Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
Tatyana N. Makarieva,
Natalia V. Ivanchina,
Pavel S. Dmitrenok,
Alla G. Guzii,
Valentin A. Stonik,
Doralyn S. Dalisay,
Tadeusz F. Molinski
Affiliations
Tatyana N. Makarieva
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
Natalia V. Ivanchina
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
Pavel S. Dmitrenok
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
Alla G. Guzii
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
Valentin A. Stonik
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
Doralyn S. Dalisay
Department of Chemistry and Biochemistry/SSPPS, University of California, San Diego, CA 92093-0358, USA
Tadeusz F. Molinski
Department of Chemistry and Biochemistry/SSPPS, University of California, San Diego, CA 92093-0358, USA
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.
