2011
DOI: 10.1248/cpb.59.499
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Microbial Mannosidation of Bioactive Chlorogentisyl Alcohol by the Marine-Derived Fungus Chrysosporium synchronum

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Cited by 26 publications
(7 citation statements)
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“…Successive normal, reversed-phase open, and flash silica gel (C 18 ) and high-performance liquid chromatography (HPLC) separation of the ethyl acetate fraction of the defatted methanol extract of P. concentricum fermented on rice medium afforded a new chlorinated xanthone, 6-chloro-3,8-dihydroxy-1-methylxanthone ( 1 ), together with 15 known compounds, identified as epoxydon ( 4 ), norlichexanthone ( 5 ), gentisyl alcohol ( 9 ), gentisyl quinone ( 10 ), ( R,S )-1-phenyl-1,2-ethanediol ( 11 ), dehydro­dechlorogriseofulvin ( 12 ), dechlorogriseofulvin ( 13 ), dehydrogriseofulvin ( 14 ), griseofulvin ( 15 ), ethylene glycol benzoate ( 16 ), alternariol ( 17 ), , griseoxanthone C ( 18 ), , drimiopsin H ( 19 ), griseophenone C ( 20 ), and griseophenone B ( 21 ) . Ethyl acetate extracts of the same strain fermented on KBr and KCl salt supplemented rice media afforded 2-bromo­gentisyl alcohol ( 2 ), 2-chloro­gentisyl alcohol ( 6 ), , an epimeric mixture of cis - and trans -bromohydrins ( 3a , 3b ), and trans - and cis -chlorohydrins ( 8a , 8b ), , together with the four known compounds identified as 4 , 5 , 13 , and 15 . Herein, we report the isolation, structure elucidation, and antiproliferative activity evaluation of these compounds of P. concentricum and discuss the in media synthesis of halogenated compounds in halogen salt-rich media.…”
mentioning
confidence: 99%
“…Successive normal, reversed-phase open, and flash silica gel (C 18 ) and high-performance liquid chromatography (HPLC) separation of the ethyl acetate fraction of the defatted methanol extract of P. concentricum fermented on rice medium afforded a new chlorinated xanthone, 6-chloro-3,8-dihydroxy-1-methylxanthone ( 1 ), together with 15 known compounds, identified as epoxydon ( 4 ), norlichexanthone ( 5 ), gentisyl alcohol ( 9 ), gentisyl quinone ( 10 ), ( R,S )-1-phenyl-1,2-ethanediol ( 11 ), dehydro­dechlorogriseofulvin ( 12 ), dechlorogriseofulvin ( 13 ), dehydrogriseofulvin ( 14 ), griseofulvin ( 15 ), ethylene glycol benzoate ( 16 ), alternariol ( 17 ), , griseoxanthone C ( 18 ), , drimiopsin H ( 19 ), griseophenone C ( 20 ), and griseophenone B ( 21 ) . Ethyl acetate extracts of the same strain fermented on KBr and KCl salt supplemented rice media afforded 2-bromo­gentisyl alcohol ( 2 ), 2-chloro­gentisyl alcohol ( 6 ), , an epimeric mixture of cis - and trans -bromohydrins ( 3a , 3b ), and trans - and cis -chlorohydrins ( 8a , 8b ), , together with the four known compounds identified as 4 , 5 , 13 , and 15 . Herein, we report the isolation, structure elucidation, and antiproliferative activity evaluation of these compounds of P. concentricum and discuss the in media synthesis of halogenated compounds in halogen salt-rich media.…”
mentioning
confidence: 99%
“…The HMBC correlations of the olefinic protons H‐2 with C‐10 and H‐6 with C‐8 and C‐9 established the geraniol moiety, and further HMBC correlation of the oxymethylene proton H 2 ‐1 with C‐1′ aided the assignment of the glycosidic linkage. The 13 C‐NMR spectrum showed carbon resonances at δ c 62.8 (CH 2 ), 68.5 (CH), 72.2 (CH), 72.5 (CH), 74.5 (CH), and 100.2 (CH), indicative of the presence of an α‐mannopyranoside …”
Section: Nmr Spectroscopic Data For Geraniol (1) and 1‐o‐(α‐d‐mannopymentioning
confidence: 99%
“…In order to clarify the structure of 2 , we synthesized 2 from 1 and 1‐ O ‐(2,3,4,6‐tetra‐ O ‐acetyl‐α‐D‐mannopyranosyl)trichloroacetimide in the same manner as described for the synthesis of 1‐ O ‐(α‐D‐mannopyranosyl)chlorogentisyl alcohol (Scheme S1 and Supporting Information p. 8). Values of [α] D , ESI‐MS, and 1 H‐NMR for the synthetic compound were identical to those of compound 2 .…”
Section: Nmr Spectroscopic Data For Geraniol (1) and 1‐o‐(α‐d‐mannopymentioning
confidence: 99%
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