海洋硅藻中的甲藻固醇

"Dinoflagellate Sterols" in marine diatoms.

机构信息

Department of Chemistry, SUNY-ESF, Syracuse, NY 13210, USA.

出版信息

Phytochemistry. 2011 Oct;72(14-15):1896-901. doi: 10.1016/j.phytochem.2011.05.002. Epub 2011 May 31.

DOI:10.1016/j.phytochem.2011.05.002

Abstract

Sterol compositions for three diatom species, recently shown to contain sterols with side chains typically found in dinoflagellates, were determined by HPLC and ¹H NMR spectroscopic analyses. The centric diatom Triceratium dubium (=Biddulphia sp., CCMP 147) contained the highest percentage of 23-methylated sterols (37.2% (24R)-23-methylergosta-5,22-dienol), whereas the pennate diatom Delphineis sp. (CCMP 1095) contained the cyclopropyl sterol gorgosterol, as well as the 27-norsterol occelasterol. The sterol composition of Ditylum brightwellii (CCMP 358) was the most complex, containing Δ⁰- and Δ⁷-sterols, in addition to the predominant Δ⁵-sterols. A pair of previously unknown sterols, stigmasta-5,24,28-trienol and stigmasta-24,28-dienol, were detected in D. brightwellii and their structures were determined by NMR spectroscopic analysis and by synthesis of the former sterol from saringosterol. Also detected in D. brightwellii was the previously unknown 23-methylcholesta-7,22-dienol.

摘要

通过高效液相色谱和 ¹H NMR 光谱分析，确定了三种刚毛藻的甾醇组成，这些刚毛藻最近被证明含有通常在甲藻中发现的侧链甾醇。中心纲刚毛藻 Triceratium dubium（=Biddulphia sp.，CCMP 147）含有最高百分比的 23-甲基甾醇（37.2%（24R）-23-甲基麦角甾-5,22-二烯醇），而羽纹纲刚毛藻 Delphineis sp.（CCMP 1095）则含有环丙基甾醇沟鞭醇，以及 27-降甾醇 occelasterol。Ditylum brightwellii（CCMP 358）的甾醇组成最为复杂，除了主要的 Δ⁵-甾醇外，还含有 Δ⁰-和 Δ⁷-甾醇。在 D. brightwellii 中检测到一对以前未知的甾醇，即麦角甾-5,24,28-三烯醇和麦角甾-24,28-二烯醇，它们的结构通过 NMR 光谱分析和从前鲨甾醇合成前一种甾醇来确定。在 D. brightwellii 中还检测到以前未知的 23-甲基胆甾-7,22-二烯醇。