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New 9?-Hydroxy-5?,6?-epoxyhydroxysterols from the Vietnamese Marine Sponge Ircinia echinata.

ABSTRACT: Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9?-hydroxy-5?,6?-epoxysterols: 5?,6?-epoxycholesta-7,22(E)-dien-3?,9?-diol (1), 5?,6?-epoxycholesta-7,24(28)-dien-3?,9?-diol (2), (24R)-5?,6?-epoxy-24-ethyl-cholesta-7-en-3?,9?-diol (3), 5?,6?-epoxycholesta-7-en-3?,9?-diol (4), (24S)-5?,6?-epoxyergosta-7,22-dien-3?,9?-diol (5), and (24R)-5?,6?-epoxy-24-methyl-cholesta-7-en-3?,9?-diol (6) along with the known 5?-6?-epoxysterols: 5?,6?-epoxystigmasta-7-en-3?-ol (7), 5?,6?-epoxystigmasta-7,22-dien-3?-ol (8), and 5?,6?-epoxyergosta-7-en-3?-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells.

SUBMITTER: Trinh TTV 

PROVIDER: S-EPMC6267468 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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New 9α-Hydroxy-5α,6α-epoxyhydroxysterols from the Vietnamese Marine Sponge <i>Ircinia echinata</i>.

Trinh Thi Thanh Van TTV   Truong Bich Ngan BN   Longeon Arlette A   Doan Thi Mai Huong TMH   Doan Thi Mai Huong TMH   Deville Alexandre A   Chau Van Minh VM   Pham Van Cuong VC   Bourguet-Kondracki Marie-Lise ML  

Marine drugs 20181101 11

Chemical investigation of the methanol extract of the Vietnamese marine sponge <i>Ircinia echinata</i> led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(<i>E</i>)-dien-3β,9α-diol (<b>1</b>), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (<b>2</b>), (24<i>R</i>)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (<b>3</b>), 5α,6α-epoxycholesta-7-en-3β,9α-diol (<b>4</b>), (24<i>S</i>)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (<b>5</b>), and (24<i>R</i>)-5α,6α-epoxy-2  ...[more]

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