title: Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492.
abstract: An aciduric fungal strain, Penicillium camemberti OUCMDZ-1492, was isolated from an acidic marine niche, mangrove soil and mud, around the roots of Rhizophora apiculata. Six new indole-diterpenoids (1-6), along with five known analogues, emindole SB (7), 21-isopentenylpaxilline (8), paspaline (9), paxilline (10), and dehydroxypaxilline (11), were isolated from the fermentation broth of P. camemberti OUCMDZ-1492 grown at pH 5.0. On the basis of spectroscopic analyses, CD spectra, quantum ECD calculations, and chemical methods, new structures 1-6 were established as 3-deoxo-4b-deoxypaxilline, 4a-demethylpaspaline-4a-carboxylic acid, 4a-demethylpaspaline-3,4,4a-triol, 2'-hydroxypaxilline, 9,10-diisopentenylpaxilline, and (6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol, respectively. Compounds 1-3 and 5-10 exhibited significant activity against the H1N1 virus with IC50 values of 28.3, 38.9, 32.2, 73.3, 34.1, 26.2, 6.6, 77.9, and 17.7 μM, respectively. The results showed that 3-oxo, 4b-hydroxy, and 9-isopentenyl substitutions tend to increase the anti-H1N1 activity of hexacyclic indole-diterpenoids.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
authors.forename: Yaqin
authors.initials: Y
authors.lastname: Fan
authors.forename: Yi
authors.initials: Y
authors.lastname: Wang
authors.forename: Peipei
authors.initials: P
authors.lastname: Liu
authors.forename: Peng
authors.initials: P
authors.lastname: Fu
authors.forename: Tonghan
authors.initials: T
authors.lastname: Zhu
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Weiming
authors.initials: W
authors.lastname: Zhu
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002681:China; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D043982:Rhizophoraceae / Q000382:microbiology
chemical_list: C475533:21-isopentenylpaxilline; D000998:Antiviral Agents; D004224:Diterpenes; D007211:Indoles; C496869:emindole; C048221:paspaline; C048220:paxilline