Planta Med 2002; 68(11): 980-985
DOI: 10.1055/s-2002-35660
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

Cytotoxic Amides from Piper sintenense

Jih-Jung Chen1 , Yu-Chun Huang2 , Yu-Chang Chen3 , Yao-Ting Huang2 , Shih-Wei Wang2 , Chieh-Yu Peng2 , Che-Ming Teng2 , Ih-Sheng Chen3
  • 1Department of Pharmacy, Tajen Institute of Technology, Pingtung, Taiwan, Republic of China
  • 2Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan, Republic of China
  • 3School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
Further Information

Publication History

Received: January 9, 2002

Accepted: July 31, 2002

Publication Date:
26 November 2002 (online)

Abstract

A new alkaloid, pipersintenamide (1), together with fourteen known compounds, have been isolated from the whole plant of Piper sintenense. The structures of these compounds were elucidated by spectroscopic analysis. Pipersintenamide, sintenpyridone, sarmentine, and 1-(3,4-methylenedioxyphenyl)-1E-dodecene at 20 μg/ml exhibited effective cytotoxicities (cell survival < 15 %) against CCRF-CEM, HL-60, PC-3, and HA22T cell lines.

References

  • 1 Lin T T, Lu S Y. Piperaceae in Flora of Taiwan. 2nd edition. Editorial Committee of the Flora of Taiwan, Taipei Taiwan; 1996 Vol. 2: 624-31
  • 2 Kan W S. Manual of Medicinal Plants in Taiwan. National Research Institute of Chinese Medicine, Taipei Taiwan; 1970 Vol. 1: 64
  • 3 Shih M H. Dissertation of Ph.D National Tsing Hua University, Hsinchu Taiwan; 39-43 104-8
  • 4 Huang Y C, Guh J H, Cheng Z J, Chang Y L, Hwang T L, Liao C H, Tzeng C C, Teng C M. Inhibition of the expression of inducible nitric oxide synthase and cyclooxygenase-2 in macrophages by 7HQ derivatives: involvement of IκB-α stabilization.  European Journal of Pharmacology. 2001;  418 133-9
  • 5 Fallo F, Pilon C, Barzon L, Pistorello M, Pagotto U, Altavilla G, Boscaro M, Sonino N. Paclitaxel is an effective antiproliferative agent on the human NCI-H295 adrenocortical carcinoma cell line.  Chemotherapy. 1998;  44 129-34
  • 6 Jagetia G C, Adiga S K. Influence of various concentrations of taxol on cell survival, micronucli induction, and LDH activity in cultured V79 cells.  Cancer Letters. 1995;  96 192-200
  • 7 Guh J H, Chueh S C, Hwang T L, Chen J, Teng C M. Cell proliferation in human prostatic smooth muscle cells involves the modulation of protein kinase C isozymes.  European Journal of Pharmacology. 1998;  359 281-4
  • 8 Likhitwitayawuid K, Ruangrungsi N, Lange G L, Decicco C P. Structural elucidation and synthesis of new components isolated from Piper sarmentosum (Piperaceae).  Tetrahedron. 1987;  43 3689-94
  • 9 Maxwell A, Rampersad D. A new amide from Piper demeraranum .  Journal of Natural Products. 1989;  52 891-2
  • 10 Kiuchi F, Nakamura N, Tsuda Y, Kaoru K, Yoshimura H. Studies on crude drugs effective on visceral larva migrans. IV. Isolation and identification of larvicidal principles in pepper.  Chemical and Pharmaceutical Bulletin. 1988;  36 2452-65
  • 11 Jacobs H, Seeram N P, Nair M G, Reynolds W F, McLean S. Amides of Piper amalago var. nigrinodum .  Journal of the Indian Chemical Society. 1999;  76 713-7
  • 12 He Q, Lu Y, Cai D, Cui Y, Lai J, Wang H. Analgesic principles from Maoju (Piper arboricola).  Zhongcaoyao. 1981;  12 433-5
  • 13 Gbewonyo W SK, Candy D J. Chromatographic isolation of insecticidal amides from Piper guineense root.  Journal of Chromatography. 1992;  607 105-11
  • 14 Moreira D L, Guimarães E F, Kaplan M AC. A C-glucosylflavone from leaves of Piper lhotzkyanum .  Phytochemistry. 2000;  55 783-6
  • 15 Mensah I A, Achenbach H, Thoithi G N, Waibel R, Mwangi J W. Epoxychiromodine and other constituents of Croton megalocarpus .  Phytochemistry. 1992;  31 2055-8
  • 16 Banerji A. Das R. Constituents of Piper sylvaticum Roxb.  Indian Journal of Chemistry. Sect B. 1977;  15B 495-6
  • 17 Della Greca M, Monaco P, Previtera L. Stigmasterols from Typha latifolia .  Journal of Natural Products. 1990;  53 1430-5
  • 18 Faijn L, Hancheng L, Xiaowei Z. Chemical constituents of Typha angustata Bory et Chaub.  Zhongcaoyao. 1985;  16 48

Prof. Ph. D. I. S. Chen

School of Pharmacy

Kaohsiung Medical University

Kaohsiung, Taiwan

Republic of China

Email: m635013@cc.kmu.edu.tw

Fax: +886-7-3210683

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