Isolation of isoflavones inhibiting dopa decarboxylase from fungi and streptomyces.

Umezawa, Hamao; Tobe, Hiroyasu; Shibamoto, Norio; Nakamura, Fukuko; Nakamura, Kenji; Matsuzaki, M; Takeuchi, Tomio

doi:10.7164/antibiotics.28.947

Cited by 50 publications

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“…Compounds 2-9 were known isoflavone derivatives. Their structures were identified as 8-chlorogenistein (2) [10], kakkatin (3) [7], 7-O-methyl genistein (4) [7], genistein (5) [14], daidzein (6) [7], glycitin (7) [16], genistin (8) [17], and daidzin (9) [18] by comparison of their spectroscopic data with those in the related literature. …”

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“…Streptomycetes are capable of biotransformation of soybean meal as major organic medium components and production of various isoflavones [5][6][7][8][9][10][11][12][13][14][15]. In our search for new metabolites from actinomycetes, a new compound, 7-O-methyl-8-chlorogenistein (1), together with eight known isoflavones, 8-chlorogenistein (2) [10], kakkatin (3) [7], 7-O-methyl genistein (4) [7], genistein (5) [14], daidzein (6) [7], glycitin (7) [16], genistin (8) [17], and daidzin (9) [18], was isolated from the Streptomyces strain YIM GS3536, which was isolated from soil sample collected from Yunnan Province, P. R. China.…”

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A new isoflavone derivative from Streptomyces sp. YIM GS3536

et al. 2013

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1 exhibited appreciable cytotoxicity against human melanoma cell lines (B16) and human leukemia cell lines (HL60) with IC 50 values of 17.5 and 19.2 PM, respectively. The MIC values of 1 for Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Candida albicans were in the range of 23-35 PM.Isoflavone intake from soy-based foods reduces the risk factors for cardiovascular disease and hormone-dependent cancers [1][2][3][4]. Streptomycetes are capable of biotransformation of soybean meal as major organic medium components and production of various isoflavones [5][6][7][8][9][10][11][12][13][14][15]. In our search for new metabolites from actinomycetes, a new compound, 7-O-methyl-8-chlorogenistein (1), together with eight known isoflavones, 8-chlorogenistein (2) [10], kakkatin (3) [7], 7-O-methyl genistein (4) [7], genistein (5) [14], daidzein (6) [7], glycitin (7) [16], genistin (8) [17], and daidzin (9) [18], was isolated from the Streptomyces strain YIM GS3536, which was isolated from soil sample collected from Yunnan Province, P. R. China. In this paper, we report the isolation and full assignment of 1 H and 13 C NMR chemical shifts for these compounds, and the biological activity of 1.The total methanol extract of the culture filtrate was chromatographed on silica gel using a gradient from chloroform to methanol, then on Sephadex LH-20 in methanol, to afford compounds 1-9.Compound 1 was obtained as pale yellow needles. Analysis of the low-resolution mass spectrum of compound 1 showed a characteristic [M + H + 2] + peak (m/z 321) indicative of the presence of a chlorine atom. Its molecular formula was deduced to be C 16 H 11 ClO 5 based on HR-ESI-MS ([M + H] + 319.0377, calcd 319.0373) and 13 C NMR data. O OH O R 1 R 2 R 3 R 4 1' 5' 3' 4 2 8 6 -9A C B 1: R 1 = OH, R 2 = H, R 3 = OCH 3 , R 4 = Cl; 2: R 1 = R 3 = OH, R 2 = H, R 4 = Cl 3: R 1 = R 4 = H, R 2 = OH, R 3 = OCH 3 ; 4: R 1 = OH, R 2 = R 4 = H, R 3 = OCH 3 5: R 1 = R 3 = OH, R 2 = R 4 = H; 6: R 1 = R 2 = R 4 = H, R 3 = OH 7: R 1 = R 4 = H, R 2 = OCH 3 , R 3 = O-Glc; 8: R 1 = OH, R 2 = R 4 = H, R 3 = O-Glc 9: R 1 = R 2 = R 4 = H, R 3 = O-Glc

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A new isoflavone derivative from Streptomyces sp. YIM GS3536

et al. 2013

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“…The result is consistent with that of Nazir et al [8], who found that 3 -hydroxygenistein was the major product of the biotransformation of genistein by the CYP57B3 from A. oryzae. In addition to the latter type of biotransformation, 3 -hydroxygenistein has also been isolated from fermented soybeans, by A. niger [9] or other bacteria [10]. However, the corresponding CYPs in the microorganisms had not been identified.…”

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Identification of 3′-hydroxygenistein as a potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris

Ding

Chiang

Tzeng

et al. 2015

Process Biochemistry

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“…Kiirzlich haben Umezawa et al [5] bei der Suche nach Substanzen mit blutdrucksenkender Wirkung Genistein sowie Hydroxy-und Methoxyderivate isoliert. Die Autoren halten auch fur diese Isoflavone eine Herkunft aus dem Sojamehl der Nahrlosung fur moglich.…”

Section: Discussionunclassified

Stoffwechselprodukte von Mikroorganismen 6‐Chlorgenistein und 6,3′‐Dichlorgenistein. 164. Mitteilung

König

Krauss

Zähner

1977

Helvetica Chimica Acta

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Metabolites from Microorganisms. 6-Chlorogenistein and 6,3'-Dichlorogenistein SummaryA strain of Streptomyces griseus produced chlorinated metabolites in media containing soybean meal. Two of these metabolites were isolated together with a chlorine free compound which could be identified as the isoflavone genistein (I) by its spectral properties and by comparison with an authentic sample. By NMR. and mass spectroscopy the chlorinated compounds were shown to be 6-chlorogenistein (TI) and 6,3'-dichlorogenistein (111).The 7-glucoside of genistein is a constituent of soybean meal; it is hydrolysed and chlorinated by Streptomyces griseus.Bei der Suche nach chlorhaltigen Metaboliten aus Mikroorganismen fanden wir einen Stamm von Streptomyces griseus, der auf sojamehlhaltiger Nahrlosung ein Gemisch chlorhaltiger Metabolite bildet. Thr Nachweis beim Screening und wahrend der Isolierung erfolgte iiber den Einbau von 3 T l in die lipophilen Fraktionen. Die Auftrennung der Fraktionen an Sephadex LH 20 lieferte die Substanzen I, chlorfrei, I1 und 111, beide chlorhaltig, und ein nicht weiter aufgetrenntes Gemisch chlorhaltiger Nebenkomponenten. In Diinnschichtchromatogrammen liessen sich 1, IT und 111 durch ihre Fluoreszenz-Loschung in UV.-Licht von 350 nm sowie durch Violettfarbung nach Bespriihen mit Eisen(II1)chlorid erkennen. Dadurch konnten die Metabolite auch ohne radioaktive Markierung isoliert werden.Alle drei Verbindungen haben das gleiche UV.-Absorptionsspektrum (Fig. I ) , dessen Maximum bei Zusatz von Natriummethylat eine bathochrome Verschiebung erfahrt. Die 1R.-Spektren sind sehr ahnlich und zeigen breite Hydroxylbanden sowie fur aromatische Verbindungen charakteristische Absorptionen von (C = C)-Valenzschwingungen bei 1600, eine Carbonylabsorption bei 1650 und die (C-0)-Valenzschwingung bei 1250 cm-1 (Fig. 2).Massenspektrometrische Untersuchungen. -a) Substanz I . Das MS. von I weist einen Molekularpik (100% rel. Int.) bei m/e 270 auf (Fig. 3). Eine exakte Massenbe-163.Mitteilung, siehe [I].

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Isolation of isoflavones inhibiting dopa decarboxylase from fungi and streptomyces.

Cited by 50 publications

References 6 publications

A new isoflavone derivative from Streptomyces sp. YIM GS3536

A new isoflavone derivative from Streptomyces sp. YIM GS3536

Identification of 3′-hydroxygenistein as a potent melanogenesis inhibitor from biotransformation of genistein by recombinant Pichia pastoris

Stoffwechselprodukte von Mikroorganismen 6‐Chlorgenistein und 6,3′‐Dichlorgenistein. 164. Mitteilung

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