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 4.745
Times Cited 24
Algae NIES-2142