title: Structures and biological activities of azaphilones produced by Penicillium sp. KCB11A109 from a ginseng field.
abstract: Twelve metabolites, including five highly oxygenated azaphilones, geumsanols A-E, along with seven known analogues were isolated from Penicillium sp. KCB11A109, a fungus derived from a ginseng field. Their structures were assigned by spectroscopic means (NMR and MS), and stereochemistries were determined by extensive spectroscopic analyses ((1)H-(1)H coupling constants, NOESY, and HETLOC) and chemical derivatizations (modified Mosher's method and acetonide formation). The isolates were evaluated for their anticancer, antimicrobial, antimalarial activities, and phenotypic effects in zebrafish development. Of these compounds possessing no pyranoquinone core, only geumsanol E exhibited cytotoxic activities and toxic effects on zebrafish embryos, suggesting that a double bond at C-11 and C-12 is important for biological activity.
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea.
authors.forename: Sangkeun
authors.initials: S
authors.lastname: Son
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea.
authors.forename: Sung-Kyun
authors.initials: SK
authors.lastname: Ko
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: Jong Won
authors.initials: JW
authors.lastname: Kim
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: Jae Kyoung
authors.initials: JK
authors.lastname: Lee
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea.
authors.forename: Mina
authors.initials: M
authors.lastname: Jang
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: In-Ja
authors.initials: IJ
authors.lastname: Ryoo
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: Gwi Ja
authors.initials: GJ
authors.lastname: Hwang
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: Min Cheol
authors.initials: MC
authors.lastname: Kwon
authors.affiliation: Microbial Resource Center, Korea Research Institute of Bioscience and Biotechnology, 125 Gwahak-ro, Daejeon 306-809, South Korea.
authors.forename: Kee-Sun
authors.initials: KS
authors.lastname: Shin
authors.affiliation: Chemical Biology Research Group, RIKEN CSRS, Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Yushi
authors.initials: Y
authors.lastname: Futamura
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea.
authors.forename: Young-Soo
authors.initials: YS
authors.lastname: Hong
authors.affiliation: College of Pharmacy, Wonkwang University, 460 Iksandae-ro, Iksan, Jeonbuk 570-749, South Korea.
authors.forename: Hyuncheol
authors.initials: H
authors.lastname: Oh
authors.affiliation: Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea; Incurable Diseases Therapeutics Research Center (WCI), Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea.
authors.forename: Bo Yeon
authors.initials: BY
authors.lastname: Kim
authors.affiliation: RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN, Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Ueki
authors.affiliation: RIKEN-KRIBB Joint Research Unit, Global Research Cluster, RIKEN, Hirosawa, Wako-shi, Saitama 351-0198, Japan; Chemical Biology Research Group, RIKEN CSRS, Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Shunji
authors.initials: S
authors.lastname: Takahashi
authors.affiliation: Chemical Biology Research Group, RIKEN CSRS, Hirosawa, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Osada
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea. Electronic address: jangjh@kribb.re.kr.
authors.forename: Jae-Hyuk
authors.initials: JH
authors.lastname: Jang
authors.affiliation: Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanji-ro, Cheongju, Chungbuk 363-883, South Korea; Department of Biomolecular Science, University of Science and Technology, 217 Gajungro, Daejeon 305-333, South Korea. Electronic address: jsahn@kribb.re.kr.
authors.forename: Jong Seog
authors.initials: JS
authors.lastname: Ahn
mesh_terms: D000818:Animals; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D005894:Panax / Q000382:microbiology*; D010407:Penicillium / Q000737:chemistry*; D010860:Pigments, Biological / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015027:Zebrafish / Q000254:growth & development
chemical_list: D001578:Benzopyrans; D010860:Pigments, Biological; C494154:azaphilone; C000610926:geumsanol E
keywords: Azaphilone; Geumsanol; Penicillium sp.; Structure elucidation; Trichocomaceae; Zebrafish screening