A New Ergosterol Analog, a New Bis-Anthraquinone and Anti-Obesity Activity of Anthraquinones from the Marine Sponge-Associated Fungus Talaromyces stipitatus KUFA 0207

Marine Drugs
Jidapa NoinartAnake Kijjoa

Abstract

A new ergosterol analog, talarosterone (1) and a newbis-anthraquinone derivative (3) were isolated, together with ten known compounds including palmitic acid, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol-5,8-endoperoxide, cyathisterone (2), emodin (4a), questinol (4b), citreorosein (4c), fallacinol (4d), rheoemodin (4e) and secalonic acid A (5), from the ethyl acetate extract of the culture of the marine sponge-associated fungusTalaromyces stipitatusKUFA 0207. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis, and in the case of talarosterone (1), the absolute configurations of its stereogenic carbons were determined by X-ray crystallographic analysis. The structure and stereochemistry of cyathisterone (2) was also confirmed by X-ray analysis. The anthraquinones4a-eand secalonic acid A (5) were tested for their anti-obesity activity using the zebrafish Nile red assay. Only citreorosein (4c) and questinol (4b) exhibited significant anti-obesity activity, while emodin (4a) and secalonic acid A (5) caused toxicity (death) for all exposed zebrafish larvae after 24 h.

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Citations

Jan 22, 2019·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Mar 6, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kun YangHu-Ri Piao
Feb 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mei-Mei ChengGuo-Qiang Li
Jul 11, 2018·International Journal of Molecular Sciences·Fedia Ben MeftehLassaad Belbahri
Apr 20, 2019·Marine Drugs·Sara FreitasRalph Urbatzka
Apr 27, 2019·Frontiers in Microbiology·José D SantosOlga M Lage
Feb 11, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hee Jae ShinHwa-Sun Lee
Mar 9, 2021·Planta medica·Boonyanoot ChaiyosangSomdej Kanokmedhakul

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Datasets Mentioned

BETA
KU500028

Methods Mentioned

BETA
X-ray
column chromatography

Software Mentioned

OMNIC
97
ORTEP
SHELXS
SHELXL
ImageJ

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