P-43 黄金色藻Ochromonas danicaから得られるクロロスルフォリピッド類の立体化学(ポスター発表の部)
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概要
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Chlorosulfolipids (CSLs) are unusual naturally occurring compounds, which were first isolated at the end of the 1960s from freshwater microalgae such as Chrysophyceae Ochromonas danica and Poterioochromonas malhamensis. They constitute 15% of total lipids. The preparation of the CSLs in sufficient purity for structural characterization has proven to be difficult because the polar lipids were extremely hydroscopic and viscously. Therefore, any bioassays have not taken in nature form and structural elucidation was not satisfied with stereochemical analysis. Herein, we report successful isolation and determination of relative and absolute configuration of eight chlorosulfolipids. The Chrysophyta O. danica (IAM CS-2) was cultured at 25℃ for 1 week in a medium containing 0.1% glucose, 0.1% tryptone, 0.1% yeast extract and 0.05% meat extract with aeration. The cells were collected by continuous centrifugation, and freeze dried. The freeze-dried cells were homogenized and extracted with 1L of MeOH (three times) and 1L of EtOAc. The combined extracts were evaporated in vacuo and sequentially extracted with hexane, CHCl_3, EtOAc, BuOH and water. The active fractions (EtOAc, BuOH) of brineshrimp assay were applied repeatedly to silica gel and flash ODS column chromatography. Finally reverse phase-HPLC using a C_<30> column and an ELSD detector yielded four known CSLs (1,6-8) and four new compounds (2-5). Compound 1 was a major component of CSL from O. danica. Planar structure of 1 was established by HR-ESI-MS, 1D, 2D NMR and ESI-MS/MS. By using the JBCA method, relative configurations of 1 were determined by measuring ^<23>_J_<C,H> from HETLOC and J-IMPEACH-MBC spectrum. The absolute configuration was determined by modified Mosher's method after the sulfatide was hydrolyzed. In conclusion, 1 was identified as 2,2,11,13,15,16-hexachlorodocosane 1,14-disulfate. In the same manner, structures of 2-8 (2: 2,2,11,13,15,16-hexachloro-14-docosanol 1-sulfate, 3: 2,2,11,13,15,16-hexachlorodocosane 1,14-diol, 4: 11,13,15,16-tetrachlorodocosane 1,14-disulfate, 5: 11,13,15-tri-chlorodocosane 1,14-disulfate, 6: 13-chlorodocosane 1,14-disulfate, 7: docosane 1,14-disulfate, 8: 14-chlorotetracosane 1,15-disulfate) were determined.
- 2008-09-01
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