Bryoamaride

Bryoamaride is a chemical compound isolated from certain plants, notably Bryonia dioica. It can be seen as a derivative of the triterpene hydrocarbon cucurbitane (C
30H
54), more specifically from cucurbitacin L or 23,24-dihydrocucurbitacin I.[1]: 65 

Bryoamaride
Names
IUPAC name
2-(β-D-Glucopyranosyloxy)-16,20,25-trihydroxy-9-methyl-19-nor-9β,10α-lanosta-1,5-diene-3,11,22-trione
Preferred IUPAC name
(1R,2R,3aS,3bS,9aR,9bR,11aR)-1-[(2R)-2,6-Dihydroxy-6-methyl-3-oxoheptan-2-yl]-2-hydroxy-3a,6,6,9b,11a-pentamethyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3,3a,3b,4,6,9a,9b,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-7,10-dione
Other names
Cucurbitacin L 2-O-β-D-glucopyranoside
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C36H54O12/c1-31(2,45)12-11-23(39)36(8,46)28-19(38)14-33(5)22-10-9-17-18(35(22,7)24(40)15-34(28,33)6)13-20(29(44)32(17,3)4)47-30-27(43)26(42)25(41)21(16-37)48-30/h9,13,18-19,21-22,25-28,30,37-38,41-43,45-46H,10-12,14-16H2,1-8H3/t18-,19-,21-,22+,25-,26+,27-,28+,30-,33+,34-,35+,36+/m1/s1 Y
    Key: QCAZYVAEXLGYLV-HPCBBFKLSA-N Y
  • C[C@@]12C[C@H]([C@@H]([C@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)[C@](C)(C(=O)CCC(C)(C)O)O)O
Properties
C36H54O12
Molar mass 678.816 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

The derivative 25-O-acetylbryoamaride is found in Trichosanthes tricuspidata.[1]: 66 

References
  1. Jian Chao Chen, Ming Hua Chiu, Rui Lin Nie, Geoffrey A. Cordell and Samuel X. Qiu (2005), "Cucurbitacins and cucurbitane glycosides: structures and biological activities" Natural Product Reports, volume 22, pages 386-399 doi:10.1039/B418841C
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