Biosynthesis and metabolic engineering of palmitoleate production, an important contributor to human health and sustainable industry

Progress in Lipid Research

Volumn 51, Issue 4, 2012, Pages 340-349

  Wu, Yongmei ^a,b   Li, Runzhi ^b   Hildebrand, David F ^b  

^a SHANXI AGRICULTURAL UNIVERSITY   (China)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

9 Desaturase; 7 Fatty acids; Biodiesel; Healthy fatty acids; Lipid biosynthesis; Metabolic engineering; Palmitoleate (16:1 9); Renewable feedstocks

Indexed keywords

ACETATE COENZYME A LIGASE; ACYL COENZYME A; ACYL COENZYME A DESATURASE; BIODIESEL; BIOFUEL; PALMITIC ACID; PALMITOLEIC ACID; PETROLEUM; PHOSPHOLIPID; ROSIGLITAZONE; SYNTHETASE; UNCLASSIFIED DRUG;

BIOACCUMULATION; BIOENGINEERING; BIOSYNTHESIS; CHEMICAL INDUSTRY; CROP; DIABETES MELLITUS; DYSLIPIDEMIA; ENERGY RESOURCE; FATTY ACID METABOLISM; FATTY ACID SYNTHESIS; HUMAN; LIPID COMPOSITION; LIPID METABOLISM; LIPIDOMICS; METABOLIC DISORDER; METABOLIC REGULATION; MOLECULAR GENETICS; MUTANT; NONHUMAN; NUTRITIONAL HEALTH; PHYTOCHEMISTRY; PLANT BREEDING; PLANT GENE; PLANT SEED; PRIORITY JOURNAL; PROTEIN EXPRESSION; RENEWABLE ENERGY; REVIEW; TRANSGENIC PLANT;

BIOFUELS; FATTY ACID DESATURASES; FATTY ACIDS, MONOUNSATURATED; HUMANS; MEMBRANE FLUIDITY; METABOLIC ENGINEERING; PLANT OILS; PLANTS, GENETICALLY MODIFIED; TRIGLYCERIDES;

ARABIDOPSIS; FUNGI; MAMMALIA;

EID: 84863466829     PISSN: 01637827     EISSN: 18732194     Source Type: Journal    
DOI: 10.1016/j.plipres.2012.05.001     Document Type: Review

References (102)

1. G. Knothe Biodiesel derived from a model oil enriched in palmitoleic acid macadamia nut oil Energy Fuels 24 2010 2098 2103
2. A.E. Griel, Y.M. Cao, D.D. Bagshaw, A.M. Cifelli, B. Holub, and P.M. Kris-Etherton A macadamia nut-rich diet reduces total and LDL-cholesterol in mildly hypercholesterolemic men and women J Nutr 138 2008 761 767
3. H. Ako, D. Okuda, and D. Gray Healthful new oil from macadamia nuts Nutrition 11 1995 286 288
4. J.D. Curb, G. Wergowske, J.C. Dobbs, R.D. Abbott, and B.J. Huang Serum lipid effects of a high-monounsaturated fat diet based on macadamia nuts Arch Intern Medicine 160 2000 1154 1158
5. H.J. Welters, E. Diakogiannaki, J.M. Mordue, M. Tadayyon, S.A. Smith, and N.G. Morgan Differential protective effects of palmitoleic acid and cAMP on caspase activation and cell viability in pancreatic beta-cells exposed to palmitate Apoptosis 11 2006 1231 1238
6. H. Hayatsu, S. Arimoto, and T. Negishi Dietary inhibitors of mutagenesis and carcinogenesis Mutat Res 202 1988 429 446
7. K. Maedler, J. Oberholzer, P. Bucher, G.A. Spinas, and M.Y. Donath Monounsaturated fatty acids prevent the deleterious effects of palmitate and high glucose on human pancreatic beta-cell turnover and function Diabetes 52 2003 726 733
8. P. Georgel, K. Crozat, X. Lauth, E. Makrantonaki, H. Seltmann, and S. Sovath A toll-like receptor 2-responsive lipid effector pathway protects mammals against skin infections with gram-positive bacteria Infect Immun 73 2005 4512 4521
9. H. Swarts, S.F. Schuurmans, and J. De Pont Binding of unsaturated fatty acids to N+, K(+)-ATPase leading to inhibition and inactivation Biochim Biophys Acta 1024 1990 32 40
10. N. Theret, J. Bard, M. Nuttens, J. Lecerf, C. Delbart, and M. Romon The relationship between the phospholipids fatty acid composition of red blood cells, [lasma lipids, and apolipoproteins Metabolism 42 1993 526 528
11. A. Rybak, P.A. Fokou, and M.A.R. Meier Metathesis as a versatile tool in oleochemistry Eur J Lipid Sci Technol 110 2008 797 804
12. M.A.R. Meier Metathesis with oleochemicals: new approaches for the utilization of plant oils as renewable resources in polymer science Macromol Chem Phys 210 2009 1073 1079
13. H.T. Nguyen, G. Mishra, E. Whittle, M.S. Pidowich, S.A. Bevan, and A.O. Merlo Metabolic engineering of seeds can achieve levels of w-7 fatty acids comparable with the highest levels found in natural plant sources Plant Physiol 154 2010 1897 1904
14. M. Bondaruk, S. Johnson, A. Degafu, P. Boora, P. Bilodeau, and J. Morris Expression of a cDNA encoding palmitoyl-acyl carrier protein desaturase from cat's claw (Doxantha unguis-cati L.) in Arabidopsis thaliana and Brassica napus leads to accumulation of unusual unsaturated fatty acids and increased stearic acid content in the seed oil Plant Breed 126 2007 186 194
15. H. Moon, J. Hazebroek, and D. Hildebrand Changes in fatty acid composition in plant tissues expressing a mammalian Δ9 desaturase Lipids 35 2000 471 479
16. M.L. Choudhary, C.K. Chin, J.J. Polashock, and C.E. Martin Agrobacterium-mediated transformation of petunia-hybrida with yeast Delta-9 fatty-acid desaturase Plant Growth Regul 15 1994 113 116
17. J.J. Polashock, C.-K. Chin, and C.E. Martin Expression of the yeast D-9 fatty acid desaturase in Nicotiana tabacum Plant Physiol 100 1992 894 901
18. W.S. Grayburn, and D.F. Hildebrand Progeny analysis of tobacco that express a mammalian Delta-9 desaturase J Am Oil Chem Soc 72 1995 317 321
19. C. Wang, C.K. Chin, and A. Chen Expression of the yeast Delta-9 desaturase gene in tomato enhances its resistance to powdery mildew Physiol Mol Plant Pathol 52 1998 371 383
20. J.S. Xing, and C.K. Chin Modification of fatty acids in eggplant affects its resistance to Verticillium dahliae Physiol Mol Plant Pathol 56 2000 217 225
21. L. Wang, A.R. Folsom, Z.J. Zheng, J.S. Pankow, and J.H. Eckfeldt Plasma fatty acid composition and incidence of diabetes in middle aged adults: the Atherosclerosis Risk in Communities (ARIC) Study Circulation 106 2002 3601
22. J.D. McGarry Dysregulation of fatty acid metabolism in the etiology of type 2 diabetes Diabetes 51 2002 7 18
23. M. Bajaj, S. Suraamornkul, A. Romanelli, G.W. Cline, L.J. Mandarino, and G.I. Shulman Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty acyl-CoAs and insulin action in type 2 diabetic patients Diabetes. 54 2005 3148 3153
24. N. Stefan, K. Kantartzis, N. Celebi, H. Staiger, J. Machann, and F. Schick Circulating palmitoleate strongly and independently predicts insulin sensitivity in humans Diabetes Care 33 2010 405 407
25. T. Scherer, J. O'Hare, K. Diggs-Andrews, M. Schweiger, B. Cheng, and C. Lindtner Brain insulin controls adipose tissue lipolysis and lipogenesis Cell Metab 13 2011 183 194
26. Y. Tsuchiya, H. Hatakeyama, N. Emoto, F. Wagatsuma, S. Matsushita, and M. Kanzaki Palmitate-induced down-regulation of sortilin and impaired GLUT4 trafficking in C2C12 myotubes J Biol Chem 285 2010 34371 34381
27. H.M. Cao, K. Gerhold, J.R. Mayers, M.M. Wiest, S.M. Watkins, and G.S. Hotamisligil Identification of a lipokine, a lipid hormone linking adipose tissue to systemic metabolism Cell 134 2008 933 944
28. E. Fabbrini, F. Magkos, X.O. Su, N.A. Abumrad, N. Nejedly, and C.C. Coughlin Insulin sensitivity is not associated with palmitoleate availability in obese humans J Lipid Res 52 2011 808 812
29. D. Mozaffarian, H.M. Cao, I.B. King, R.N. Lemaitre, X.L. Song, and D.S. Siscovick Circulating palmitoleic acid and risk of metabolic abnormalities and new-onset diabetes Am J Clin Nutr 92 2010 1350 1358
30. N. Dimopoulos, M. Watson, K. Sakamoto, and H.S. Hundal Differential effects of palmitate and palmitoleate on insulin action and glucose utilization in rat L6 skeletal muscle cells Biochem J 399 2006 473 481
31. W.J. Yoon, M.J. Kim, J.Y. Moon, H.J. Kang, G.O. Kim, and N.H. Lee Effect of Palmitoleic Acid on melanogenic protein expression in murine B16 melanoma J Oleo Sci 59 2010 315 319
32. O. Kuda, B. Stankova, E. Tvrzicka, M. Hensler, T. Jelenik, and M. Rossmeisl Prominent role of liver in elevated plasma palmitoleate levels in response to rosiglitazone in mice fed high-fat diet J Physiol Pharmacol 60 2009 135 140
33. Y. Akazawa, S. Cazanave, J.L. Mott, N. Elmi, S.F. Bronk, and S. Kohno Palmitoleate attenuates palmitate-induced Bim and PUMA up-regulation and hepatocyte lipoapoptosis J Hepatol 52 2010 586 593
34. A. Kadotani, Y. Tsuchiya, H. Hatakeyama, H. Katagiri, and M. Kanzaki Different impacts of saturated and unsaturated free fatty acids on COX-2 expression in C2C12 myotubes Am J Physiol Endocrinol Metab 297 2009 E1291-E303
35. E. Diakogiannaki, and N.G. Morgan Differential regulation of the ER stress response by long-chain fatty acids in the pancreatic beta-cell Biochem Soc Trans 36 2008 959 962
36. E. De Fabiani The true story of palmitoleic acid: between myth and reality Eur J Lipid Sci Technol 113 2011 809 811
37. Cahoon EB, Nguyen HT, Collins-Silva JE, Nazarenus TJ, Cahoon RE, Reddy AK. Biotechnological Development of Camelina as a Biofuel and Biolubricant Crop. In: AOCS Annual Meeting. Cincinnati; 2011.
38. Nguyen TH, Mishra G, Whittle E, Bevan SA, Owens-Merlo A, Walsh TA, et al. Metabolic Engineering of Seeds Can Achieve Levels of ω-7 Fatty Acids Comparable to the Highest Levels Found in Natural Plant Sources. In: AOCS Annual Meeting. Cincinnati; 2011.
39. J.L. Harwood, L.W. Morgan, and T. Greatrex Aveolar surfactants E.E. Bittar, Pulmonary Biology in Health and Disease 2002 Springer-Verlag New York 44 58
40. B.R. Yang, and H.P. Kallio Fatty acid composition of lipids in sea buckthorn (Hippophae rhamnoides L.) berries of different origins J Agric Food Chem 49 2001 1939 1947
41. L.F. Gutierrez, and K. Belkacemi Palmitoleic acid enrichment of seabuckthor (Hippophae rhamnoides L.) pulp oil by crystallization process Sep Sci Technol 43 2008 2003 2022
42. M.R.G. Klaas, and P.U. Meurer A palmitoleic acid ester concentrate from seabuckthorn pomace Eur J Lipid Sci Technol 106 2004 412 416
43. S. Polat, and Y. Ozogul Biochemical composition of some red and brown macro algae from the Northeastern Mediterranean Sea Int J Food Sci Nutr 59 2008 566 572
44. T. Matsunaga, H. Takeyama, Y. Miura, T. Yamazaki, H. Furuya, and K. Sode Screening of marine cyanobacteria for high palmitoleic acid production FEMS Microbiol Lett 133 1995 137 141
45. I.K. Lang, L. Hodac, T. Friedl, and I. Feussner Fatty acid profiles and their distribution patterns in microalgae: a comprehensive analysis of more than 2000 strains from the SAG culture collection Bmc Plant Biol 11 2011 124 140
46. J.B. Ohlrogge, and J.G. Jaworski Regulation of fatty acid synthesis Annu Rev Plant Physiol Plant Mol Biol 48 1997 109 136
47. P. Dormann, M. Frentzen, and J.B. Ohlrogge Specificities of the acyl-acyl carrier protein (ACP) thioesterase for octadecenoyl-ACP isomers Plant Physiol 104 1994 839 844
48. K.M. Mayer, and J. Shanklin Identification of amino acid residues involved in substrate specificity of plant acyl-ACP thioesterases using a bioinformatics-guided approach Bmc Plant Biol 7 2007
49. J.J. Salas, and J.B. Ohlrogge Characterization of substrate specificity of plant FatA and FatB acyl-ACP thioesterases Arch Biochem Biophys 403 2002 25 34
50. J.A. Schnurr, J.M. Shockey, G.-J. de Boer, and J.A. Browse Fatty acid export from the chloroplast. Molecular characterization of a major plastidial Acyl-coenzyme A synthetase from arabidopsis Plant Physiol 129 2002 1700 1709
51. J.M. Shockey, M.S. Fulda, and J.A. Browse Arabidopsis contains nine long-chain acyl-coenzyme A synthetase genes that participate in fatty acid and glycerolipid metabolism Plant Physiol 129 2002 1710 1722
52. McKeon T, Kang S-T, Turner C, He X, Chen G, Lin J-T. Enzymatic synthesis of intermediates in castor oil biosynthesis. In: 97th AOCS Annual Meeting & Expo. vol. 15; 2006.
53. T.A. McKeon The enzymology of castor oil biosynthesis J. Janick, A. Whipkey, Issues in New Crops and New Uses 2007 ASHS Press Alexandria, VA
54. U. Stahl, A.S. Carlsson, M. Lenman, A. Dahlqvist, B.Q. Huang, and W. Banas Cloning and functional characterization of a Phospholipid: Diacylglycerol acyltransferase from Arabidopsis Plant Physiol 135 2004 1324 1335
55. M. Zhang, J. Fan, D.C. Taylor, and J.B. Ohlrogge DGAT1 and PDAT1 Acyltransferases have overlapping functions in Arabidopsis triacylglycerol biosynthesis and are essential for normal pollen and seed development Plant Cell 21 2009 3885 3901
56. F.M. Jackson, L. Michaelson, T.C.M. Fraser, A.K. Stobart, and G. Griffiths Biosynthesis of triacylglycerol in the filamentous fungus Mucor circinelloides Microbiology-Sgm 144 1998 2639 2645
57. J.G. Wallis, and J. Browse Lipid biochemists salute the genome Plant J 61 2010 1092 1106
58. C. Lu, Z. Xin, Z. Ren, M. Miquel, and J. Browse An enzyme regulating triacylglycerol composition is encoded by the ROD1 gene of Arabidopsis Proc Nat Acad Sci 106 2009 18837 18842
59. K.D. Chapman, and J.B. Ohlrogge Compartmentation of Triacylglycerol accumulation in plants J Biol Chem 287 2012 2288 2294
60. J. Hill, E. Nelson, D. Tilman, S. Polasky, and D. Tiffany Environmental, economic, and energetic costs and benefits of biodiesel and ethanol biofuels Proc Nat Acad Sci 103 2006 11206 11210
61. B. Shen, W.B. Allen, P.Z. Zheng, C.J. Li, K. Glassman, and J. Ranch Expression of ZmLEC1 and ZmWRI1 increases seed oil production in Maize Plant Physiol 153 2010 980 987
62. S. Baud, A.B.F. Bourrellier, M. Azzopardi, A. Berger, J. Dechorgnat, and F. Daniel-Vedele PII is induced by WRINKLED1 and fine-tunes fatty acid composition in seeds of Arabidopsis thaliana Plant J 64 2010 291 303
63. T. Masaki, N. Mitsui, H. Tsukagoshi, T. Nishii, A. Morikami, and K. Nakamura Activator of Spo(min): LUC1/WRINKLED1 of a Arabidopsis thaliana transactivates sugar-inducible promoters Plant Cell Physiol 46 2005 547 556
64. S. Baud, M.S. Mendoza, A. To, E. Harscoet, L. Lepiniec, and B. Dubreucq WRINKLED1 specifies the regulatory action of LEAFY COTYLEDON2 towards fatty acid metabolism during seed maturation in Arabidopsis Plant J 50 2007 825 838
65. E.B. Cahoon, J.M. Shockey, C.R. Dietrich, S.K. Gidda, R.T. Mullen, and J.M. Dyer Engineering oilseeds for sustainable production of industrial and nutritional feedstocks: solving bottlenecks in fatty acid flux Curr Opin Plant Biol 10 2007 236 244
66. J.M. Dyer, and R.T. Mullen Engineering plant oils as high-value industrial feedstocks for biorefining: the need for underpinning cell biology research Physiologia Plantarum 132 2008 11 22
67. T.P. Durrett, C. Benning, and J. Ohlrogge Plant triacylglycerols as feedstocks for the production of biofuels Plant J 54 2008 593 607
68. H.G. Damude, and A.J. Kinney Enhancing plant seed oils for human nutrition Plant Physiol 147 2008 962 968
69. J.J. Salas, E. Martinez-Force, and R. Garces Biochemical characterization of a high-palmitoleic acid Helianthus annuus mutant Plant Physiol Biochem 42 2004 373 381
70. J.J. Salas, A.J. Moreno-Perez, E. Martinez-Force, and R. Garces Characterization of the glycerolipid composition of a high-palmitoleic acid sunflower mutant Eur J Lipid Sci Technol 109 2007 591 599
71. S.R. Schnebly, W.R. Fehr, G.A. Welke, E.G. Hammond, and D.N. Duvick Inheritance of reduced and elevated palmitate in mutant lines of soybean Crop Sci. 34 1994 829 833
72. K. Aghoram, R.F. Wilson, J.W. Burton, and R.E. Dewey A Mutation in a 3-Keto-Acyl-ACP synthase II gene is associated with elevated Palmitic Acid levels in soybean seeds Crop Sci 46 2006 2453 2459
73. J. Shanklin, and C. Somerville Stearoyl-acyl-carrier-protein desaturase from higher plants is structurally unrelated to the animal and fungal homologs Proc Nat Acad Sci 88 1991 2510 2514
74. J. Shanklin, C. Mullins, and C. Somerville Sequence of a complementary DNA from Cucumus sativus L. encoding the stearoyl-acyl-carrier protein desaturase Plant Physiol 97 1991 467 468
75. M.T. Kaup, C.D. Froese, and J.E. Thompson A role for diacylglycerol acyltransferase during leaf senescence Plant physiol 129 2002 1616 1626
76. E.B. Cahoon, S.J. Coughlan, and J. Shanklin Characterization of a structurally and functionally diverged acyl-acyl carrier protein desaturase from milkweed seed Plant Mol Biol 33 1997 1105 1110
77. E.B. Cahoon, A.M. Cranmer, J. Shanklin, and J.B. Ohlrogge D6 hexadecenoic acid is synthesized by the activity of a soluble D6 palmitoyl-acyl carrier protein desaturase in Thunbergia alata endosperm J Biol Chem 269 1994 27519 27526
78. W.S. Grayburn, G.B. Collins, and D.F. Hildebrand Fatty acid alteration by a D9 desaturase in transgenic tobacco tissue Biotechnol 10 1992 675 678
79. C. Wang, C.-K. Chin, C.-T. Ho, C.-F. Hwang, J.J. Polashoc, and C.E. Martin Changes of fatty acids and fatty acid-derived flavor compounds by expressing the yeast D-9 desaturase gene in tomato J Agric Food Chem 44 1996 3399 3402
80. W. Liu, R.S. Torisky, K.P. McAllister, S. Avdiushko, D. Hildebrand, and G.B. Collins A mammalian desaturase gene lowers saturated fatty acid levels in transgenic soybean embryos Plant Cell Tissue Organ Culture 47 1996 33 42
81. H. Moon, J. Hazebroek, and D.F. Hildebrand Changes in fatty acid composition in plant tissues expressing a mammalian Delta 9 desaturase Lipids 35 2000 471 479
82. E.B. Cahoon, S. Shah, J. Shanklin, and J. Browse A determinant of substrate specificity predicted from the acyl-acyl carrier protein desaturase of developing cat's claw seed Plant Physiol 117 1998 593 598
83. Shockey J, Gidda S, Burgal J, Chapital D, Kuan J-C, Rothstein S, et al. A new magic bullet? Type-2 diacylglycerol acyltransferases are key components to novel fatty acid accumulation in transgenic systems. In: 17th International Symposium on Plant Lipids. East Lansing, MI2006.
84. J. Burgal, J. Shockey, C.F. Lu, J. Dyer, T. Larson, and I. Graham Metabolic engineering of hydroxy fatty acid production in plants: RcDGAT2 drives dramatic increases in ricinoleate levels in seed oil Plant Biotechnol J 6 2008 819 831
85. R. Li, K. Yu, and D. Hildebrand DGAT1, DGAT2 and PDAT expression in seeds and other tissues of epoxy and hydroxy fatty acid accumulating plants Lipids 45 2010 145 157
86. R. Li, K. Yu, T. Hatanaka, and D.F. Hildebrand Vernonia DGATs increase accumulation of epoxy fatty acids in oil Plant Biotechnol J 8 2010 184 195
87. R. Li, K. Yu, Y. Wu, M. Tateno, T. Hatanaka, and D.F. Hildebrand Vernonia DGATs can complement the disrupted oil and protein metabolism in epoxygenase-expressing soybean seeds Metab Eng 14 2012 29 38
88. A.J. Moreno-Pérez, A. Sánchez-García, J.J. Salas, R. Garcés, and E. Martínez-Force Acyl-ACP thioesterases from macadamia (Macadamia tetraphylla) nuts: cloning, characterization and their impact on oil composition Plant Physiol Biochem 49 2011 82 87
89. A. Sanchez-Garcia, A.J. Moreno-Perez, A.M. Muro-Pastor, J.J. Salas, R. Garces, and E. Martinez-Force Acyl-ACP thioesterases from castor (Ricinus communis L.): an enzymatic system appropriate for high rates of oil synthesis and accumulation Phytochem 71 2010 860 869
90. E.B. Cahoon, C.R. Dietrich, K. Meyer, H.G. Damude, J.M. Dyer, and A.J. Kinney Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds Phytochem 67 2006 1166 1176
91. S.C.A. Thomaeus, and S. Stymne Distribution of fatty acids in polar and neutral lipids during seed development in Arabidopsis thaliana genetically engineered to produce acetylenic, epoxy and hydroxyl fatty acids Plant sci 161 2001 997 1003
92. J.M. Shockey, S.K. Gidda, D.C. Chapital, J.-C. Kuan, P.K. Dhanoa, and J.M. Bland Tung tree DGAT1 and DGAT2 have nonredundant functions in triacylglycerol biosynthesis and are localized to different subdomains of the endoplasmic reticulum Plant Cell 18 2006 2294 2313
93. W.C. Man, M. Miyazaki, K. Chu, and J. Ntambi Colocalization of SCD1 and DGAT2: implying preference for endogenous monounsaturated fatty acids in triglyceride synthesis J Lipid Res 47 2006 1928 1939
94. M. Chisholm, and C. Hopkins Fatty acids of doxantha seed oil J Am Oil Chem Soc 42 1965 49 50
95. B. Yang, and H.P. Kallio Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoides L.) berries of different origins J Agric Food Chem 49 2001 1939 1947
96. G. Spencer, and R. Kleiman Palmitoleic acid in Roureopsis obliquifoliata (Connaraceae) Seed oil J Am Oil Chem Soc 55 1978 689
97. P.O. Gummeson, M. Lenman, M. Lee, S. Singh, and S. Stymne Characterisation of acyl-ACP desaturases from Macadamia integrifolia Maiden & Betche and Nerium oleander L Plant Sci 154 2000 53 60
98. N. Tsevegsuren, K. Aitzetmuller, and K. Vosmann Isomers of hexadecenoic and hexadecadienoic acids in Androsace septentrionalis (Primulaceae) seed oil Lipids 38 2003 1173 1178
99. J.R. Vickery Fatty acid composition of seed oils of proteaceae - a chemotaxonomic study Phytochemistry 10 1971 123
100. Cattaneo P, Bertoni MH, Desutton GK. Aceites de semilla de proteaceas. 2. genero grevillea. Anales De La Asociacion Quimica Argentina. 1966;54:117.
101. A.H. Gentry Generic delimitations of central-american bignoniaceae Brittonia 25 1973 226 242
102. S. Rawsthorne Carbon flux and fatty acid synthesis in plants Prog. Lipid Res. 41 2002 182 196