title: Terphenyl derivatives and drimane - Phathalide/isoindolinones from Hypoxylon fendleri BCC32408.
abstract: The genus Hypoxylon, a member of the family Xylariaceae, has been known to produce significant secondary metabolites in terms of chemical diversity. Moreover, the compounds isolated can also be used as chemotaxonomic characters for differentiation among the two sections, which are sect. Annulata and sect. Hypoxylon. In our continuing chemical screening programme for novel compounds, the crude extracts of H. fendleri BCC32408 gave significant chemical profiles in HPLC analyses. Thus, the chemical investigation of these crude extracts was then carried out. The investigation led to the isolation of ten previously undescribed compounds including three terphenylquinones (fendleryls A - C), one terphenyl (fendleryl D), and six novel drimane - phthalide-type lactone/isoindolinones derivatives (fendlerinines A - F) along with seven known compounds (2-O-methylatromentin, rickenyl E, atromentin, rickenyls C - D, (+)-ramulosin, and O-hydroxyphenyl acetic acid). The chemical structures were determined on the basis of spectroscopic analyses, including 1D, 2D NMR and high-resolution mass spectrometry, as well as chemical transformations. In addition, these isolated compounds were assessed for antimicrobial activity including antimalarial (against Plasmodium falciparum, K-1 strain), antifungal (against Candida albicans), antibacterial (against Bacillus cereus) activities. Cytotoxicity against both cancerous (KB, MCF-7, NCI-H187) and non-cancerous (Vero) cells of these compounds were also evaluated.
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Chakapong
authors.initials: C
authors.lastname: Intaraudom
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Nantiya
authors.initials: N
authors.lastname: Bunbamrung
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Aibrohim
authors.initials: A
authors.lastname: Dramae
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Nattawut
authors.initials: N
authors.lastname: Boonyuen
authors.affiliation: Department of Chemistry, Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, 10400, Thailand; Center for Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, 10400, Thailand.
authors.forename: Palangpon
authors.initials: P
authors.lastname: Kongsaeree
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Kitlada
authors.initials: K
authors.lastname: Srichomthong
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand.
authors.forename: Sumalee
authors.initials: S
authors.lastname: Supothina
authors.affiliation: National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand. Electronic address: pattamap@biotec.or.th.
authors.forename: Pattama
authors.initials: P
authors.lastname: Pittayakhajonwut
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001409:Bacillus cereus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007624:KB Cells; D007783:Lactones / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010648:Phenylacetates / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013730:Terphenyl Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014709:Vero Cells; D013098:Xylariales / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000962:Antimalarials; D007783:Lactones; D010648:Phenylacetates; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013730:Terphenyl Compounds; C437376:drimane; C005756:2-hydroxyphenylacetic acid
keywords: Antimicrobial; Cytotoxicity; Fendlerinines; Fendleryls; Hypoxylon fendleri; Xylariaceae