Plant Profiler

Jojoba (Simmondsia chinensis)


Jojoba (Simmondsia chinensis) Image
Synonyms / Common Names / Related Terms
D-pinitol, docosenyl eicosenoate (C22:1-C20:1), eicosenyl docosenoate (C20:1-C22:1), eicosenyl eicosenoate (C20:1-C20:1), eicosenyl octadecenoate (C20:1-C18:1), jojoba beans, jojoba bean oil, jojoba cotyledons, jojoba esters, jojoba liquid wax (JLW), JLW, jojoba meal, jojoba meal phospholipids, jojoba oil (Joj), jojoba protein, jojoba seed, jojoba seedlings, jojoba seed meal, jojoba seed xyloglucan, jojoba wax, jojoba xyloglucan oligosaccharides, lysophosphatidylcholine (LPC), myo-inositol sucrose, phosphatidylcholine (PC), pinitol alpha-D-galactosides, rimethylsilyl derivatives, Simmondsia chinensis, Simmondsiaceae (family), simmondsin, simmondsin ferulates, simmondsins, simmondsin derivative, tetracosenyl eiosenoate (C24:1-C20:1).


Mechanism of Action

Pharmacology:

  • Constituents: In jojoba meal, the major proteins are albumins (79%) and globulins (21%).1 Residual meal analysis resulted in crude protein 25.24%; ether extract 14.73%; crude fiber 10.07%; ash 4.72, nitrogen-free extract 45.25, and trypsin inhibitor factors 11,197TIU/g.5 A trypsin-inhibitory substance, able to inhibit the enzymic activity of trypsin, chymotrypsin, and pepsin, but not the protease from Aspergillus saotoi, has been identified in commercially processed jojoba seed meal and the albumin fraction of seed proteins.11 It is unclear whether consumption of jojoba seed meal by humans would inhibit trypsin activity in the intestine.
  • In jojoba meal, 1-oleoyl-3-lysophosphatidylcholine and 1,2-dioleoyl-3-phosphatidylcholine12, the pinnitol alpha-D-galactosides 5-O-(alpha-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol or 5-alpha-D-galactopyranosyl-D-pinitol and 2-O-(alpha-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol or 2-alpha-D-galactopyranosyl-D-pinitol13,14, and simmondsin [2-(cyanomethylene)-3 hydroxy 4,5 dimethoxy cyclohexyl beta-D-glucoside] and simmondsin ferulates7,15 were identified. Simmondsin, 4-demethylsimmondsin, 5-demethylsimmondsin and 4,5-didemethylsimmondsin were isolated from jojoba seed meal.16
  • With fermentation, five strains of simmondsin-degrading, lactic-acid-producing bacteria were isolated from jojoba meal.17
  • Seed analysis resulted in crude protein 14.03%; ether extract 48.89%; crude fiber 10.03%; ash 1.59, nitrogen-free extract 25.46, and trypsin inhibitor factors 13.747TIU/g.5
  • The jojoba plant synthesizes liquid wax.3 Wax levels may represent up to 70% (by weight) of the oil present in jojoba seeds.18,19,20 The main constituents in jojoba wax are the wax esters, eicosenyl octadecenoate (C20:1-C18:1), eicosenyl eicosenoate (C20:1-C20:1), docosenyl eicosenoate (C22:1-C20:1), eicosenyl docosenoate (C20:1-C22:1) and tetracosenyl eiosenoate (C24:1-C20:1).4 A wax ester hydrolase is active in developing jojoba cotyledons.21
  • Jojoba seed is a source of xyloglucan oligosaccharides, which may be a convenient source of individual oligosaccharides.22
  • Aminopeptidase activity has been determined in germinated jojoba cotyledon extracts.23 This protein is thought to be involved in the degradation of globulin reserve proteins during cotyledon senescence.
  • Anti-inflammatory effects: Habashy examined the anti-inflammatory effects of jojoba liquid wax in several animal and in vitro models.2 Jojoba liquid wax reduced carrageenin-induced rat paw edema and prostaglandin E2 (PGE2) levels in inflammatory exudates. In a chick embryo chroioallantoic membrane model, jojoba liquid wax caused a reduction in granulation tissue formation. In rats, croton oil induced ear edema was reduced. In this model, there was also a reduction in neutrophil infiltration (decreased myeloperoxidase activity) and histopathological changes. Jojoba liquid wax reduced nitric oxide levels and tumor necrosis factor-alpha release in a lipopolysaccharide-induced inflammation rat air pouch model.
  • Anti-insect effects: Topical application of the prepupae of Rhynchophorus ferrugineous with one of three dose-levels (0.1, 0.005 or 0.001mcg per insect) of jojoba oil decreased daily O2 consumption and CO2 release of early and late pupae.8 This suggests jojoba oil may have use a general insecticide.
  • Appetite suppressant effects: The appetite suppressing effects of jojoba seed meal is reduced when the meal is treated with 1N NaOH at 20oC, resulting in the destruction of simmondsin.6
  • Cholesterol reducing effects: The effects of jojoba oil on blood cholesterol levels have been investigated in an animal model.10

Pharmacodynamics/Kinetics:

  • In an animal model, absorption of jojoba 14C-labelled liquid wax was investigated.9 Intragastric administration resulted in the majority of the wax being excreted. A small amount was absorbed, and distributed in internal organs, epididymal fat, and body lipids.
  • The final step in liquid wax biosynthesis in the jojoba seed is catalyzed by fatty-acyl-coenzyme A (CoA): fatty alcohol acyltransferase.3 Beta-Ketoacyl-coenzyme A (CoA) synthase activity, involved in the formation of very long chain fatty acids, such as found in jojoba waxes, is present in developing jojoba embryos.24
  • The appetite suppressing effects of jojoba seed meal is reduced when the meal is treated with 1N NaOH at 20oC resulting in the destruction of simmondsin.6 End products include d-glucose and 2-hydroxy-3-methoxyphenylacetonitrile and intermediates included isosimmondsin and a simmondsin lactone derivative.
  • Boiling of jojoba meal has been suggested to inactivate protease inhibitors and the denaturation of proteins, resulting in increased digestibility.1

References

  1. Shrestha, M. K., Peri, I., Smirnoff, P., Birk, Y., and Golan-Goldhirsh, A. Jojoba seed meal proteins associated with proteolytic and protease inhibitory activities. J Agric Food Chem 9-25-2002;50(20):5670-5675. 12236696
  2. Habashy, R. R., Abdel-Naim, A. B., Khalifa, A. E., and Al Azizi, M. M. Anti-inflammatory effects of jojoba liquid wax in experimental models. Pharmacol Res 2005;51(2):95-105. 15629254
  3. Shockey, J. M., Rajasekharan, R., and Kemp, J. D. Photoaffinity Labeling of Developing Jojoba Seed Microsomal Membranes with a Photoreactive Analog of Acyl-Coenzyme A (Acyl-CoA) (Identification of a Putative Acyl-CoA:Fatty Alcohol Acyltransferase. Plant Physiol 1995;107(1):155-160. 12228351
  4. Tada, A., Jin, Z. L., Sugimoto, N., Sato, K., Yamazaki, T., and Tanamoto, K. Analysis of the constituents in jojoba wax used as a food additive by LC/MS/MS. Shokuhin Eiseigaku Zasshi 2005;46(5):198-204. 16305174
  5. Perez-Gil, F., Sangines, G. L., Torreblanca, R. A., Grande, M. L., and Carranco, J. M. [Chemical composition and content of antiphysiological factors of jojoba (Simmondsia chinensis) residual meal]. Arch Latinoam Nutr 1989;39(4):591-600. 2490896
  6. Van Boven, M., Laga, M., Leonard, S., Busson, R., Holser, R., Decuypere, E., Flo, G., Lievens, S., and Cokelaere, M. Mechanism of simmondsin decomposition during sodium hydroxide treatment. J Agric Food Chem 2-26-2003;51(5):1260-1264. 12590465
  7. Flo, G., Van Boven, M., Vermaut, S., Daenens, P., Decuypere, E., and Cokelaere, M. The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat. Appetite 2000;34(2):147-151. 10744903
  8. Bream, A. S., Ghoneim, K. S., Tanani, M. A., and Nassar, M. I. Respiratory metabolic responsiveness during the pupal stage of the red palm weevil, Rhynchophorus ferrugineus (Coleoptera: Curculionidae) to certain plant extracts. Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet 2001;66(2a):491-502. 12425070
  9. Yaron, A., Samoiloff, V., and Benzioni, A. Absorption and distribution of orally administered jojoba wax in mice. Lipids 1982;17(3):169-171. 7087693
  10. Clarke, J. A. and Yermanos, D. M. Effects of ingestion of jojoba oil on blood cholesterol levels and lipoprotein patterns in New Zealand white rabbits. Biochem Biophys Res Commun 10-30-1981;102(4):1409-1415. 7317057
  11. Samac, D. and Storey, R. Proteolytic and Trypsin Inhibitor Activity in Germinating Jojoba Seeds (Simmondsia chinensis). Plant Physiol 1981;68(6):1339-1344. 16662104
  12. Leon, F., Van Boven, M., de Witte, P., Busson, R., and Cokelaere, M. Isolation and identification of molecular species of phosphatidylcholine and lysophosphatidylcholine from jojoba seed meal (Simmondsia chinensis). J Agric Food Chem 3-10-2004;52(5):1207-1211. 14995122
  13. Van Boven, M., Leyssen, T., Busson, R., Holser, R., Cokelaere, M., Flo, G., and Decuypere, E. Identification of 4,5-didemethyl-4-O-alpha-D-glucopyranosylsimmondsin and pinitol alpha-D-galactosides in jojoba seed meal (Simmondsia chinensis). J Agric Food Chem 2001;49(9):4278-4283. 11559123
  14. Kornienko, A., Marnera, G., and d'Alarcao, M. Synthesis of a jojoba bean disaccharide. Carbohydr Res 1998;310(1-2):141-144. 9794077
  15. Van Boven, M., Holser, R., Cokelaere, M., Flo, G., and Decuypere, E. Gas chromatographic analysis of simmondsins and simmondsin ferulates in jojoba meal. J Agric Food Chem 2000;48(9):4083-4086. 10995318
  16. Lein, S., Van Boven, M., Holser, R., Decuypere, E., Flo, G., Lievens, S., and Cokelaere, M. Simultaneous determination of carbohydrates and simmondsins in jojoba seed meal (Simmondsia chinensis) by gas chromatography. J Chromatogr A 11-22-2002;977(2):257-264. 12456116
  17. Swezey, J. L., Nakamura, L. K., Abbott, T. P., and Peterson, R. E. Lactobacillus arizonensis sp. nov., isolated from jojoba meal. Int J Syst Evol Microbiol 2000;50 Pt 5:1803-1809. 11034490
  18. Lardizabal, K. D., Metz, J. G., Sakamoto, T., Hutton, W. C., Pollard, M. R., and Lassner, M. W. Purification of a jojoba embryo wax synthase, cloning of its cDNA, and production of high levels of wax in seeds of transgenic arabidopsis. Plant Physiol 2000;122(3):645-655. 10712527
  19. Moreau, R. A. and Huang, A. H. Gluconeogenesis from Storage Wax in the Cotyledons of Jojoba Seedlings. Plant Physiol 1977;60(2):329-333. 16660087
  20. Metz, J. G., Pollard, M. R., Anderson, L., Hayes, T. R., and Lassner, M. W. Purification of a jojoba embryo fatty acyl-coenzyme A reductase and expression of its cDNA in high erucic acid rapeseed. Plant Physiol 2000;122(3):635-644. 10712526
  21. Huang, A. H., Moreau, R. A., and Liu, K. D. Development and Properties of a Wax Ester Hydrolase in the Cotyledons of Jojoba Seedlings. Plant Physiol 1978;61(3):339-341. 16660288
  22. Hantus, S., Pauly, M., Darvill, A. G., Albersheim, P., and York, W. S. Structural characterization of novel L-galactose-containing oligosaccharide subunits of jojoba seed xyloglucans. Carbohydr Res 10-28-1997;304(1):11-20. 9403992
  23. Johnson, R. and Storey, R. Aminopeptidase Activity from Germinated Jojoba Cotyledons. Plant Physiol 1985;79(3):641-645. 16664465
  24. Lassner, M. W., Lardizabal, K., and Metz, J. G. A jojoba beta-Ketoacyl-CoA synthase cDNA complements the canola fatty acid elongation mutation in transgenic plants. Plant Cell 1996;8(2):281-292. 8742713




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