Cadinane sesquiterpenes from Curcuma phaeocaulis with their inhibitory activities on nitric oxide production in RAW 264.7 cells

Jianghao Ma; Ying Wang; Yue Liu; Suyu Gao; Liqin Ding; Feng Zhao; Lixia Chen; Feng Qiu

doi:10.1016/j.fitote.2015.03.020

Cadinane sesquiterpenes from Curcuma phaeocaulis with their inhibitory activities on nitric oxide production in RAW 264.7 cells

Fitoterapia. 2015 Jun:103:90-6. doi: 10.1016/j.fitote.2015.03.020. Epub 2015 Mar 24.

Authors

Jianghao Ma¹, Ying Wang¹, Yue Liu¹, Suyu Gao¹, Liqin Ding², Feng Zhao³, Lixia Chen⁴, Feng Qiu⁵

Affiliations

¹ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
² Tianjin State Key Laboratory of Modern Chinese Medicine, School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China.
³ School of Pharmacy, Yantai University, Yantai 264005, People's Republic of China.
⁴ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China. Electronic address: syzyclx@163.com.
⁵ Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China; Tianjin State Key Laboratory of Modern Chinese Medicine, School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China. Electronic address: fengqiu20070118@163.com.

PMID: 25819006
DOI: 10.1016/j.fitote.2015.03.020

Abstract

Four new cadinane-type sesquiterpenes named phacadinanes A-D (1-4) were isolated from the rhizomes of Curcuma phaeocaulis. Their structures were elucidated by 1D and 2D NMR, as well as accurate mass measurements. Compound 4 was the first example of a rare 4,5-seco-cadinane sesquiterpene isolated from the Zingiberaceae family. Furthermore, inhibitory effects of the isolated compounds on nitric oxide production in LPS-activated macrophages were evaluated. Compounds 1 and 2 showed strong inhibitory activities on NO production with IC50 values of 3.88±0.58 and 2.25±0.71 μM, respectively. A possible biogenetic pathway for 4,5-seco-cadinane sesquiterpene (4) was postulated.

Keywords: Biogenetic pathway; Cadinane; Curcuma phaeocaulis; Nitric oxide; Sesquiterpenes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Line
Curcuma / chemistry*
Macrophages / drug effects*
Mice
Molecular Structure
Nitric Oxide / metabolism*
Polycyclic Sesquiterpenes
Rhizome / chemistry
Sesquiterpenes / pharmacology*

Substances

Polycyclic Sesquiterpenes
Sesquiterpenes
cadinane
Nitric Oxide