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

Abstract

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.

Toporosides A and B, Cyclopentenyl-Containing ω-Glycosylated Fatty Acid Amides, and Toporosides C and D from the Northwestern Pacific Marine Sponge Stelodoryx toporoki

“…Its spectroscopic properties were similar to those of melonoside A, 6 The positions of the keto groups and the double bonds in the alkyl chain were confirmed when 3 was subjected to ozonolysis in MeOH at −70 °C. Analysis of the obtained degradation products (5,6) by HRESIMS and NMR spectra of 3 confirmed the double-bond positions at C-5 and C-19 and the carbonyl groups at C-11 and C-16 in 3 (Scheme 1). In comparison melonoside A contains double bonds at C-5 and C-21 and the carbonyl groups at C-11 and C-18.…”

“…3 Cyclopentenyl fatty acids can also be formed as artifacts from conventional unsaturated fatty acids during food processing. 4 In the course of our continuing search for bioactive marine natural products, 5 we have found two unusual ω-glycosylated fatty acid amides containing a cyclopentenyl α,β-unsaturated carbonyl moiety in the polymethylene chain in the chemically unstudied sponge Stelodoryx toporoki. Herein we report the structures and biological activities of four new ω-Oglycosylated polyoxygenated fatty acid amides, toporosides A−D (1−4).…”

Marine natural products

“…1 Two long chain fatty acid butenolides 967 and 968 were obtained from a Chinese specimen of Hippospongia , 411 while a new sphingoid glycoside 969 was reported from a dredged Oceanapia . 412 A dredged Cladocroce sp. (245 m, Japan) was the source of sphingosine calyxoside B 970 .…”

Catecholamine Derivatives: Natural Occurrence, Structural Diversity, and Biological Activity

“…In 2016, two unique N -acetyl dopamine glycolipids, myxillins A and B ( 215 and 216 ), were isolated from the sponge Myxilla incrustans Johnston . More recently, the rare sphingoid tetrahydoisoquinoline galactoside, oceanalin B ( 217 ), was isolated from the marine sponge Oceanapia sp …”