title: Terpecurcumins A-I from the rhizomes of Curcuma longa: absolute configuration and cytotoxic activity.
abstract: Terpecurcumins A-I (1-9), together with three known analogues (10-12), were isolated from the rhizomes of Curcuma longa (turmeric). They were derived from the hybridization of curcuminoids and bisabolanes. The structures and absolute configurations of 1-9 were elucidated on the basis of extensive spectroscopic data analysis, including NMR and electronic circular dichroism spectra. The configuration of 10 was further confirmed by X-ray crystallography. A plausible biogenetic relationship for 1-12 is proposed. Compounds 4, 6, 7, 10, and 11 showed higher cytotoxic activities (IC(50), 10.3-19.4 μM) than curcumin (IC(50), 31.3-49.2 μM) against human cancer cell lines (A549, HepG2, and MDA-MB-231).
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, People's Republic of China.
authors.forename: Xionghao
authors.initials: X
authors.lastname: Lin
authors.forename: Shuai
authors.initials: S
authors.lastname: Ji
authors.forename: Rui
authors.initials: R
authors.lastname: Li
authors.forename: Yinhui
authors.initials: Y
authors.lastname: Dong
authors.forename: Xue
authors.initials: X
authors.lastname: Qiao
authors.forename: Hongbo
authors.initials: H
authors.lastname: Hu
authors.forename: Wenzhi
authors.initials: W
authors.lastname: Yang
authors.forename: Dean
authors.initials: D
authors.lastname: Guo
authors.forename: Pengfei
authors.initials: P
authors.lastname: Tu
authors.forename: Min
authors.initials: M
authors.lastname: Ye
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D030024:Curcuma / Q000737:chemistry*; D003474:Curcumin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D027343:Rhizome / Q000737:chemistry / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D003474:Curcumin