title: Chemical constituents of the bark of Machilus wangchiana and their biological activities.
abstract: Eleven new metabolites, butanolides 1-6, lignan derivatives 7-9, sesquiterpene 10, and 3',4'-seco-flavane derivative 11, have been isolated from an ethanol extract of Machilus wangchiana. Twenty known compounds, including ginkgolides A and B (16 and 17), were also isolated. Their structures and absolute configurations were determined by spectroscopic and chemical methods. Compounds 7, 8a, 8b, 9, 11, (+)-guaiacin (12), meso-dihydroguaiaretic acid (13), and hamabiwalactone A (15) showed potent in vitro activities against the release of beta-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with 42.5-75.6% inhibition at 10(-5) M. Compounds 8, 8a, 8b, 9, and 11 reduced dl-galactosamine (GalN)-induced hepatocyte (WB-F344 cells) damage with 39.4 +/- 6.3% to 53.6 +/- 3.5% inhibition at 10(-4) M. Isomahubannolide-23 (14) was cytotoxic against human stomach cancer (BGC-823) and ovarian cancer (A2780) cell lines, with IC(50) values of 0.13 and 2.66 muM, respectively.
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College (Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education), Beijing 100050, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Cheng
authors.forename: Chenggen
authors.initials: C
authors.lastname: Zhu
authors.forename: Wendong
authors.initials: W
authors.lastname: Xu
authors.forename: Xiaona
authors.initials: X
authors.lastname: Fan
authors.forename: Yongchun
authors.initials: Y
authors.lastname: Yang
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Chen
authors.forename: Wenjie
authors.initials: W
authors.lastname: Wang
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005260:Female; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D046934:Ginkgolides / Q000302:isolation & purification; D005966:Glucuronidase / Q000097:blood / Q000187:drug effects; D006801:Humans; D007783:Lactones / Q000302:isolation & purification; D019770:Lauraceae / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects; D024301:Plant Bark / Q000737:chemistry; D051381:Rats; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D005419:Flavonoids; D046934:Ginkgolides; D007783:Lactones; D017705:Lignans; D012717:Sesquiterpenes; C045856:ginkgolide B; D005966:Glucuronidase; D015107:4-Butyrolactone; C477042:ginkgolide A