First finding of Daidzein 7- O -phosphate and Genistein 7- O -phosphate that are hydrolyzed by sulfatase

Kanakubo, Akira; Koga, Kazushi; Isobe, Mitsuaki; Fushimi, Takashi; Saitoh, Takanobu; Ohshima, Yoshifumi; Tsukamoto, Yoshinori

doi:10.1016/s0040-4020(01)00863-8

Cited by 23 publications

(12 citation statements)

References 14 publications

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“…15) The concentrated EtOAc layer (16 g) was subjected to column chromatography over silica gel and eluted with a gradient of i-Pr 2 O-MeOH (5 : 1 to pure MeOH) to give nine fractions. Purification of fraction 2 by silica gel column with CHCl 3 -MeOH (9 : 1) furnished daidzein (2 mg), 32) protocatechuic acid (6 mg), 33) protocatechuic acid methyl ester (11 mg), 34) 4-hydroxybenzoic acid (5 mg), 9) and pcoumaric acid (1 mg). 9) Further separation of fraction 3 on silica gel column with a gradient of CHCl 3 -MeOH (9 : 1 to pure MeOH) yielded begonanline (1, 5 mg), methyl (S)-glycerate (3, 9 mg), and (Ϫ)-catechin (13, 998 mg).…”

Section: )mentioning

confidence: 99%

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Cytotoxic and Anti-HIV Principles from the Rhizomes of Begonia nantoensis

Lin

et al. 2004

Chem. Pharm. Bull.

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Section: )mentioning

confidence: 99%

“…All intensity measurements were performed using graphite monochromated Mo-Ka radiation (lϭ0.71073 Å). Cucurbitacin E (6), C 32 , 2q max ϭ56.66°, crystal dimensions 0.30ϫ0.20ϫ0.10 mm 3 . The crystal structure was solved by a direct method.…”

Section: )mentioning

confidence: 99%

Cytotoxic and Anti-HIV Principles from the Rhizomes of Begonia nantoensis

Lin

et al. 2004

Chem. Pharm. Bull.

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“…The EtOAc, n-BuOH, and water fractions were analyzed by HPLC-DAD and all of the increased peaks, newly appearing and decreased peaks were found in the ethyl acetate fraction. HPLC-DAD-guided fractionation of the EtOAc fraction produced five pure compounds, and their structures were identified by MS, 1 H-, and 13 C-NMR and compared with published data (Kinjo et al, 1987;Pouchert and Behnke J, 1993a;Pouchert and Behnke, 1993b;Kanakubo et al, 2001;Choi et al, 2010).…”

Section: Resultsmentioning

confidence: 99%

Bioconversion Constituents of Galgeun-tang Fermented by Lactobacillus plantarum

Min¹,

Kim²,

Jeong³

et al. 2011

Korean Journal of Medicinal Crop Science

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: Galgeun-tang (GGT) is a traditional medicinal formula that is widely prescribed to treat cold, asthma, and hives in Korea. Fermented herbal medicines can be made more effective than normal herbal medicines by increasing the absorption and bioavailability of the active compounds. In this study, we fermented Galgeun-tang to produce bioconversion constituents using Lactobacillus plantarum (GGT144), and found that four peaks were decreased, three peaks were increased and two new peaks appeared in the HPLC-DAD chromatogram. After HPLC-DAD-guided fractionation of the newly-appearing compounds (1 and 5) and the increased (6, 7, and 9) compounds, the structure of the compounds was determined using NMR and MS. Using this approach the compounds were identified to be pyrogallol (1), daidzein (5), liquiritigenin (6), cinnamyl alcohol (7), and formononetin (9), respectively. In addition, the decreased compounds were identified to be daidzin (2), liquiritin (3), ononin (4), and cinnam aldehyde (8) using HPLC-DAD analysis with standard compounds. The high performance liquid chromatography method was used to quantify the nine constituents in GGT and GGT144. All calibration curves of the standard compounds displayed excellent linearity with a R 2 > 0.9968.

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“…Acylation of a hydroxy moiety as a sulfate or phosphate usually leads to a downfield shift of the adjacent carbon atom [13]. As shown in Table 1, large downfield shifts (bottom row in Table 1) were observed for C-6 00 in the glucose moiety of puerarin, from 61.5 to 64.9 ppm, implying that the transferred sulfate or phosphate unit was attached to C-6 00 in the glucose moiety of puerarin.…”

Section: Isolation and Purification Of Transformed Productmentioning

confidence: 95%

Biotransformation of puerarin into puerarin-6″-O-phosphate by Bacillus cereus

Gao

Yang

et al. 2012

Journal of Industrial Microbiology and Biotechnology

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The biotransformation of puerarin catalyzed by Bacillus cereus NT02 was studied. A primary screening was carried out using 307 strains of bacteria isolated from soil which were able to grow in the presence of puerarin. Strain NT02, identified as B. cereus, was able to convert puerarin into puerarin-6″-O-phosphate. Under the optimum conditions, resting cells of B. cereus NT02 converted 27% of added 0.4 g/l puerarin into puerarin-6″-O-phosphate that was characterized by MS, ¹³C NMR, ³¹P NMR. The activity of puerarin-6″-O-phosphate was 25 times higher than that of puerarin in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging system. The water solubility of puerarin-6″-O-phosphate was 85.4 times higher than that of puerarin.

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First finding of Daidzein 7- O -phosphate and Genistein 7- O -phosphate that are hydrolyzed by sulfatase

Cited by 23 publications

References 14 publications

Cytotoxic and Anti-HIV Principles from the Rhizomes of Begonia nantoensis

Cytotoxic and Anti-HIV Principles from the Rhizomes of Begonia nantoensis

Bioconversion Constituents of Galgeun-tang Fermented by Lactobacillus plantarum

Biotransformation of puerarin into puerarin-6″-O-phosphate by Bacillus cereus

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