Simmondsin

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Simmondsin
Simmondsin.svg
Systematic (IUPAC) name
(2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,
Identifiers
CAS Number 51771-52-9
ATC code none
PubChem CID: 6437384
ChemSpider 4941947
Chemical data
Formula C16H25NO9
Molecular mass 375.371 g/mol
  • 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=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 an extract of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis), it was traditionally thought to be a toxic substance due to jojoba seed meal causing weight loss in animals, but recently it has been researched as a potential treatment for reducing appetite of obese individuals by helping to reduce craving for food.[1] Several mechanisms of action are thought to be involved in the appetite suppressant effect.[2][3][4][5]

References

  1. ↑ United States Department of Agriculture, Agricultural Research Service. Simmondsin From Jojoba - Checked for Appetite Suppression
  2. ↑ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M. Devazepide reverses the anorexic effect of simmondsin in the rat. Journal of Endocrinology. 1995 Dec;147(3):473-7. PMID 8543917
  3. ↑ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, Kühn E, Cokelaere M. Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats. Hormone and Metabolic Research. 1998 Aug;30(8):504-8. PMID 9761380
  4. ↑ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M. The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat. Appetite. 2000 Apr;34(2):147-51. PMID 10744903
  5. ↑ Boozer CN, Herron AJ. Simmondsin for weight loss in rats. International Journal of Obesity (London). 2006 Jul;30(7):1143-8. PMID 16462820

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