GC-MS analysis and in vitro anti-androgenic activity of  Kaempferia rotunda Linn extract

Nungruthai Suphrom; Witsanu Sonyot; Kamonluk Insumrong; Pimtawan Sawangsup; Phitchaporn Sutamuang; Kornkanok Ingkaninan

Authors

Nungruthai Suphrom Department of Chemistry, Faculty of Science and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000
Witsanu Sonyot Department of Chemistry, Faculty of Science and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000
Kamonluk Insumrong Department of Chemistry, Faculty of Science and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000
Pimtawan Sawangsup Department of Chemistry, Faculty of Science and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000
Phitchaporn Sutamuang Department of Chemistry, Faculty of Science and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000
Kornkanok Ingkaninan Bioscreening Unit, Department of Pharmaceutical Chemistry and Pharmacognosy, Faculty of Pharmaceutical Sciences and Center of Excellence for Innovation in Chemistry, Naresuan University, Muang, Phitsanulok, 65000

Keywords:

Kaempferia rotunda, Anti-androgen, 5α-Reductase, GC-MS, Sesquiterpenes

Abstract

Testosterone is converted to a more potent androgen, dihydrotestosterone (DHT) by 5α-reductase and causes various hormonal actions. Anti-androgen can be used for the treatment of several disorders related to male sex hormone. In this study, the in vitro anti-androgenic activity and chemical components of hexane, dicholomethane and ethanolic extracts of Kaempferia rotunda Linn. rhizome were investigated. The various concentrations of extracts were tested on anti-androgenic activity by acting against the conversion of testosterone. The hexane extract was the most potent (IC₅₀ = 0.43 ± 0.10 mg/mL) and showed the IC₅₀ value in the same range to that of positive control; ethinylestradiol (IC₅₀ = 0.26 ± 0.02 mg/mL). The different chemical profiles of all extracts studied were observed by GC-MS. The results indicated that most of volatile components including mono- and sesquiterpenes were present in hexane extract. Further studies on isolation and identification of active components are needed. This plant might be a new source for anti-androgens.

References

Afzal, A., Oriqat, G., Akram Khan, M., Jose, J., & Afzal, M. (2013). Chemistry and Biochemistry of Terpenoids from Curcuma and Related Species. Journal of Biologically Active Products from Nature, 3(1), 1-55.

Aggarwal, S., Thareja, S., Verma, A., Bhardwaj, T. R., & Kumar, M. (2010). An overview on 5α-reductase inhibitors. Steroids, 75(2), 109-153.

Agrawal, S., Bhawsar, A., Choudhary, P., Singh, S., Keskar, N., & Chaturvedi, M. (2011). In-vitro anthelmintic activity of Kaempferia rotunda. International Journal of Pharmacy & Life science, 2(9), 1062-1064.

Andersen, J. T., Nickel, J. C., Marshall, V. R., Schulman, C. C., & Boyle, P. (1997). Finasteride significantly reduces acute urinary retention and need for surgery in patients with symptomatic benign prostatic hyperplasia. Urology, 49(6), 839-845.

Atun, S., Arianingrum, R., Sulistyowati, E., & Aznam, N. (2013). Isolation and antimutagenic activity of some flavanone compounds from Kaempferia rotunda. International Journal of Chemical and Analytical Science, 4(1), 3-8.

Atun, S., & Arianingrum, R. (2015). Anticancer activity of bioactive compounds from Kaempferia rotunda rhizome against human breast cancer. International Journal of Pharmacognosy and Phytochemical Research, 7(2), 262-269.

Babushok, V. I., Linstrom, P. J., Reed, J. J., Zenkevich, I. G., Brown, R. L., Mallard, W. G., & Stein, S. E. (2007). Development of a database of gas chromatographic retention properties of organic compounds. Journal of Chromatography A, 1157(1–2), 414-421.

Bartsch, G., Rittmaster, R., & Klocker, H. (2002). Dihydrotestosterone and the concept of 5α-reductase inhibition in human benign prostatic hyperplasia. World Journal of Urology, 19(6), 413-425.

Chayamarit, K., Pooma, R., & Pattharahirantricin, N. (2014). A checklist of plants in Thailand (Vol. 1). Bangkok, Thailand: Office of Natural Resources and Environmental Policy and Planing.

Gormley, G. J. (1995). Finasteride: a clinical review. Biomedicine and Pharmacotherapy, 49(7-8), 319-324.

Hirata, N., Tokunaga, M., Naruto, S., Iinuma, M., & Matsuda, H. (2007). Testosterone 5α-reductase inhibitory active constituents of Piper nigrum leaf. Biological and Pharmaceutical Bulletin, 30(12), 2402-2405.

Imam, S. A., Rout, S. K., Sutar, N., Sharma, U. S., & Sutar, R. (2013). Wound healing activity of Kaempferia rotunda Linn leaf extract. Int J Curr Microbiol App Sci, 2(12), 74-78.

Jantan, I., Pisar, M., Sirat, H. M., Basar, N., Jamil, S., Ali, R. M., & Jalil, J. (2004). Inhibitory effects of compounds from Zingiberaceae species on platelet activating factor receptor binding. Phytotherapy Research, 18(12), 1005-1007.

Jantan, I., Raweh, S. M., Sirat, H. M., Jamil, S., Mohd Yasin, Y. H., Jalil, J., & Jamal, J. A. (2008). Inhibitory effect of compounds from Zingiberaceae species on human platelet aggregation. Phytomedicine, 15(4), 306-309.

Kabir, S. R., & Reza, M. A. (2014). Antibacterial activity of Kaempferia rotunda rhizome lectin and its induction of apoptosis in Ehrlich ascites carcinoma cells. Applied Biochemistry and Biotechnology, 172(6), 2866-2876.

Kumar, A. (2014). Chemical characterization of essential oil from the rhizomes of Kaempferia rotunda L. by GC/MS technique International Journal of Pharma and Bio Sciences, 5(4), 458-462.

Kupchan, S. M., Hemingway, R. J., Coggon, P., McPhail, A. T., & Sim, G. A. (1968). Crotepoxide, a novel cyclohexane diepoxide tumor inhibitor from Croton macrostachys. Journal of the American Chemistry Society, 90(11), 2982-2983.

Larsen, K., & Larsen, S. S. (2006). Gingers of Thailand. Chiang Mai, Thailand: Queen Sirikit Botanic Garden, the Botanical Garden Organization.

Linstrom, P. J., & Mallard, W. G. (2016 ). NIST Chemistry WebBook. NIST Standard Reference Database Number 69. Retrieved from http://webbook. nist.gov/chemistry

Lotulung, P. D., Minarti, Kardono, L. B. S., & Kawanishi, K. (2008). Antioxidant compound from the rhizomes of Kaempferia rotunda L. Pakistan Journal of Biological Sciences, 11(20), 2447-2450.

Madaka, F., & Tewtrakul, S. (2011). Anti-allergic activity of some selected plants in the genus Boesenbergia and Kaempferia. Songklanakarin Journal of Science and Technology, 33(3), 301-304.

Matsuda, H., Yamazaki, M., Matsuo, K., Asanuma, Y., & Kubo, M. (2001). Anti-androgenic activity of Myricae Cortex—Isolation of active constituents from bark of Myrica rubra. Biological and Pharmaceutical Bulletin, 24(3), 259-263.

Nugroho, B. W., Schwarz, B., Wray, V., & Proksch, P. (1996). Insecticidal constituents from rhizomes of Zingiber cassumunar and Kaempferia rotunda. Phytochemistry, 41(1), 129-132.

Nukui, F. (1997). Effects of chlormadinone acetate and ethinylestradiol treatment on epididymal 5α-reductase activities in patients with prostate cancer. Endrocrine Journal, 44(1), 127-132.

Prasad, S., Yadav, V. R., Sundaram, C., Reuter, S., Hema, P. S., Nair, M. S., . . . Aggarwal, B. B. (2010). Crotepoxide chemosensitizes tumor cells through inhibition of expression of proliferation, invasion, and angiogenic proteins linked to proinflammatory pathway. The Journal of Biological Chemistry, 285(35), 26987-26997.

Pratiwi, S. U. T., Lagendijk, E. L., Hertiani, T., De Weert, S., Cornellius, A. M., & Van Den Hondel, J. J. (2015). Antimicrobial effects of indonesian medicinal plants extracts on planktonic and biofilm growth of Pseudomonas aeruginosa and Staphylococcus aureus. International Journal of Pharmacy and Pharmaceutical Sciences, 7(4), 183-191.

Russell, D. W., & Wilson, J. D. (1994). Steroid 5α-reductase: two genes/two enzymes. Annual review of biochemistry, 63(1), 25-61.

Sirata, H. M., Jamila, S., & Siew, L. W. (2005). The rhizome oil of Kaempferia rotunda Val. Journal of Essential Oil Research, 17(3), 306-307.

Srivilai, J., Khorana, N., Waranuch, N., & Ingkaninan, K. (2011). Anti-androgenic activity of furanodiene isolated from Curcuma aeruginosa Roxb. extract. Naresuan University Journal (Special Issue), 33-37.

Stevenson, P. C., Veitch, N. C., & Simmonds, M. S. J. (2007). Polyoxygenated cyclohexane derivatives and other constituents from Kaempferia rotunda L. Phytochemistry, 68(11), 1579-1586.

Sultana, Z., Imam, K. M. S. U., Azam, F. M. S., Rahman, S., Rahman, S., Islam, F., & Rahmatullah, M. (2012). Evaluation of antihyperglycemic and antinociceptive activities of methanolic extract of Kaempferia rotunda L. (Zingiberaceae) rhizomes. Advances in Natural and Applied Sciences, 6(8), 1302-1306.

Suphrom, N., Pumthong, G., Khorana, N., Waranuch, N., Limpeanchob, N., & Ingkaninan, K. (2012). Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb. Fitoterapia, 83(5), 864-871.

van Den Dool, H., & Dec. Kratz, P. (1963). A generalization of the retention index system including linear temperature programmed gas—liquid partition chromatography. Journal of Chromatography A, 11, 463-471.

Woerdenbag, H. J., Windono, T., Bos, R., Riswan, S., & Quax, W. J. (2004). Composition of the essential oils of Kaempferia rotunda L. and Kaempferia angustifolia Roscoe rhizomes from Indonesia. Flavour and Fragrance Journal, 19(2), 145-148.