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2019•Journal of Natural ProductsRequires access

Cytotoxic Pregnane Steroidal Glycosides from Chonemorpha megacalyx

Fang-Yu Yuan, Wang Xiao-ling, Wang Xiao-ling, Tian Wang, Tao Shen, Dong‐Mei Ren, Hong‐Xiang Lou, Xiao‐Ning Wang, Xiao‐Ning Wang

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Abstract

Three new C 21 pregnane steroids, chonemorphols A–C ( 1, 3, and 4 ), 11 new C 21 steroidal glycosides, chonemorphosides A–K ( 2 and 5 – 14 ), and 11 known compounds ( 15 – 25 ) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC 50 values of 2.0–3.6 μM.

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What this paper is about

Three new C 21 pregnane steroids, chonemorphols A–C ( 1, 3, and 4 ), 11 new C 21 steroidal glycosides, chonemorphosides A–K ( 2 and 5 – 14 ), and 11 known compounds ( 15 – 25 ) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC 50 values of 2.0–3.6 μM.

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Available abstract

Three new C 21 pregnane steroids, chonemorphols A–C ( 1, 3, and 4 ), 11 new C 21 steroidal glycosides, chonemorphosides A–K ( 2 and 5 – 14 ), and 11 known compounds ( 15 – 25 ) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC 50 values of 2.0–3.6 μM.

Key concepts: Pregnane, Glycoside, Stereochemistry, Chemistry, Biology, Traditional medicine, Medicine

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