• 약학회지
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• 제47권5호
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• pp.283-287
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• 2003

Isoflavonoids are abundant in natural products and reported with many synthetic variations. However, relatively few quinolone analogs of isoflavonoids have been described. As part of our endeavor to pursue biologically active novel isoflavonoids, we report an efficient synthetic route for quinolone analogs of isoflavonoids. The key intermediate, 2'-aminochalcone 2 was obtained from substituted aniline and cyclized to afford quinolones 6, 8a, and 8b.

• 한국미생물·생명공학회지
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• 제21권2호
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• pp.139-143
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• 1993

Three isoflavonoids having tyrosinase-inhibiting activity were isolated from the culture filtrate of Streptomyces sp. 20747. Their structures were determined by UV, EI-MS, 1H-NMR, 13C-NMR to be daidzein, daidzein 7-rhamnoside, and genistein 7-rhamnoside, which were competitive with substrate and had IC50 value of 14, 19, and 16 ng/ml, respectively to mushroom tyrosinase and did not inhibit melanin production of Streptomyces bikiniensis. Soybean meal as well as peptone were found to be a good nitrogen source for tyrosinase-inhibiting isoflavonoids production, susgesting that soybean meal is not the origin of tyrosinase inhibiting isoflavonoids formation in Streptomyces sp. 20747 strain.

• Archives of Pharmacal Research
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• 제26권9호
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• pp.756-762
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• 2003

In the current study, our research focused on the estrogenic activity of isoflavonoids, mainly genistein, biochanin A and daidzein. Genistein enhanced the reporter gene expression of MCF-7-ERE-Luc cells, at a concentration as low as 10 nM, with a concentration of 100 nM the achieved gene expression effects were similar to those of 10 pM 17$\beta$-estradiol. Based on the estrogenic activities of biochanin A and daidzein, hydroxyl groups at the 4 and 5 positions are needed for the maximal effect of the genistein. The estrogenic effects of these isoflavonoids were inhibited by the concomitant treatment with tamoxifen. The data showed that the estrogenic effects of isoflavonoids were mediated through estrogen receptors. When the isoflavonoids were tested as mixtures, the estrogenic effects were lower than the arithmetic sum of those induced by each individual isoflavonoid. The estrogenic potency of each isoflavonoid was presented at EC50 levels with a 17$\beta$-estradiol equivalent concentration (EEQ) based on the dose response of each chemical. The EC50s and EEQs of genistein, biochanin A and daidzein were 4.15, 0.89 and 0.18 $\mu$M, and 15.0, 5.12 and 1.83 $\mu$ M/M, respectively. Our data clearly demonstrated that the pERE-luciferase reporter gene assay was suited for the sensitive and quantitative measurement, and large scale screening, of the estrogenicity of chemicals in vitro.

• Archives of Pharmacal Research
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• 제17권1호
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• pp.31-35
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• 1994

For comparing with flavones/flavonols, isoflavonoids isolated from Pueraria radix and chemically synthesized from biochanin A were evaluated for the antiinflammatory activity using mouse ear edema test, Isoflavonoids such as daildzein and puerarin hsowed the significant antiinflammatory activity at a dose of 2 mg/mouse, although their activity was generally less than that of flavones/flavonols. 7-O-Substitution of biochanin A was not facorable for the antiinflammatory activity.

• Molecules and Cells
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• 제37권2호
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• pp.172-177
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• 2014

A glycosyltransferase, YjiC, from Bacillus licheniformis has been used for the modification of the commercially available isoflavonoids genistein, daidzein, biochanin A and formononetin. The in vitro glycosylation reaction, using UDP-${\alpha}$-D-glucose as a donor for the glucose moiety and aforementioned four acceptor molecules, showed the prominent glycosylation at 4' and 7 hydroxyl groups, but not at the $5^{th}$ hydroxyl group of the A-ring, resulting in the production of genistein 4'-O-${\beta}$-D-glucoside, genistein 7-O-${\beta}$-D-glucoside (genistin), genistein 4',7-O-${\beta}$-D-diglucoside, biochanin A-7-O-${\beta}$-D-glucoside (sissotrin), daidzein 4'-O-${\beta}$-D-glucoside, daidzein 7-O-${\beta}$-D-glucoside (daidzin), daidzein 4', 7-O-${\beta}$-D-diglucoside, and formononetin 7-O-${\beta}$-D-glucoside (ononin). The structures of all the products were elucidated using high performance liquid chromatography-photo diode array and high resolution quadrupole time-of-flight electrospray ionization mass spectrometry (HR QTOF-ESI/MS) analysis, and were compared with commercially available standard compounds. Significantly higher bioconversion rates of all four isoflavonoids was observed in both in vitro as well as in vivo bioconversion reactions. The in vivo fermentation of the isoflavonoids by applying engineered E. coli $BL21(DE3)/{\Delta}pgi{\Delta}zwf{\Delta}ushA$ overexpressing phosphoglucomutase (pgm) and glucose 1-phosphate uridyltransferase (galU), along with YjiC, found more than 60% average conversion of $200{\mu}M$ of supplemented isoflavonoids, without any additional UDP-${\alpha}$-D-glucose added in fermentation medium, which could be very beneficial to large scale industrial production of isoflavonoid glucosides.

• 생약학회지
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• 제22권1호
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• pp.13-17
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• 1991

Dimethyltectorigenin, irisflorentin, muningin and iristectorigenins A and B were isolated from the rhizomes of Belamcanda chinensis.

• Food Science and Biotechnology
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• 제14권3호
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• pp.399-404
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• 2005

The aim of this study was to investigate the in vitro antioxidant profiles of genistein and other isoflavonoids. The reactivity of genistein towards stable radical and reactive oxygen species including ${\bullet}\;ABTS^+$, ${\bullet}{O_2}^-$, $H_2O_2$ and HOCl has been investigated, and the effects were compared with other isoflavonoids and antioxidants. All the tested isoflavonoids showed remarkable ${\bullet}\;ABTS^+$ scavenging activity and genistein was more potent than BHT and ascorbic acid. Genistein was more effective in scavenging hypochlorous acid than superoxide and hydrogen peroxide. At $10\;{\mu}M$ concentrations of genistein and genistin showed about 90% inhibitory effect on HOCl, while BHT and ascorbic acid showed lower than 50% inhibitory effect. Moreover, genistein could inhibit plasmid DNA cleavage, protein degradation and cell death from HOCl attack, while daidzein, BHT and ascorbic acid could not protect them effectively. These results suggest that genistein is a more potent radical scavenger than other isoflavonoids, and it can remarkably reduce cellular damage induced by HOCl.

• Natural Product Sciences
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• 제16권4호
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• pp.211-216
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• 2010

A new 3-indolyl propionate alkaloid; (-) abrine (1), was isolated from the alcohol extract of Erythrina caffra stem bark together with the alkaloid (-) hypaphorine (2). Phytochemical investigation of the chloroform extract led to the isolation of one fatty alcohol; 1-octacosanol, isolated for the first time from genus Erythrina, two dienoid alkaloids; erythraline and erysodine, and three isoflavonoids; 3S (+) 2'-O-methylphaseollidinisoflavan (3), (6aR, 11aR)- 3-hydroxy-10-dimethylallyl-9-methoxypterocarpan, known as sandwicensin (4) and 3R (-) rythbidin A (5). It is worth mentioning that this is the first report for the isolation of these isoflavonoids from E. caffra. The absolute configuration of 3S (+) 2'-O-methylphaseollidinisoflavan (3) was not previously reported. The isolated isoflavonoids showed promising antibacterial activity against Staphylococcus aureus.

• 임산에너지
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• 제20권2호
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• pp.28-33
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• 2001

Bacillus licheniformis의 액체배지를 부탄올(butanol)로 추출한 후 헥산(n-hexane), 에틸아세테이트(EtOAc)등의 용매를 사용하여 순차 연속추출하여 분획하였다. 이중 에틸아세데이트 가용부에 대해서 칼럼 크로마토그라피법을 사용하여 물질을 분리하였으며, 여기서 단리되어진 화합물들을 Mass, NMR등의 분광학적 방법을 사용하여 그 화학구조를 조사한 결과, 이소플라보노이드인 diadzein, genistein 그리고 그 배당체인 genistin으로 각각 동정하였다.

• Natural Product Sciences
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• 제17권3호
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• pp.206-211
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• 2011

High-performance liquid chromatography coupled to an online $ABTS^+$-based assay (online HPLC-$ABTS^+$) system was used to determine the principal antioxidants in Cudrania tricuspidata fruits. Six prenylated isoflavonoids (1 - 6) were isolated from C. tricuspidata fruits according to the online HPLC-$ABTS^+$ system. The structures of isolated compounds, alpiniumisoflavone (1), 6,8-diprenylorobol (2), 6,8-diprenylgenistein (3), pomiferin (4), 4'-methylalpiniumisoflavone (5), and osajin (6) were identified by their retention time, UV spectra, ESI-MS, and NMR data. Among these compounds, 6,8-diprenylorobol (2) and pomiferin (4) reduced A2E photooxidation in a dose dependent manner.