9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

Steroids
Jun ZhangShi-Hai Xu

Abstract

Nine new 9,11-secosterols (1-9), containing the same 3β,6α,11-trihydroxy-9,11-seco-5α-cholest-7-en-9-one steroidal nucleus, whereas possessing an array of structurally diverse side chains, along with fourteen known 9,11-secosterol compounds (10-23), were isolated from the South China Sea gorgonian coral Subergorgia suberosa, of which 3/4, 5/6, 7/8, and the known compounds 11/12, 20/21 were five pairs of inseparable C-24 epimers. Their structures were established by the extensive analyses of 1D and 2D NMR spectra, high-resolution chemical ionization mass spectrometry (HRCIMS), and by the comparison with literature data. Cytotoxic effect of these metabolites against the growth of HeLa cell lines was evaluated. The result showed that the inhibitory effect of compounds 1-23 varied considerably depending on the nature of the side chain in spite of sharing the same steroidal nucleus. Compound 19, featuring both the absence of hydroxyl group and the presence of double bond in the stigmasterol side chain, exhibited the most potent cytotoxicity with IC50 being 15.1 μM. The preliminary structure activity relationship studies identified some important structural features considerably influencing the biological effect deserved, providing v...Continue Reading

References

Feb 9, 2002·Natural Product Letters·R JäälaidU Lille
Dec 8, 2004·Steroids·Donato Sica, Domenica Musumeci
Sep 25, 2007·Steroids·María F Rodríguez BrascoJorge A Palermo
May 27, 2009·Bioorganic & Medicinal Chemistry·Efstathia IoannouVassilios Roussis
Mar 25, 2011·Organic & Biomolecular Chemistry·Bo-Wei ChenJyh-Horng Sheu
Jun 8, 2012·Bioorganic & Medicinal Chemistry Letters·Chiung-Yao HuangJyh-Horng Sheu
Aug 30, 2013·Marine Drugs·Yen-Ju TsengChang-Yih Duh

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Citations

Jun 1, 2016·Natural Product Research·Mu-Wu Xu, Yuan-Tao Hao
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dario MatuljaDean Marković
Oct 7, 2020·Natural Product Research·Mohamed ShaabanMaha M Soltan

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