RRC ID 20870
Author Kawahara T, Kumaki Y, Kamada T, Ishii T, Okino T.
Title Absolute configuration of chlorosulfolipids from the chrysophyta Ochromonas danica.
Journal J Org Chem
Abstract We isolated eight chlorosulfolipids (1-8) from the chrysophyta Ochromonas danica (IAM CS-2), including five new chlorosulfolipids (2-5, 8). The planar structures of all the compounds were elucidated by 1D and 2D NMR and ESI-MS/MS analyses. We determined the relative configuration of seven chlorosulfolipids (1-7), including the most commonly known chlorosulfolipid, 2,2,11,13,15,16-hexachlorodocosane-1,14-disulfate (1), by J-based configuration analysis (JBCA). The absolute configuration of each compound was determined using a modified Mosher's method after chemical degradation. 2,2,11,13,15,16-Hexachloro-14-docosanol-1-sulfate (2) was the most toxic to brine shrimp (Artemia salina) larvae (LC(50) 0.27 microg/mL). Compounds 1 and 4-8 were less toxic (LC(50) 2.2-6.9 microg/mL). Compound 3 was not toxic at 30 microg/mL.
Volume 74(16)
Pages 6016-24
Published 2009-8-21
DOI 10.1021/jo900860e
PMID 19627129
MeSH Animals Artemia / drug effects Lipids / chemistry* Lipids / isolation & purification* Lipids / toxicity Magnetic Resonance Spectroscopy Ochromonas / chemistry* Spectrometry, Mass, Electrospray Ionization
IF 4.335
Times Cited 30
Algae NIES-2142