一种石竹烯型倍半萜，来自黑水缬草的石竹烯醇A。

A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis.

作者信息

Wu Junkai, Wang Guangshu, Du Xiaowei, Song Ning, Zou Zhongmei, Chen Jiashuai, Zhang Yu, Li Tingli, Wang Xijun, Kuang Haixue

机构信息

Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.

School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun 130021, China.

出版信息

Fitoterapia. 2014 Jul;96:18-24. doi: 10.1016/j.fitote.2014.03.025. Epub 2014 Apr 4.

DOI:10.1016/j.fitote.2014.03.025

PMID:24704552

Abstract

A new caryophyllane derivative, caryophyllenol A, and a new germacrane derivative, isovolvalerenal D, together with 11 known sesquiterpenoids, were isolated from a petroleum ether partition of the roots and rhizomes of Valeriana amurensis. Structure elucidation of caryophyllenol A and isovolvalerenal D was accomplished on the basis of various spectroscopic techniques including HRESIMS and 2D NMR analyses. The structure of caryophyllenol A was further confirmed by X-ray crystallography and using quantum-chemical ECD calculation adopting TDDFT method. Caryophyllenol A and other eight sesquiterpenoids were evaluated for sedative activity with the model of Drosophila melanogaster, and eight of them showed the effect of prolonging the total sleeping time (TST) of D. melanogaster, displaying significant sedative action.

摘要

从黑水缬草的根和根茎的石油醚提取物中分离出一种新的石竹烷衍生物——石竹烯醇A和一种新的吉马烷衍生物——异缬草烯醛D，以及11种已知的倍半萜类化合物。通过包括高分辨电喷雾电离质谱（HRESIMS）和二维核磁共振（2D NMR）分析在内的各种光谱技术对石竹烯醇A和异缬草烯醛D进行了结构解析。石竹烯醇A的结构通过X射线晶体学进一步确证，并采用含时密度泛函理论（TDDFT）方法进行量子化学电子圆二色谱（ECD）计算。以黑腹果蝇为模型对石竹烯醇A和其他8种倍半萜类化合物进行了镇静活性评价，其中8种化合物表现出延长黑腹果蝇总睡眠时间（TST）的作用，显示出显著的镇静作用。