Temnosides A and B, Two New Glycosphingolipids from the Sea Urchin Temnopleurus toreumaticus of the Indian Coast

Abstract

Two new glycosphingolipids, temnosides A (1) and B (2), have been isolated from a MeOH extract of the sea urchin Temnopleurus toreumaticus. The proposed structures 1-O-(β-d-glucopyranosyl)-d-(+)-(2S,3R)-2-[(2‘(R)-hydroxytricosanoyl]amido]-1,3-eicosanediol (1) and 1-O-(β-d-glucopyranosyl)-d-(+)-(2S,3R)-2-(docosanoylamido)-1,3-eicosanediol (2) were established by FABMS, 2D NMR, and chemical degradation studies.

New Cytotoxic Secondary Metabolites from Marine Bryozoan Cryptosula pallasiana

“…The resulting CCl 4 portion was separated by column chromatography (CC) and high-performance liquid chromatography (HPLC) to afford a new sterol ( 1 ) and two new ceramides ( 6 and 7 ), along with six known compounds ( 2 – 5 , 8 and 9 ) ( Figure 1 ). The known compounds were identified as cholest-5-en-3β-ol ( 2 ) [ 7 ], (22 E )-cholesta-7,22-dien-3β,5α,6β-triol ( 3 ) [ 8 ], (24 S ,22 E )-methylcholesta-7,22-dien-3β,5α,6β-triol ( 4 ) [ 8 ], loliolide ( 5 ) [ 9 ], (2 S ,3 R ,4 E )-2-(tetradecanoylamino)-4-octadecen-l,3-diol ( 8 ) [ 10 ] and (2 S ,3 R ,4 E ,8 E )-2-(hexadecanoylamino)-4,8-octadecadien-l,3-diol ( 9 ) [ 11 ], respectively, by comparison of their spectroscopic data (see supplementary information ) with those reported in the literature.…”

Glycolipids from Marine Invertebrates

“…Ceramides of the Dihydrosphingosine Type Two series of new b-glucocerebrosides, temnosides, were identified in lipid extracts of the sea urchin Temnopleurus toreumaticus, collected from the India coasts (Babu, Bhandari, and Garg, 1997) (Table 5.3).…”

Astonishing diversity of natural surfactants: 4. Fatty acid amide glycosides, their analogs and derivatives

“…Another sponge species, Agelas mauritianus, from Okinawa Island contained a series of glycosphingolipids termed agelasphins: AGL-10 111 and AGL-12 112 (two major components), AGL-7A 113, AGL-7B (mixture), AGL-9A 114, AGL-9B 115, AGL-11 116, and AGL-13 117 (113). Three glycosphingolipids, regulosides A-C 118-120, were obtained from extracts of the starfish Pentaceraster regulus (114), and two related compounds, temnosides A 121 and B 122, were isolated from the sea urchin Temnopleurus toreumaticus; both specimens were collected from the Mandapam coast of India (115).…”