All plants contain oils (ex. olive oil) or fats (ex. cocoa butter)
and mainly in their seeds. As an exception, tubers of Cyperus esculentus
(sedge or tigernut tubers) contain up to 27% oil (Eteshola E et al., JAOCS
1996, 2, 255).
Accumulation of triglycerides may also occur in certain yeasts and moulds. Thus,
up to 86% lipid has been recorded in the mould, Mortierella isabellina.
The analysis of the distribution of the fatty acyl groups in triglycerides from
numerous yeasts and mould indicates that these microbial lipids are similar to
their plant counterparts mainly in locating the unsaturated chains at the sn-2
position.
In most plants storage lipids are in the form of triglycerides (Murphy DJ,
Prog Lipid Res 1990, 29, 299). There are a very few examples of alternative
forms of storage lipid in higher plants. The most known of these is the desert
shrub, jojoba, which stores its seed lipid as a liquid wax. Storage lipids may
be accumulated in one or both of the main types of seed tissue, embryo or
endosperm. In oilseeds such as sunflower, linseed or rapeseed, the cotyledons of
the embryo are the major sites of lipid accumulation. In species such as castor
bean, coriander or carrot, the endosperm is the main site of lipid accumulation.
Finally, in tobacco, both embryo and endosperm tissues store lipids.
Vegetal oils are frequently classified in two main
groups, according to their source: pulp oil (palm, olive, avocado) and seed oil (other
sources). The amount of lipids in plant parts varies from as low as 0.1% in potatoes to
about 70% in pecan nuts. Some vegetal products are fat poor (1% in lentils, 3% in
mushrooms), some seeds have a middle range amount (about 10% in wheat germ, 20% in
soybeans) while some are very oily (44% in peanuts, 55% in almonds, 65% in walnuts).
Plants store their energy production first as
carbohydrates, but during ripening they transform these oxygen containing compounds in
carbon-rich triglycerides. Thus, a minimum of volume is required to stock a maximum of
energy content. Conversely, the triglyceride stock is reconverted into carbohydrates
during germination along with an incorporation of high amount of water. One gram of
oil is converted into 2.7 g of carbohydrates.
Global oilseed production had reached a record 319 million metric tons in 2001.
Part of the total production of each oilseed is used directly as food, but most
is crushed to extract oil. In average, all the seeds crushed gave oil in about
26% yield (min. cottonseed 15%, max. coprah 62%). The global vegetable oil
consumption has more than doubled between 1980 and 2000, reaching about 76
million tons.
The following picture shows the gross fatty acid composition of the most important
vegetal (seed) oils for human or animal consumption.
It can be seen that cocoa butter (as coconut oil or
hydrogenated palm oil) is rich in saturated fatty
acids and poor in essential fatty acids (n-6 and n-3). A number of plant
families have seed fats characterized by low amounts of palmitic, oleic and linoleic acids.
These acids have been replaced by lauric (12:0) and myristic (14:0) acids, as well as
capric (10:0) and caprylic (8:0) acids. Among Lauracaea, Laurus nobilis fat
contains about 58% lauric acid, while among Lythracaea, Cuphea salvadorensis contains
about 65% myristic acid, C. calophylla 85% lauric acid, C. koehneana
92% capric acid, and C. pulcherrina 94% caprylic acid (Isbell TA et
al., Inform 2003, 14, 513).
Peanut, olive and rapeseed oils are the richest in monoene (n-9) fatty
acids.
Rapeseed oil (or colza oil from Brassica sp) was
originally available as a high-erucic oil (almost 50% of 22:1n-9) used mainly in the
oleochemical industry. Several studies in animal models have shown that erucic acid may
have detrimental effects on cardiovascular physiology, therefore, a low erucic acid oil is
now produced and can be used safely in the food industry.
Soya, corn,
sunflower and walnut oils are very rich in one diene
(n-6) fatty acid, linoleic acid (18:2n-6)
while rapeseed, walnut and soya oils are precious sources of one triene (n-3) fatty
acid,
linolenic acid (18:3n-3).
The seed oils of watercress (Nasturtium)
and Honesty (Lunaria
annua) have relatively high proportions of C22:1 (38-48%) and C24:1(22-25%) fatty acids in their triglyceride
molecules, these peculiarities make them potentially suitable for production of
high-temperature lubricants and engineering nylons. The seeds of Crambe
abyssinica (Cruciferae), a cabbage-like annual herb cultivated in
Northern Europe, contain an oil high in erucic acid (about 56%). The seed
oil of meadowfoam (Limnanthes
alba) contains triglycerides with over 98% fatty acids over 20 carbon atoms.
Among them, are found 20:1 n-15 (about 60%), 22:1 n-17 (about 4%) and cis 5, 13
-22:2 (about 17%). Furthermore, this oil is liquid at room temperature even
though it is of high molecular weight, it is one of the most stable lipids
known, and it is highly resistant to oxidation. Meadowfoam oil has many
potential applications in cosmetics, lubricants, waxes, polymers, surfactants,
water repellents, and in textile and leather manufacturing
Positional
distribution of major fatty acids in triglycerides of some plant oils
The composition and structure of natural vegetal oils may be modified by
chemical or enzymatic processes known as interesterification
or hydrogenation.
Some seed oils contain also hydroxy
fatty acids and are known as hydroxy acid oils. Thus, castor bean (Ricinus
communis) produces a seed oil which contains about 90% ricinoleic acid (hydroxy oleic
acid) and 1-2% dihydroxystearic acid. Glycerides of Strophantus oils contain 6-15%
9-hydroxy-octadec-12-enoic acid. Coriaria seed oil contains 66-68% of a rare fatty
acid, coriolic acid (13-hydroxy-9c,11t-octadecadienoic acid). Seed oil of
Cardamine
impatiens contains C18, C20, C22 and C24 dihydroxy acids in which one of the hydroxyl
groups is acetylated, thus forming triglyceride molecules named estolide
triglycerides.
In one of these molecules found in seed oil from Sebastiana commersoniana
(Euphorbiaceae) an hydroxy allenic acid was discovered (Spitzer V et
al. Lipids 1997, 32, 549).
Some seed oils contain epoxy fatty acids
and are known as epoxy acid oils. Thus, vernolic acid (cis-12,13-epoxy-cis-9-octadecenoic
acid) is found in Vernonia, Euphorbia and Cephalocroton.
Curiously, acetic acid was shown to be a component of
natural triglycerides in some plant species. It is known that Celastraceae,
Lardizabalaceae, Ranunculaceae and Rosaceae plants contain monoaceto
triglycerides (Kleimann R et al., Lipids 1967, 2, 473). 2- or 3-Acetyl
glycerides (liliosides) were isolated from Lilium longiflorum (Kaneda
M et al., Tetrahedron Lett 1974, 3937). The seed oil of Impatiens roylei and
Euonymus
verrucosus contain as major triglyceride species the sn-glycerol-1,2-diacyl-3-acetins
(Kleiman R et al., Lipids 1966, 1, 286; Bagby MO et al., Biochim Biophys Acta
1967, 137, 475). Monoacetyldiglycerides were also
isolated from an animal tissue, bovine udder. 1,2-Diacyl 3-acetin,
distearoacetin, stearo-oleaoacetin and stearo-linoleo-acetin have been isolated
from lipids of the insect Icerya purchasi (Hashimoto A et al., Jap J
Appl Ent Zool 1974, 18, 121).
In some rare vegetals,
phenolic triacylglycerols have been described. Thus, phenolic acid triglycerides
were isolated in the bud excretion of Populus lasiocarpa, a tree native in China
(Asakawa Y et al., Phytochemistry 1976, 15, 811). These lipids were
identified as 1,3-di-p-coumaryl-2-acetyl-glycerol (see fig below). A similar compound with
methylated coumaryl groups was also identified. Several other phenolic
triglycerides have been isolated from lipophilic excretion of winter buds of
many species of Populus : 1-p-coumaryl-3-caffeyl-2-acetyl
glycerol, 1,3-di-caffeyl-2-acetyl glycerol (Asakawa Y et al., Phytochemistry
1977, 16, 1791).

1,3-p-Coumaryl-2-acetyl-glycerol
Several other
phenolic triglycerides have been detected in propolis, a bee glue that honeybees
collect from living plants, which is used, mixed with wax, in the construction
of bee hive. Whereas the composition of propolis depends on the vegetal sources,
specific structures have been determined in Russian (Popravko SA et al., Chim
Prir Soed 1982, 2, 169) and European propolis (Bankova V et al., Z
Naturforsch 2002, 57c, 530). Thus, dicoumaroyl acetyl glycerol, diferuloyl acetyl
glycerol and feruloyl coumaroyl acetyl glycerol have been isolated in bud
exudates of various Populus species.
A phenolic triglyceride displaying a cytotoxic activity, 1,3-dibehenyl-2-ferulyl
glyceride, has been isolated from Aquilaria malaccensis, a plant (Thymelaeaceae)
distributed in India, Thailand and Philippines (Gunasekera SP et al., J Nat
Prod 1981, 44, 569).

1,3-dibehenyl-2-ferulyl glyceride
Ferulyl dioleine, which is a useful sunscreen ingredient, has been produced by
lipase-catalyzed transesterification of ethyl ferulate with trioleine (Compton
DL et al., JAOCS 2000, 77, 513).
Jojoba fruit (Simmondsia
chinensis) contain an oily product which is not triglycerides but contain about
80% wax made up of long-chain alcohols
(C20 to 24) and long-chain fatty acids (C18 to C22), each complex chain having one double
bond.
A translation table of seed oils (6 languages) including the botanical
sources may be found in a page of the AOCS
Analytical Divisions.
An important database for seed oil fatty acids established by the Institute for
Chemistry and Physics of Lipids in Műnster is now electronically searchable :
the Database SOFA.
This internet database allows to search for plant species, genera and families,
for individual fatty acids (start by adding an asterisk after each entry) and
combinations of fatty acids in their seed oils, and for their percentage
contents. It contains literature references and numerous unpublished data.
Moreover, fatty acid partial structures or functional groups can also be
searched for, using the "delta-notation" system of chemists as
described above. The use of the database is mostly straightforward and
self-explanatory but several examples for search operations have been published
to help anybody interested in seed oils and their fatty acid composition (Aitzetmüller
K et al., Eur J Lipid Sci Technol 2003, 105, 92).
The fatty acid profiles of 80 vegetable oils with regard to their
nutritional potential has been reported (Dubois V et al., Eur J Lipid Sci
Technol 2007, 109, 710). Triacylglycerols profiling of 26 plant oils
important in food industry, dietetics and cosmetics has been done, reporting the
distribution of 264 triacylglycerol species consisting of 28 fatty acids (Lisa
M et al., J Chromatogr A 2008, 1198-1199, 115).
Since about 1990, genetically modified oils have been developed using either
mutation/selection breeding or the tools of biotechnology and represent some of
the most significant new products developed for the oils and fats industry .
Many of these new oils possess fatty acid contents that are unique to the plant
in which they have been developed. Thus, they convey different functional and/or
nutritional characteristics compared to the classic or natural types.
Genetically modified oils fall into two main categories. The first group has
been designed to give products with enhanced oxidative stability. These oils are
targeted mainly to salad dressing or frying applications and are best
represented by the high oleate and low linolenate types. The second general
group is characterized by oils with altered levels of saturated fatty acids. In
the future, it may be expected that oils will be genetically created possessing
novel fatty acyl substitutions, such as hydroxyl or epoxy groups, as well as
alkyne or conjugated double bonds. These types represent potential alternatives
to industrial oils derived currently from undomesticated species. An extensive
review of genetically modified oils and the utilization of analytical procedures
for characterizing these oils may be consulted with interest (Hazebroek JP,
Prog Lipid Res 2000, 39, 477).
![]()
According to OIL
WORLD, ten oilseeds can be divided into three groups based on their levels
of production. Soybean dominates representing over 30% of the ten seeds. This is
followed by four seeds (rapeseed/canola, cottonseed, sunflower and groundnut,
each in the range 3-13% of the total) making up a further 40% and five others (corn,
palm kernel, coprah, sesame, linseed, and castor), each in the range 0.5-2% of
the total.
The expected relative values of world seed oil production in 2003-2004 for ten
major sources are given below:

The world oilseed production is expected to be about 340 million tons for
2003-2004 and jumped by an average 13 million tons per year during the last 10
years. The world supply of vegetable oils from the ten major sources in 2004-2005
is about 110 million tons
Recent world statistics for the production of main vegetable oils may be found
at the FEDIOL
web site.
Oil sources can be easily sorted according to the importance and use of
the extracted oil.
Thus, information on near the totality of oil sources are distributed below
among 5 groups:
Palm oil
Rape oil
Soja oil
Sunflower oilArachis (groundnut)
Cotton
Coprah
Palmkernel
Maize (corn)
Olive
SesameAlmond seed
Camelina
Carthame
Grape seed
Hazel-nut
Linseed
Poppy seed
Walnut4. Oils used in dietetics, cosmetics, and lipochemistry
Avocado pear
Black-currant
Borage
Cacao
Castor bean
Evening primrose
Kukui oil
Wheat germ
5. Vegetal butters and Margarine