A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis.
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.
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Junkai
J
Wu
School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun 130021, China.
Guangshu
G
Wang
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China. Electronic address: xiaoweidu@hotmail.com.
Xiaowei
X
Du
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Ning
N
Song
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing 100193, China. Electronic address: zmzou@implad.ac.cn.
Zhongmei
Z
Zou
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Jiashuai
J
Chen
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Yu
Y
Zhang
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Tingli
T
Li
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Xijun
X
Wang
Key laboratory of Chinese Materia Medica, Ministry of Education, Pharmaceutical College, Heilongjiang University of Chinese Medicine, 24 Heping Road, Harbin 150040, China.
Haixue
H
Kuang
D000818:Animals; D018360:Crystallography, X-Ray; D004331:Drosophila melanogaster / Q000187:drug effects* / Q000502:physiology; D005260:Female; D006993:Hypnotics and Sedatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D027343:Rhizome / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054830:Sesterterpenes; D014632:Valerian / Q000737:chemistry*
D006993:Hypnotics and Sedatives; D011134:Polysaccharides; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; D054830:Sesterterpenes; C441250:caryophyllan; C000596882:caryophyllenol A
Caryophyllane; Germacrane; Sedative; Sesquiterpenoid; Valeriana amurensis