• Title/Summary/Keyword: dalbergioidin

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Inhibitory Effect of Dalbergioidin Isolated from the Trunk of Lespedeza cyrtobotrya on Melanin Biosynthesis

  • Baek, Seung-Hwa;Kim, Jin-Hee;Kim, Dong-Hyun;Lee, Chan-Yong;Kim, Ji-Young;Chung, Dae-Kyun;Lee, Choong-Hwan
    • Journal of Microbiology and Biotechnology
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    • v.18 no.5
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    • pp.874-879
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    • 2008
  • Tyrosinase is a key enzyme for melanin biosynthesis, and hyperpigmentation disorders are associated with abnormal accumulation of melanin pigments, which can be reduced by treatment with depigmenting agents. The methanol extract of Lespedeza cyrtobotrya $M_{IQ}$ showed inhibitory activity against mushroom tyrosinase. The active compound was purified from the methanol extract of L. cyrtobotrya, followed by several chromatographic methods, and identified as dalbergioidin (DBG) by spectroscopic methods. The results showed that DBG exhibited tyrosinase inhibitory activity with an $IC_{50}$ of $20\;{\mu}M$. The kinetic analysis of tyrosinase inhibition revealed that DBG acted as a noncompetitive inhibitor. In addition, DBG showed a melanin biosynthesis inhibition zone in the culture plate of Streptomyces bikiniensis that has commonly been used as an indicator organism. Furthermore, $27\;{\mu}M$ DBG decreased more than 50% of melanin contents on the pigmentation using the immortalized mouse melanocyte, melan-a cell.

Melanin Synthesis Inhibition and Radical Scavenging Activities of Compounds Isolated from the Aerial Part of Lespedeza cyrtobotrya

  • Lee, Mi-Yeon;Kim, Jin-Hee;Choi, Jung-Nam;Kim, Ji-Young;Hwang, Geum-Sook;Lee, Choong-Hwan
    • Journal of Microbiology and Biotechnology
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    • v.20 no.6
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    • pp.988-994
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    • 2010
  • The EtOAc fraction of Lespedeza cyrtobotrya showed mushroom tyrosinase inhibitory and radical scavenging activities. Four active compounds were isolated based on Sephadex LH-20 chromatography and HPLC, and the structures were elucidated, on the basis of their LC-MS and NMR spectral data, as 2-(2,4-dihydroxyphenyl)-6-hydroxybenzofuran (1), eriodictyol-7-O-glucopyranoside (2), haginin A (3), and dalbergioidin (4), respectively. Compound (1) showed mushroom tyrosinase inhibitory activity with an $IC_{50}$ value of $5.2\;{\mu}M$ and acted as a competitive inhibitor. Furthermore, $37.3\;{\mu}M$ of compound 1 reduced 50% of the melanin content on human melanoma (MNT-1) cells. The radical scavenging activities of compounds 1, 2, 3, and 4 were shown to have $IC_{50}$ values of 11.0, 24.5, 9.0, and $36.5\;{\mu}M$, respectively, in an ABTS system and $IC_{50}$ values of 42.7, 36.0, 37.7, and $61.7\;{\mu}M$, respectively, in a DPPH system. The mushroom tyrosinase inhibitory activity of the EtOAc fraction of Lespedeza cyrtobotrya was contributed by compounds 1, 3, and 4, and its radical scavenging activity was contributed by compounds 1-4.

Cytotoxic Isoflavanones from Uraria clarkei

  • Huang, Xiang-Zhong;Bai, Xi-Shan;Liang, Hui;Wang, Chao;Li, Wen-Juan;Guo, Jun-Ming;Jiang, Zhi-Yong
    • Bulletin of the Korean Chemical Society
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    • v.34 no.5
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    • pp.1421-1424
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    • 2013
  • Two new isoflavanones, (3R) 5,7,3',4'-tetrahydroxy-2'-methoxyisoflavanone (1) and (3R) 5',8-di-(${\gamma}$,${\gamma}$-dimethylallyl)-2',5-dihydroxyl-4',7-dimethoxyl-isoflavanone (2), were isolated from Uraria clarkei, together with two known compounds dalbergioidin (3), 5,7-dihydroxy-2',4'-dimethoxyisoflavanone (4). The structures involving the absolute configuration of the new compounds were well elucidated by MS, IR, UV, CD, 1D and 2D NMR analyses. Cytotoxicity of the four compounds were assessed, results suggested that compound 2 possessed well cytotoxic activity, against the Hela, K562, and HL60 cell lines with $IC_{50}$ values of 28.0, 40.6 and $35.1{\mu}M$, respectively.