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2020•Natural Product ResearchRequires access

Polyhydroxylated steroid derivatives from the starfish Pentaceraster regulus

Le Thi Vien, Trần Thị Hồng Hạnh, Trần Hồng Quang, Nguyễn Xuân Cường, Đỗ Thị Thảo, Nguyễn Hoài Nam, Đỗ Công Thung, Phan Văn Kiệm, Châu Văn Minh

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Abstract

A new polyhydroxysteroid glycoside, regulusoside D (1), and a new polyhydroxylated steroid, (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), together with seven known compounds were purified from the starfish Pentaceraster regulus collected near Con Co Islands, Vietnam. The structure elucidation was confirmed by extensive analysis of their NMR and HR-QTOF mass experiments. Among isolated compounds, regulusoside D (1), (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), granulatoside A (4), 5α-cholestane-3β,6β,7α,15α,16β,26-hexol (6), 5α-cholestane-3β,6β,7α,8β,15α,16β,26-heptol (7) and 5α-cholestane-3β,6α,8,15α,16β,26-hexol (8) exhibited strong inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 9.13 ± 1.17, 9.19 ± 0.77, 8.63 ± 3.31, 12.61 ± 0.51, 14.83 ± 3.02 and 10.98 ± 1.22 µM, respectively.

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What this paper is about

A new polyhydroxysteroid glycoside, regulusoside D (1), and a new polyhydroxylated steroid, (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), together with seven known compounds were purified from the starfish Pentaceraster regulus collected near Con Co Islands, Vietnam. The structure elucidation was confirmed by extensive analysis of their NMR and HR-QTOF mass experiments. Among isolated compounds, regulusoside D (1), (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), granulatoside A (4), 5α-cholestane-3β,6β,7α,15α,16β,26-hexol (6), 5α-cholestane-3β,6β,7α,8β,15α,16β,26-heptol (7) and 5α-cholestane-3β,6α,8,15α,16β,26-hexol (8) exhibited strong inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 9.13 ± 1.17, 9.19 ± 0.77, 8.63 ± 3.31, 12.61 ± 0.51, 14.83 ± 3.02 and 10.98 ± 1.22 µM, respectively.

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Available abstract

A new polyhydroxysteroid glycoside, regulusoside D (1), and a new polyhydroxylated steroid, (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), together with seven known compounds were purified from the starfish Pentaceraster regulus collected near Con Co Islands, Vietnam. The structure elucidation was confirmed by extensive analysis of their NMR and HR-QTOF mass experiments. Among isolated compounds, regulusoside D (1), (24S)-cholestane-3β,5,6β,8,15α,24-hexol (2), granulatoside A (4), 5α-cholestane-3β,6β,7α,15α,16β,26-hexol (6), 5α-cholestane-3β,6β,7α,8β,15α,16β,26-heptol (7) and 5α-cholestane-3β,6α,8,15α,16β,26-hexol (8) exhibited strong inhibitory effects on LPS-induced NO production in RAW264.7 cells with IC50 values of 9.13 ± 1.17, 9.19 ± 0.77, 8.63 ± 3.31, 12.61 ± 0.51, 14.83 ± 3.02 and 10.98 ± 1.22 µM, respectively.

Key concepts: Cholestane, Starfish, Steroid, Chemistry, Stereochemistry, Glycoside, Sterol, Biochemistry

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