Diterpenoid constituents of Euphorbia macrorrhiza

Jie Gao; Qi-Bin Chen; Yong-Qiang Liu; Xue-Lei Xin; Ablimiti Yili; Haji Akber Aisa

doi:10.1016/j.phytochem.2015.12.003

Diterpenoid constituents of Euphorbia macrorrhiza

Phytochemistry. 2016 Feb:122:246-253. doi: 10.1016/j.phytochem.2015.12.003. Epub 2015 Dec 17.

Authors

Jie Gao¹, Qi-Bin Chen¹, Yong-Qiang Liu², Xue-Lei Xin², Ablimiti Yili², Haji Akber Aisa³

Affiliations

¹ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China; University of Chinese Academy of Sciences, Beijing 100039, PR China.
² The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China.
³ The Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China; State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China. Electronic address: haji@ms.xjb.ac.cn.

PMID: 26706317
DOI: 10.1016/j.phytochem.2015.12.003

Abstract

Ten diterpenoids, named macrorilone A-B, macroripremyrsinone A, macrorilathyrone A-B, macrorieuphorone A-B and macroricasbalone A-C, together with ten known diterpenoids, jatrophalone, sikkimenoids A-D, jatrophodione A, latilagascenes F, jolkinol B, 15β-O-benzoyl-5α-hydroxyisolathyrol and jatrophalactone were isolated from the whole plant of Euphorbia macrorrhiza C.A. Mey. These diterpenoids belong to six skeleton-types, including jatropholane, premyrsinane, lathyrane, euphoractin, casbene and rhamnofolane diterpenoids. Their structures were elucidated by extensive analysis of 1D, 2D NMR and HRESIMS spectroscopic data. The absolute configurations of macrorilone B, macroripremyrsinone A and macrorilathyrone A were established by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Several of the isolated compounds exhibited weak cytotoxicity against the KB and KBv200 cell lines with IC50 values ranging from 21.19 to 47.87μM. Some also showed multidrug resistance (MDR) reversal activity, among which macrorilathyrone B exhibited a remarkable inhibitory effect on P-gp-mediated drug exclusion.

Keywords: Cytotoxicity; Diterpenoids; Euphorbia macrorrhiza C.A. Mey; Euphorbiaceae; Multidrug resistance reversal activity.

Publication types

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

MeSH terms

ATP Binding Cassette Transporter, Subfamily B, Member 1 / drug effects
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Diterpenes / chemistry
Diterpenes / isolation & purification*
Diterpenes / pharmacology
Drug Resistance, Multiple / drug effects
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification*
Drugs, Chinese Herbal / pharmacology
Euphorbia / chemistry*
Inhibitory Concentration 50
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots / chemistry

Substances

ATP Binding Cassette Transporter, Subfamily B, Member 1
Antineoplastic Agents, Phytogenic
Diterpenes
Drugs, Chinese Herbal
lathyrane
latilagascene F
jolkinol B