Cytotoxic scalarane sesterterpenoids from the South China Sea sponge Carteriospongia foliascens

Organic & Biomolecular Chemistry
Fei CaoChang-Yun Wang

Abstract

Eleven new scalarane sesterterpenoids, including three 20,24-bishomo-25-norscalaranes, carteriofenones A–C (1–3), and eight 20,24-bishomoscalaranes, carteriofenones D–K (4–11), along with two known analogues (12 and 13), were obtained from the marine sponge Carteriospongia foliascens collected from the South China Sea. Their planar structures and relative configurations were elucidated by extensive NMR spectroscopic data. The absolute configuration of 3 was determined using the modified Mosher's method on its hydrolysis product. Scalarane sesterterpenoids with 4-methylpentanate or pentanoate substituents at the 12-position (1–8) were reported for the first time. Carteriofenones E–H (5–8) represented rare naturally occurring scalarane sesterterpenoids with a cyclobutane ring. Compound 4 showed cytotoxicity against the mouse lymphocytic leukemia cell line (P388) with an IC50 value of 0.96 μM.

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Citations

Jan 10, 2017·Marine Drugs·Huawei ZhangPhillip Crews
Nov 16, 2019·Magnetic Resonance in Chemistry : MRC·Xiao-Lu LiYue-Wei Guo
Mar 16, 2017·Natural Product Reports·John W BluntMichèle R Prinsep
Apr 5, 2018·Frontiers in Chemistry·Haishan LiuWeiming Zhu
Dec 23, 2020·Natural Product Reports·Keke Li, Kirk R Gustafson
Jul 3, 2021·Marine Drugs·Valery M DembitskyVladimir V Poroikov

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