Occurrence of Melibiose‐Containing Glycosphingolipids in a Sample of a Sponge‐Coral Association (Desmapsamma anchorata/Carijoa riisei). Issue 1 (17th January 2019)

• Record Type: Journal Article
• Authors: Santalova, Elena A.; Denisenko, Vladimir A.; Dmitrenok, Pavel S.; Ha, Dinh T.; Hung, Nguyen A.; Drozdov, Anatoly L.; Malyarenko, Olesya S.; Thuy, Tran T. T.; Quan, Pham M.; Long, Pham Q.
• Is Part Of: Chemistry & biodiversity. Volume 16:Issue 1(2019)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2019-01-17
• Subjects: glycolipids -- sphingolipids -- Carijoa riisei -- Desmapsamma anchorata -- sphingoid bases -- biological activity; Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201800401
• Languages: English
• ISSNs: 1612-1872

Abstract

Abstract: In our research on biologically active compounds from Vietnamese marine invertebrates, rare melibiose‐containing glycosphingolipids were found in a sample of a sponge‐coral association ( Desmapsamma anchorata / Carijoa riisei ). Melibiosylceramides were analyzed as constituents of some multi‐component RP‐HPLC fractions, and the structures of 14 new (1b, 3b, 4a –4c, 6a –6c, 8b, 9a, 9b, 10b, 11a, 11b ) and five known (2b, 5a –5c, 7b ) natural compounds were elucidated using NMR, mass spectrometry, optical rotation, and chemical transformations. These α ‐d ‐Gal p ‐(1→6)‐ β ‐d ‐Glc p ‐(1 ↔ 1)‐ceramides (presumably sponge‐derived compounds) were shown to contain phytosphingosine‐type n ‐t17:0 (1 ), (6 E )‐ n ‐t17:1 (2 ), i ‐t17:0 (3 ), n ‐t18:0 (4 ), (6 E )‐ n ‐t18:1 (5 ), i ‐t18:0 (6 ), (6 E )‐ i ‐t18:1 (7 ), i ‐t19:0 (8 ), (6 E )‐ i ‐t19:1 (9 ), ai ‐t19:0 (10 ), and (6 E )‐ ai ‐t19:1 (11 ) backbones N ‐acylated with saturated straight‐chain (2 R )‐2‐hydroxy C21 (a ), C22 (b ), and C23 (c ) acids. Characteristic trends in the fragmentations of the terminal parts of tetraacetylated normal ‐chain and iso ‐ and anteiso ‐branched sphingoid bases were observed using GC/MS. The total sum of melibiosylceramides and compound5b caused a reduction in colony formation of human melanoma cells. Abstract :