New ceramides from Rantherium suaveolens

Abstract

A mixture of five new ceramides was isolated from the aerial parts of Rantherium suaveolens and characterized by spectroscopic and chemical methods. Their structures were elucidated by spectroscopic and chemical methods as (2S,3S, 4R,2'R, 14E)-2-(2'-hydroxydocosanoylamino) - 14 - octadecene -1,3,4-triol (1), (2S,3S,4R,2'R, 14E)-2-(2'-hydroxytricosanoylamino)-14-octadecene-1,3,4-triol (2), (2S,3S,4R,2'R, 14E)-2-(2'-hydroxytetracosanoylamino)- 14 - octadecene - 1,3,4 - triol (3), (2S, 3S,4R,2'R, 14E) - 2 - (2'- hydroxypentacosanoylamino) - 14 - octadecene - 1,3,4-triol (4), and (2S,3S,4R,2'R,14E)-2-(2'-hydroxyhexacosanoylamino)-14-octadecene-1,3,4-triol (5).

Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from Zephyranthes candida

“…The length of the LCB and the fatty acid (FA), together with the presence of 2-amino and 1, 2 0 , 3, 4 tetrahydroxyl groups as well as C-8, C-9 double bond were established due to EIMS and ESIMS fragment pattern analysis (Schemes 5, 6). The fragmentation pattern of compound 2 in EI mode was HN (CH 2 ) 19 Regarding the stereochemistry, the formulated relative configuration of compound 2 was based on the carbon chemical shifts at d C 61.9 (C-1), 53.1 (C-2), 76.8 (C-3), 73.3 (C-4), 174.0 (C-1 0 ), 76.3 (C-2 0 ), which happened to be fairly close to those previously reported for (2S, 3S, 4R, 2 0 R) sphingosine moieties [31][32][33]. Including biogenetic considerations, compound 2 was determined to be (2S,3S, 4R,8E,2 0 R)-2-[N-(2 0 -hydroxyoctadecanoyl)-N-(1 00 ,2 00 -dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol.…”

Another two novel ceramides from Zephyranthes candida

“…In the 1 H NMR spectrum of compound 1, however, there were no signals between the G H 8-9, which indicated a tertiary amide may be present [10]. Furthermore, the lengths of the long-chain base (LCB) and the fatty acid (FA), together with the presence of 2-amino and 1,2c,3,4-tetrahydroxyl groups, as well as the C-21 and C-22 double bonds, were established by ESI-MS fragment pattern analysis ( Regarding the stereochemistry, the formulated relative configuration of compound 1 was based on the carbon chemical shifts at G C 61.9 (C-1), 53.1 (C-2), 76.8 (C-3), 73.7 (C-4), 174.0 (C-1c), and 76.3 (C-2c), which happened to be fairly close to those previously reported for (2S, 3S, 4R, 2cR) sphingosine moieties [13,14]. Including biogenetic considerations, the structure of compound 1 was therefore concluded to be (2S,3S,4R,21E,2cR)-2-[N-(2c-hydroxynonadecanoyl)-N-(1cc,2cc-dihydroxyethyl)amino]-21-hexacosene-1,3,4-triol, and we have named compound 1 zephyranamide C.…”

Use of Bodipy-labeled sphingolipid and cholesterol analogs to examine membrane microdomains in cells

“…As noted below, alterations in the stereochemistry of the long-chain base drastically changes the biophysical and biological behavior of LacCer. Interestingly, SLs with different ( l - threo or 2S,3S) stereochemistry occur in plants, marine invertebrates, and fungi (Emura et al 2005; Gao et al 2004; Inagaki et al 2006; Ishii et al 2006; Ling et al 2006; Oueslati et al 2005; Yamada et al 2000; Zhang et al 2007). While all mammalian GSLs possess the β -anomeric linkage between the first sugar and Cer, an unusual set of α -linked GSLs from microbes and marine sponges have been found to activate natural killer T cells.…”