Taxonomy and secondary metabolites of Pseudobotrytis sp. FKA-25

Yamaguchi, Yuichi; Masuma, Rokuro; Kim, Yong-Pil; Uchida, Ryuji; Tomoda, Hiroshi; Ōmura, Satoshi

doi:10.1007/s10267-003-0148-6

Cited by 31 publications

(32 citation statements)

References 15 publications

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“…This compound was first isolated from Aspergillus versicolor as a new ultraviolet light-absorbing substance (Arai and Sano, 1994), and was also found to be produced as a major secondary metabolite by the fungus Pseudobotrytis sp. FKA-25 (Yamaguchi et al, 2004). However, the stereochemistry of the hydroxyl group at C-12 has not been defined.…”

Section: Resultsmentioning

confidence: 96%

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Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor

et al. 2010

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As part of an ongoing search for bioactive metabolites from the fungus Aspergillus versicolor derived from a marine sponge Petrosia sp., an aromatic polyketide derivative (1), two xanthones (2 and 3), and five anthraquinones (4-8) were isolated by bioactivity-guided fractionation. The gross structures were determined based on the NMR and MS spectroscopic data, and the absolute configurations were defined by comparison of optical rotation data with those of reported. Compounds 2, 4, 5, and 7 exhibited significant cytotoxicity against five human solid tumor cell lines (A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15) with IC50 values in the range of 0.41-4.61 microg/mL. Compounds 4 and 7 exhibited antibacterial activity against several clinically isolated Gram-positive strains with MIC values of 0.78-6.25 microg/mL.

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Section: Resultsmentioning

confidence: 96%

“…1. Chemical structures of compounds 1-8 (Yamaguchi et al, 2004). This compound was first isolated from Aspergillus versicolor as a new ultraviolet light-absorbing substance (Arai and Sano, 1994), and was also found to be produced as a major secondary metabolite by the fungus Pseudobotrytis sp.…”

Section: Resultsmentioning

confidence: 99%

Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor

et al. 2010

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“…1) produced by Pseudobotrytis terrestris FKA-25 [1] is a potent inhibitor of lipid droplet synthesis in macrophages. The fermentation, isolation and biological activities of 1 were described previously [2].…”

Section: Introductionmentioning

confidence: 99%

Structure Elucidation of Fungal Sespendole, an Inhibitor of Lipid Droplet Synthesis in Macrophages

et al. 2006

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A new fungal metabolite named sespendole was isolated as an inhibitor of lipid droplet synthesis in mouse macrophages from the culture broth of the fungal strain Pseudobotrytis terrestris FKA-25. The structure and stereochemistry of sespendole were elucidated by spectroscopic studies including various NMR spectral analyses, exciton chirality experiments and the modified Mosher method. Sespendole was found to possess a new indolosesquiterpene skeleton modified with two isoprenes.Keywords sespendole, indolosesquiterpene, fungal metabolites, structure elucidation Introduction Sespendole (1, Fig. 1) produced by Pseudobotrytis terrestris FKA-25 [1] is a potent inhibitor of lipid droplet synthesis in macrophages. The fermentation, isolation and biological activities of 1 were described previously [2].In this report, we describe the structure elucidation of 1 and show that 1 possesses an indolosesquiterpene core with two additional isoprenyl side chains. A number of indoloditerpenes have been reported from fungi [3], such as paspalicine [4], paxilline [5,6], janthitrems [7,8] Results and Discussion Physico-chemical PropertiesThe physico-chemical properties of 1 are summarized in Table 1. Compound 1 is a colorless amorphous solid, and is soluble in chloroform, methanol, acetone and ethyl acetate. The molecular formula was revealed to be C 33 H 45 NO 4 by HR-EI-MS (m/z 519.3339; calcd. 519.3349). The UV spectrum exhibited characteristic absorption maxima at 239 and 288 nm in methanol, suggesting the presence of an indole moiety in the structure. The IR spectrum showed -OH and/or -NH absorption at 3426 cm Ϫ1 and carbonyl absorption at 1693 cm Ϫ1. Structure of SespendoleThe 1 H and 13 C NMR spectra of 1 showed 45 protons and 33 carbons in pyridine-d 5 as shown in Table 2. The carbon signals were classified into 8 methyl, 6 methylene, 6 methine, and 13 quaternary carbons by analysis of the

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“…1) [2,3]. A number of fungal metabolites having the indoloditerpene core structure and their biosynthesis have been reported [4ϳ6].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Sespendole

2006

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Sespendole is the first reported fungal metabolite having an indolosesquiterpene core structure. Materials and Methods Spectroscopic MeasurementsThe patterns and rates of incorporation of 13 C-labeled 1 were determined using 13 C NMR spectra obtained using a JEOL EX-270 (270 MHz) spectrometer and the 13 C-15 N coupling of 15 N-labeled 1 was determined from the 13 C NMR spectra obtained using a Varian Inova 600 (600 MHz). Materials Sespendole ProductionA stock culture of strain P. terrestris FKA-25 was grown on slants adjusted to pH 6.0 and containing 0.1% glycerol, 0.02% yeast extract (Oriental Yeast Co.), 0.02% MgSO 4 ·7H 2 O, 0.08% KH 2 PO 4 , 0.08% K 2 HPO 4 , 0.02% KCl, 0.02% NaNO 3 and 1.0% agar. The slants were incubated at 27°C and stored in tubes sealed with screw caps at 27°C. Prior to production of 1, P. terrestris ORIGINAL ARTICLE Biosynthesis of SespendoleRyuji Uchida, Hiroshi Tomoda, Satoshi Ō mura

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Taxonomy and secondary metabolites of Pseudobotrytis sp. FKA-25

Cited by 31 publications

References 15 publications

Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor

Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor

Structure Elucidation of Fungal Sespendole, an Inhibitor of Lipid Droplet Synthesis in Macrophages

Biosynthesis of Sespendole

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