Synthetic Studies on Echinulin and Related Natural Products. IV. : Isolation, Structure and Synthesis of Flavoglaucin-Auroglaucin Type Natural Products isolated from Aspergillus amstelodami

Inoue, Shoji; Hashizume, Kiyomatsu; Takamatsu, N.; Nagano, Hideo; Kishi, Yoshito

doi:10.1248/yakushi1947.97.5_569

Cited by 11 publications

(11 citation statements)

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“…Each peak in the two extracts was separated by preparative HPLC and examined for its DPPH radical scavenging capacity. Five antioxidants were isolated from the extract; they were assigned and identified as isodihydroauroglaucin (IDAG), 19) auroglaucin (AG), 20) dihydroauroglaucin (DAG), 21) tetrahydroauroglaucin (TAG), 22) and flavoglaucin (FG) 23) by reference to reported data from 1 H-NMR, 13 C-NMR, and EI-MS analyses (Fig. 1).…”

Section: Identification Of the Antioxidants Produced By Filamentous Fmentioning

confidence: 99%

“…Their structures were fully characterized on the basis of spectroscopic data, especially by using the 2D NMR spectrum, and were identified by comparing the 1 H-NMR and MS spectra with those data reported in the literature. [19][20][21][22][23] IDAG, AG, DAG, TAG, and FG have been reported to be secondary metabolites produced by filamentous fungi of A. ruber, 19) A. amstelodami, 20) A. chevalieri, 21) Penicillum charlesii, 22) and E. repens, 23) respectively. All compounds were disubstituted gentisaldehyde (2,5-dihydroxybenzaldehyde) derivatives with a prenyl group at C-3 and a seven-carbon unbranched aliphatic chain at C-6 in the molecule.…”

Section: Identification Of the Antioxidants Produced By Filamentous Fmentioning

confidence: 99%

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Antioxidants Produced byEurotium herbariorumof Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)

Miyake

Ito

Itoigawa

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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Extracts prepared by culturing ten filamentous fungi from Aspergillus and Eurotium species isolated from dried bonito (katsuobushi) were examined for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging capacity. The extracts prepared by culturing E. herbariorum NE-1 and NE-4, which are used in the molding process for the manufacture of karebushi (a kind of katsuobushi), were shown to have higher activity than the others. Five antioxidants were isolated from the extracts and identified as isodihydroauroglaucin (IDAG), auroglaucin (AG), dihydroauroglaucin (DAG), tetrahydroauroglaucin (TAG), and flavoglaucin (FG) by 1 H-NMR, 13 C-NMR, and EI-MS analyses. Compared with -tocopherol, the isolated antioxidants exhibited high antioxidative activity for the radical scavenging capacity of DPPH and superoxide, but low activity for inhibiting the autoxidation of docosahexaenoic acid (DHA). The isolated antioxidants were produced by the Eurotium species, but not by the Aspergillus species. DAG and TAG exhibited higher radical scavenging capacity than the other antioxidants and were abundantly contained in the extracts of E. herbariorum NE-1 and NE-4.

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Section: Identification Of the Antioxidants Produced By Filamentous Fmentioning

confidence: 99%

Section: Identification Of the Antioxidants Produced By Filamentous Fmentioning

confidence: 99%

Antioxidants Produced byEurotium herbariorumof Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)

Miyake

Ito

Itoigawa

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…By comparison of their NMR data with those reported in the literature, the structures of these compounds were identified as chaetopyranin (5), 9) flavoglaucin (6), 19) aspergin (7), 19) isotetrahydroauroglaucin (8), 18) isodihydroauroglaucin (9), 18) 2-(2Ј,3-epoxy-1Ј,3Ј-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (10), 9) and 2-(2Ј,3-epoxy-1Ј,3Ј,5Ј-heptatrienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (11). 19) Compounds 1-11 were tested for cytotoxic effects on the P-388, K-562 and HL-60 cell lines using the MTT method and on A-549 cell line using the SRB method. None of these compounds showed cytotoxic activities against any of the four cell lines (IC 50 Ͼ10 mg/ml).…”

mentioning

confidence: 93%

“…The molecular formula of 1 was determined to be C 19 Table 1). The 13 C-NMR spectrum of 1 exhibited 19 carbon signals attributable to three methyls, three methylenes, seven methines, and six quaternary carbon atoms according to the DEPT experiments (Table 2).…”

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confidence: 99%

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Benzaldehyde Derivatives from Eurotium rubrum, an Endophytic Fungus Derived from the Mangrove Plant Hibiscus tiliaceus

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Endophytic fungi are a large group of microorganisms which were defined as fungi colonizing healthy plant tissue without causing overt symptoms in or apparent injury to the host. Endophytes have been proven to be a well-established source for structurally diverse and biologically active secondary metabolites.2-4) Marine mangrove plants were proven to be a rich source of endophytic fungi. Many secondary metabolites with novel structures and biological activities have been characterized from mangrove-derived endophytic fungi. [5][6][7][8] In the course of our ongoing project directed toward the discovery of new natural products from endophytic fungi that were isolated from marine organisms from the Chinese sea coasts, [9][10][11][12][13][14] we have investigated the chemical constituents of an endophytic fungal strain Eurotium rubrum that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus collected from Hainan island. This paper describes the isolation, structure elucidation, and cytotoxicity of four new (1-4) and seven known (5-11) benzaldehyde derivatives. To our knowledge, compound 1, which was named as eurotirumin, possesses a new carbon skeleton with a cyclopentabenzopyran ring system. Results and DiscussionThe fungus E. rubrum was grown in potato-dextrose broth (PDB) media. The combined extracts from the culture broth and from the mycelium were fractionated by repeated column chromatography on silica gel, reversed-phase silica gel C 18 , and Sephadex LH-20, as well as by preparative TLC, to afford eleven metabolites (1-11).Compound 1 was obtained as a yellowish amorphous powder. The IR spectrum exhibited absorptions at 3442 (OH), 1729 (carbonyl), and 1632 cm Ϫ1 (double bond). The EI-MS of 1 displayed a molecular ion peak at m/z 316 [M] (Table 1). The 13 C-NMR spectrum of 1 exhibited 19 carbon signals attributable to three methyls, three methylenes, seven methines, and six quaternary carbon atoms according to the DEPT experiments (Table 2). Detailed comparison of 1D and 2D NMR spectral data of 1 with those of our recently reported data for chaetopyranin (5), a benzaldehyde derivative that was identi- Four new (1-4) and seven known (5-11) benzaldehyde derivatives were characterized from the liquid fermentation cultures of Eurotium rubrum, an endophytic fungus that was isolated from the inner tissue of stems of the mangrove plant Hibiscus tiliaceus. The structures of these compounds were determined by extensive analysis of their spectroscopic data. Among these metabolites, compound 1, which was named as eurotirumin, possesses a new carbon skeleton with a cyclopentabenzopyran ring system.

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ChemInform Abstract: SYNTHETIC STUDIES ON ECHINULIN AND RELATED NATURAL PRODUCTS. IV. ISOLATION, STRUCTURE AND SYNTHESIS OF FLAVOGLAUCIN‐AUROGLAUCIN TYPE NATURAL PRODUCTS ISOLATED FROM ASPERGILLUS AMSTELODAMI

Inoue¹,

Hashizume²,

Takamatsu³

et al. 1977

Chemischer Informationsdienst

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Synthetic Studies on Echinulin and Related Natural Products. IV. : Isolation, Structure and Synthesis of Flavoglaucin-Auroglaucin Type Natural Products isolated from Aspergillus amstelodami

Cited by 11 publications

References 0 publications

Antioxidants Produced byEurotium herbariorumof Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)

Antioxidants Produced byEurotium herbariorumof Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)

Benzaldehyde Derivatives from Eurotium rubrum, an Endophytic Fungus Derived from the Mangrove Plant Hibiscus tiliaceus

ChemInform Abstract: SYNTHETIC STUDIES ON ECHINULIN AND RELATED NATURAL PRODUCTS. IV. ISOLATION, STRUCTURE AND SYNTHESIS OF FLAVOGLAUCIN‐AUROGLAUCIN TYPE NATURAL PRODUCTS ISOLATED FROM ASPERGILLUS AMSTELODAMI

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