Exploring Phylogenetic Relationships between Hundreds of Plant Fatty Acids Synthesized by Thousands of Plants. more details ...

Key literature and reviews on plant fatty acids with links to full text (if available).    DOI (digital object identifier) shown in bold will provide link to full text in most cases 

A few reviews:

Avato, P., and Tava, A. (2021). Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity. Phytochemistry Reviews, 1-28.  10.1007/s11101-021-09770-4

Badami , R.C., and Patil, K.B.  (1981). Structure and Occurrence of Unusual Fatty Acids in Minor Seed Oils. Progress in Lipid Research 19,119-153.    10.1016/0163-7827(80)90002-8

Baud, S. (2018) Seeds as Oil Factories . Plant Reproduction /10.1007/s00497-018-0325-6

Christensen, L.P., and Brandt, K.  (2006). Acetylenes and Psoralens , in Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet 137-173.    10.1002/9780470988558.ch5  

Dembitsky , V.M., and Srebnik, M.  (2002). Natural Halogenated Fatty Acids: Their Analogues and Derivatives. Progress in Lipid Research 41, 315-367.     10.1016/s0163-7827(02)00003-6

    Gunstone, F.D., Harwood, J.L, Dkjkstra, A.J. (2007) The Lipid Handbook with CD-ROM, Third Edition.  ISBN-10: 0849396883   (This book and the CD-ROM are highly recommended and provide a superb database for over 12,000 lipid structures, including >1000 fatty acids)

Hildebrand, D.  (2010) Production of Unusual Fatty Acids in Plants        http://lipidlibrary.aocs.org/Biochemistry/content.cfm?ItemNumber=40317

Mangold , H.K. and Spener, F.,  (1977). The cyclopentenyl fatty acids. In Lipids and Lipid Polymers in Higher Plants (pp. 85-101). Springer Berlin Heidelberg.  ISBN: 978-3-642-66632-2 

Mawlong , I., Sujith Kumar, M.S., and Singh, D. ( 2014). Furan Fatty Acids: Their Role in Plant Systems.  Phytochemistry  Reviews 15, 121-127.     10.1007/s11101-014-9388-7

McKeon, T., Hayes, D., Hildebrand, D., & Weselake, R. (Eds.).   (2016).Industrial Oil Crops. Elsevier. eBook ISBN :9780128053850

Napier, J.A.  (2007). The Production of Unusual Fatty Acids in Transgenic Plants. Annu Rev Plant Biol 58, 295-319.   10.1146/annurev.arplant.58.032806.103811

Shanklin, J., & Cahoon, E. B. (1998). Desaturation and related modifications of fatty acids. Annual Review of Plant Biology, 49, 611-641.  DOI:  10.1146/annurev.arplant.49.1.611

Smith Jr, CR (1971)  "Occurrence of unusual fatty acids in plants."  Progress in the chemistry of fats and other lipids  11: 137-177.  doi.org/10.1016/0079-6832(71)90005-X

Spitzer, V. (1999)  Screening analysis of unknown seed oils   Lipid/Fett , 101 (1), 2-19.  doi:10.1002/(SICI)1521-4133(19991)101:1<2::AID-LIPI2>3.0.CO;2-H

     van de Loo, Frank J., Brian G. Fox, and Chris Somerville. (1993) "Unusual fatty acids." Chapter 3 in Lipid Metabolism in Plants: T.S. Moore ed. CRC Press p91-126.  ISBN: 1315894971 9781315894973

Selection of ~70 publications that include larger datasets


Appelqvist , L.A.  (1971). Lipids in Cruciferae: Viii. The Fatty Acid Composition of Seeds of Some Wild or Partially Domesticated Species.Journal of the American Oil Chemists Society 48, 740-744.    10.1007/BF02638533

              A total of 75 seed samples of 29 species of Cruciferae have been analyzed for fatty acid composition by gas chromatography. All but three species contained erucic acid in the seed oils at levels ranging from 1% to 57%. Linolenic acid was present in all samples; the levels ranged from 2% to 55%. A considerable variation in fatty acid patterns was observed at the intraspecific level for Sinapis arvensis. Species from five of the generas studied may have potential as new crops, namely BarbareaConringiaErysimumHesperis and Sisymbrium.

Averna , V., Lotti, G., and Tartaglia, F.P.  (1969).  Further Investigations on Leguminosae Seed Oils.  Rivista  Italiana delle Sostanze Grasse 46,602-606.                             

              Oils extracted with petroleum ether (bp 40-70°C) from the seeds of 15 species of Leguminosae were analysed for unsaponifiablematter, % fatty acids, refractive index, I number and saponification number.Purified fatty acids were examined spectrophotometrically in the 232-308 nm range. DM, total N, ash, and ether extract were determined for the seeds. Palmitic, stearic, oleic, and linoleic acids were present in all the cases, the last 2 predominating. Conjugated double bonds were found in almost all the oils, whereas small amounts of acids with conjugated triple bonds were present in only a few cases. Of the 15 species studied only 2 had been previously investigated.

Banerji , R., Chowdhury, A.R., Misra, G., and Nigam, S.K.  (1984). Butter from Plants. Fette Seifen Anstrichmittel 86, 279-284.   10.1002/lipi.19840860706         

Barclay, A.S., and Earle, F.R.  (1974). Chemical Analyses of Seeds Iii Oil and Protein Content of 1253 Species. Economic Botany 28, 178-236.    10.1007/BF02861984

Bohannon, M.B., and Kleiman, R.  (1976). Γ-Linolenic Acid in Acer Seed Oils. Lipids 11, 157-159.    10.1007/BF02532667

              The octadecatrienoic acids in Acer negundo L. (maple family) seed oil include both 9,12,15- (1%) and 6.9,12-(7%) isomers. The chiefmonoenoic acids identified were 9-octadecenoic (21%), 11-eicosenoic (7%), 13-docosenoic (15%), and 15-tetracosenoic (7%). Also present is a considerable amount of 9,12-octadecadienoic acid. Investigation of ten other Aceraceae revealed their seed oils to have a similar fatty acid composition.

Bohannon, M.B., and Kleiman, R.  (1978).  Cyclopropene  Fatty Acids of Selected Seed Oils from BombacaceaeMalvaceae, andSterculiaceae. Lipids 13, 270-273.    10.1007/BF02533669

              Fatty acid compositions of seed oils from three species of Bombacaceae, eleven from Malvaceae, and six from Sterculiaceae were determined. Each of the seed oils contains varying amounts of both malvalic and sterculic acids accompanied by one or both of the corresponding cyclopropane fatty acids. In addition, the seed oil of Pachira aquatic Aubl. (Bombacaeae) contains 12.8% α-hydroxysterculicacid.

Brown, A.J., Cherikoff, V., and Roberts, D.C.K.  (1987).  Fatty Acid Composition of Seeds from the Australian Acacia Species. Lipids 22, 490-494.    10.1007/BF02540364

              Presented are the lipid content and fatty acid composition of 20 species of edible Australian Acacia seeds. Aborigines reportedly have used at least 18 of these as foods. Seed lipid content ranged from 3% to 22%, with an average of 11% on a dry weight basis. Linoleic (12-71%), oleic (12-56%) and plamitic (7-35%) acids were the major fatty acids. Smaller proportions of behenic, stearic and vaccenic acids were detected. Seventeen of the 20 species were found to have polyunsaturated to saturated (P/S) fatty acid ratios greater than 1, with four species having ratios in excess of 4. The persistent arils attached to the seeds of certain Australian Acacias and containing a portion of the total lipid were associated with a significantly reduced proportion of linoleic acid in the total seed material. This observation was explained by the aril lipid possessing a markedly different fatty acid composition from that of the seed lipid. For comparison, seeds from two non-Australian Acacia species (A. farnesiana and A. cavenia) were analyzed. Australian and non-Australian were found to exhibit markedly different fatty acid profiles.

Chowdhury , A.R., Banerji, R., Misra, G., and Nigam, S.K.  (1983). Chemical Composition of Acacia Seeds. Journal of the American Oil Chemists' Society 60, 1893-1894.    10.1007/BF02901545

              Several plants of Acacieae (family Leguminosae) have been recommended under aforestation programs. The seeds of some such plants have been examined for their fatty acid composition with special reference to epoxy acids. Epoxy 18:1 in Acacia auriculiformis, A. catechu, A. coriacea and A. mellifera was 4.9, 0.1, 2.1, and 0.6%,respectively..

Chowdhury , A.R., Banerji, R., Tiwari, S.R., Misra, G., and Nigam, S.K.  (1986). Studies on Leguminous Seeds .3. Fette Seifen Anstrichmittel 88, 144-146.    10.1002/lipi.19860880407

Christensen, L.P., and Brandt, K.  (2006). Acetylenes and Psoralens 137-173.    10.1002/9780470988558.ch5         

Corneliu.Ja , Hammonds, T.W., Leiceste.JbNdabahwe.Jk, Rosie, D.A., and Shone, G.G.  (1970). New Tropical Seed Oils .3. Component Acids of Leguminous and Other Seed Oils. Journal of the Science of Food and Agriculture 21, 49-&.    10.1002/jsfa.2740210114   

Dembitsky , V.M., and Srebnik, M.  (2002). Natural Halogenated Fatty Acids: Their Analogues and Derivatives. Progress in Lipid Research 41,315-367.    10.1016/s0163-7827(02)00003-6  

Dubois, V., Breton, S., Linder, M., Fanni, J., and Parmentier, M.  (2007).  Fatty Acid Profiles of 80 Vegetable Oils with Regard to Their Nutritional Potential. European Journal of Lipid Science and Technology 109, 710-732.    10.1002/ejlt.200700040

              The current concern for fat intake in western countries has raised the question of the individual fatty acid (FA) impact on health. This important issue has strengthened the awareness of nutritionists and food manufacturers for the control of the FA profile of food products. The aim of this review is to provide a classification of the FA profiles of 80 vegetable oil sources, according to their nutritional potential. The first part of the review focuses on lipoprotein metabolism, and on the impact of each dietary FA on blood lipid composition (LDL-cholesterol, HDL-cholesterol and circulating triacylglycerols). In the second part of the review, the oil sources are clustered by similar FA profiles, and the classification is discussed with regard to the individual FA action on blood lipid composition. Apart from the major vegetable seeds, the clustering high-lighted some interesting nutritional oil sources containing mainly α-linolenic acid (camelina, linseed, perilla and stock oils), or interesting amounts of the two essential FA (purslane, chia, raspberry seed, sea buckthorn seed and salicorn oils). Furthermore, this classification provides a useful tool for the formulation of the FA profile of food products.

Earle, F.R., and Jones, Q.  (1962). Analyses of Seed Samples from 113 Plant Families. Economic Botany 16, 221-250.   10.1007/BF02860181

Gaydou , E.M., and Ramanoelina, A.R.P.  (1983). A Survey of the Sarcolaenaceae for Cyclopropene Fatty Acids. Phytochemistry 22, 1725-1728.    10.1016/S0031-9422(00)80259-9

              An investigation of the fatty acid composition of 22 representative species of the 10 genera of the family Sarcolaenaceae yielded some results of chemotaxonomic interest. Two cyclopropene fatty acids, malvalic and sterculic acids, were detected and quantitated in the seed oil of most species. The occurrence of cyclopropene fatty acids shows that this family has more biochemical affinities with the orderMalvales than with the order Parietales.

Gaydou , E.M., and Ramanoelina, A.R.P.  (1983). Study on Fatty-Acid Composition of Vegetable Seed Oils from Madagascar. RevueFrancaise Des Corps Gras 30, 21-25.                 

Gaydou , E.M., and Ramanoelina, A.R.P.  (1984). Cyclopropenoic Fatty-Acids of Malvaceae Seed Oils by Gas-Liquid-Chromatography. Fette Seifen Anstrichmittel 86, 82-84.    10.1002/lipi.19840860208

Gaydou , E.M., Ramanoelina, A.R.P., Rasoarahona, J.R.E., and Combres, A.  (1993). Fatty-Acid Composition of Sterculia Seeds and Oils from Madagascar. Journal of Agricultural and Food Chemistry 41, 64-66.    10.1021/jf00025a014

              The percentage contents of oil and protein in the seeds of 17 species belonging to 9 genera of the Sterculiaceae family, growing in Madagascar, were determined. The major fatty acids were palmitic (11.6-27.5%), oleic (8.3-32.6%), linoleic (4.2-45.8%), malvalic (tr-53.7%), and sterculic (1.3-24.8%) acids. Heritiera littoralis seed oil was characterized by a high content of malvalic (53.7 %) and sterculic acids(12.4%). Cyclopropene fatty acids were identified and determined by using a combination of gas chromatographic and H-1 and C-13 NMR analyses. Dihydrosterculic acid was also detected in all samples at a low concentration.

Goffman , F.D., Thies, W., and Velasco, L.  (1999).  Chemotaxonomic Value of Tocopherols in Brassicaceae. Phytochemistry 50, 793-798.   10.1016/S0031-9422(98)00641-4

              The significance of tocopherols as chemotaxonomic markers and their relationship with oil content and fatty acid profile was investigated in a collection of 91 species of the family Brassicaceae. Total tocopherols content ranged from 68 mg kg-1 oil in Diplotaxis viminea to 2479 mg kg-1 oil in Schivereckia doerfleri. The collection also showed wide variability for tocopherol composition. The averagetocopherol profile consisted of 65.4% γ-, 28.7% α-, 5.1% δ- and 0.8 β-tocopherol . Individual tocopherols were found to have great taxonomic value in the Brassicaceae.

Graham, S.A.  (1989). Cuphea - a New Plant Source of Medium-Chain Fatty-Acids. Critical Reviews in Food Science and Nutrition 28, 139-173.                    

Graham, S.A., and Kleiman, R.  (1987).  Seed Lipids of the Lythraceae. Biochemical Systematics and Ecology 15, 433-439.    10.1016/0305-1978(87)90057-3

              Fatty acid composition of seed lipids for 20 of the 26 genera in the Lythraceae and seed oil and protein content for nine genera are reported. The percent oil ranges from 2.7 to 34% of total weight and protein from 11.3 to 24.9%. Linoleic acid is the dominant fatty acid in seed lipids of all genera surveyed. Variations in pattern emphasize palmitic or oleic acid or both as second most abundant lipid component. There are three exceptions: in Diplusodon capric acid ranks second in abundance; in Adenaria lauric acid and oleic acid occur in approximately equal amounts as second most abundant fatty acid; in Decodon an unusual trienoic acid, previously reported only from theCompositae, is the main secondary component. Fatty acid composition of seeds in the genera is compared to that of the previously studiedlythraceous genus Cuphea. Among all the genera, only Cuphea seed produces large quantities of lauriccapric, or caprylic acids, as well as a diversity of fatty acid patterns. No relationship between oil content or seed weight and habit is apparent in any genus studied, nor are differences in seed morphology reflected in composition of the seed lipids. The fatty acid patterns are judged evolutionarily conservative, with the strong exception of Cuphea, which remains unique in the Lythraceae and among all angiosperms for the diversity of patterns displayed.

Guil -Guerrero, J.L., Gómez-Mercado, F., García-Maroto, F., and Campra-Madrid, P.  (2000).  Occurrence and Characterization of Oils Rich in Γ-Linolenic Acid Part I: Echium Seeds from MacaronesiaPhytochemistry 53, 451-456.    10.1016/S0031-9422(99)00549-X

              Nineteen species of the genus Echium (Fam. Boraginaceae) collected in Macaronesia were surveyed in a search for new sources of γ-linolenic acid (GLA, 18:3ω6). High amounts of this acid were found in all of them, ranging from 9.15% (E. plantagineum) to 26.31% (E.callithyrsum) of total seed fatty acids. The amounts of GLA related to total seed weight were also significant, ranging from 1.77% (E.sventenii) to 5.02% (E. nervosum). In addition, considerable amounts of stearidonic acid (SA, 18:4ω3) were detected, ranging from 3.03% (E. auberianum) to 12.94% (E. plantagineum) of total fatty acids. These data allow us to consider the members of the genus Echium fromMacaronesia as one of the richest sources of γ-linolenic acid found so far in nature. The results obtained from multivariable data analysis and the taxonomic relationships among the species is discussed.

Guil -Guerrero, J.L., López-Martínez, J.C., Gómez-Mercado, F., and Campra-Madrid, P.  (2006).  Gamma-Linolenic and Stearidonic Acids from Moroccan Boraginaceae. European Journal of Lipid Science and Technology 108, 43-47.    10.1002/ejlt.200500251

              Seeds from 20 species belonging to Boraginaceae, subfamilies Boraginoideae and Heliotropioideae, were surveyed in a search for new sources of γ-linolenic acid (GLA) and stearidonic acid (SDA). Seed oil content ranged from 7.5% in Echium humile ssp. pycnanthum to 28.8% in Anchusa undulata. GLA ranged from 0.2% of total fatty acids in Heliotropium undulatum to 20.2% in Lithodora maroccana. This last species may be considered as new source of GLA. GLA content was also tested in other Lithodora species from the south east of Spain, to compare GLA percentages among related taxa. GLA amounts in all Echium species reached approximately 12%, in good agreement with previous findings in other European Echium species. SDA ranged from an absence in several Cynoglossum species to 16.2% in Echium humile ssp. pycnanthum, which may be considered as a new source of this fatty acid.

Gunstone , F.D., Hammonds, T.W., Steward, S.R., and Corneliu.Ja.  (1972). New Tropical Seed Oils .4. Component Acids of Leguminous and Other Seed Oils Including Useful Sources of Crepenynic and Dehydrocrepenynic Acid. Journal of the Science of Food and Agriculture23, 53-&.    10.1002/jsfa.2740230108

Gunstone , F.D., Taylor, G.M., Corneliu.Ja, and Hammonds, T.W.  (1968). New Tropical Seed Oils .2. Component Acids of Leguminous and Other Seed Oils. Journal of the Science of Food and Agriculture 19, 706-&.    10.1002/jsfa.2740191205  

Hagemann , J.M., Earle, F.R., Wolff, I.A., and Barclay, A.S.  (1967). Search for New Industrial Oils. Xiv. Seed Oils of Labiatae. Lipids 2, 371-380.    10.1007/BF02531850

              Seed of 194 species in 56 genera of Labiatae, representing six of the eight subfamilies, were analyzed for oil and protein and for fatty acid composition of the oil. The oils are diverse and include some that contain up to 70% oleic acid, 79% linoleic acid, or 72% linolenic acid. An allenic function occurs in a third of the samples from the subfamily Stachyoideae and in the one sample analyzed from the Prasioideae. A method for determining the allene was devised. Oils from Teucrium species contain trans unsaturation in unidentified components. Oils from two Lamium species have both allenic and trans unsaturation. Two species of Thymus appear to produce hydroxy acids.

Hayes, D.G., Kleiman, R., and Phillips, B.S.  (1995). The Triglyceride Composition, Structure, and Presence of Estolides in the Oils ofLesquerella and Related Species. Journal of the American Oil Chemists’ Society 72, 559-569.    10.1007/BF02638857

              Members of the genus Lesquerella, native to North America, have oils containing large amounts of hydroxy fatty acids and are under investigation as potential new crops. The triglyceride structure of oils from twenty-five Lesquerella species in the seed collection at our research center has been examined after being hydrolysis-catalyzed by reverse micellar-encapsulated lipase and alcoholysis-catalyzed by immobilized lipase. These reactions, when coupled with supercritical-fluid chromatographic analysis, provide a powerful, labor-saving method for oil triglyceride analysis. A comprehensive analysis of overall fatty acid composition of these oils has been conducted as well.Lesquerella oils (along with oils from two other Brassicaceae: Physaria floribunda and Heliophilia amplexicaulis) have been grouped into five categories: densipolic acid-rich (Class I); auricolic acid-rich (Class II); lesquerolic acid-rich (Class III); an oil containing a mixture of hydroxy acids (Class IV); and lesquerolic and erucic acid-rich (Class V). The majority of Class I and II triglycerides contain one or twomonoestolides at the 1- and 3-glycerol positions and a C18 polyunsaturated acyl group at the 2-position. Most Class III and IV oil triglycerides contain one or two hydroxy acids at the 1- and 3-positions and C18 unsaturated acid at the 2-position. A few of the Class III oils have trace amounts of estolides. The Class V oil triglycerides are mostly pentaacyl triglycerides and contain monestolide and small amounts of diestolide. Our triglyceride structure assignments were supported by1H nuclear magnetic resonance data and mass balances.

Idiemopute , F.  (1979). Seed Lipids of the Palm Family. Journal of the American Oil Chemists Society 56, 528-530.                    

Jamieson, G.R., and Reid, E.H.  (1972). The Leaf Lipids of Some Conifer Species. Phytochemistry 11, 269-275.    10.1016/S0031-9422(00)90002-5

              Conifer leaf lipids contain, in addition to the fatty acids found in angiosperms, a series of polyunsaturated acids with Δ5 olefinicunsaturation. All the species contain Δ5 C20 acids and the members of the family, Pinaceae, contain, in addition a series of C18 Δ5 acids. Significant amounts of a saturated C17 branched-chain acid were present in many of the species. The distribution of polyunsaturated acids among certain lipid classes was investigated and it was found that C16 and C18 polyunsaturated acids with ω3 unsaturation are concentrated in the galactosyl diglycerides.

Jart , A.  (1978). The Fatty Acid Composition of Various Cruciferous Seeds. Journal of the American Oil Chemists' Society 55, 873-875.   10.1007/BF02671410

              Seeds from 26 Cruciferae species in 7 genera have been investigated for fat content and fatty acid composition of the oil. The GLC retention data have been verified by mass spectrometry. The oil from Cardamine graeca contained 54% of cis-15-tetracosenoic acid; it is the highest content of this acid so far reported in any seed fat.

Jones, Q., and Earle, F.R.  (1966). Chemical Analyses of Seeds Ii: Oil and Protein Content of 759 Species. Economic Botany 20, 127-155.   10.1007/BF02904010

Kleiman , R., Earle, F.R., Wolff, I.A., and Jones, Q.  (1964). Search for New Industrial Oils. Xi. Oils of Boraginaceae. Journal of the American Oil Chemists' Society 41, 459-460.    10.1007/BF02670021

              Analysis of seed oils from 29 species of the family Boraginaceae revealed widespread occur-rence of 6,9,12-octadecatrienoic and C18 noncon-jugated tetraenoic acids in addition to linolenic and other common C16 and C18 acids. The 6,9,12-octadecatrienoic acid ranged in amount from 0-27%, tetraene from 0-17%, and linolenic acid from 0.3-50%. Iodine values of the oils ranged from 88-225.

Kleiman , R., and Payne-Wahl, K.L.  (1984). Fatty Acid Composition of Seed Oils of the Meliaceae, Including One Genus Rich in Cis-VaccenicAcid. Journal of the American Oil Chemists' Society 61, 1836-1838.    10.1007/BF02540810

              The seed lipids of three species of Entandraphragma (Meliaceae) contain the largest proportion (31-50%) of cis-vaccenic acid ever found in nature. The acid is not indicative of the family as a whole and is found as a major fatty acid in the seed of only one additional species, besides Entandraphragma, out of the 30 analyzed from this family. With the total oil comprising between 45 and 62% ofEntandraphragma seed, these species should be considered as a source of undecadioic acid for the production of nylon 11.

Kleiman , R., Smith Jr, C.R., Yates, S.G., and Jones, Q.  (1965). Search for New Industrial Oils. Xii. Fifty-Eight Euphorbiaceae Oils, Including One Rich in Vernolic Acid. Journal of the American Oil Chemists' Society 42, 169-172.    10.1007/BF02541123

              Seed oil of Euphorbia lagascae Sprengcontains 57% of cis-12,13-epoxy-cis-9-octadecenoic (vernolic) acid. The amt of trivernolin in the glycerides of this species indicates random or restricted random distribution of the vernolic acid. Seed from 57 additional species in theEuphorbiaceae were analyzed for oil and protein contents and also for fatty acid composition of the oils. Iodine values (I.V.) of the oils ranged from 87-221. Among these oils, samples were encountered with as much as 76% linolenic, 77% linoleic or 84% oleic acid.

Kleiman , R., and Spencer, G.F.  (1982). Search for New Industrial Oils: Xvi.  Umbelliflorae -Seed Oils Rich in Petroselinic Acid. Journal of the American Oil Chemists' Society 59, 29-38.    10.1007/BF02670064

              Seed oils of the order Umbelliflorae, including those from the families UmbelliferaeGarryaceaeAraliaceaeCornaceaeDavidiaceae,Nyssaceae and Alangiaceae, were analyzed for fatty acid composition by gas liquid chromatography (GLC) of their methyl esters. The characteristic fatty acid of the order, petroselinic acid, occurred in the Umbelliferae in amounts up to 85%. In the Araliaceae, the content was as high as 83% and in the Garryaceae as high as 81%. The other major acids were palmitic, oleic and linoleic acids, with small amounts of hexadecenoic, stearic, linolenic, and, in some cases, C20 acids.  petroselinic  acid was determined by microscale ozonolysis of the C18 monoenoic esters and subsequent GLC of the ozonolysis products. The occurrence of high oil contents (up to 46%) combined with exceptionally high (up to 83%) single component purity is notable and emphasizes the potential of the Umbelliflorae as a raw material source for the chemical industry.

Koiwai , A., Suzuki, F., Matsuzaki, T., and Kawashima, N.  (1983).  The Fatty Acid Composition of Seeds and Leaves of Nicotiana Species. Phytochemistry 22, 1409-1412.    10.1016/S0031-9422(00)84024-8

              Fatty acid analyses of seeds in 62 Nicotiana species and leaves in 56 Nicotiana species are presented. The total fatty acid content on a dry wt basis ranged from 25 to 40 %of seeds and from 2.1 to4.4% of green leaves. Linolenate was the dominant fatty acid in the leaves of all species studied, comprising 50-63% of the total fatty acid content. In seeds of most species linoleate predominated, constituting 69-79% of the total fatty acid content. Fourteen of 21 species in the section Suaveolentes and one species in the section Noctiflorae had relatively high proportions (10-38%) of linolenate. In two linolenate-rich species studied, linolenate was the major fatty acid of triacylglycerols which predominated in the seed lipids.

Kumar, P.R., and Tsunoda, S.  (1978). Fatty Acid Spectrum of Mediterranean Wild Cruciferae. Journal of the American Oil Chemists' Society55, 320-323.    10.1007/BF02669920

              Seed samples of 54 species of wild Cruciferae were newly collected from natural populations of the west Mediterranean and adjacent areas in a search for "new" oil crops. Oil contents and fatty acid compositions were determined simultaneously by gas liquid chromatography using methyl heptadecanoate as the internal standard. The study revealed large variations in oil content (6-48.8%), oleic acid (5-31.3%), linoleic acid (2-24.8%), linolenic acid (1.7-64.1%), and erucic acid (0-55.1%). Correlation coefficients between component fatty acids inter se and oil content were determined separately for all species, the tribe Brassiceae, and the genus Brassica. The promising species identified are being studied further.

Lotti , G., and Galoppini, C.  (1965). Nature of the Lipids in the Germ and Reserve Tissues of Seeds.  Rivista  Italiana delle Sostanze Grasse42, 289-297.                             

              The content of oil and its characteristics and fatty acid composition were determined in the germ and reserve tissue of 42 species of vegetables from 14 families. Appreciable differences in fatty acid composition were often shown in the oil from the germ and reserve tissue, particularly in the proportion of linoleic and oleic acids.

Lotti , G., Paradossi, C., and Marchini, F.  (1985). Analytical Characterization of New Seed Oils. Rivista  della  Societa Italiana di Scienza dell'Alimentazione 14, 263-270.                    Analytical characteristics are given for novel seed oils from 37 plant species from 27 families, including data for oil content, UV extinction values at 8 wavelengths in the range 232-315 nm, and fatty acid compositions. Individual oils are discussed in detail.

Lotti , G., Paradossi, C., and Marchini, F.  (1991). Composition of New Seed Oils. Agrochimica 35, 58-68.                     

              The behaviour in the U.V. and I.R.-lights and the fatty acid composition by gaschromatography of the oils extracted from the seeds of 30 plant species belonging to different families were determined. Results have shown in many oils, in addition to the fundamental fatty acids, the presence of particular acids, such as octadecatetraenoiceicosenoic and eicosentrienoic, besides epoxiacidsallenic acids andtrienoic acids with an isolated trans double bond.

Marin, P., Sajdl, V., Kapor, S., and Tatić, B.  (1989).  Fatty Acid Composition of Seeds of the Papaveraceae and Fumariaceae. Phytochemistry 28, 133-137.    10.1016/0031-9422(89)85024-1

              Fatty acids were analysed in the seeds of 40 species from 12 genera of the Papaveraceae and 14 species from four genera of theFumariaceaeLinoleate was predominant in both families; however, its content was 11% greater on average in the Papaveraceae. WithPapaver orientale and Corydalis cava intraspecific variability of fatty acid patterns of seed lipids was studied; no large differences between samples were encountered. Triacylglycerols were the dominant lipid class. Members of Papaveraceae show a higher triacylglycerol but lower free fatty acid content than members of Fumariaceae.

Marin, P.D., Sajdl, V., Kapor, S., Tatic, B., and Petkovic, B.  (1991).  Fatty Acids of the SaturejoideaeAjugoideae and Scutellarioideae(Lamiaceae).  Phytochemistry  30, 2979-2982.    10.1016/S0031-9422(00)98235-9

              Fatty acid composition of nutlet lipids in 62 species from the Saturejoideae, seven species from the Ajugoideae and four species from the Scutellarioideae have been analysedLinolenate was the predominant acid in all species from the Saturejoideae but in the Ajugoideae,linoleate and linolenate were the major fatty acids. In the Scutellarioideaelinoleate was the dominant fatty acid. Results showed that the fatty acid composition of nutlet lipids and their linolenate/linoleate ratios may be useful as taxonomic markers for the differentiation of genera belonging to different subfamilies of the Lamiaceae.

Matthaus , B., Vosmann, K., Pham, L.Q., and Aitzetmuller, K.  (2003).  Fa  and Tocopherol Composition of Vietnamese Oilseeds. Journal of the American Oil Chemists Society 80, 1013-1020.    10.1007/s11746-003-0813-y

              Seeds of 40 oilseed species from 23 different plant families (Brassicaceae, CucurbitaceaeFabaceaeSapindaceaeMalvaceae,GnetaceaeClusiaceaeBruseraceaeRanunculaceaeConvolvulaceaeAmaranthaceaeTiliaceaeBasellaceaeSolanaceae,UmbelliferaeLabiataeCompositaeTheaceaeEuphorbiaceaeCaesalpiniaceaeSapotaceaeAnacardiaceae, and Connaraceae) grown in Vietnam were analyzed for oilseed oil content, FA, and vitamin E. The seed oil content varied between 0.2 g/100 g for Mangifera indicaand 75.7 g/100 g for Calophyllum inophyllum, whereas only nine seeds contained more than 40% oil. The tocopherol content ranged from 26 (Sapindus mukorossi) to 9361 mg/kg (Litchi chinensis). In nine seed oils unusual FA such as conjugated, cyclopropenoic, or epoxy FA were found.

Mawlong , I., Sujith Kumar, M.S., and Singh, D.  (2014). Furan Fatty Acids: Their Role in Plant Systems. Phytochemistry Reviews 15, 121-127.    10.1007/s11101-014-9388-7

Mikolajczak , K.L., Miwa, T.K., Earle, F.R., Wolff, I.A., and Jones, Q.  (1961). Search for New Industrial Oils. V. Oils of Cruciferae. Journal of the American Oil Chemists Society 38, 678-681.    10.1007/BF02633053

              Seeds from 37 species of plants in the family Cruciferae were analyzed for oil and protein, and the fatty acid composition of the oils was determined by gas-liquid chromatography. Erucic acid, generally considered characteristic of crucifer oils, occurs in about three-fourths of these species in amounts ranging from 3 to 59%. Some oils free of erucic acid contain up to 63% linolenic acid or up to 58% eicosenoic.

Miller, R.W., Earle, F.R., Wolff, I.A., and Barclay, A.S.  (1968). Search for New Seed Oils. Xv. Oils of Boraginaceae. Lipids 3, 43-45.   10.1007/BF02530967

              In a search for a preferred source of γ-linolenic (all-cis-6,9,12-octadecatrienoic) acid, seed oils of 33 species of Boraginaceae were examined. The desired triene was found primarily in the subfamily Boraginoideae in amounts ranging from 0.2 to 18%. Oils of this subfamily also contain 0.2 to 15% of the tetraene, all-cis-6,9,12,15-octadecatetraenoic acid. Total unsaturation and the relative proportions of the common acids varied widely in oils of the family. Monoene predominated in the subfamily Cordioideaediene in Heliotropioideae, and a diverse composition among the Boraginoideae; seven had iodine values of 200 or above. Cordia verbenacea seed oil was unique among those examined in having 43% of C 20 acids and 23% of components more volatile in gas chromatography than the usual triglycerides.

Miller, R.W., Earle, F.R., Wolff, I.A., and Jones, Q.  (1965). Search for New Industrial Oils. Xiii. Oils from 102 Species of Cruciferae. Journal of the American Oil Chemists' Society 42, 817-821.    10.1007/BF02541165

              Seed from additional species of Cruciferae have been analyzed for crude protein, oil and fatty acids in the oil. Oils were like those reported earlier from other crucifers, except for Cardamine impatiens which is unique among known seed oils because it contains some 25% dihydroxy acids. Erucic acid is present (0.3-55%) in about three-fourths of the 102 samples. Eicosenoic acid is a major constituent (32-53%) in four species and monohydroxy acids (45-72%) in another four. Linolenic acid occurs (2-66%) in oil of all species.

Miller, R.W., Gentry, H.S., Daxenbichler, M.E., and Earle, F.R.  (1964).  Search for New Industrial Oils .8. Genus Limnanthes. Journal of the American Oil Chemists Society 41, 167-&.             

Miralles , J., and Pares, Y.  (1980). Fatty-Acid Composition of Some Oils from Senegalese Seeds. Revue Francaise Des Corps Gras 27, 393-396.                       

Morice , I.M.  (1967). Seed Fats of Astelia and Collospermum Family Liliaceae. Journal of the Science of Food and Agriculture 18, 343-&.   10.1002/jsfa.2740180804        

Mukherjee, K.D., Kiewitt, I., and Hurka, H.  (1984). Lipid-Content and Fatty-Acid Composition of Seeds of Capsella Species from Different Geographical Locations. Phytochemistry 23, 117-119.     

Muuse , B.G., Essers, M.L., and Vansoest, L.J.M.  (1988). Oenothera Species and Borago-Officinalis - Sources of Gamma-Linolenic Acid. Netherlands Journal of Agricultural Science 36, 357-363.                             

Ngiefu , C.K., Paquot, C., and Vieux, A.  (1977). Oil-Bearing Plants of Zaire. Iii. Botanical Families Providing Oils of Relatively High Unsaturation. Oleagineux 32, 535-537.                   

               Data are tabulated on the seed oil compostion of 16 spp. of Leguminosae (including Albizia lebbeckCaesalpinia pulcherrima, andDelonix regia), 6 spp. of Euphorbiaceae (including Aleurites moluccanaHevea brasiliensis and Jatropha curcas) and 1 sp. (Kigelia africana) of Bignoniaceae. The most interesting for food and industrial purposes appear to be Afzelia bellaAdenanthera pavonina andPentaclethra macrophylla, in addition to A. moluccana and H. brasiliensis. (For part II, see HcA 47, 9822.)

Özcan , T.  (2007).  Characterization of Turkish Quercus L. Taxa Based on Fatty Acid Compositions of the Acorns. JAOCS, Journal of the American Oil Chemists' Society 84, 653-662.    10.1007/s11746-007-1087-8

              Total oil content and the composition of fatty acids were analyzed in the acorns of 16 Quercus taxa from Turkey. The range of total fat varied between 0.7 and 7.4%. Oleic (10.2-54.4%), linoleic (24.2-49.1%), palmitic (13.4-30.4%), alpha linolenic (1.5-8.6%) and stearic acid (1.5-4.5%) were major fatty acids for all taxa. Significantly differences at section level were found (p < 0.05) for palmitic, stearic and oleic acid concentration. Saturated (17.0-38.6%), mono unsaturated (11.0-55.5%) and unsaturated fatty acids (57.4-81.6%) in total oil were also significantly different between section QuercusCerris and Ilex (p < 0.05). In addition, sectional differences were significant (p < 0.02) for the relative concentrations of saturated fatty acids compared to mono, poly and total unsaturated fatty acids. Considerable variation of individual fatty acid levels were observed in related species and varieties. The species from section Ilex Loudon exhibited the highest levels of saturated fatty acid while the lowest levels were found in Q. brantii, Q. libani and Q. trojana from section Cerris Loudon. These species also had the highest levels of unsaturated fatty acids. Whereas the lowest values were detected in the species of section Ilex. Both varieties of Q. cerris showed significant differences (p < 0.05) from the other species in section Cerris for all parameters, except for stearic acid and exhibited little variations among their individual populations. Different concentrations of fatty acids may be useful biochemical markers for the characterization of Quercus at the infrageneric level. Interesting ratios of linoleic-linolenic acid especially in Q. robur ssp. robur, Q.hartwissiana, Q. vulcanica, Q. ithaburensis ssp. macrolepis and Q. libani also were detected with respect to dietary reference for fatty acid intake.

Pina , M., Graille, J., Grignac, P., Lacombe, A., Quenot, O., and Garnier, P.  (1984).  Research on Oenothera Rich in Gamma-Linolenic Acid. Oleagineux 39, 593-596.                       

Ralaimanarivo , A., Gaydou, E.M., and Bianchini, J.P.  (1982). Fatty Acid Composition of Seed Oils from Six Adansonia Species with Particular Reference to Cyclopropane and Cyclopropene Acids. Lipids 17, 1-10.    10.1007/BF02535115

              The oil content of six Adansonia species (Bombacaceae family) of Madagascar (Adansonia grandidieri, A. za, A. digitata, A. fony, A.madagascariensis and A. suarenzensis) and Africa (A. digitata) ranges from 8 to 46%. All the oils give a positive response to the Halphentest. Malvalicsterculic and dihydrosterculic acids were detected using gas liquid chromatography-mass spectrometry (GLC-MS). Epoxy or hydroxy fatty acids were not found in these oils. Fatty acid composition was determined by GLC using glass capillary columns coated with BDS and Carbowax 20 M. Results obtained for cyclopropenic fatty acids (CPEFA) were compared to those given by glass capillary GLC after derivatization with silver nitrate in methanol, by hydrogen bromide titration and by proton magnetic resonance (PMR). Good agreement was observed for the results given by the various methods. Malvalic acid content ranges from 3 to 28%, sterculic acid from 1 to 8% anddihydrosterculic acid from 1.5 to 5.1%. Odd-numbered fatty acids (Pentadecanoic and hepatadecanoic) were also observed in minute amounts (0.1-1.1%). Among the normal fatty acids, we observed mainly palmitic (21-46%), oleic (15-40%) and linoleic (12-32%). The relationship between fatty acid composition and Adansonia species is discussed.

Sanchez, M.A., and Cattaneo, P.  (1987). On the Contents and Fatty-Acid Composition Values of Total Lipids (Folch) from Non Gily Pulps of Edible Fruits. Anales De La Asociacion Quimica Argentina 75, 531-549.                  

Sayanova , O., Napier, J.A., and Shewry, P.R.  (1999).  Δ6-Unsaturated Fatty Acids in Species and Tissues of the Primulaceae. Phytochemistry 52, 419-422.    10.1016/S0031-9422(99)00256-3

              The Δ6-unsaturated fatty acids γ-linolenic acid (GLA; 18:3Δ6,9,12) and octadecatetraenoic acid (OTA; 18:4Δ6,9,12,15) were present in seed lipids of the tribe Primuleae, but not in other tribes of the Primulaceae. Within the genus Primula both fatty acids were present in seed lipids from 22 species (from 12 sections), with combined levels increasing from 1.1 to 27.4%. High levels of Δ6- unsaturated fatty acids were also present in leaves of ten species (from nine sections), but with lower levels generally being present in root lipids. In general, the levels of octadecatetraenoic acid were higher than that of γ- linolenic acid. The results indicate that Δ6-unsaturated fatty acids could be used as taxonomic markers within the genus Primula.

Seher , A., and Gundlach, U.  (1982). Isomeric Monoenoic Acids in Vegetable-OilsFette Seifen Anstrichmittel 84, 342-349.   10.1002/lipi.19820840904

Takagi, T., and Itabashi, Y.  (1982).  Cis-5-Olefinic Unusual Fatty Acids in Seed Lipids of Gymnospermae and Their Distribution inTriacylglycerols. Lipids 17, 716-723.    10.1007/BF02534657

              Open-tubular gas chromatographic analysis of fatty acids in the lipids from the seeds of 20 species of Gymnospermae showed that they all contained nonmethylene-interrupted polyenoic (NMIP) acids as minor components and palmitic, oleic, linoleic and α-linolenic acids as major components. The NMIP acids have an additional 5,6-ethylenic bond in ordinary plant unsaturated fatty acids and the following C2 elongation acids:cis-5, cis-9-octadecadienoic acid (5,9-18:2) (I); 5,9,12-18:3 (II); 5,9,12,15-18:4, 5,11-20:2, 5,11,14-20:3 (III); and 5,11,14,17-20:4 (IV). The main NMIP acids found in neutral lipids are I in two species of Taxus, II in seven species of Pinaceae, III in two species of PodocarpaceaeTorreya nuciferaCycas revoluta, and Ginkgo biloba, and III and IV in each of three species of Taxodiaceae, and Cupressaceae. The polar lipids constitute the minor fraction of seed lipids in general. The content and composition of NMIP acids in these lipids differe considerably from those in neutral lipids. Analysis of the partial cleavage products of triacylglycerols showed that the NMIP acids distribute mainly in the 1,3-position.

Ucciani , E.  (1995). Nouveau Dictionnaire Des Huiles  Végétales  : Compositions En Acides Gras. (Paris; Londres; New York: Tec et doc).

Velasco, L., and Goffman, F.D.  (1999). Chemotaxonomic Significance of Fatty Acids and Tocopherols in Boraginaceae. Phytochemistry 52,423-426.    10.1016/S0031-9422(99)00203-4

              A collection of 45 accessions (36 species, 20 genera) of the family Boraginaceae was evaluated for oil content, fatty acid composition,tocopherol content and composition. All the accessions contained γ-linolenic acid, the lowest content (0.7%) being found in Cerinthe major L. and the highest (24.4%) in Borago officinalis L. Three tocopherol profiles were characterized by the extremes of more than 90% of α-, δ- and γ-tocopherol, respectively. Fatty acids and tocopherols were suggested to have potential chemotaxonomic value in this family.

Vickery, J.R.  (1971). The Fatty Acid Composition of the Seed Oils of Proteaceae: A Chemotaxonomic Study. Phytochemistry 10, 123-130.   10.1016/S0031-9422(00)90259-0

              The fatty acid composition and the amounts of the positional isomers of the monoene acids have been determined in 26 Proteaceaesp. representing two sub families and seven tribes. Fatty acids containing from 12 to 24 carbon atoms were detected, the major components being monoene acids. The amounts of cis-hexadecenoic acid exceeded 10% in 13 species. Each of the four monoenesstudied had several positional isomers of which Δ9 and Δ11 predominated in hexadecenoic acid, Δ9 in octadecenoic acid and Δ11 and Δ15 in eicosenoic acid. The regression of the concentration of cis-hexadec-9-enoic acid on that of cis-octadec-11-enoic in 14 species was not statistically significant. The two sub families, Grevilleoideae and Proteoideae, have several distinct differences, the former, for instance, having a much wider range of acids. Differences between tribes were reflected mainly in the differing patterns of the monoene and dieneacids, whereas these patterns were rather uniform within genera. The data for Placospermum and Bellendena tend to support the claim that the former represents the primitive form of the Proteaceae.

Vickery, J.R.  (1980).  The Fatty Acid Composition of Seed Oils from Ten Plant Families with Particular Reference to Cyclopropene andDihydrosterculic Acids.  Journal of the American Oil Chemists' Society  57,  87-91.     10.1007/BF02674370   Oil contents and fatty acid compositions of 40 seed oils of the plant families  Elaecarpaceae Thymelaeceae Malvaceae , Sterculiaceae  (order  Malvales );  Anacardiaceae Celestraceae Sapindaceae  ( Sapindales );  Ebenaceae Sapotaceae  ( Ebenales ) and Rhamnaceae  ( Rhamnales ) are presented.  Cyclopropene  fatty acids (CPFA) occur in two families in the order  malvales  not hitherto assayed. CPFA contents of seed oils of 12 Australian and Pacific species of  Malvaceae  and  Sterculiaceae  are given. CPFA occur randomly in small amounts in at least six families not in the order  Malvales Dehydrosterculic  acid (DHS) occurs in small amounts in many species of Anacardiaceae Celestraceae Elaeocarpaceae Malvaceae Sapindaceae Sapotaceae  and  Sterculiaceae . Linoleic acid was predominant in 28 of 40 seed oils, being as high as 63.9% in two species. The sum of 18:1 and 18:2 esters exceeded 70% in 20 oils.

Vioque , J., Pastor, J.E., and Vioque, E.  (1994). Study of the Fatty-Acid Composition of the Seed Oils of Some Wild Plants in Spain. Grasas YAceites 45, 161-163.                            

               The fatty acid composition of 34 species of plants from a variety of families that grow wild in the Iberian Peninsula was analysed. The aim to the survey was to indentify oils that contain a mix of fatty acids that from a qualitative or quantitative point of view have a commercial value. Because of the diverse taxonomic origin of the samples, the oil content between species was very variable, fluctuating between an average value of 3.4% in the Caryphyllaceae and 31.1% in Euphorbiaceae. Like the oil content, the fatty acid composition was quite variable, but, in general, the main fatty acids were palmitic, oleic, linoleic and linolenic acid, while in the Brassicaceae and in the Apiaceae erucic acid and petroselinic acid were the principal fatty acids respectively.

Wang, J.-P., Meng, S.-J., Zhang, Q.-H., and He, G.-F.  (1981). The Fatty Acid Compositions of Seed Oils and Their Significance in the Taxonomy of the Family Ulmaceae. Acta Phytotaxonomica Sinica 19, 416-420.                 

     22 kinds of seed oils were extracted from 8 genera of the family Ulmaceae in China

              The seed oils were examined for their characteristics and fatty acid compositions by gas liquid chromatography.  The fatty acid compositions of these oils were found tofall into two classes. Some genera (such as  Ulmus ,  Zelkova)  contain  mainly   lower  saturated acids, in which the chief acid is  capric  acid 10:0, while the genera   ( such  as  Celtis Pteroceltis Aphananthe Trema Gironniera ) contain mainly  unsaturat ed  acids, in which the chief acid is linoleic acid  18:2.   Hemiptelea   davidii   ( Hance )   Planch contain however either certain amount of short-chain saturated acids or higher   unsaturated  acids, it appears a intermediate genus between the two classes.  According  to  the component acids we support that the  Ulmaceae  be split into two subfamilies.  The genera arrangement based on the component acids corresponds basically with the   view  based on  mophological  characters and flavonoids found in leaves of  Ulmaceae , but  there  are some discrepancies in certain genera, for example, the  Aphananthe  should be  placed  in  Celtoid  instead of  Ulmoid  by the present study.

Wissebach , H.  (1969).  Fette  Und Lipoide (Lipids). (Berlin, Heidelberg: Springer Berlin Heidelberg).

Wolf, R.B., Kleiman, R., and England, R.E.  (1983). New Sources of Γ-Linolenic Acid. Journal of the American Oil Chemists' Society 60,1858-1860.    10.1007/BF02901538

              γ-Linolenic acid (18:3Δ6,9,12) occurs in significant amounts in various species of plants surveyed. Of the species analyzed in this study, Nonnea macrospernia, with 5.1% 7-linolenic acid in the seed, is the richest source of this fatty acid. Other species in the same family (Boraginaceae) are also good sources: Adelocaryum coelestinumAlkanna froediniiAlkanna orientalis and Brunnera orientalis.Scrophularia marilandica (family Scrophulariaceae) seeds contain 37.9% oil, of which 9.6% is γ-linolenic acid. All species mentioned above are better sources, when the total amount of γ-linolenic acid in the seed is considered, than that used traditionally, Evening Primrose (Oenothera biennis, family Onagraceae). None of the other Onagraceae nor any of the Ribes (family Saxifragaceae) species analyzed areas rich in γ-linolenic acid as Evening Primrose. Octadecatetraenoic acid (18:4Δ,6,9,12,15) was found in significant amounts in most of theBoraginaceae and Ribes surveyed. The Onagraceae and Scrophulariaceae lack detectable amounts of this fatty acid.

Wolff, R.L., Deluc, L.G., and Marpeau, A.M.  (1996). Conifer Seeds: Oil Content and Fatty Acid Composition. Journal of the American Oil Chemists Society 73, 765-771.    10.1007/bf02517953

              The seed oils from twenty-five Conifer species (from four families-PinaceaeCupressaceaeTaxodiaceae, and Taxaceae) have been analyzed, and their fatty acid compositions were established by capillary gas-liquid chromatography on two columns with different polarities. The oil content of the seeds varied from less than 1% up to 50%. Conifer seed oils were characterized by the presence of several Delta 5-unsaturated polymethylene-interrupted polyunsaturated fatty acids (Delta 5-acids) with either 18 (cis-5, cis-9 18:2, cis-5, cis-9, cis-12 18:3, and cis-5, cis-9, cis-12, cis-15 18:4 acids) or 20 carbon atoms (cis-5, cis-11 20:2, cis-5, cis-11, cis-14 20:3, and cis-5, cis-11, cis-14, cis-17 20:4 acids). Pinaceae seed oils contained 17-31% of Delta 5-acids, mainly with 18 carbon atoms. The 20-carbon acids present were structurally derived from 20:1n-9 and 20:2n-6 acids. Pinaceae seed oils were practically devoid of 18:3n-3 acid and did not contain either Delta 5-18:4 or Delta 5-20:4 acids. Several Pinaceae seeds had a Delta 5-acid content higher than 50 mg/g of seed. The only Taxaceaeseed oil studied (Taxus baccata) had a fatty acid composition related to those of Pinaceae seed oils. Cupressaceae seed oils differed fromPinaceae seed oils by the absence of Delta 5-acids with 18 carbon atoms and high concentrations in 18:3n-3 acid and in Delta 5-acids with 20 carbon atoms (Delta 5-20:3 and Delta 5-20:4 acids). Delta 5-18:4 Acid was present in minute amounts. The highest level of Delta 5-20:4acid was found in Juniperus communis seed oil, but the best source of Delta 5-acids among Cupressaceae was Thuja occidentalis.Taxodiaceae seed oils had more heterogeneous fatty acid compositions, but the distribution of Delta 5-acids resembled that found inCupressaceae seed oils. Except for Sciadopytis verticillata, other Taxodiaceae species are not interesting sources of Delta 5-acids. The distribution profile of Delta 5-acids among different Conifer families appeared to be linked to the occurrence of 18:3n-3 acid in the seed oils.

Wolff, R.L., Deluc, L.G., Marpeau, A.M., and Comps, B.  (1997). Chemotaxonomic Differentiation of Conifer Families and Genera Based on the Seed Oil Fatty Acid Compositions: Multivariate Analyses. Trees - Structure and Function 12, 57-65.    10.1007/s004680050122

              The fatty acid compositions of seed oils from 34 conifer species, mainly Pinaceae and secondarily Cupressaceae, have been determined by gas-liquid chromatography of the methyl esters. As noted in earlier studies, these oils were characterized by the presence of several Δ5-olefinic acids, i.e., 5,9-18:2, 5,9,12-18:3, 5,9,12,15-18:4, 5,11-20:2, 5,11,14-20:3, and 5,11,14,17-20:4 acids, in addition to the more common saturated, oleic, linoleic and α-linolenic acids. Based on these fatty acid compositions, and on those established in earlier systematic studies (totalling 82 species), we established a chemotaxonomic grouping of the main conifer families, i.e., of the Pinaceae,TaxodiaceaeCupressaceae, and Taxaceae. This was achieved using multivariate analyses (principal component analysis and discriminant analysis). The fatty acids that discriminate best in this classification are the 5,11,14,17-20:4, 9,12,15-18:3 and 5,9,12-18:3 acids. Moreover, it was possible to differentiate between several genera of the PinaceaePinus (including Tsuga and Pseudotsuga), AbiesCedrus, andPicea plus Larix, represented quite distinct groups. Other fatty acids such as oleic, linoleic, and 5,9-18:2 acids were also important for this purpose. The fatty acid compositions, and particularly the Δ5-olefinic acid contents of conifer seed oils, may thus be applied to thechemosystematic distinction among conifer families as well as genera of the Pinaceae.

Wolff, R.L., Lavialle, O., Pedrono, F., Pasquier, E., Deluc, L.G., Marpeau, A.M., and Aitzetmuller, K.  (2001).  Fatty Acid Composition ofPinaceae as Taxonomic Markers. Lipids 36, 439-451.    10.1007/s11745-001-0741-5

               Following our previous review on Pinus spp. seed fatty acid (FA) compositions, we recapitulate here the seed FA compositions of Larix (larch),Picea (spruce), and Pseudotsuga (Douglas iir) spp. Numerous seed FA compositions not described earlier are included. Approximately 40% of all Piceataxa and one-third of Larix taxa have been analyzed so Car for their seed FA compositions. Qualitatively, the seed FA compositions in the three genera studied here are the same as in Pinus spp., including in particular the same Delta5-olefinic acids. However, they display a considerably lower variability inLarix and Picea spp. than in Pinus spp. An assessment of geographical Variations in the seed FA composition of P. abies was made, and intraspecific dissimilarities in this species were found to be of considerably smaller amplitude than interspecific dissimilarities among other Picea species. This observation supports the use of seed FA compositions as chemotaxonomic markers, as they practically do not depend on edaphic or climatic conditions. This also shows that Picea spp. are coherently united as a group by their seed FA compositions. This also holds for Larix spp. Despite a close resemblance between Picea and Larix spp. seed FA compositions, principal component analysis indicates that the minor differences in seed FA compositions between the two genera are sufficient to allow a clear-cut individualization of the two genera. in both cases, the main FA is linoleic acid (slightly less than one-half of total FA), followed by pinolenic (5,9,12-18:3) and oleic acids. A maximum of 34% of total Delta5-olefinic acids is reached in L. sibirica seeds, which appears to be the highest value found in Pinaceae seed FA. This apparent limit is discussed in terms of regio- and stereospecific distribution of Delta5-olefinic acids in seed triacylglycerols. Regarding the single species of Pseudotsuga analyzed so far (P. menziesii) its seed FA composition is quite distinct from that of the other two genera, and in particular, it contains 1.2% of 14-methylhexadecanoic (anteiso-17:0) acid. In the three genera studied here, as well as in most Pinus spp., the C-18 Delta5-olefinic acids (5,9-18:2 and 5,9,12-18:3 acids) are present in considerably higher amounts than the C-20 Delta5-olefinic acids (5,11-20:2 and 5,11,14-20:3 acids).

Wolff, R.L., Pedrono, F., Pasquier, E., and Marpeau, A.M.  (2000).  General Characteristics of Pinus Spp. Seed Fatty Acid Compositions, and Importance of Delta 5-Olefinic Acids in the Taxonomy and Phylogeny of the Genus. Lipids 35, 1-22.    10.1007/s11745-000-0489-y

               The Delta 5-unsaturated polymethylene-interrupted fatty acid (Delta 5-UPIFA) contents and profiles of gymnosperm seeds are useful chemometricdata for the taxonomy and phylogeny of that division, and these acids may also have some biomedical or nutritional applications. We recapitulate here all data available on pine (Pinus; the largest genus in the family Pinaceae) seed fatty acid (SFA) compositions, including 28 unpublished compositions. This overview encompasses 76 species, subspecies, and varieties, which is approximately one-half of all extant pines officially recognized at these taxon levels; Qualitatively, the SFA from all pine species analyzed so far are identical. The genus Pinus is coherently united-but this qualitative feature can be extended to the whole family Pinaceae-by the presence of Delta 5-UPIFA with C-18 [taxoleic (5,9-18:2) and pinolenic (5,9,12-18:3) acids] and C-20 chains [5,11-20.2, and sciadonic 15,11,14-20:3) acids]. Not a single pine species was found so far with any of these acids missing. Linoleic acid is almost always, except in a few cases, the prominent SFA, in the range 40-60% of total fatty acids. The second habitual SFA is oleic acid, from 12 to 30%. Exceptions, however, occur, particularly in the Cembroides subsection, where oleic acid reaches ca. 45%, a value higher than that of linoleic acid. alpha-Linolenic acid, on the other hand, is a minor constituent of pine SFA, almost always less than 1%, but that would reach 2.7% in one species (P. merkusii). The sum of saturated acids [16:0 (major) and 18:0 (minor) acids principally] is most often less than 10% of total SFA, and anteiso-17:0 acid is present in all species in:amounts  up to 0.3%. Regarding C18 Delta 5-UPIFA, taxoleic acid reaches a maximum of 4.5% of total SFA, whereas pinolenic acid varies from 0.1 to 25.3%. The very minor coniferonic (5,9,12,15-18:4) acid is less than 0.2% in all species. The C20 elongation product of pinolenic acid,bishomo-pinolenic (7,11,14-20:3) acid, is a frequent though minor SFA constituent (maximum, 0.7%). When considering C20 Delta 5-UPIFA, a difference is noted between the subgenera Strobus and Pinus. In the former subgenus, 5,11-20:2 and sciadonic acids are less than or equal to 0.3 and less than or equal to 1.9%, respectively, whereas in the latter subgenus, they are most often greater than or equal to 0.3 and greater than or equal to 2.0%, respectively. The highest values for 5,11-20:2 and sciadonic acids are 0.5% (many species) and 7.0% (P. pinaster). The 5,11,14,17-20:4 (juniperonic) acidis present occasionally in trace amounts. The highest level of total Delta 5-UPIFA is 30-31% (P. sylvestris), and the lowest level is 0.6% (P. monophylla). Uniting as well as discriminating features that may complement the knowledge about the taxonomy and phylogeny of pines are emphasized.