Bryoamaride

Bryoamaride

IUPAC name (9R,10R,13R,14S,16R,17R)-17-(1,5-Dihydroxy-1,5-dimethyl-2-oxo-hexyl)-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Other names Cucurbitacin L 2-O-β-D-glucopyranoside
Identifiers
CAS number	61105-51-9^Y
PubChem	44584115
ChemSpider	23264945^Y
Jmol-3D images	Image 1
SMILES 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
InChI 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
Properties
Molecular formula	C₃₆H₅₄O₁₂
Molar mass	678.81 g mol⁻¹
Exact mass	678.361527192 g mol^-1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bryoamaride is a chemical compound isolated from certain plants, notably Bryonia dioica. It can be seen as a derivative of the triterpene hydrocarbon cucurbitane (C₃₀H₅₄), more specifically from cucurbitacin L or 23,24-dihydrocucurbitacin I.^[1]^:65

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

References

^ ^a ^b 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