title: Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima.
abstract: Pseudoguaianolide sesquiterpene lactones minimolides A (1), B (2), C (3) and D (4) and two guaianolide sesquiterpene lactones minimolides E (5) and F (6), along with seven known ones (7-13), were isolated from the supercritical fluid extract of Centipeda minima. The structures of these compounds were elucidated by extensive spectroscopic methods (IR, UV, HRESIMS, 1D-NMR and 2D-NMR), and the complete structure and stereochemistry of 1 was further confirmed by X-ray diffraction analysis. Compounds 1, 5-8,11 and 13 displayed inhibitory activity against human nasopharyngeal cancer cells (CNE) with IC(50) values ranging from 1.1 to 20.3 μM. Compound 13 containing both α-methylene-γ-lactone and α, β-unsaturated cyclopentenone moieties exhibited even stronger inhibitory activity than that of cisplatin (positive control) through cell cycle arrest at G2/M phase. Isolation of six sesquiterpene lactones from Centipeda minima highlighted the potential of supercritical fluid extraction for enrichment of minor constituents for phytochemical study.
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, People's Republic of China.
authors.forename: Peng
authors.initials: P
authors.lastname: Wu
authors.forename: Miao-Xian
authors.initials: MX
authors.lastname: Su
authors.forename: Ying
authors.initials: Y
authors.lastname: Wang
authors.forename: Guo-Cai
authors.initials: GC
authors.lastname: Wang
authors.forename: Wen-Cai
authors.initials: WC
authors.lastname: Ye
authors.forename: Hau-Yin
authors.initials: HY
authors.lastname: Chung
authors.forename: Juan
authors.initials: J
authors.lastname: Li
authors.forename: Ren-Wang
authors.initials: RW
authors.lastname: Jiang
authors.forename: Yao-Lan
authors.initials: YL
authors.lastname: Li
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D059447:Cell Cycle Checkpoints; D045744:Cell Line, Tumor; D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D002945:Cisplatin / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045788:Sesquiterpenes, Germacrane / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045789:Sesquiterpenes, Guaiane; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: C558353:(6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide; D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; D045789:Sesquiterpenes, Guaiane; C572815:florilenalin-2alpha-O-isobutyrate; C001329:helenalin; D002945:Cisplatin