title: [Aromatic constituents of Heteroplexis micocephal and their bioactivities].
abstract: OBJECTIVE
  To investigate the chemical constituents of Heteroplexis micocephal and their bioactivities.
  
  
  METHODS
  The constituents were isolated by using a combination of various chromatographic techniques including column chromatography over macroporous adsorbent resin, silica gel, Pharmadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. In vitro cytotoxic, HIV-1 replication, neuroprotective, and anti-inflammatory activities were screened by using cell-based models.
  
  
  RESULTS
  Thirty-one compounds were obtained. Twelve of them are phenylpropanols, and the structures were elucidated as (+)-(7S,8R)-guaiacylglycerol (1), ferulic acid (2), cinnamate methyl ester (3), 1-eicosanyl 3,4-dihydroxycinnamate (4), morinin B (5), sinapyl diangelate (6), chlorogenic acid (7), 4-O-caffeoylquinic acid (8), 5-O-caffeoylquinic acid (9), 5-O-caffeoylquinic acid methyl ester (10), 1,5-di-O-caffeoylquinic acid (11) and 4,5-di-O-caffeoylquinic acid methyl ester (12). Three lignans, (+)-pinoresinol (13), prinsepiol (14) and (+)-pinoresinol-O-beta-D-glucopyranoside (15). Four acetophenones, 2,4-diacetylanisole (16), espeleton (17), viscidone (18) and 12-hydroxytremetone-12-O-beta-D-glucopyranoside (19). Nine flavones, isosakuranetin (20), hesperetin (21), 3-methoxy-5,7,3',4'-tetrahydroxyflavone (22), acacetin (23), 5-hydroxy-7,4'- dimethoxyflavone (24), 7-methoxy-4',5, 6-trihydroxyflavone (25), 3,3'-dimethylquercetin (26), kaempferol 3-O-rutinoside (27), rutin (28). And three coumarins scopoletin (29), umbelliferone (30) and ayapin (31). Compound 6 and 22 showed selective cytotoxicities against a human stomach cancer cell line(BGC-823) and a human lung cancer cell line (A549) with IC50 values of 3.74 x 10(-5) and 7.17 x 10(-5) mol L(-1), respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 x 10(-6) mol L(-1), while 22 showed neuroprotective activity Against the MPP+ induced PC12-syn cell damage, with a relative protection ratio of 105.2% (P < 0.01) at a concentration of 10(-5) mol L(-1). Compound 26 and 31 showed inhibitory activities against the release of beta-glucuronidase of the polymorphous nuclear leukocytes induced by platelet activating factor (PAF), with inhibitory rates of 75.6% (P < 0.001) and 53. 9% (P < 0.01), respectively.
  
  
  CONCLUSIONS
  Compounds 1-31 were obtained from the genus Heteroplexis for the first time. Compound 6 and 22 possessed selective cytotoxicities against human cancer cell lines BGC-823 and A549, respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication while 22 showed neuroprotective activity against the MPP+ induced PC12-syn cell damage. Compound 26 and 31 were potent anti-inflammatory agents.
authors.affiliation: Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Xiaona
authors.initials: X
authors.lastname: Fan
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Chenggen
authors.initials: C
authors.lastname: Zhu
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.forename: Jinfeng
authors.initials: J
authors.lastname: Hu
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Chen
authors.forename: Wenjie
authors.initials: W
authors.lastname: Wang
authors.forename: Naihong
authors.initials: N
authors.lastname: Chen
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000032:analysis / Q000494:pharmacology; D045744:Cell Line, Tumor; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D006801:Humans; D027822:Myrtaceae / Q000737:chemistry*; D009474:Neurons / Q000166:cytology / Q000187:drug effects; D018696:Neuroprotective Agents / Q000032:analysis / Q000494:pharmacology; D010936:Plant Extracts / Q000032:analysis* / Q000494:pharmacology*; D051381:Rats; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D018696:Neuroprotective Agents; D010936:Plant Extracts