Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge Oceanapia sp.

Marine Drugs

Tadeusz F. Molinski¹  Doralyn S. Dalisay¹  Alla G. Guzii²  Pavel S. Dmitrenok²  Tatyana N. Makarieva²  Valentin A. Stonik²  Natalia V. Ivanchina² 

[1] Department of Chemistry and Biochemistry/SSPPS, University of California, San Diego, CA 92093-0358, USA;G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, Russia;

关键词: Oceanapia sp.;    marine sponge;    oceanalin B;    bipolar sphingolipids;    tetrahydroisoquinoline;    glycoside;   

DOI  :  10.3390/md19110635

来源: DOAJ

【 摘 要 】

Oceanalin B (1), an α,ω-bipolar natural product belonging to a rare family of sphingoid tetrahydoisoquinoline β-glycosides, was isolated from the EtOH extract of the lyophilized marine sponge Oceanapia sp. as the second member of the series after oceanalin A (2) from the same animal. The compounds are of particular interest due to their biogenetically unexpected structures as well as their biological activities. The structure and absolute stereochemistry of 1 as a α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside was elucidated using NMR, CD and MS spectral analysis and chemical degradation. Oceanalin B exhibited in vitro antifungal activity against Candidaglabrata with a MIC of 25 μg/mL.

【 授权许可】

Unknown