14,15-Didehydrohellebrigenin

Tong Yu,Xiao-Feng Yuan,Hai-Yan Tian,Ren-Wang Jiang,Shu-Zhi Hu

doi:10.1107/s1600536812018570

Tong Yu, Xiao-Feng Yuan + Show 3 more

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https://doi.org/10.1107/s1600536812018570

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Abstract

The title compound, C24H30O5, is the didehydro product of the steroid hellebrigenin (systematic name: 3β,5,14-trihydroxy-19-oxo-5β-bufa-20,22-dienolide). It consists of three cyclohexane rings (A, B and C), a five-membered ring (D) and a six-membered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclohexane rings A, B and C have normal chair conformations. The five-membered ring D with the C=C bond adopts an envelope conformation. Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is β-oriented at the C atom of ring D to which it is attached. There is an O—H⋯O hydrogen bond in the molecule involving the hydroxy groups. In the crystal, O—H⋯O hydrogen bonds link the molecules into chains propagating along [010]. The chains are linked by C—H⋯O contacts into a three-dimensional network.

Highlights

Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Institute of Traditional
The title compound, C24H30O5, is the didehydro product of the steroid hellebrigenin. It consists of three cyclohexane rings (A, B and C), a five-membered ring (D) and a sixmembered lactone ring (E)
Lactone ring E is essentially planar with a mean derivation of 0.006 (4) Å and is -oriented at the C atom of ring D to which it is attached

Summary

Structure Reports

Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People’s Republic of China. The title compound, C24H30O5, is the didehydro product of the steroid hellebrigenin (systematic name: 3,5,14-trihydroxy-19oxo-5-bufa-20,22-dienolide). It consists of three cyclohexane rings (A, B and C), a five-membered ring (D) and a sixmembered lactone ring (E). The stereochemistry of the ring junctions are A/B cis, B/C trans and C/D cis. Cyclohexane rings A, B and C have normal chair conformations. The fivemembered ring D with the C C bond adopts an envelope conformation. There is an O—H O hydrogen bond in the molecule involving the hydroxy groups. O—H O hydrogen bonds link the molecules into chains propagating along [010].

CCD diffractometer

This work was supported by a grant from the National

Graphite monochromator ω scan

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