Two New Steroidal Monoglycosides, Anthenosides A₁ and A₂, and Revision of the Structure of Known Anthenoside A with Unusual Monosaccharide Residue from the Starfish Anthenea aspera

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Timofey V MalyarenkoAlla A Kicha

Abstract

Two new polyhydroxysteroidal glycosides, anthenosides A₁ (1) and A₂ (2), and one previously known steroidal glycoside anthenoside A (3) were isolated from extract of the tropical starfish Anthenea aspera. Structures of 1⁻3 were determined by analysis of the spectroscopic data as well as chemical transformations. As a result, the structure of anthenoside A has been revised and the structures of 1 and 2 were established. Glycosides 1⁻3 contain a 2-acetamido-2-deoxy-4-O-methyl-β-d-glucopyranosyl residue, found in the starfish steroidal glycosides for the first time. All the isolated compounds slightly inhibited cell viability of human cancer T-47D cells and did not show cytotoxic effects against RPMI-7951 cells. Glycoside 1 slightly inhibited colony formation of human cancer RPMI-7951 cells by 16% while compound 2 decreased the number of colonies of T-47D cells by 40%.

References

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Citations

Jan 8, 2020·Chemistry & Biodiversity·Jin-Mei XiaXian-Wen Yang
Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Mar 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alla A KichaNatalia V Ivanchina

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Methods Mentioned

BETA
NMR
column chromatography
Assay

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