• Title/Summary/Keyword: (-)-Medicarpin

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Two Isoflavonoid Glucoside Derivatives from Ononis serrata Growing in Egypt

  • Abdel-Kader, Maged S.
    • Natural Product Sciences
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    • v.10 no.6
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    • pp.321-324
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    • 2004
  • The n-butanol soluble fraction of the extract obtained from the whole plants of Ononis serrata afforded the pterocarpan derivative medicarpin-3-O-glucoside and the isoflavone glucoside rothindin. Structures were elucidated by chemical methods, detailed spectral analyses as well as comparison with the literature data.

Isoflavonoids from the Root Cortex of Robinia pseudo-acacia

  • Kwon, Yong-Soo;Jeon, Seung-Ho;Kim, Chang-Min
    • Natural Product Sciences
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    • v.6 no.3
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    • pp.139-141
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    • 2000
  • From the $CHCl_3-fraction$ of the root cortex of Robinia pseudo-acacia, five compounds have been isolated. On the basis of spectral data, these compounds were identified as medicarpin, biochanin A, formononetin, 3'-methoxydaidzein.

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Anti-Helicobacter pylori Compounds from Maackia amurensis

  • Park, Woo Sung;Bae, Ji-Yeong;Kim, Hye Jin;Kim, Min Gab;Lee, Woo-Kon;Kang, Hyung-Lyun;Baik, Seung-Chul;Lim, Kyung Mook;Lee, Mi Kyeong;Ahn, Mi-Jeong
    • Natural Product Sciences
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    • v.21 no.1
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    • pp.49-53
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    • 2015
  • Eight isoflavonoid compounds were isolated from the EtOAc fraction of Maackia amurensis which had shown the highest anti-Helicobacter pylori activity among the fractions, using medium pressure liquid chromatography and recrystallization. Based on the spectroscopic data including $^1H$-NMR, $^{13}C$-NMR, HMBC and MS data, the chemical structures of the isolates were determined to be (-)-medicarpin (1), afromosin (2), formononetin (3), tectorigenin (4), prunetin (5), wistin (6), tectoridin (7) and ononin (8). Anti-H. pylori activity of each compound was evaluated with broth dilution assay. As a result, (-)-medicarpin (1), tectorigenin (4) and wistin (6) showed anti-H. pylori activity. (-)-Medicarpin (1) exhibited the most potent growth inhibitory activity against H. pylori with the minimal inhibitory concentration $(MIC)_{90}$ of $25{\mu}M$, and tectorigenin (4) with $MIC_{90}$ of $100{\mu}M$ ranked the second. This is the first study to show the anti-H. pylori activity of M. amurensis, and it is suggested that the stem bark of M. amurensis or the EtOAc fraction or the isolated compounds can be a new natural source for the treatment of H. pylori infection.

Medicarpin induces lipolysis via activation of Protein Kinase A in brown adipocytes

  • Imran, Khan Mohammad;Yoon, Dahyeon;Lee, Tae-Jin;Kim, Yong-Sik
    • BMB Reports
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    • v.51 no.5
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    • pp.249-254
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    • 2018
  • Natural pterocarpan Medicarpin (Med) has been shown to have various beneficial biological roles, including inhibition of osteoclastogenesis, stimulation of bone regeneration and induction of apoptosis. However, the effect of the Med on lipolysis in adipocytes has not been reported. Here, we show the effect of Med on lipolysis in different mouse adipocytes and elucidate the underlying mechanism. We observed that Med treatment promoted release of glycerol in the media. Differentiated mouse brown adipose tissue cells were treated with Med. RNA-Seq analysis was performed to elucidate the effect of med and subsequently was confirmed by qRT-PCR and western blotting analyses. Med treatment increased both protein and gene expression levels of hormone-sensitive lipase (Hsl) and adipose triglyceride lipase (Atgl), which are two critical enzymes necessary for lipolysis. Mechanistic study showed that Med activates Protein Kinase A (PKA) and phosphorylates Hsl at PKA target position at $Serine^{660}$. Silencing of PKA gene by short interfering RNA attenuated the Med-induced increase in glycerol release and Hsl phosphorylation. The results unveil that Med boosts lipolysis via a PKA-dependent pathway in adipocytes and may provide a possible avenue of further research of Med mediated reduction of body fat.

Flavonoids from Spatholobus Suberectus

  • Yoon, Jeong-Seon;Sung, Sang-Hyun;Park, Jong-Hee;Kim, Young-Choong
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.589-593
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    • 2004
  • Two pterocarpans [(6aR,11aR)-maackiain, (6aR,11aR)-medicarpin], one flavanone [(2S)-7-hydroxy-G-methoxy-flavanone], one isoflavan (sativan) and two isoflavones (pseudobaptigenin, genistein) were isolated from the Spatholobus suberectus (Leguminosae). Their chemical structures were determined by comparison of their spectroscopic parameters of CD, ElMS, 1D-NMR and 2D-NMR with those reported in the literatures. All of these compounds are reported for the first time from this plant through the present study.

Anti-inflammatory Constituents of Robinia pseudoacacia Root Bark (아까시나무 뿌리껍질의 항염증활성물질)

  • Kang, Dong-Min;Park, Woo Sung;Kim, Hye-Jin;Jeong, Woo-Jin;Kang, Kwon Kyoo;Ahn, Mi-Jeong
    • Korean Journal of Pharmacognosy
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    • v.53 no.1
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    • pp.8-15
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    • 2022
  • Robinia pseudoacacia L. (Leguminosae) is widely distributed in Asia, North America and Europe. The root bark has been traditionally used for hemostasis, arthritis and hypertension. Therefore, this study was conducted to identify the biological activity and the bioactive constituents of the root bark. We found that the methanol extract obtained from the root bark of R. pseudoacacia reduced the level of ROS and NO production in LPS-induced inflammation of RAW 264.7 cell line. Among the fractions, methylene chloride fraction showed the highest inhibitory activity against the inflammation. Seven constituents (1-7) were isolated from this fraction, and the chemical structures were determined to be medicarpin (1), (-)-vestitol (2), indole 3-carboxaldehyde (3), 3-acetylindole (4), liquiritigenin (5), 4(1H)-quinolone (6) and 8-methoxyononin (7). Among the isolates, medicarpin (1), (-)-vestitol (2), 3-acetylindole (4) and liquiritigenin (5) inhibited ROS and NO production in a dose-dependent manner. This is the first study to show the anti-inflammatory activity of the root bark of R. pseudoacacia, and it is suggested that the four constituents (1, 2, 4, and 5) could play a role in the biological activity.

Constituents of the Roots of Pueraria Iobata Inhibit Formation of Advanced Glycation End Products (AGEs)

  • Kim, Jong-Min;Lee, Yun-Mi;Lee, Ga-Young;Jang, Dae-Sik;Bae, Ki-Hwan;Kim, Jin-Sook
    • Archives of Pharmacal Research
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    • v.29 no.10
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    • pp.821-825
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    • 2006
  • Two isoflavone C-glucosides, puerarin (1) and PG-3 (2), a but-2-enolide, $({\pm})-puerol$ B (3), two isoflavone O-glucosides, daidzin (4) and genistin (5), and three pterocarpans, (-)-medicarpin (6), (-)-glycinol (7) and (-)-tuberosin (8), were isolated from a MeOH extract of the roots of Pueraria Iobata, using an in vitro bioassay based on the inhibition of the formation of advanced glycation end products (AGEs) to monitor chromatographic fractionation. The structures of 1-8 were determined by spectroscopic data interpretation, particularly by 1D- and 2D-NMR studies, and by comparison of these data with values in the literature. All of the isolates (1-8) were evaluated for their inhibitory activity on AGEs formation in vitro. Of these, puerarin (1), PG-3 (2), and $({\pm})-puerol$ B (3) exhibited more potent inhibitory activity than the positive control aminoguanidine.