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Official Journal of the Japan Wood Research Society

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5α-Reductase inhibitory compounds produced by polymerization of resveratrol with horseradish peroxidase

Abstract

To produce 5α-reductase inhibitory compounds, resveratrol was enzymatically oxidized in a horseradish peroxidase (HRP)/H2O2 system. Ethyl acetate extract of the oxidation products showed strong 5α-reductase inhibitory activity with 10%–15% organic solvents in the system, whereas without organic solvent little inhibitory activity was exhibited. The optimum pH of enzymatic oxidation for acquisition of the inhibitory activity was 4.5. The inhibitory compounds were isolated and identified as resveratroltrans-dehydrodimer and resveratrolcis-dehydrodimer by comparing with published nuclear magnetic resonance data. The two resveratrol dehydrodimers have stronger inhibitory activity than natural resveratrol dimers and trimers found inShorea species.

References

  1. Bruchovsky N, Wilson JD (1968) The conversion of testosterone to 5α-androstan-17β-o1-3-one by rat prostate in vivo and in vitro. J Biol Chem 243:2012–2021

    CAS  PubMed  Google Scholar 

  2. Stephan VF (1996) Inhibitors of 5α-reductase. Curr Pharm Des 2:59–84

    Google Scholar 

  3. Hirano Y, Kondo R, Sakai K (2001) Compounds inhibitory to rat liver 5α-reductase from tropical commercial wood species: resveratrol trimers from melapi (Shorea sp.) heartwood. J Wood Sci 47:308–312

    Article  CAS  Google Scholar 

  4. Potter DW, Miller DW, Hinson JA (1985) Identification of acetaminophen polymerization products catalyzed by horseradish peroxidase. J Biol Chem 260:12174–12180

    CAS  PubMed  Google Scholar 

  5. Breuil AC, Adrian M, Pirio N, Meunier P, Bessis R, Jeandet P (1998) Metabolism of stilbene phytoalexines byBotrytis cinerea. 1. Characterization of a resveratrol dehydrodimer. Tetrahed Lett 39:537–540

    Article  CAS  Google Scholar 

  6. Kurihara H, Kawabata J, Ichikawa S, Mishima M, Mizutani J (1991) Oligostilbenes fromCarex kobomugi. Phytochemistry 30:649–653

    Article  CAS  Google Scholar 

  7. Tanaka T, Ito T, Ido Y, Son TK, Nakaya K, Iinuma M, Ohyama M, Chelladurai V (2000) Stilbenoids in the stem bark ofHopea parviflora. Phytochemistry 53:1015–1019

    Article  CAS  PubMed  Google Scholar 

  8. Shimizu K, Hukuda M, Kondo R, Sakai K (2000) The 5α-reductase inhibitory components from heartwood ofArtocapus incisus; structure-activity investigations. Planta Med 66:16–19

    Article  CAS  PubMed  Google Scholar 

  9. Liangcake P, Pryce RJ (1977) A new class of phytoalexins from grapevines. Experientia 33:151–152

    Article  Google Scholar 

  10. Liangcake P, Pryce RJ (1977) Oxidative dimerisation of 4-hydroxystilbenes in vitro: production of a grapevine phytoalexin mimic. JCS Chem Commun 1412:208–210

    Article  Google Scholar 

  11. Liang T, Liao S (1992) Inhibition of steroid 5α-reductase by specific aliphatic unsaturated fatty acids. Biochem J 285:557–562

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. McConnell JD, Wilson JD, George FW, Geller J, Pappas F, Stoner E (1992) Finasteride, an inhibitor of 5α-reductase, suppresses prostatic dihydrotestosterone in men with benign prostatic hyperplasia. J Clin Endocrinol Metab 74:505–508

    CAS  PubMed  Google Scholar 

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Correspondence to Yoshio Hirano.

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Hirano, Y., Kondo, R. & Sakai, K. 5α-Reductase inhibitory compounds produced by polymerization of resveratrol with horseradish peroxidase. J Wood Sci 48, 64–68 (2002). https://doi.org/10.1007/BF00766240

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  • DOI: https://doi.org/10.1007/BF00766240

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