Skip to main content

Official Journal of the Japan Wood Research Society

  • Original Article
  • Published:

Compounds inhibitory to rat liver 5α-reductase from tropical commercial wood species: resveratrol trimers from melapi (Shorea sp.) heartwood


5α-Reductase inhibitory activity of methanol extracts of the heartwood of 13 tropical wood species were examined. Strong 5α-reductase inhibitory activity was observed withShorea species. From melapi (Shorea sp.), two known resveratrol trimers, vaticanol A and ampelopsin C, and two novel trimers were isolated as active compounds. The structures of the two novel resveratrol trimers were elucidated by one- and two-dimensional nuclear magnetic resonance spectroscopic analyses, including1H-1HCOSY, HMQC, and HMBC. The compounds were named melapinol A and melapinol B. There were no significant differences among the 5α-reductase inhibitory activities of the four resveratrol trimers, which were significantly stronger than those ofα-linolenic acid and epigallocatechin gallate, known 5α-reductase inhibitors.


  1. Bruchovsky N, Wilson JD (1968) The conversion of testosterone to 5α-androstan-17β-ol-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 Design 2:59–84

    Google Scholar 

  3. Liang T, Heiss CE (1981) Inhibition of 5α-reductase, receptor binding, and nuclear uptake of androgens in the prostate by a 4-methyl-4-aza-steroid. J Biol Chem 256:7998–8005

    CAS  PubMed  Google Scholar 

  4. McConnell JD, Wilson JD (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 

  5. Price VH (1999) Treatment of hair loss. N Engl J Med 341:964–973

    Article  CAS  PubMed  Google Scholar 

  6. Tanaka T, Ito T, Nakaya K, Iinuma M, Riswan S (2000) Oligostilbenoids in stem bark ofVatica rassak. Phytochemistry 54:63–69

    Article  CAS  PubMed  Google Scholar 

  7. Wen WL, Li SD, Bo GL, Yao ZC (1996) Oligostilbenes fromVitis heyneana. Phytochemistry 42:1163–1165

    Article  Google Scholar 

  8. Shimizu K, Fukuda 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. Dahms KG. Tropical timber atlas. Part II. Asia Australia. Association Technique Internationale des Bois Tropicaux, Paris, pp 31–231

  10. Oshima Y, Ueno Y, Hikino H (1990) Ampelopsin A, B, and C, new oligostilbenes ofAmpelopsis brevipedunculata var.Hancei. Tetrahedron 46:5121–5126

    Article  CAS  Google Scholar 

  11. Satyajit DS, Pensri W, Laurence D (1999) Identification and ecdysteroid antagonist activity of three resveratrol trimers (suffruticosols A, B and C) fromPaeonia suffruticosa. Tetrahedron 55:513–524

    Article  Google Scholar 

  12. 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 

  13. Shutsung L, Richard AH (1995) Selective inhibition of steroid 5α-reductase isozymes by tea epicatechin-3-gallate and epigallocatechin-3-gallate. Biochem Biophys Res Commun 214:833–838

    Article  Google Scholar 

  14. Ishibashi K, Nakajima K, Sugioka Y, Sugiyama M, Hamada T, Horikoshi H, Nishi T (1999) Synthesis of 2-phenylbenzofran derivatives as testosterone 5α-reductase inhibitor. Chem Pharm Bull (Tokyo) 47:226–240

    Article  CAS  Google Scholar 

  15. Gunawardena YAGP, Sotheeswaran S, Sultanbawa MUS, Surendrakumar S, Bladon P (1986) Another antibacterial polyphenol, copalliferol B, fromVateria copallifera (Dipterocarpaceae). Phytochemistry 25:1498–1500

    Article  CAS  Google Scholar 

  16. Bokei M, Diyasena MNC, Gunatilaka AAL, Kraus W, Sotheeswaran S (1988) Canaliculatol, an antifungal resveratrol trimer fromStemonoporous canaliculatus. Phytochemistry 27:377–380

    Article  Google Scholar 

  17. Nozaki H, Hayashi H, Hayashi K, Ohira S, Ikeda S, Iinuma M, Tanaka T, Ohyama M, Tsutsui K, Tsutsui K, Takaoka D, Yamada M (1997) Plant polyphenols exhibiting DNA topoisomerase II inhibition. In: 39th Symposium on the chemistry of natural products, pp 571–576

  18. Kitanaka S, Ikezawa T, Yasukawa K, Yamanouchi S, Takido M, Hung KS, Il HK (1990) (+)-α-Viniferin, an anti-inflammatory compound fromCaragana chamlagu root. Chem Pharm Bull (Tokyo) 38:432–435

    Article  CAS  Google Scholar 

  19. Sotheeswaran S, Pasupathy V (1993) Distribution of resveratrol oligomers in plants. Phytochemistry 32:1083–1092

    Article  CAS  Google Scholar 

  20. Uvais M, Sultanbawa S, Surendrakumar S, Bladon P (1987) Distichol, an antibacterial polyphenol fromShorea disticha. Phytochemistry 26:799–801

    Article  Google Scholar 

  21. Ohyama M, Ichise M, Tanaka T, Iinuma M, Charles L, Burandt J (1996) Davidiol D, first naturally occurring resveratrol pentamer isolated fromSophora davidii. Tetrahedron Lett 37:5155–5158

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Yoshio Hirano.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hirano, Y., Kondo, R. & Sakai, K. 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 (2001).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI:

Key words