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5α-Reductase inhibitory component from leaves ofArtocarpus altilis


The inhibitory effects of 17 samples prepared from Thailand plants on 5α-reductase activity were examined. The acetone extract of leaves ofArtocarpus altilis showed potent 5α-reductase inhibitory activity. Fractionation guided by 5α-reductase inhibition led to the isolation of 2-geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone from the acetone extract of leaves ofA. altilis. This compound showed more potent inhibitory effect (IC50=38ΜM) thanα-linolenic acid known as a naturally occurring potent inhibitor.


  1. 1.

    Pilotti CA, Kondo R, Shimizu K, Sakai K (1995) An examination of the anti-fungal components in the heartwood extracts ofPterocarpus indicus. Mokuzai Gakkaishi 41:593–597

    CAS  Google Scholar 

  2. 2.

    Shimizu K, Kondo R, Sakai K, Lee SH, Sato H (1998) The inhibitory components fromArtocarpus incisus on melanin biosynthesis. Planta Med 64:408–412

    CAS  Article  PubMed  Google Scholar 

  3. 3.

    Anderson KM, Liao S (1968) Selective retention of 5α-dihydrotestosterone by prostatic nuclei. Nature 219:277–279

    CAS  Article  PubMed  Google Scholar 

  4. 4.

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

    CAS  PubMed  Google Scholar 

  5. 5.

    Liao S, Kokontis J, Sai T, Hiipakka RA (1989) Androgen receptors: structures, mutations, antibodies and cellular dynamics, J Steroid Biochem 34:41–51

    CAS  Article  PubMed  Google Scholar 

  6. 6.

    Russell DW, Wilson JD (1994) Steroid 5α-reductase: two genes/two enzymes. Annu Rev Biochem 63:25–61

    CAS  Article  PubMed  Google Scholar 

  7. 7.

    Brooks JR, Baptista EM, Berman C, Ham EA, Hichens M, Jobnston DB, Primka RL, Rasmusson GH, Reynolds GF, Schmitt SM, Arth GE (1981) Response of rat ventral prostate to a new and novel 5α-reductase inhibitor. Endocrinology 169:830–836.

    Article  Google Scholar 

  8. 8.

    Liang T, Cascieri MA, Cheung AH, Reynolds GF, Rasmusson GH (1985) Species differences in prostatic steroid 5α-reductases of rat, dog, and human. Endocrinology 117:571–579.

    CAS  Article  PubMed  Google Scholar 

  9. 9.

    Jones CD, Audia JE, Lawhorn DE, McQuaid LA, Neubauer BL, Pike AJ, Pennington PA, Stamm NB, Toomev RE, Hirsch KS (1993) Nonsteroidal inhibitors of human type I steroid 5α-, reductase. J Med Chem 36:421–423

    CAS  Article  PubMed  Google Scholar 

  10. 10.

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

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  11. 11.

    Liao S, Hiipakka RA (1995) Selective inhibition of steroid 5α-reductase isozymes by tea epicatechin-3-gallate and epigallocatechin-3-gallate. Biochem Biophys Res Commun 214:833–838

    CAS  Article  PubMed  Google Scholar 

  12. 12.

    Garzon NL, Cuca SLE, Martinez VJC, Yoshida M, Gottlieb OR (1987) Flavonolignoid from the fruit ofIryanthera laevis. Phytochemistry 26:2835–2837

    Article  Google Scholar 

  13. 13.

    Achenbach H, Stöcker M, Constenla MA (1988) Flavonoid and other constituents ofBauhinia manca. Phytochemistry 27:1835–1841

    CAS  Article  Google Scholar 

  14. 14.

    Fujimoto Y, Uzawa J, Suhanda S, Soemartono A, Sumatra M, Koshihara Y (1987) Isolation and structural elucidation of new lipoxygenase inhibitors from indonesianArtocarpus communis (in Japanese). In: 29th Symposium on the chemistry of natural products, Sapporo, Symposium Papers, pp 721–728

  15. 15.

    Koshihara Y, Fujimoto Y, Inoue H (1987) A new 5-lipoxygenase selective inhibitor derived fromArtocarpus communis strongly inhibits arachidonic acid-induced ear edema. Biochem Pharmacol 37:2161–2165

    Article  Google Scholar 

  16. 16.

    Nakano J, Uchida K, Fujimoto Y (1989) An efficient total synthesis of AC-5-1: novel 5-lipoxygenase inhibitor isolated fromArtocarpus communis. Heterocycles 29:427–430

    CAS  Article  Google Scholar 

  17. 17.

    Chu-sheng H, Yu-lin L (1998) A facile total synthesis of 2-geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone with highly 5-lipoxygenase inhibiting activity. Chem Res Chin Univ 4:428–429

    Google Scholar 

  18. 18.

    Cooke GM, Robaire B (1985) Modulation of epididymal δ4-steroid 5α-reductase activity in vitro by the phospholipid environment. J Biol Chem 260:7489–7495

    CAS  PubMed  Google Scholar 

  19. 19.

    Nomura T, Hano Y, Aida M (1998) Isoprenoid-substituted flavonoids fromArtocarpus plants (Moraceae). Heterocycles 47:1179–1205

    CAS  Article  Google Scholar 

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Correspondence to Ryuichiro Kondo.

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Shimizu, K., Kondo, R., Sakai, K. et al. 5α-Reductase inhibitory component from leaves ofArtocarpus altilis . J Wood Sci 46, 385–389 (2000).

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Key words

  • Artocarpus altilis (Parkins) Fosberg
  • Moraceae
  • Leaves
  • 5α-Reductase inhibitor
  • 2-Geranyl-2′,3,4,4′-tetrahydroxydihydrochalcone