In:
Chemistry & Biodiversity, Wiley, Vol. 16, No. 1 ( 2019-01)
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.
Type of Medium:
Online Resource
ISSN:
1612-1872
,
1612-1880
DOI:
10.1002/cbdv.201800401
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
2139001-0
SSG:
12
Bookmarklink