Chemical constituents of the bark of Machilus wangchiana and their biological activities.
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.
Cheng
Wei
W
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.
Zhu
Chenggen
C
Xu
Wendong
W
Fan
Xiaona
X
Yang
Yongchun
Y
Li
Yan
Y
Chen
Xiaoguang
X
Wang
Wenjie
W
Shi
Jiangong
J
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
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