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http://dx.doi.org/10.5352/JLS.2009.19.5.671

Purification and Identification of Apoptosis Modulator Pipernonaline from Piper longum Linn. against Prostate Cancer Cells  

Kim, Kwang-Youn (Pusan National University School of Medicine)
Kim, Yun-Jin (Pusan National University School of Medicine)
Lee, Wan (Department of Urology, Pusan National University Hospital)
Yu, Sun-Nyoung (Pusan National University School of Medicine)
Cho, Hyo-Jin (Division of Translational Clinical Research I, National Cancer Center)
Lee, Sun-Yi (Rural Development Administration, National Institute Horticultural & Herbal Science)
Lee, Han-Seung (Department of Bio-Food Materials, College of Medical and Life Sciences, Silla University)
Sohn, Jae-Hak (Department of Bio-Food Materials, College of Medical and Life Sciences, Silla University)
Oh, Hyuncheol (Department of Bio-Food Materials, College of Medical and Life Sciences, Silla University)
Ahn, Soon-Cheol (Pusan National University School of Medicine)
Publication Information
Journal of Life Science / v.19, no.5, 2009 , pp. 671-675 More about this Journal
Abstract
Prostate cancer has been a critical health problem due to an increase of prostate cancer-related deaths worldwide. Also, a frequent treatment option for prostate cancer is androgen ablation, but this treatment has a limited scope, especially for hormone-refractory cancer. There is an urgent need for the identification of alternative therapeutic strategies for prostate cancer. Previously, over one hundred species of dried-plant methanol extracts were tested for inhibitory effects on proliferation. One of them, Piper longum Linn. was selected based on its potent anti-proliferation effect. The dried root of P. longum Linn. was extracted with 100% methanol for 2-3 days and its extract was fractionated using chloroform. The chloroform layer was then subjected to column chromatography on silica gel, reverse phase-18 (RP-18) and Sephadex LH-20, in turn. Finally, the pure compound was obtained and identified as pipernonaline by NMR spectroscopic and physico-chemical analysis. In this study, anti-proliferation and cell cycle arrest effects of pipernonaline on human prostate cancer PC-3 cells were investigated using the MTT and PI staining, respectively. Our findings suggest that pipernonaline represents a dose-dependent growth inhibition pattern on PC-3 cells and, moreover, its growth inhibition is associated with sub-G1 and G0/G1 cell cycle accumulation in PC-3 cells. Also, these results provide an anticancer candidate for human prostate cancer.
Keywords
Prostate cancer; purification; pipernonaline; Piper longum; growth inhibition;
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1 Swanson, G. P., M. Riggs, and J. Earle. 2004. Failure after primary radiation or surgery for prostate cancer; differences in response to androgen ablation. J. Urol. 172, 525-528   DOI   ScienceOn
2 Swanson, G. P. 2006. Management of locally advanced prostate cancer; past, present, future. J. Urol. 176, S34-41   DOI   ScienceOn
3 Tabuneng, W., H. Bando, and T. Amiya. 1983. Studies on the constituents of the crude drug "Piperis Longi Frutus" on the alkaloids of fruits of Piper longum L. Chem. Pham. Bull. 31, 3562-3565   DOI
4 Tyagi, O. D., S. Jensen, P. M. Boll, N. K. Sharma, K. S. Bish, and V. S. Parmer. 1993. Lignans and neolignans from Piper schmidtii. Phytochemistry 32, 445-448   DOI   ScienceOn
5 Yang, Y. C., S. G. Lee, H. K. Lee, M. K. Kim, S. H. Lee, and H. S. Lee. 2002. A Piperidine Amide Extracted from Piper longum L. Fruit Shows Activity against Aedes aegypti Mosquito Larvae. J. Argic. Food Chem. 50, 3765-3767   DOI   ScienceOn
6 Duh, C. Y. and Y. C. Wu. 1990. Cytotoxic pyridone alkaloids from the leaves of Piper aborescens. Jornal of Natural Products 53, 1575-1577   DOI
7 Duh, C. Y., Y. C. Wu, and S. K. Wang. 1990. Cytotoxic pyridone alkaloids from Piper aborescens. Phytochemistry 29, 2689-2691   DOI   ScienceOn
8 Lee, S. E., B. S. Park, M. K. Kim, W. S. Choi, H. T. Kim, K. Y. Choi, S. G. Lee, and H. S. Lee. 2001. Fungicidal activity of pipernonaline, a piperidine alkaloid derived from long pepper, Piper longum L. against phytopathogenic fungi. Crop. Prot. 20, 523-528   DOI   ScienceOn
9 Mann, J. 2002. Natural products in cancer chemotherapy; past, present and future. Nature Reviews/Cancer 2, 143-148   DOI
10 Miyakado, M., M. I. Nakayama, H. Yoshioka, and N. Nakatani. 1979. The piperanceae amides I: structure of pipericide, a new insecticidal amide from Piper nigrum L. Agri. Biol. Chem. 43, 1609-1611   DOI
11 Parmer, V. S., S. C. Jains, K. S. Bisht, R. Jain, P. Taneja, A. Jha, O. D. Tyagi, A. K. Prasad, J. Wengel, C. E. Olsen, and P. M. Boll. 1997. Phytochemistry of the genus Piper. Phytochemistry 46, 597-673   DOI   ScienceOn
12 Reddy, L., B. Odhav, and K. D. Bhoola. 2003. Natural products for canerprevention: a global perspective. Phamacology and Therapeutics 99, 1-13   DOI   ScienceOn
13 Rao, J. M, K. Subrahmayam, and K. V. J. Rao. 1974. Alkaloids from the fruits of Piper auranticum Wall. (Piperaceae). Cur. Sci. 43, 76-77
14 Sengupta, S. and A. G. Ray. 1987. The chemistry of Piper species: a review. Fitoterapia 58, 147-166   DOI   ScienceOn
15 Su, H. C. F. and R. Horvat. 1981. Isolation, identification and insecticidal properties of Piper nigrum amides. J. Agri. Food Chem. 29, 115-118   DOI
16 Cho, H. J., S. N. Yu, K. Y. Kim, J. H. Sohn, H. C. Oh, and S. C. Ahn 2009. Screening and purification of an anti-prostate cancer compound, deoxypodophyllotoxin, from Anthriscus sylvestris Hoffm. Journal of Life Science 19, 9-14   DOI   ScienceOn
17 Ahn, J. W., M. J. Ahn, O. P. Zee, E. J. Kim, S. G. Lee, H. J. Kim, and I. Kubo. 1992. Piperidine alkaloids from Piper restrofractum fruits. Phytochemistry 31, 3609-3612   DOI   ScienceOn
18 Bezerra, D. P., C. Pessoa, M. O. Moraes, E. R. Silveira, M. A. S. Lima, F. J. M Elmiro, and L. V. Costa-Lotufo. 2005. Antiproliferative effects of two amides, piperine and piplatine, from Piper species. Zeitschrift fur Naturforschung 60, 539-543
19 Chaetterjee, A. and C. P. Dutta. 1967. Alkaloids of Piper longum Linn. I. structure and synthesis of piperlongumine and piperlonguminene. Tetrahedron 23, 1769-1781   DOI   ScienceOn