Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb.

Fitoterapia

Volumn 83, Issue 5, 2012, Pages 864-871

  Suphrom, Nungruthai ^a   Pumthong, Ganniga ^a   Khorana, Nantaka ^a   Waranuch, Neti ^a   Limpeanchob, Nanteetip ^a   Ingkaninan, Kornkanok ^a  

^a NARESUAN UNIVERSITY   (Thailand)

Author keywords

5 reductase; Anti androgen; Curcuma aeruginosa; Germacrone; LNCaP cell; Sesquiterpenes

Indexed keywords

ANDROGEN; ANDROGEN RECEPTOR; ANTIANDROGEN; CURCUMENOL; DEHYDROCURDIONE; FINASTERIDE; GERMACRONE; ISOCURCUMENOL; SESQUITERPENE DERIVATIVE; STEROID 5ALPHA REDUCTASE; TESTOSTERONE; UNCLASSIFIED DRUG; ZEDERONE; ZEDOARONDIOL;

ANTIANDROGIC ACTIVITY; ARTICLE; CELL PROLIFERATION; CELL STRAIN LNCAP; CELL VIABILITY; CURCUMA AERUGINOSA; DRUG ACTIVITY; DRUG ISOLATION; DRUG POTENCY; ENZYME INHIBITION; GROWTH INHIBITION; HAMSTER; IC 50; IN VITRO STUDY; IN VIVO STUDY; MEDICINAL PLANT; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; RHIZOME; ZINGIBERACEAE;

5-ALPHA REDUCTASE INHIBITORS; ANDROGEN ANTAGONISTS; ANIMALS; CELL LINE; CRICETINAE; CURCUMA; FINASTERIDE; HUMANS; INHIBITORY CONCENTRATION 50; MALE; PLANT EXTRACTS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, ANDROGEN; RHIZOME; SESQUITERPENES; SESQUITERPENES, GERMACRANE; TESTOSTERONE;

CURCUMA AERUGINOSA; MESOCRICETUS AURATUS; ZINGIBERACEAE;

EID: 84861628071     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2012.03.017     Document Type: Article

References (37)

1. D.W. Russell, and J.D. Wilson Steroid 5α-reductase: two genes/two enzymes Annu Rev Biochem 63 1994 25 61
2. C. Iehle, S. Delos, O. Guirou, R. Tate, J.P. Raynaud, and P.M. Martin Human prostatic steroid 5α-reductase isoforms, a comparative study of selective inhibitors J Steroid Biochem Mol Biol 54 1995 273 279
3. G. Bartsch, R.S. Rittmaster, and H. Klocker Dihydrotestosterone and the concept of 5α-reductase inhibition in human benign prostatic hyperplasia Eur Urol 37 2000 367 380
4. G. Gormley Finasteride: a clinical review Biomed Pharmacother 49 1995 319 324
5. S. Aggarwal, S. Thareja, A. Verma, T.R. Bhardwaj, and M. Kumar An overview on 5α-reductase inhibitors Steroids 75 2010 109 153
6. Pumthong G. Studies of a 5α-reductase inhibitory activity of Curcuma aeruginosa extract. Doctoral dissertation Ph.D. (2010), Naresuan University, Phitsanulok, Thailand.
7. G. Pumthong, P. Asawanonda, S. Varothai, V. Jariyasethavong, D. Triwongwaranat, and P. Suthipinittharm Curcuma aeruginosa, a novel botanically derived 5α-reductase inhibitor in the treatment of male-pattern baldness: a multicenter, randomized, double-blind, placebo-controlled study Ahead of Print J Dermatol Treat 2011 1 8
8. P. Thaina, P. Tungcharoen, M. Wongnawa, W. Reanmongkol, and S. Subhadhirasakul Uterine relaxant effects of Curcuma aeruginosa Roxb. rhizome extracts J Ethnopharmacol 121 2009 433 443
9. W. Reanmongkol, S. Subhadhirasakul, N. Khaisombat, P. Fuengnawakit, S. Jantasila, and A. Khamjun Investigation the antinociceptive, antipyretic and antiinflammatory activities of Curcuma aeruginosa Roxb. extracts in experimental animals Songklanakarin J Sci Technol 28 2006 999 1008
10. T. Otake, H. Mori, M. Morimoto, N. Ueba, S. Sutardjo, and I.T. Kusumoto Screening of Indonesian plant extracts for anti-human immunodeficiency virus-type 1 (HIV-1) activity Phytother Res 9 1995 6 10
11. A. Jitoe, T. Masuda, I.G.P. Tengah, D.N. Suprapta, I.W. Gara, and N. Nakatani Antioxidant activity of tropical ginger extracts and analysis of the contained curcuminoids J Agric Food Chem 40 1992 1337 1340
12. I. Jantan, I.A. Rafi, and J. Jalil Platelet-activating factor (PAF) receptor-binding antagonist activity of Malaysian medicinal plants Phytomedicine 12 2005 88 92
13. I. Takano, I. Yasuda, K. Takeya, and H. Itokawa Guaiane sesquiterpene lactones from Curcuma aeruginosa Phytochemistry 40 1995 1197 1200
14. C. Kitamura, T. Nagoe, M. Prana, A. Agusta, K. Ohashi, and H. Shibuya Comparison of Curcuma sp. in Yakushima with C. aeruginosa and C. zedoaria in Java by trn K gene sequence, RAPD pattern and essential oil component J Nat Med 61 2007 239 243
15. M.A.H. Sukari, S.M. Saad, N.H. Lajis, M. Rahmani, R. Muse, and U.K. Yusuf Chemical constituents and bioactivity of Curcuma aeruginosa Roxb Nat Prod Sci 13 2007 175 179
16. H. Matsuda, M. Yamazaki, K. Matsuo, Y. Asanuma, and M. Kubo Anti-androgenic activity of Myricae Cortex - isolation of active constituents from bark of Myrica rubra Biol Pharm Bull 24 2001 259 263
17. F. Nukui Effects of chlormadinone acetate and ethinylestradiol treatment on epididymal 5α-reductase activities in patients with prostate cancer Endocr J 44 1997 127 132
18. H. Matsuda, N. Sato, M. Yamazaki, S. Naruto, and M. Kubo Testosterone 5α-reductase inhibitory active constituents from Anemarrhenae Rhizoma Biol Pharm Bull 24 2001 586 587
19. S. Liao, J. Lin, M.T. Dang, H. Zhang, Y.H. Kao, and J. Fukuchi Growth suppression of hamster flank organs by topical application of catechins, alizarin, curcumin, and myristoleic acid Arch Dermatol Res 293 2001 200 205
20. T. Liang, and S. Liao Growth suppression of hamster flank organs by topical application of gamma-linolenic and other fatty acid inhibitors of 5α-reductase J Invest Dermatol 109 1997 152 157
21. J. Liu, K. Shimizu, F. Konishi, S. Kumamoto, and R. Kondo The anti-androgen effect of ganoderol B isolated from the fruiting body of Ganoderma lucidum Bioorg Med Chem 15 2007 4966 4972
22. J. Yan, G. Chen, S. Tong, Y. Feng, L. Sheng, and J. Lou Preparative isolation and purification of germacrone and curdione from the essential oil of the rhizomes of Curcuma wenyujin by high-speed counter-current chromatography J Chromatogr A 1070 2005 207 210
23. M. Kuroyanagi, A. Ueno, K. Ujiie, and S. Sato Structures of sesquiterpenes from Curcuma aromatica SALISB Chem Pharm Bull 35 1987 53 59
24. K. Firman, T. Kinoshita, A. Itai, and U. Sankawa Terpenoids from Curcuma heyneana Phytochemistry 27 1988 3887 3891
25. F.Q. Yang, S.P. Li, Y. Chen, S.C. Lao, Y.T. Wang, and T.T. Dong Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry J Pharm Biomed Anal 39 2005 552 558
26. H. Hikino, S. Takahashi, Y. Sakurai, T. Takemoto, and N.S. Bhacca Structure of zederone Chem Pharm Bull 16 1968 1081 1087
27. H. Hikino, C. Konno, and T. Takemoto Sesquiterpenoids XLIII. Structure of dehydrocurdione, a sesquiterpenoid of Curcuma zedoaria Chem Pharm Bull 20 1972 987 989
28. H. Matsuda, M. Yamazaki, S. Naruo, Y. Asanuma, and M. Kubo Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5α-reductase Biol Pharm Bull 25 2002 622 626
29. N. Hirata, M. Tokunaga, S. Naruto, M. Iinuma, and H. Matsuda Testosterone 5α-reductase inhibitory active constituents of Piper nigrum Leaf Biol Pharm Bull 30 2007 2402 2405
30. Z. Zhong, X. Chen, W. Tan, Z. Xu, K. Zhou, and T. Wu Germacrone inhibits the proliferation of breast cancer cell lines by inducing cell cycle arrest and promoting apoptosis Eur J Pharmacol 667 2011 50 55
31. J.S. Horoszewicz, S.S. Leong, T.M. Chu, Z.L. Wajsman, M. Friedman, and L. Papsidero The LNCaP cell line, a new model for studies on human prostatic carcinoma Prog Clin Biol Res 37 1980 115 132
32. J.S. Horoszewicz, S.S. Leong, E. Kawinski, J.P. Karr, H. Rosenthal, and T.M. Chu LNCaP model of human prostatic carcinoma Cancer Res 43 1983 1809 1818
33. P. Negri-Cesi, A. Poletti, A. Colciago, P. Magni, P. Martini, and M. Motta Presence of 5α-reductase isozymes and aromatase in human prostate cancer cells and in benign prostate hyperplastic tissue Prostate 34 1998 283 291
34. J. Liu, S. Tamura, K. Kurashiki, K. Shimizu, K. Noda, and F. Konishi Anti-androgen effects of extracts and compounds from Ganoderma lucidum Chem Biodivers 6 2009 231 243
35. H.G. Bull, M. Garcia-Calvo, S. Andersson, W.F. Baginsky, H.K. Chan, and D.E. Ellsworth Mechanism-based inhibition of human steroid 5α-reductase by finasteride: enzyme-catalyzed formation of NADP-dihydrofinasteride, a potent bisubstrate analog inhibitor J Am Chem Soc 118 1996 2359 2365
36. G.S. Harris, and J.W. Kozarich Steroid 5α-reductase inhibitors in androgen-dependent disorders Curr Opin Chem Biol 1 1997 254 259
37. L. Drake, M. Hordinsky, V. Fiedler, J. Swinehart, W.P. Unger, and P.C. Cotterill The effects of finasteride on scalp skin and serum androgen levels in men with androgenetic alopecia J Am Acad Dermatol 41 1999 550 554