- Original Article
- Published:
Compounds inhibitory to rat liver 5α-reductase from tropical commercial wood species: resveratrol trimers from melapi (Shorea sp.) heartwood
Journal of Wood Science volume 47, pages 308–312 (2001)
Abstract
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.
References
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
Stephan VF (1996) Inhibitors of 5α-reductase. Curr Pharm Design 2:59–84
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
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
Price VH (1999) Treatment of hair loss. N Engl J Med 341:964–973
Tanaka T, Ito T, Nakaya K, Iinuma M, Riswan S (2000) Oligostilbenoids in stem bark ofVatica rassak. Phytochemistry 54:63–69
Wen WL, Li SD, Bo GL, Yao ZC (1996) Oligostilbenes fromVitis heyneana. Phytochemistry 42:1163–1165
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
Dahms KG. Tropical timber atlas. Part II. Asia Australia. Association Technique Internationale des Bois Tropicaux, Paris, pp 31–231
Oshima Y, Ueno Y, Hikino H (1990) Ampelopsin A, B, and C, new oligostilbenes ofAmpelopsis brevipedunculata var.Hancei. Tetrahedron 46:5121–5126
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
Liang T, Liao S (1992) Inhibition of steroid 5α-reductase by specific aliphatic unsaturated fatty acids. Biochem J 285:557–562
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
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
Gunawardena YAGP, Sotheeswaran S, Sultanbawa MUS, Surendrakumar S, Bladon P (1986) Another antibacterial polyphenol, copalliferol B, fromVateria copallifera (Dipterocarpaceae). Phytochemistry 25:1498–1500
Bokei M, Diyasena MNC, Gunatilaka AAL, Kraus W, Sotheeswaran S (1988) Canaliculatol, an antifungal resveratrol trimer fromStemonoporous canaliculatus. Phytochemistry 27:377–380
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
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
Sotheeswaran S, Pasupathy V (1993) Distribution of resveratrol oligomers in plants. Phytochemistry 32:1083–1092
Uvais M, Sultanbawa S, Surendrakumar S, Bladon P (1987) Distichol, an antibacterial polyphenol fromShorea disticha. Phytochemistry 26:799–801
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
Author information
Authors and Affiliations
Corresponding author
Rights 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). https://doi.org/10.1007/BF00766718
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00766718