title: Isochromans and Related Constituents from the Endophytic Fungus Annulohypoxylon truncatum of Zizania caduciflora and Their Anti-Inflammatory Effects.
abstract: Six new isochroman derivatives (annulohypoxylomans A-C, 1-3; annulohypoxylomanols A and B, 6 and 7; and annulohypoxyloside, 8), an isocoumarin (annulohypoxylomarin A, 4), and an azaphilone derivative (xylariphilone, 5) were isolated from an ethyl acetate extract derived from cultures of the endophytic fungus JS540 found in the leaves of Zizania caduciflora. The JS540 strain was identified as Annulohypoxylon truncatum. The structures of the isolated compounds were elucidated by one- and two-dimensional nuclear magnetic resonance and mass spectrometry and by comparison with related compounds from the literature. The anti-inflammatory activities of the isolated compounds were evaluated in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells. Xylariphilone (5) exhibited significant inhibitory effects on LPS-induced interleukin (IL)-6, IL-12 p40, and tumor necrosis factor (TNF)-α production with IC50values of 5.3, 19.4, and 37.6 μM, respectively.
authors.affiliation: KM Application Center, Korea Institute of Oriental Medicine , Daegu 41062, Republic of Korea.
authors.forename: Wei
authors.identifier: 0000-0001-7272-7290
authors.initials: W
authors.lastname: Li
authors.affiliation: College of Pharmacy, Duksung Women's University , Seoul 01369, Republic of Korea.
authors.forename: Changyeol
authors.initials: C
authors.lastname: Lee
authors.affiliation: College of Pharmacy, Duksung Women's University , Seoul 01369, Republic of Korea.
authors.forename: Sung Hee
authors.identifier: 0000-0001-6085-193X
authors.initials: SH
authors.lastname: Bang
authors.affiliation: KM Application Center, Korea Institute of Oriental Medicine , Daegu 41062, Republic of Korea.
authors.forename: Jin Yeul
authors.initials: JY
authors.lastname: Ma
authors.affiliation: National Institute of Biological Resources , Incheon 22689, Republic of Korea.
authors.forename: Soonok
authors.initials: S
authors.lastname: Kim
authors.affiliation: School of Medicine and Brain Korea 21 PLUS Program and Institute of Medical Science, Jeju National University , Jeju 690-756, Republic of Korea.
authors.forename: Young-Sang
authors.initials: YS
authors.lastname: Koh
authors.affiliation: College of Pharmacy, Duksung Women's University , Seoul 01369, Republic of Korea.
authors.forename: Sang Hee
authors.initials: SH
authors.lastname: Shim
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002839:Chromans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003713:Dendritic Cells / Q000166:cytology / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D018664:Interleukin-12 / Q000819:agonists* / Q000737:chemistry / Q000378:metabolism*; D015850:Interleukin-6 / Q000819:agonists* / Q000737:chemistry / Q000378:metabolism*; D049934:Isocoumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry*; D006109:Poaceae / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism; D013098:Xylariales / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D002839:Chromans; D015850:Interleukin-6; D049934:Isocoumarins; D008070:Lipopolysaccharides; D014409:Tumor Necrosis Factor-alpha; C000621611:annulohypoxyloman A; C000621612:annulohypoxyloman B; C000621613:annulohypoxyloman C; C000609425:xylariphilone; D018664:Interleukin-12