS et al.,
Biochemistry 1962, 1, 624).
1963
Steim JM et al. first described the presence of monogalactosyl diacylglycerol in
an animal tissue, the bovine brain (Fed Proc Fed Am Soc Exp Biol 1963, 22, 299).
A sulfonated glycolipid (sulfoquinovosyl diacylglycerol) was discovered in the
green alga Chlorella (Benson AA, Adv Lipid Res 1963, 1, 387). That
acidic lipid was later shown to be a universal component of photosynthetic
tissues.
Hirsch J reported the reversed-phase separation of non polar lipids on a column
of polymerized vegetable oil (Factice) (J Lipid Res 1963, 4, 1).
Klenk E et al. showed that the Refsum's disease in human is associated with
accumulation of phytanic acid in blood and tissues (Hoppe Seyler's Z Physiol
Chem 1963, 333, 133).
First demonstration of the presence of sphingophosphonolipids in lipid extracts
of the sea anemone, Anthopleura elegantissima (Rouser G et al., J Am
Oil Chem Soc 1963, 40, 425).
Ceramide phosphorylethanolamine was for the first time demonstrated to be
present in lipid extract of an insect, Musca domestica (Crone HD et
al., Biochem J 1963, 89, 11).
First demonstration of a stimulation of the mitochondrial oxidation of
long-chain fatty acids, observations which led the authors to propose for the
first time that carnitine played a specific role in the transport of acyl groups
through mitochondrial membranes (Fritz IB et al., J Lipid Res 1963, 4, 279).
A uniform nomenclature for the gangliosides was proposed by Svennerholm L (J
Neurochem 1963, 10, 613).
The exact structure of four major gangliosides (GM1, GD1a, GD1b, and GT1b) have
been reported (Kuhn R et al., Chem Ber 1963, 96, 866; Kuhn R et al., Z
Naturforsch 1963, 18b, 541).
1964
Holman RT proposed a new numbering system for the
unsaturation of fatty acids, the "omega nomenclature".
Block KE and Lynen F were Nobel laureates in physiology and medicine for their
discoveries concerning the mechanism and regulation of the cholesterol and fatty
acid metabolism (pathway from "activated acetic acid" to the terpenes
and fatty acids).
Bergström S et al. demonstrated the enzymatic conversion of arachidonic acid to
prostaglandin E2.
Morrison WR et al. described the famous preparation of fatty acid methyl esters with
boron trifluoride (J Lipid Res 1964, 5, 600).
Vaughan M et al. described in detail and assigned the term
"hormone-sensitive lipase" to the neutral triacylglycerol lipase
activity in adipose tissue which could be increased by lipolytic hormones (catecholamines,
glucagon) (J Biol Chem 1964, 239, 401).
Hokin MR et al. suggested that the phosphoinositide effect is initiated by a
receptor-activated cleavage of phosphatidylinositol bisphosphate to yield
diacylglycerol (Metabolism and physiological significance of lipids, Dawson
RMC et al. Eds, J Wiley, London, pp423-434, 1964).
Sophorolipids were first described as surface-active glycolipids in some fungi (Tulloch
AP, Can J Microbiol 1964, 10, 359).
The term "phosphonolipids" was proposed by Baer E et al. to
describe phospholipids carrying a covalent bond (C-P) between posphorus and the carbon
of the nitrogenous base (Baer E et al., J Biol Chem 1964, 239, 3209).
First description of a glycosphingolipid containing a large quantity of fucose
(1 out of 4 carbohydrate residues) ("fucolipid") in adenocarcinoma cells
from human stomach (Hakomori S et al., J Biol Chem 1964, 239, 3606).
1965
Brockerhoff H described an enzymatic procedure to
determine the stereo chemical position of fatty acids in triglyceride molecules
(combination of a pancreatic lipase and a phospholipase A2) (J Lipid Res 1965,
6, 10).
Renkonen O for the first time was able to effectively characterize molecular
species of phospholipids after enzymatic removal of the phosphate group (J Am
Oil Chem Soc 1965, 42, 298).
Pabon HJJ et al. made the first total synthesis of docosahexaenoic acid (Recl
Trav Chim Pays-Bas 1965, 84, 1319).
Cyclohexyl fatty acids were
first found in butter (Schogt JC et al., J Lipid Res 1965, 6, 466)
First description of phospholipid vesicles (liposomes) made by mechanical
shaking of dried egg phosphatidylcholine with a salt solution (Bangham AD et
al., J Mol Biol 1965, 13, 238).
1966
Morris LJ et al. discovered furanoid fatty acids
in seed oil from Santalaceae (Tetrahedron Lett 1966, 36, 4249).
The structure of a C55 isoprenoid alcohol was described in Lactobacillus
and named bactoprenol (Thorne KJL et al. Biochem J 1966, 99, 123).
The presence of compounds similar to insect ecdysteroids (phytoedysteroids) in
plants was documented (Galbraith MN et al., J Chem Soc, Chem Comm 1966, 24,
905).
The first issue of the journal "Chemistry and Physics of Lipids"
appeared that year.
1967
Rouser G et al. isolated digalactosyl
diacylglycerol from human brain tissue (Lipids 1967, 2, 37).
Diphosphatidylglycerol (cardiolipin) was definitively shown to be localized
exclusively to liver mitochondria (Parsons DF et al., in Mitochondrial
structure and compartmentation, Quagliariello E et al. Eds, Adriatica Editrice,
Bari, 1967, pp. 29-70).
The first component protein of an enzyme of fatty acid biosynthesis, fatty acid
synthase, was purified (Simoni RD et al., J Biol Chem 1967, 242, 573).
Polyprenol diphosphates were shown to be involved in the biosynthesis of
polysaccharides in Salmonella (Wright A et al., Proc Natl Acad Sci USA
1967, 57, 1798) and in the biosynthesis of peptidoglycans in Micrococcus
(Higashi Y et al., Proc Natl Acad Sci USA 1967, 57, 1878).
1968
First indication by Fisher DB et al. of a
relationship between inositol lipids and cell proliferation (lymphocytes
stimulated with phytohaemagglutinin) (Proc Natl Acad Sci USA 1968, 60, 1396).
First description of a "peptidelipid" surfactant (surfactin) composed
of seven amino acids and one fatty acid (cyclic lipopeptide) produced by Bacillus subtilis (Arima K
et al., Biochem Biophys Res Comm 1968, 31, 488).
1969
First description of the structure
of a cyanogenic lipid found in a Boraginaceae (Cordia verbenacea) (Mikolajczak
KL et al., Lipids 1969, 4, 617).
First report of the exact structure of a ceramide phosphorylethanolamine and a
ceramide phosphorylglycerol in the lipids of an anaerobic bacterium (LaBach
JP et al., J Lipid Res 1969, 10, 528).
Discovery of
glucosylated phosphatidylglycerol in the gram-positive bacteria Bacillus megaterium
(MacDougall JC et al., Biochem J 1969, 114,
361).
The structure of complex phosphorylated glycolipids (glycophosphoceramides or
"phytoglycolipids") were elucidated by the group of Carter HE in plant
extracts (Carter HE et al., Biochemistry 1969, 8, 383).
The b-oxidation
of fatty acids was demonstrated to take place in a newly discovered organelle,
the glyoxysome (Cooper TG et al., J Biol Chem 1969, 244, 3514; Hutton D et
al., Plant Physiol 1969, 44, 508).
1970
Stoffel (Hoppe-Seyler's Z Physiol Chem 1970, 351, 635) reported the formation of
sphingosine-1-phosphate in erythrocytes, a kind of
phosphosphingolipid which appeared later involved in cellular proliferation.
The name lipoteichoic was coined when teichoic acid lipid complexes were
detected in the wall of gram-positive bacteria (Wicken AJ et al., J Gen
Microbiol 1970, 60, 293).
1971
Boyle IT et al. demonstrated that 1,25-dihydroxyvitamin D3 was the most potent component for calcium absorption by the intestine (Proc Ntl Acad Sci USA 1971, 68, 2131).
1972
Bretscher MS proposed that both leaflets of the
lipid bilayer of biological membranes have different lipid compositions, thus
defining an asymmetric structure (Nature
New Biol 1972, 236,11)
Yavin E et al. demonstrated that the cleavage of the vinyl-ether linkage of
plasmalogens may be done via an oxygen-dependent reaction (ferrous-ascorbate
complex) which is inhibited by
antioxidants (Eur J Biochem 1972, 25, 437).
Borensztajn J et al. reported an increase of adipose lipoprotein lipase activity
in rats after insulin injection (Am J Physiol 1972, 223, 1271).
Bang HO et al. reported that Greenland Eskimos had lower levels of serum
cholesterol, low density lipoprotein and triglycerides correlated with a low
myocardial infarction rate as compared with Danish
controls (Acta med Scand 1972, 192, 85).
Kornblatt MJ et al. discovered
the presence of sulfate esters of glycoglycerolipids (a mixture of
sulfated alkylacyl, known as seminolipids, and diacyl glycerol) in rat testis (Biochem
Biophys Res Commun 1972, 48, 1489).
Galliard T et al. described the structure of two new divinyl ether fatty acids (colneleic
and colnelenic acids) generated in potato homogenates by the action of
9-lipoxygenase and divinyl ether synthase (Galliard T et al., Biochem J 1972,
129, 743).
Discovery of the platelet activating factor (PAF) as an alkyl acetyl
phosphatidylcholine, one of the first and the most important lipid mediator
known (Benveniste J et al., J Exp Med 1972, 136, 1356).
A model of cell membrane, known as the fluid mosaic model, with globular
proteins floating within the lipid bilayer was proposed by Singer S J et al. (Science
1972, 175, 720).
It was established that lipid compounds containing arsenic and bromine are present in marine
organisms (fish and seaweed oils) (Lunde G, JAOCS 1972, 49, 44).
1973
Gordesky SE et al. demonstrated that nearly all
phosphatidylserine and a minimum of 70% of phosphatidylethanolamine is on the
inside surface of the human erythrocyte membrane, thus "presenting a strong
evidence for an asymmetric arrangement of phospholipids" (Biochem
Biophys Res Comm 1973, 50, 1027).
First demonstration of an inhibition of sterol biosynthesis (HMG-CoA reductase
activity) by oxygenated derivatives of cholesterol in cultured mammalian cells (Kandutsch
AA et al., J Biol Chem 1973, 248, 8408-8417).
1974
Riley CA et al. first reported
that hydrocarbon gases were released by mice upon treatment with CCl4 due
to lipid peroxidation (Science 1974, 183, 208).
Banschbach MW et al. demonstrated that acetylcholine is able to increase
diglyceride levels in incubated pancreatic tissue (Biochem Biophys Res Comm
1974, 58, 714).
Inositol phosphorylceramide was shown to be a novel phospholipid in yeast (Smith
SW et al., J Biol Chem 1974, 249, 3395).
The first structure of a betain lipid (diacylglyceryl hydroxymethyl
trimethylhomoserine) was reported in a vegetal Ochromonas danica (Brown
AE et al., Biochemistry 1974, 13, 3476).
1975
Michell RH in a famous review proposed for the
first time that the "phosphoinositide effect" discovered in 1953 by
Hokin plays a role in cellular calcium mobilization (Biochim Biophys Acta
1975, 415, 81).
Flynn TJ et al. reported the isolation of sulfogalactosyl diacylglycerol from
the brain of young rats (Biochem Biophys Res Comm 1975, 65, 122).
1976
Fisher KA demonstrated by freeze-fracture and
biochemical analysis in human erythrocytes that cholesterol is asymmetrically
distributed across the plane of the membrane, being more present on the exterior
side than on the interior side (Proc Nat Acad Sci USA 1976, 73, 173)
Sporn MB et al. introduced the term retinoid to cover all natural as well as
synthetic structural analogs of retinol (Fed Proc 1976, 35, 1332).
1977
Discovery in the gram-positive
bacteria Streptococcus of glucosylated diphosphatidylglycerol (cardiolipin)
(Fisher W, Biochim Biophys Acta 1977, 487, 74).
Pieringer J et al. demonstrated a close association of the sulfogalactosyl
diacylglycerol of rat brain with the process of myelination (Biochem J 1977,
166, 421).
1978
A new membrane lipid, archaeol (diphytanyl
glycerol ether) is discovered by Kates M in halophilic bacteria (Prog Chem Fats
Lipids 1978, 15, 301).
Dyerberg J et al. make the hypothesis that eicosapentaenoic acid (EPA) plays a
role in the prevention of thrombosis and atherosclerosis (Lancet 1978, 2, 117).
Discovery of sulfated glyceroglycolipids in rat brain (Ishizuka I et al., J
Biol Chem 1978, 253, 898).
1979
Murphy RC et al. elucidated the structure of the slow reacting substance
(SRS-A) of anaphylaxis as a new hydroxylated derivative of arachidonic acid
which was named leukotriene (Proc
Ntl Acad Sci USA 1979, 76, 4275).
Demopoulos CA et al. elucidated the structure of the Platelet-Activating Factor
(PAF) as an acetylated alkyl phosphatidylcholine (J
Biol Chem 1979, 254, 9355).
Takai Y et al. described a protein kinase (now protein kinase C) requiring
calcium, phosphatidylserine, and diacylglycerol for complete activation (Biochem
Biophys Res Comm 1979, 91, 1218).
Bell RL et al. provided evidence that arachidonate release from stimulated
platelets involves a diglyceride lipase acting on the diglycerides produced by a
phosphatidylinositol-specific phospholipase C (Proc
Natl Acad Sci 1979, 76, 3238).
Dyerberg J et al. suggested for the first time a close relationship between platelet aggregation, bleeding time and n-3 polyunsaturated fatty acids (Lancet 1979, 2, 433).
Walker IC et al. identified a new epoxy-hydroxy fatty acid (hepoxilin) after
incubation of blood platelets with arachidonic acid (Prostaglandins 1979, 18,
173).
1980
Porter NA et al. demonstrated for the first
time the free radical oxidation
of membrane phospholipids (Lipids 1980, 15, 163)
Low MG et al. demonstrated clearly that alkaline phosphatase is attached to membranes
of Staphylococcus aureus by a strong interaction with
phosphatidylinositol (Low
MG et al., Biochemistry 1980, 19, 3913). The discovery of these
"anchor" molecules had a significant impact on several areas of cell
biology.
1981
Michell RH et al. identified
phosphatidylinositol-4,5-bisphosphate as the main phospholipid subject to a
turnover in stimulated cells in connection with calcium mobilization (Philos
Trans R Soc, London B, 1981, 296, 123).
Fredrikson G et al. described the first extensive purification of the
hormone-sensitive lipase of adipose tissue (J Biol Chem 1981, 256, 6311).
1982
Bergström SK , Samuelsson BI and Sir Vane JR
received the Nobel Prize for medicine "for their discoveries concerning prostaglandins and related biologically active substances".
Their work established the relationships between fatty acids, prostaglandins,
thromboxanes and leukotrienes (they discovered) and helped explain the effects on the body of aspirin, the world's most widely used drug.
Nakamura T et al. discovered 4-hydroxynonenal (4-HNE) in autoxidized linseed oil (Bull Jap
Soc Sci Fish 1982, 48, 1357).
Bevers EM et al. reported that the activation of blood platelets triggered a
change in the distribution of lipids in the plasma membrane: phosphatidylserine
become exposed at the outer surface (Eur J Biochem 1982, 122, 429).
Grove RI et al. demonstrated that a tumor promoter (phorbol ester) caused in
chick embryo myoblasts increased diacylglycerol levels generated via the
hydrolysis of phosphatidylcholine (Biochim
Biophys Acta 1982, 711, 272).
Macrae R et al. used for the time a HPLC detection system for lipids based on evaporative
light-scattering (Chromatographia 1982, N° 7, july).
Agrawal HC et al. demonstrated for the first time that proteolipids contain
covalently-bound fatty acids (Agrawal HC et al., J Biol Chem 1982, 257, 4588).
Schwartz RS et al. described the mechanism of the regulation of lipogenesis by
fatty acids in measuring the rate of synthesis of fatty acid synthase in mouse
liver (Schwartz RS et al., Biochim Biophys Acta 1982, 711, 316).
1983
Streb H et al. have shown that inositol-1,4,5-trisphosphate (IP3) is capable to release calcium from non-mitochondrial pools in pancreatic cells, this report providing information on the role of phosphatidylinositol 4,5-bisphosphate in stimulus-coupled responses (Nature 1983, 306, 67).
1984
Serhan CN et al. discovered new biologically active compounds formed from arachidonic acid in
human leukocytes, lipoxins A and B (Proc
Ntl Acad Sci USA 1984, 81, 5335).
Seigneuret M et al. discovered in erythrocytes an ATP-dependent aminophospholipid-specific
transporter (translocase) which transports phosphatidylserine and
phosphatidylethanolamine from the outer to inner leaflet of plasma membranes (Proc Natl Acad Sci 1984, 81,
3751).
Evidence was given for a post-translational modification of proteins by
incorporation of isoprenoid lipids (Schmidt RA et al., J Biol Chem 1984, 259,
10175).
New aldehydic products of the cyclooxygenase pathway, levuglandins, have been
discovered
(Salomon RG et al., J Am Chem Soc 1984, 106, 6049).
1985
Brown MS and Golstein JL received the Nobel prize
for medicine "for their discoveries concerning the regulation of cholesterol
metabolism".
Bocckino SB et al. brought evidence that phosphatidylcholine breaks down in
response to several agonists generating diacylglycerols (J
Biol Chem 1985, 260, 14201).
First demonstration by Wolf RA et al. of a plasmalogen selective phospholipase
A2 in heart tissue (J
Biol Chem 1985, 260, 7295).
Pentchev PG et al. demonstrated that Niemann-Pick disease type C is a disease of
cholesterol metabolism (Proc
Natl Acad Sci USA 1985, 82, 8247).
Sucrose esters were characterized in lipids of
tobacco leaf (Severson RF et al. J Agric Food Chem 1985, 33, 870). These
particular glycolipids were later shown to have antibiotic and insecticide
properties.
The composition and the structure of a novel phosphatidylinositol-containing
glycolipid, now known as membrane anchor, were reported in a protozoan Trypanosoma
brucei (Ferguson
MAJ et al., J Biol Chem 1985, 260, 14547).
Experiments on Torpedo electric organ led to the suggestion that
acetylcholinesterase is anchored to the plasma membrane by one or more
phosphatidylinositol molecules linked to a short amino acid sequence at one end
of the catalytic subunit of the enzyme (Futerman
AH et al. Biochem J 1985, 226, 369).
First report that fish oils reduced thickening of vein intimal in graft
experiments in dogs (Landymore RW et al., J Thorac Cardiovasc Surg 1985, 89,
351).
First published paper in which mutants of Arabidopsis thaliana were used
to elucidate the role of a plant lipid, tr-3-hexadecenoic acid (Browse JA et
al., Science 1985, 227, 763).
1986
Serhan CN et al. described the structure and
formation of various lipoxins by leukocytes (J
Biol Chem 1986, 261, 16340).
Stremmel W et al. brought evidence that movement of free fatty acids through
hepatocyte plasma membrane is facilitated by a specific binding protein (FABP) (Proc
Natl Acad Sci USA 1986, 83, 3584).
Brassell SC et al. first demonstrates the reliability of a new stratigraphic
technique for climatic assessment utilizing the relative abundance of two C37
alkenones in marine sediments (Brassell SC et al., Nature 1986, 320, 129).
First demonstration of a specific receptor-mediated release of 20:4n-6 and
22:6n-3 from plasmalogen phospholipids (Horrocks LA et al., Adv Cyclic Nucl
Prot Phosphoryl Res 1986, 20, 263).
Evidence is given that phosphatidic acid is a lipid second messenger with growth
factor-like properties, stimulating the breakdown of phosphoinositides and
calcium release (Moolenaar
WH et al., Nature 1986, 323, 171).
Demonstration of an inhibition of protein kinase C by sphingosine which
suggested an important role for that lipid in the regulation of the signal
transduction pathways (Hannun
YA et al., J Biol Chem 1986, 261, 12604).
1987
Whitman M et al. identified a
phosphatidylinositol kinase that phosphorylates the D-3 position on the inositol
ring to produce phosphatidylinositol 3-phosphate (PI-3-P) (Biochem
J 1987, 247, 165).
Bocckino SB et al. provided evidence that in hormone-treated hepatocytes
phosphatidic acid levels increase by a mechanism involving phospholipase B (J
Biol Chem 1987, 262, 15309).
Investigating the carcinogenic components of grilled beef, Ha YL et al.
demonstrated for the first time the presence of conjugated linoleic acids (CLA)
in animal products which were shown to inhibit mutagenesis in bacteria and the
initiation of epidermal carcinogenesis in mice (Carcinogenesis
1987, 8, 1881).
Discovery of a hormone-like compound, a sesquiterpenoid (methyl farnesoate) in
crustaceans, now considered as the crustacean juvenile hormone (Borst DW et al.,
Insect Biochem 1987, 17, 1123).
1988
Description by Bitbol M et al. of an
ATP-dependent flippase in erythrocytes which transports aminophospholipids and
cholinephospholipids from the inner to outer leaflet (Proc Natl Acad Sci 1988,
85, 6783).
Demonstration by Hungund BL et al. of fatty acid ethyl ester synthesis in liver
of mice treated with ethanol inhalation (J Chem Pharmacol 1988, 37, 3001).
First literature use of the term biodiesel in a Chinese paper by Wang R et al. (Taiyangneng
Xuebao 1988, 9, 434).
Description of a specific phosphatidylinositol kinase (PI3K) which produces a
novel phospholipid, phosphatidylinositol-3-phosphate (Whitman M et al.,
Nature 1988, 332, 644).
First report of the receptor-activation of phospholipase D in mammalian cells
with generation of diacylglycerol from phosphatidylcholine (Pai JK et al.,
Biochem Biophys Res Comm 1988, 150, 355).
1989
First description of a "sphingomyelin
cycle" related to cell differentiation which generates ceramide and choline
phosphate through the stimulation by vitamin D3 (Okazaki T et al., J Biol
Chem 1989, 264, 19076).
Sphingosine, a constituent and metabolite of membrane sphingolipids, was shown
to inhibit protein kinase C, thus playing a pivotal role in a specific signal
transduction system (Merrill
AH et al., Biochim Biophys Acta 1989, 1010, 131).
1990
Morrow JD et al. discovered new
prostaglandin-like molecules produced by free-radical-catalyzed mechanism which were termed isoprostanes (Proc Natl Acad Sci
1990, 87, 9383).
Issemann I et al. identified a peroxisome proliferator-activated receptor (PPAR)
and cloned a novel member of the nuclear receptor superfamily (steroid hormone
receptors). Among activators, a variety of endogenously present lipids were
described (Nature
1990, 347, 645).
An antiphosphatidylcholine antibody was described in the
serum of a patient diagnosed with hemolytic anemia (Cabral AR et al., J
Autoimmun 1990, 3, 773).
Phosphatidylserine was shown to be recognized by specific antibodies in patients
with lupus anticoagulant (Zuazu-Jausoro I et al., Med Clin 1990, 95, 210).
The "Nod factors" produced in legumes by Rhizobia as a class of
signalling molecules was identified as lipo-chitooligosaccharides (Lerouge
P et al., Nature 1990, 344, 781).
First demonstration of phosphatidylinositol anchor on the lipopolysaccharides of
a prokaryotic species, Mycobacterium tuberculosis ( Hunter
SW et al., J Biol Chem 1990, 265, 9272).
1991
The cloning of cDNA for a lipid transfer protein
in maize (Zea mays) introduced for the first time molecular biology into plant
lipid research (Arondel
V et al., Gene. 1991, 99, 133)
Evidence that sphingosine-1-phosphate is a component of the intracellular second
messenger-mediated calcium release is presented (Zhang
H et al., J Cell Biol 1991, 114, 155).
Evidence that sphingosylphosphorylcholine is a potent mitogenic mediator is
presented (Desai
NN et al., Biochem Biophys Res Comm 1991, 481, 361).
1992
Fadok VA et al. discovered the exposure of phosphatidylserine at the lymphocytes outer surface during apoptosis triggering their recognition and removal by macrophages (J Immunol 1992, 148, 2207).
A gene from Arabidopsis that encodes a n-3 desaturase was cloned and an increased production of n-3 fatty acids was obtained by genetic manipulation of the plant (Arondel V et al., Science 1992, 258, 1353).
A novel family of nuclear hormone
receptors controlling the peroxisomal b-oxidation
pathway (PPARs) was described and cloned on Xenopus eggs (Dreyer
C et al., Cell 1992, 68, 879-887).
Anandamide (arachidonoyl ethanolamine) is the first endocannabinoid substance to
be discovered in brain tissue (Devane WA et al., Science 1992,258,1946
– 9).
Identification of lysophosphatidic acid as the albumin-bound lipid
responsible for various cellular messenger properties (Tigyi
G et al., J Biol Chem 1992, 267, 21360).
Identification of cyclic phosphatidic acid as a bioactive lipid at the nuclear
level (Murakami-Murofushi
K et al., J Biol Chem 1992, 267, 21512).
The name bio-diesel was introduced in the USA by the National Soy Diesel
Development Board for an alternative diesel fuel made from renewable sources
such as vegetable oil and animal fats.
Gottlicher M et al. demonstrated that fatty acids can regulate gene expression
mediated by a member of the steroid nuclear receptor superfamily (Gottlicher
M et al., PNAS 1992, 89, 4653).
1993
An experimental mutant of a plant, Arabidopsis,
deficient in oleic acid desaturase, was shown to be very sensitive to cold
temperature (Miquel M et al., Proc Natl Acad Sci USA 1993, 90, 6208).
Glucose was shown to react with a phospholipid, phosphatidylethanolamine, giving
glycosylation end products which are able to enhance free radical formation (Bucala
R et al., PNAS 1993, 90, 6434).
Ceramide was shown to be potent agent involved in the programmed cell death
(apoptosis) (Obeid LM et al., Science 1993, 259, 1769).
Demonstration of a control of peroxisomal beta-oxidation of fatty acids by fatty
acids and retinoids through activation of PPARs (Keller
H et al., PNAS 1993, 90, 2160).
1994
First analysis of individual phospholipids by high-performance capillary electrophoresis (Ingvardsen L et al., JAOCS 1994, 71, 183-188).
1995
A new vitamin E constituent, a-tocomonoenol
was discovered in palm oil (Matsumoto
A et al., J Jap Oil Chem Soc 1995, 44, 593).
A monoglyceride, 2-arachidonoyl glycerol, has been shown to be endogenous
ligands for cannabinoid receptors in brain tissue (Sugiura T et
al., Biochem Biophys Res Comm 1995, 215, 89) and in gut (Mechoulam R et
al., Biochem Pharmacol 1995, 50, 83).
1996
Morrow JD et al. discovered
isothromboxanes which are produced by non-enzymatic free radical-catalyzed
peroxidation of arachidonoyl lipids (J
Biol Chem 1996, 271, 23185).
First report of the genetic engineering of plants to modify oil crops (Murphy
DJ, Trends Biotechnol 1996, 14, 206).
First demonstration of a modification of proteins (hedgehog signaling proteins)
by linking of cholesterol to an amino-terminal signaling domain (Porter JA et
al., Science 1996, 274, 255).
1997
Rafts are presented as a new aspect
of cell membrane based on the dynamic clustering of sphingolipids and
cholesterol. They were mainly proposed as platform for the attachment of
proteins (Simons K et al., Nature 1997, 387, 569).
Yu M et a. report for the first time a new class of prostaglandins, prostamides,
formed from anandamide by cyclooxygenase action (Yu
M et al., J Biol Chem 1997, 272, 21181).
Evidence was provided that new oxidation products (F3-Isoprostanes) could be
formed in vitro from eicosapentaenoic acid ((Nourooz-Zadeh J
et al., Biochem Biophys Res Commun 1997, 236, 467).
A sesquiterpene, methyl farnesoate, is demonstrated to be the
crustacean juvenile hormone, synthesized by the mandibular organs (Homola E et al., Comp Biochem Physiol 1997,
117B, 347).
Presqualene
diphosphate, a metabolic intermediate between farnesyl
diphosphate and squalene, was shown to carry biological activity in human neutrophiles and
to serve as a negative intracellular signal preventing superoxide anion generation
(Levy
BD et al., Nature 1997, 389, 985).
1998
Roberts LJ described the oxidative formation of isoprostane-like compounds
(F4-neuroprostanes) in nervous tissues from docosahexaenoic acid (J
Biol Chem 1998, 273, 13605).
Discovery of a major aminated phospholipid (about 18% of the lipid phosphorus), alanylcardiolipin,
in a gram-positive bacteria, Vagococcus fluvialis (Fisher
W et al., J Bacteriol 1998, 180, 2950).
First description of lysylcardiolipin in a gram-positive bacteria Listeria
welshimeri (Peter-Katainic
J et al., J Lipid Res 1998, 39, 2286).
Experiments on tobacco cell culture suggested that N-acetylethanolamine may
participate in the early signal transduction events leading to plant defense
responses (Chapman KD et al., Plant Physiol 1998, 116, 1163).
1999
Nitrogen dioxide was shown to induce cis-trans-isomerization of arachidonic acid within cellular phospholipids generating new compounds termed trans-arachidonic acids (Jiang H et al., J Biol Chem 1999, 274, 16235).
2000
The endocannabinoid
2-arachidonoylglycerol has been shown to be metabolized by cyclooxygenase-2 into
glyceryl prostaglandins (Kozak
KR et al., J Biol Chem 2000, 275, 33744).
The first issue of the journal "European Journal of Lipid Science and
Technology" appeared that year.
First experimental evidence that seminolipid, sulfated galactosyl-alkyl-acyl-glycerol
is essential for normal spermatogenesis in mice (Fujimoto
H et al., J Biol Chem 2000, 275, 22623).
2001
Autoantibodies to
phosphatidylethanolamine were shown to recognize coagulation
factor XI and prekallikrein (Sugi T et al., J Autoimmun 2001, 17, 207).
a-Tocomonoenol
discovered in 1995 has been shown to provide enhanced antioxidant protection in
marine fish adapted to cold-water environments (Yamamoto
Y et al., PNAS 2001, 98, 13144).
Identification of a new phosphoinositide in plants, phosphatidylinositol
5-monophosphate which was shown to be accumulated upon osmotic stress (Meijer
HJ et al., Biochem
J. 2001, 360, 491).
The alkyl monoglyceride, 2-arachidonoylglyceryl ether (noladin ether), was shown
to belong to the endocannabinoid family (Hanus
L et al., PNAS 2001, 98, 3662).
2002
Discovery of new arachidonic acid
peroxidation products, the isofurans, preferentially generated by increased
oxygen tension (Fessel
JP et al., PNAS 2002, 99, 16718).
Discovery of the function of sterol glucoside as primer for the synthesis of
cellulose (Peng
L et al., Science 2002, 295, 147).
Characterization of a novel family of bioactive fatty acids carrying conjugated
triene structures formed formed from eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) termed resolvins
which have anti-inflammation effects (Serhan
CN et al., J Exp Med 2002, 196, 1025).
Arachidonoyl dopamine was shown to be present in bovine and rat brain and to be
agonist of cannabinoid and vanilloid receptors (Huang L et al., Proc Natl
Acad Sci USA 2002, 99, 8400).
Nitrolinoleate, formed from NO-derived reactive nitrogen species and linoleic
acid, was shown to inhibit platelet aggregation via cAMP-dependent mechanisms (Coles
B et al., J Biol Chem 2002, 277, 5832).
First description of fatty acids and fatty alcohols containing four-membered
aliphatic cyclobutane rings in bacteria (order Planctomycetales) capable of
anaerobic ammonium oxidation (Sinninghe
Damsté JS et al., Nature 2002, 419, 708). They were named
ladderane molecules.
2003
NAD(P)H steroid dehydrogenase-like,
involved in the conversion of lanosterol into cholesterol, may be a new
mechanism for the regulation of the levels and sites of accumulation of
intracellular cholesterol (Ohashi
M et al., Human Mol Gen 2003, 12, 2981).
A new brain messenger, 10,17S-docosatriene formed from docosahexaenoic acid (DHA),
is shown to elicit several responses suggesting that it may have a potent
neuroprotective effect (Marcheselli
VL
et al., J Biol Chem 2003, 278, 43807).
Ceramide-1-phosphate was shown to be a specific and potent inducer of
arachidonic acid and prostanoid synthesis in cells (Pettus
BJ et al., J Biol Chem 2003, 278, 38206)
2004
The docosanoid 10,17S-docosatriene,
or Neuroprotectin D1, was shown to protect human retinal pigment epithelial
cells from oxidative stress (Mukherjee
PK et al., PNAS 2004, 101, 8491).
Nitrolinoleate, which was previously shown to mediate signaling reactions, was
reported to be present in plasma and in red cell membranes representing a large
pool of bioactive oxides of nitrogen in the vasculature (Baker PRS et al.,
PNAS 2004, 101, 11577).
The G2A receptor was shown to mediate T lymphoid cell migration via
lysophosphatidylcholine interaction. This function may be relevant to
the autoimmune syndrome (Radu
CG et al., PNAS 2004, 101, 245).
2005
Nitrolinoleic acid is shown to be a
potent endogenous ligand for peroxisome proliferator-activated receptor gamma (PPARgamma)
(Schopfer
FJ et al., PNAS 2005, 102, 2340).
Fucosylated glycosphingolipids containing polyunsaturated very long chain fatty
acids were demonstrated to be essential for spermatogenesis and fertility in
mice (Sandhoff
R et al., J Biol Chem 2005, 280, 27310).
2006
Evidence was provided that F3-isoprostanes are formed in vivo from eicosapentaenoic acid in mice ((Gao L et al., J Biol Chem 2006, 281, 14092).
2008
Discovery of neurofurans,
isodocosanoids derived from docosahexaenoic acid, which may serve as indices of
oxidant stress. They are elevated in brain cortex of animal model of Alzheimer
disease (Song
WL et al., J Biol Chem 2008, 283, 6).
Cyclopentenone isoprostanes (A3/J3-isoprostanes) are produced in vitro and in
vivo by the free radical-catalyzed peroxidation of eicosapentaenoic acid. They
are likely related to the beneficial effects
of fish oil consumption on human health (Brooks
JD et al., J Biol Chem 2008, 283, 12043).
