Anticancer activities of polyynes from the root bark of Oplopanax horridus and their acetylated derivatives.
Six polyynes OH-1~6, some of which are occur naturally in acetylated form, had been isolated and identified from the root bark of Oplopanax horridus (Devil's Club), a natural dietary supplement and medicinal plant in North America. During the evaluation of the polyynes' potential anticancer activities, sixteen more acetylated derivatives OHR-1~16 have synthesized and their anti-proliferation activity on MCF-7, MDA-MB-231, A549, HepG2 and LO2 cells assayed to elucidate their structure-activity relationships. The results showed that OH-1 ((3S, 8S)-falcarindiol) had the most potent anticancer activity, with IC50 values of 15.3, 23.5, 7.7 and 4.7 μM on MCF-7, A549, HepG2 and MDA-MB-231 cells, respectively. For the primary structure-activity relationship, the anticancer activities of polyynes become weaker if their hydroxyl groups are acetylated, the terminal double bonds transformed into single bonds or they contain one more methylene group in the main skeleton chain.
Department of Clinical Pharmacology, Xiangya Hospital, Central South University, Changsha, Hunan 410008, China. endeavor34852@aliyun.com.
Wei-Hua
WH
Huang
School of Pharmacy, Hunan University of Chinese Medicine, Changsha, Hunan 410128, China. shaoli82@aliyun.com.
Li
L
Shao
Tang Center for Herbal Medicine Research, The Pritzker School of Medicine, University of Chicago, 5841 South Maryland Avenue, MC 4028, Chicago, IL 60637, USA. CWang@dacc.uchicago.edu.
Chong-Zhi
CZ
Wang
Tang Center for Herbal Medicine Research, The Pritzker School of Medicine, University of Chicago, 5841 South Maryland Avenue, MC 4028, Chicago, IL 60637, USA. CYuan@dacc.uchicago.edu.
Chun-Su
CS
Yuan
Department of Clinical Pharmacology, Xiangya Hospital, Central South University, Changsha, Hunan 410008, China. hhzhou2003@163.com.
Hong-Hao
HH
Zhou
D000107:Acetylation / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy*; D009656:North America; D028002:Oplopanax / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000008:administration & dosage* / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D053279:Polyynes / Q000008:administration & dosage* / Q000737:chemistry / Q000302:isolation & purification; D013329:Structure-Activity Relationship
D010936:Plant Extracts; D053279:Polyynes