Absolute configuration of chlorosulfolipids from the chrysophyta Ochromonas danica.
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.
Kawahara
Teppei
T
Graduate School of Environmental Science, Hokkaido University, North-10, West-5, Kita-ku, Sapporo 060-0810, Japan.
Kumaki
Yasuhiro
Y
Kamada
Takashi
T
Ishii
Takahiro
T
Okino
Tatsufumi
T
D000818:Animals; D001156:Artemia / Q000187:drug effects; D008055:Lipids / Q000737:chemistry* / Q000302:isolation & purification* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D044663:Ochromonas / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D008055:Lipids; C015518:sulfolipids