Planta Med 2003; 69(1): 72-74
DOI: 10.1055/s-2003-37028
Letter
© Georg Thieme Verlag Stuttgart · New York

Inhibition of 5α-Reductase Activity by Diarylheptanoids from Alpinia officinarum

Yong-ung Kim1 , Hyun Kyong Son1 , Hye Kyoung Song1 , Mi-Jeong Ahn1 , Sang Sup Lee1 , Seung Ki Lee1
  • 1College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, Republic of Korea
Further Information

Publication History

Received: April 30, 2002

Accepted: August 13, 2002

Publication Date:
04 February 2003 (online)

Abstract

The acetone extract from the rhizomes of Alpinia officinarum was evaluated for activity against 5α-reductase which had been prepared from rat prostate. The fraction responsible for the inhibition of the enzyme was purified, analyzed, and the active constituents were identified as four diarylheptanoids, 1,7-diphenylhept-4-en-3-one, dihydroyashabushiketol (1,7-diphenyl-5-hydroxy-3-heptanone), 5-hydroxy-7-(4″-hydroxy-3″-methoxyphenyl)-1-phenyl-3-heptanone and 5-hydroxy-7-(4″-hydroxyphenyl)-1-phenyl-3-heptanone.

References

  • 1 Russell D W, Wilson J D. Steroid 5α-reductase: two genes/two enzymes.  Annu Rev Biochem. 1994;  63 25-61
  • 2 Dukker E M, Kopanski L, Schweikert H U. Inhibition of 5α-reductase activity by extracts from Sabal serrulata .  Planta Med. 1989;  55 587
  • 3 Komoda Y. Isolation of flavonoids from Populus nigra as Δ4-3-ketosteroid (5α) reductase inhibitors.  Chem Pharm Bull. 1989;  37 3128-30
  • 4 Lesuisse D, Berjonneau J, Ciot C, Devaux P, Doucet B, Gourvest J F, Khemis B, Lang C, Legrand R, Lowinski M, Maquin P, Parent A, Schoot B, Teutsch G, Chodounska H, Kasal A. Determination of oenothein B as the active 5α-reductase-inhibiting principle of the folk medicine Epilobium parviflorum .  J Nat Prod. 1996;  59 490-2
  • 5 Ducrey B, Marston A, Gohring S, Hartmann R W, Hostettmann K. Inhibition of 5α-reductase and aromatase by the ellagitannins oenothein A and oenothein B from Epilobium species.  Planta Med. 1997;  63 111-4
  • 6 Kim Y, Kim C Y, Son H K, Song H K, Han J, Lee S S, Lee S K. Testosterone 5α-reductase inhibitors, menaquinone 7 produced by a Bacillus and phenazine methosulfate.  Biol Pharm Bull. 1999;  22 1396-9
  • 7 Ishiguro K, Oku H, Kato T. Testosterone 5α-reductase inhibitor bisnaphthoquinone derivative from Impatiens balsamina .  Phytother Res. 2000;  14 54-6
  • 8 Shimizu K, Kondo R, Sakai K, Buabarn S, Dilokkunanant U. A geranylated chalcone with 5α-reductase inhibitory properties from Artocarpus incisus .  Phytochemistry. 2000;  54 737-9
  • 9 Itokawa H, Morita M, Mihashi S. Two new diarylheptanoids from Alpinia officinarum Hance.  Chem Pharm Bull. 1981;  29 2383-5
  • 10 Suga T, Ohta S, Aoki T, Hirata T. An X-ray crystallographic study on the absolute configuration of dihydroyashabushiketol and the solvent-dependence of its optical rotation.  Bull Chem Soc Jpn. 1983;  56 3353-7
  • 11 Inoue T, Shinbori T, Fujioka M, Hashimoto K, Masada Y. Studies on the pungent principle of Alpinia officinarum Hance.  Yakugaku Zasshi. 1978;  98 1255-7
  • 12 Kiuchi F, Shibuya M, Sankawa U. Inhibitors of prostaglandin biosynthesis from Alpinia officinarum .  Chem Pharm Bull. 1982;  30 2279-82
  • 13 Liao S, Lin J, Dang M T, Zhang H, Kao Y H, Fukuchi J, Hiipakka R A. Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid.  Arch Dermatol Res. 2001;  293 200-5

Prof. Dr. Seung Ki Lee

College of Pharmacy

Seoul National University

San 56-1

Sillim-dong

Gwanak-gu

Seoul 151-742

Republic of Korea

Fax: 82-2-889-0751

Email: sklcrs@plaza.snu.ac.kr

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