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.

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%.

• Authors: Timofey V Malyarenko, Natalia V Ivanchina, Olesya S Malyarenko, Anatoly I Kalinovsky, Pavel S Dmitrenok, Evgeny V Evtushenko, Chau Van Minh, Alla A Kicha
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 23 Issue 5 (05 03 2018) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 29751557 (Publication Type: Journal Article)

Chemical References

• Glycosides
• Monosaccharides
• Steroids

Topics

• Animals
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cell Survival (drug effects)
• Glycosides (chemistry)
• Humans
• Hydrolysis
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Monosaccharides (chemistry)
• Starfish (chemistry)
• Steroids (chemistry)