title: Ailanthusins A-G and nor-lupane triterpenoids from Ailanthus triphysa.
abstract: Bioactivity-guided chemical investigation of the CH2Cl2and CH2Cl2MeOH extracts of the stem and stem bark material of Ailanthus tryphysa (Simaroubaceae) led to the isolation of five cycloapotirucallanes, ailanthusins A-E, two malabaricanes, ailanthusins F-G, and one nor-lupane triterpenoid, 29-nor-lup-1-ene-3,20-dione along with twenty known compounds. Their structures were elucidated through the application of extensive spectroscopic methods, and the structure of ailanthusin A was further confirmed by single crystal X-ray analysis. Several malabaricane derivatives were prepared from malabaricol and, together with some of the isolates, were evaluated for their cytotoxic activities against human cancer and normal cell lines.
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand. Electronic address: sanit@cri.or.th.
authors.forename: Sanit
authors.initials: S
authors.lastname: Thongnest
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.
authors.forename: Jutatip
authors.initials: J
authors.lastname: Boonsombat
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.
authors.forename: Hunsa
authors.initials: H
authors.lastname: Prawat
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand; Chulabhorn Graduate Institute and Center for Environmental Health and Toxicology (EHT), Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.
authors.forename: Chulabhorn
authors.initials: C
authors.lastname: Mahidol
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand; Chulabhorn Graduate Institute and Center for Environmental Health and Toxicology (EHT), Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
mesh_terms: D000072283:A549 Cells; D032268:Ailanthus / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053978:Pentacyclic Triterpenes
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D014315:Triterpenes; C000614555:ailanthusin A; C480546:lupane; D053978:Pentacyclic Triterpenes
keywords: Ailanthus triphysa; Cycloapotirucallane; Cytotoxicity; Lupane; Malabaricane; Octanor-triterpenoid; Simaroubaceae