title: Cytotoxic sesquiterpenes from the endophytic fungus Pseudolagarobasidium acaciicola.
abstract: Twenty previously unknown compounds and two known metabolites, merulin A and merulin D, were isolated from the endophytic fungus Pseudolagarobasidium acaciicola, which was isolated from a mangrove tree, Bruguiera gymnorrhiza. Structures of the 20 compounds were elucidated by analysis of spectroscopic data. The absolute configuration of seven of these compounds was addressed by a single crystal X-ray analysis using CuKα radiation and an estimate of the Flack parameter. Three compounds also possessed a tricyclic ring system. Terpene endoperoxides isolated exhibited cytotoxic activity, while those without an endoperoxide moiety did not show activity. The endoperoxide moiety of sesquiterpenes has significant impact on cytotoxic activity, and thus is an important functionality for cytotoxicity. One terpene endoperoxide displayed potent cytotoxic activity (IC50 0.28μM), and selectively exhibited activity against the HL-60 cell line.
authors.affiliation: Chulabhorn Graduate Institute, Chemical Biology Program, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
authors.forename: Mario
authors.initials: M
authors.lastname: Wibowo
authors.affiliation: Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
authors.forename: Vilailak
authors.initials: V
authors.lastname: Prachyawarakorn
authors.affiliation: Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
authors.forename: Thammarat
authors.initials: T
authors.lastname: Aree
authors.affiliation: Chulabhorn Graduate Institute, Chemical Biology Program, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
authors.forename: Chulabhorn
authors.initials: C
authors.lastname: Mahidol
authors.affiliation: Chulabhorn Graduate Institute, Chemical Biology Program, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Center of Excellence on Environmental Health and Toxicology (EHT), CHE, Ministry of Education, Bangkok, Thailand.
authors.forename: Somsak
authors.initials: S
authors.lastname: Ruchirawat
authors.affiliation: Chulabhorn Graduate Institute, Chemical Biology Program, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand; Center of Excellence on Environmental Health and Toxicology (EHT), CHE, Ministry of Education, Bangkok, Thailand. Electronic address: prasat@cri.or.th.
authors.forename: Prasat
authors.initials: P
authors.lastname: Kittakoop
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D015394:Molecular Structure; D010545:Peroxides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020072:Polyporales; D043982:Rhizophoraceae / Q000382:microbiology*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D053833:Wetlands
chemical_list: D000970:Antineoplastic Agents; D010545:Peroxides; D012717:Sesquiterpenes; C550059:merulin A
keywords: Chamigrane; Cytotoxic activity; Endoperoxides; Endophytic fungi; Fungal metabolites; Mangrove derived fungi; Norsesquiterpene; Pseudolagarobasidium acaciicola; Sesquiterpene