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

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 (&l...

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Autores principales:	Tatyana N. Makarieva, Natalia V. Ivanchina, Pavel S. Dmitrenok, Alla G. Guzii, Valentin A. Stonik, Doralyn S. Dalisay, Tadeusz F. Molinski
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Oceanapia</i> sp. marine sponge oceanalin B bipolar sphingolipids tetrahydroisoquinoline glycoside Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/d3086b6f6eec4f80aa73bd3c04bba392
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spelling	oai:doaj.org-article:d3086b6f6eec4f80aa73bd3c04bba3922021-11-25T18:12:58ZOceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.10.3390/md191106351660-3397https://doaj.org/article/d3086b6f6eec4f80aa73bd3c04bba3922021-11-01T00:00:00Zhttps://www.mdpi.com/1660-3397/19/11/635https://doaj.org/toc/1660-3397Oceanalin B (<b>1</b>), 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 <i>Oceanapia</i> sp. as the second member of the series after oceanalin A (<b>2</b>) 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 <b>1</b> 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 <i>Candida</i><i>glabrata</i> with a MIC of 25 μg/mL.Tatyana N. MakarievaNatalia V. IvanchinaPavel S. DmitrenokAlla G. GuziiValentin A. StonikDoralyn S. DalisayTadeusz F. MolinskiMDPI AGarticle<i>Oceanapia</i> sp.marine spongeoceanalin Bbipolar sphingolipidstetrahydroisoquinolineglycosideBiology (General)QH301-705.5ENMarine Drugs, Vol 19, Iss 635, p 635 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Oceanapia</i> sp. marine sponge oceanalin B bipolar sphingolipids tetrahydroisoquinoline glycoside Biology (General) QH301-705.5
spellingShingle	<i>Oceanapia</i> sp. marine sponge oceanalin B bipolar sphingolipids tetrahydroisoquinoline glycoside Biology (General) QH301-705.5 Tatyana N. Makarieva Natalia V. Ivanchina Pavel S. Dmitrenok Alla G. Guzii Valentin A. Stonik Doralyn S. Dalisay Tadeusz F. Molinski Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
description	Oceanalin B (<b>1</b>), 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 <i>Oceanapia</i> sp. as the second member of the series after oceanalin A (<b>2</b>) 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 <b>1</b> 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 <i>Candida</i><i>glabrata</i> with a MIC of 25 μg/mL.
format	article
author	Tatyana N. Makarieva Natalia V. Ivanchina Pavel S. Dmitrenok Alla G. Guzii Valentin A. Stonik Doralyn S. Dalisay Tadeusz F. Molinski
author_facet	Tatyana N. Makarieva Natalia V. Ivanchina Pavel S. Dmitrenok Alla G. Guzii Valentin A. Stonik Doralyn S. Dalisay Tadeusz F. Molinski
author_sort	Tatyana N. Makarieva
title	Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
title_short	Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
title_full	Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
title_fullStr	Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
title_full_unstemmed	Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.
title_sort	oceanalin b, a hybrid α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge <i>oceanapia</i> sp.
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/d3086b6f6eec4f80aa73bd3c04bba392
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Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge <i>Oceanapia</i> sp.

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