title: Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia.
abstract: Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.
authors.affiliation: Department of Traditional Chinese Medicine and Natural Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310031, People's Republic of China. dryuzhao@zjuem.zju.edu.cn
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhao
authors.forename: Xiaojiang
authors.initials: X
authors.lastname: Hao
authors.forename: Wei
authors.initials: W
authors.lastname: Lu
authors.forename: Junchao
authors.initials: J
authors.lastname: Cai
authors.forename: Hong
authors.initials: H
authors.lastname: Yu
authors.forename: Thierry
authors.initials: T
authors.lastname: Sevénet
authors.forename: Françoise
authors.initials: F
authors.lastname: Guéritte
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D002384:Catalysis; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells / Q000187:drug effects; D008175:Lung Neoplasms; D008516:Medicine, Chinese Traditional; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000438:Alcohols; D000972:Antineoplastic Agents, Phytogenic