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Occurrence of Melibiose‐Containing Glycosphingolipids in a Sample of a Sponge‐Coral Association ( Desmapsamma anchorata / Carijoa riisei )
Author(s) -
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.
Publication year - 2019
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800401
Subject(s) - chemistry , coral , sponge , melibiose , association (psychology) , biochemistry , ecology , botany , biology , psychology , psychotherapist , enzyme , maltose
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 C 21 ( a ), C 22 ( b ), and C 23 ( 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 compound 5b caused a reduction in colony formation of human melanoma cells.