Chemical Constituents of Heteroplexis micocephala

• Published in: Journal of natural products (Washington, D.C.) Vol. 72; no. 6; pp. 1184 - 1190
• Main Authors: Fan, Xiaona, Zi, Jiachen, Zhu, Chenggen, Xu, Wendong, Cheng, Wei, Yang, Sen, Guo, Ying, Shi, Jiangong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2009; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Anti-HIV Agents; Anti-HIV Agents - chemistry; Anti-HIV Agents - isolation & purification; Anti-HIV Agents - pharmacology; antiviral properties; Asteraceae; Asteraceae - chemistry; Biological and medical sciences; cell lines; chemical structure; chemistry; Chemistry, Medicinal; cytotoxicity; Diterpenes; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; diterpenoids; drug crops; drug effects; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; General pharmacology; herbal medicines; Heteroplexis micocephala; HIV-1; HIV-1 - drug effects; Human immunodeficiency virus 1; Humans; Inhibitory Concentration 50; isolation & purification; lactones; Life Sciences & Biomedicine; Medical sciences; medicinal plants; medicinal properties; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; pharmacology; Pharmacology & Pharmacy; Pharmacology. Drug treatments; plant extracts; Plant Sciences; Plants, Medicinal; Plants, Medicinal - chemistry; Science & Technology; Sesquiterpenes; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; sesquiterpenoids; virus replication; Asia; China; GLYCOSIDES; DITERPENOIDS; COLORIMETRIC ASSAY; BARK; HYDROXYACETOPHENONE; IMMUNODEFICIENCY-VIRUS TYPE-1; GAMMA-LACTONES; DERIVATIVES; TERPENOIDS; SESQUITERPENE LACTONES; Antineoplastic agent; Five membered ring; HIV-1 virus; Epimer; Ketol; Cytotoxicity; Compositae; Oxygen heterocycle; Medicinal plant; Ester; Ovary; Ketoether; Folk medicine; Dicotyledones; Sesquiterpenes; Angiospermae; Bicyclic compound; Antiviral; Inhibition; Secondary alcohol; Tumor cell; Human; Terpenoid; Ether; Aliphatic compound; Pharmacognosy; Retroviridae; Virus replication cycle; Lactone; Tetracyclic compound; Lentivirus; Ketone; In vitro; Biological activity; Virus; Cell line; Absolute configuration; Plant origin; Diterpene; Phenols; Isolation; Spermatophyta; Human immunodeficiency virus; Enone; Structural analysis
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/np900213w

Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3−7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9−11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC50 value of 4.37 μM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 μM.