Simmondsin

Simmondsin
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H25NO9
Molar mass375.374 g·mol−1
3D model (JSmol)
SMILES
  • N#C\C=C2/[C@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C[C@H](OC)[C@H](OC)[C@H]2O
InChI
  • InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10-,11+,12-,13+,14-,15+,16-/m1/s1
  • Key:KURSRHBVYUACKS-XGYNEUJOSA-N
  (verify)

Simmondsin is a component of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis). While it had been considered toxic due to jojoba seed meal causing weight loss in animals, in recent years its appetite suppressant effect has also been researched as a potential treatment for obesity.[1] Several mechanisms of action are thought to be involved in the appetite suppressant effect.[2][3][4][5]

References

  1. ↑ "Simmondsin From Jojoba - Checked for Appetite Suppression". United States Department of Agriculture, Agricultural Research Service.
  2. ↑ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M (December 1995). "Devazepide reverses the anorexic effect of simmondsin in the rat". The Journal of Endocrinology. 147 (3): 473–7. doi:10.1677/joe.0.1470473. PMID 8543917.
  3. ↑ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, et al. (August 1998). "Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats". Hormone and Metabolic Research. 30 (8): 504–8. doi:10.1055/s-2007-978921. PMID 9761380.
  4. ↑ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M (April 2000). "The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat". Appetite. 34 (2): 147–51. doi:10.1006/appe.1999.0299. PMID 10744903. S2CID 42949049.
  5. ↑ Boozer CN, Herron AJ (July 2006). "Simmondsin for weight loss in rats". International Journal of Obesity. 30 (7): 1143–8. doi:10.1038/sj.ijo.0803251. PMID 16462820.
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