来自泡叶楠的奥科布勒酮三种非对映异构体的立体结构与抗炎活性

Stereostructure and anti-inflammatory activity of three diastereomers of ocobullenone from Ocotea bullata.

作者信息

Zschocke S, van Staden J, Paulus K, Bauer R, Horn M M, Munro O Q, Brown N J, Drewes S E

机构信息

Research Centre for Plant Growth and Development, School of Botany and Zoology, University of Natal Pietermaritzburg, Scottsville, South Africa.

出版信息

Phytochemistry. 2000 Jul;54(6):591-5. doi: 10.1016/s0031-9422(00)00163-1.

DOI:10.1016/s0031-9422(00)00163-1

PMID:10963452

Abstract

A novel diastereomer of ocobullenone. designated as sibyllenone, was isolated from the stem bark of mature Ocotea bullata in the course of a search for anti-inflammatory compounds from this plant. The stereostructure was established by X-ray crystallography and corroborated by NOESY analysis. Ocobullenone, obtained previously, was re-isolated and crystallised successfully for X-ray analysis, thus making possible an accurate spatial comparison of ocobullenone, iso-ocobullenone and the new stereoisomer. Tested pharmacologically for cyclooxygenase-1 and 2, and 5-lipoxygenase inhibition, sibyllenone was the only compound from O. bullata which showed good inhibitory activity towards 5-lipoxygenase.

摘要

一种新的奥科布勒酮非对映异构体，命名为西碧勒酮，是在从成熟的奥科特亚·布拉塔树的茎皮中寻找抗炎化合物的过程中分离得到的。其立体结构通过X射线晶体学确定，并经NOESY分析证实。之前获得的奥科布勒酮被重新分离并成功结晶用于X射线分析，从而能够对奥科布勒酮、异奥科布勒酮和新的立体异构体进行精确的空间比较。在对环氧化酶-1和-2以及5-脂氧合酶抑制进行药理测试时，西碧勒酮是来自奥科特亚·布拉塔树的唯一对5-脂氧合酶显示出良好抑制活性的化合物。