Metabolic Activities of Ginsenoside Rb1, Baicalin, Glycyrrhizin and Geniposide to Their Bioactive Compounds by Human Intestinal Microflora

Yim, Jang-Shim; Kim, Young-Suk; Moon, Sang-Kwan; Cho, Ki-Ho; Bae, Hyung-Sup; Kim, Jung-Jin; Park, Eunkyung; Kim, Dong-Hyun

doi:10.1248/bpb.27.1580

Cited by 79 publications

(57 citation statements)

References 18 publications

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“…These constituents exhibit anti-inflammatory, antiallergic, anti-oxidant, and hepatoprotective, and antitumor effects (Chou et al, 2003;Jang et al, 2003;Lim, 2003;Kim et al, 2005). These components are poorly absorbed from the gastrointestinal tract in its native form due to their hydrophilic properties and must be hydrolyzed by intestinal microflora in the intestine to their aglycones in human and rats (Akao et al, 2000;Yim et al, 2004). The absorbed metabolite, baicalein, is subsequently conjugated to baicalin in the gut mucosae by UDP-glucuronyl transferase and approximately half of the conjugate is excreted back into the gut.…”

Section: Introductionmentioning

confidence: 99%

Metabolism of Wogonoside by Human Fecal Microflora and Its Anti-pruritic Effect

Trinh¹,

Jang²,

Han³

et al. 2009

Biomolecules and Therapeutics

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-To understand the relationship between the metabolism of wogonoside from the rhizome of Scutellaria baicalensis, and its anti-pruritic effect, we anaerobically incubated it with human fecal microflora, identified its metabolite identified, and investigated its anti-pruritic effect in compound 48/80 or histamineinduced pruritic mice. Wogonoside was metabolized to wogonin, with metabolic activity of 6.9 ± 5.1 nmol/h/ mg wet weight of fecal microflora. Orally administered wogonoside had more potent anti-scratching behavioral effect in compound 48/80 or histamine-treated mice than intraperitoneally treated one, apart from orally administered its metabolite, wogonin, which was more potent than the orally administered one. Wogonoside showed more potent anti-pruritic effects when administered at 5 h prior to the pruritic agent treatment than when administered at 1 h before. However, wogonin orally administered 1 h before the treatment with pruritic agents showed a more potent anti-pruritic effect than when treated at 5 h before. Orally administered wogonoside may be metabolized to wogonin in the intestine and its anti-scratching behavioral effect may be dependent on its metabolism by intestinal microflora.

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Section: Introductionmentioning

confidence: 99%

Metabolism of Wogonoside by Human Fecal Microflora and Its Anti-pruritic Effect

Trinh¹,

Jang²,

Han³

et al. 2009

Biomolecules and Therapeutics

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“…Since the intestinal microflora vary among individuals, about 20% of people cannot efficiently, or even at all, transform ginsenosides. 10) This may explain why some people using ginseng achieved their expectations while others did not. Moreover, deglycosylated ginsenosides show more efficient activity than the undeglycosylated forms.…”

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Korean Ginseng Berry Fermented by Mycotoxin Non-producing <i>Aspergillus niger</i> and <i>Aspergillus oryzae</i>: Ginsenoside Analyses and Anti-proliferative Activities

Ahn

Kim

et al. 2016

Biological & Pharmaceutical Bulletin

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To transform ginsenosides, Korean ginseng berry (KGB) was fermented by mycotoxin non-producing Aspergillus niger and Aspergillus oryzae. Changes of ginsenoside profile and anti-proliferative activities were observed. Results showed that A. niger tended to efficiently transform protopanaxadiol (PPD) type ginsenosides such as Rb1, Rb2, Rd to compound K while A. oryzae tended to efficiently transform protopanaxatriol (PPT) type ginsenoside Re to Rh1 via Rg1. Butanol extracts of fermented KGB showed high cytotoxicity on human adenocarcinoma HT-29 cell line and hepatocellular carcinoma HepG2 cell line while that of unfermented KGB showed little. The minimum effective concentration of niger-fermented KGB was less than 2.5 µg/mL while that of oryzae-fermented KGB was about 5 µg/mL. As A. niger is more inclined to transform PPD type ginsenosides, niger-fermented KGB showed stronger anti-proliferative activity than oryzaefermented KGB.

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“…Deglycosylation of ginsenosides in the human body varies greatly depending upon the enzyme activity of microbial flora in the intestines. Since this activity varies between individuals, the medicinal effects of ginseng also vary significantly (39). To understand the exact pharmacological effects of the deglycosylated ginsenosides, a pure compound of deglycosylated ginsenoside should be used or administered.…”

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confidence: 99%

Identification and Characterization of the Rhizobium sp. Strain GIN611 Glycoside Oxidoreductase Resulting in the Deglycosylation of Ginsenosides

Kim

Seo

et al. 2012

Appl Environ Microbiol

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Using enrichment culture, Rhizobium sp. strain GIN611 was isolated as having activity for deglycosylation of a ginsenoside, compound K (CK). The purified heterodimeric protein complex from Rhizobium sp. GIN611 consisted of two subunits with molecular masses of 63.5 kDa and 17.5 kDa. In the genome, the coding sequence for the small subunit was located right after the sequence for the large subunit, with one nucleotide overlapping. The large subunit showed CK oxidation activity, and the deglycosylation of compound K was performed via oxidation of ginsenoside glucose by glycoside oxidoreductase. Coexpression of the small subunit helped soluble expression of the large subunit in recombinant Escherichia coli. The purified large subunit also showed oxidation activity against other ginsenoside compounds, such as Rb1, Rb2, Rb3, Rc, F2, CK, Rh2, Re, F1, and the isoflavone daidzin, but at a much lower rate. When oxidized CK was extracted and incubated in phosphate buffer with or without enzyme, (S)-protopanaxadiol [PPD(S)] was detected in both cases, which suggests that deglycosylation of oxidized glucose is spontaneous.

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Metabolic Activities of Ginsenoside Rb1, Baicalin, Glycyrrhizin and Geniposide to Their Bioactive Compounds by Human Intestinal Microflora

Cited by 79 publications

References 18 publications

Metabolism of Wogonoside by Human Fecal Microflora and Its Anti-pruritic Effect

Metabolism of Wogonoside by Human Fecal Microflora and Its Anti-pruritic Effect

Korean Ginseng Berry Fermented by Mycotoxin Non-producing <i>Aspergillus niger</i> and <i>Aspergillus oryzae</i>: Ginsenoside Analyses and Anti-proliferative Activities

Identification and Characterization of the Rhizobium sp. Strain GIN611 Glycoside Oxidoreductase Resulting in the Deglycosylation of Ginsenosides

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