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In this study we investigated the inhibitory effects and possible mechanisms of action of 8'-hydroxydaidzein and 3'-hydroxydaidzein, two ortho-dihydroxyisoflavone derivatives from Korean fermented soybean paste, on melanogenesis in B16 murine melanoma cells. The two hydroxydaidzeins reduced melanin synthesis comparably to treatment with kojic acid, a proven whitening agent, in B16 melanoma cells. Furthermore, when in vitro human skin equivalents were treated with the hydroxydaidzeins, the levels of melanogenesis were significantly reduced relative to a kojic acid control. The RT-PCR results demonstrated that depigmentation was due to transcriptional repression of several melanogenesis genes, including microphthalmia-associated transcription factor (MITF), by the hydroxydaidzeins. The immunoblotting results confirmed that diminution of MITF expression subsequently decreased expression of tyrosinase, and tyrosinase-related proteins 1 and 2. Cumulatively, these results suggest that hydroxydaidzeins would be potent attenuators of melanin synthesis as well as effective inhibitors of hyperpigmentation in human skin.

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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.