Planta Med 2004; 70(2): 174-177
DOI: 10.1055/s-2004-815497
Letter
© Georg Thieme Verlag Stuttgart · New York

A New Aristolactam Alkaloid and Anti-Platelet Aggregation Constituents from Piper taiwanense

Yu-Chang Chen1 , Jih-Jung Chen2 , Ya-Ling Chang3 , Che-Ming Teng3 , Wei-Yu Lin1 , Chin-Chung Wu4 , Ih-Sheng Chen1
  • 1Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
  • 2Department of Pharmacy, Tajen Institute of Technology, Pingtung, Taiwan, Republic of China
  • 3Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan, Republic of China
  • 4Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
This work was supported by a grant (NSC 89-2314-B-037-044) from the National Science Council of the Republic of China
Further Information

Publication History

Received: August 26, 2003

Accepted: November 9, 2003

Publication Date:
02 March 2004 (online)

Abstract

A new alkaloid, piperolactam E, and fourteen known compounds have been isolated from the stem of Piper taiwanense. Bioassay-guided fractionation of the methanolic extract led to the isolation, from the chloroform-soluble part, of 4-allylcatechol, eugenol, trans-caffeic aldehyde, 2-hydroxy-1-methoxy-4H-dibenzo[de,g]quinoline-4,5-(6H)-dione, piperolactam B, piperolactam C, and piperolactam E as the active principles of anti-platelet aggregation in vitro. The derived 1,2-diacetoxy-4-allyl-benzene and eugenol acetate exhibit stronger anti-platelet aggregation activities induced by arachidonic acid than 4-allylcatechol and eugenol, respectively.

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 Olsen C E, Tyagi O D, Boll P M, Hussaini F A, Parmar V S, Sharma N K, Taneja P, Jain S C. An aristolactam from Piper acutisleginum and revision of the structures of piperolactam B and D.  Phytochemistry. 1993;  33 518-20
  • 3 Coolen H KAC, Meeuwis J AM, van Leeuwen P WNM, Nolte R JM. Substrate selective catalysis by rhodium metallohosts.  J Am Chem Soc. 1995;  117 11 906-13
  • 4 Kelm M A, Nair M G. Mosquitocidal compounds and a triglyceride, 1,3-dilinoleneoyl-2-palmitin, from Ocimum sanctum .  J Agric Food Chem. 1998;  46 3092-4
  • 5 Duran E, Duran H, Gorrichon L. Synthesis of para-hydroxycinnamaldehyde substrates of cinnamic alcohol dehydrogenase.  Holzforschung. 1992;  46 21-4
  • 6 Achenbach H, Fietz W, Wörth J, Waibel R, Portecop J. Constituents of tropical medicinal plants, IXX GC/MS-investigations of the constituents of Piper amalago - 30 new amides of the piperine-type.  Planta Med. 1986;  52 12-8
  • 7 Nishioka T, Watanabe J, Kawabata J, Niki R. Isolation and activity of N-p-coumaroyltyramine, an α-glucosidase inhibitor in Welsh onion (Allium fistulosum).  Biosci Biotech Biochem. 1997;  61 1138-41
  • 8 Lewis F D, Elbert J E, Upthagrove A L, Hale P D. Structure and photoisomerization of (E)- and (Z)-cinnamamides and their Lewis acid complexes.  J Org Chem. 1991;  56 553-61
  • 9 Singh S K, Prasad A K, Olsen C E, Jha A, Jain S C, Parmar V S, Wengel J. Neolignans and alkaloids from Piper argyrophyllum .  Phytochemistry. 1996;  43 1355-60
  • 10 Achari B, Chakrabarty S, Bandyopadhyay S, Pakarashi S C. A new 4,5-dioxoaporphine and other constituents of Aristolochia .  Heterocycles. 1982;  19 1203-6
  • 11 Galbraith M N, Horn D HS. Structures of the natural products blumenols A, B, and C. Chem Commun 1972: 113-4
  • 12 Desai S J, Prabsu B R, Mulchandani N B. Aristolactams and 4,5-dioxoaporphines from Piper longum .  Phytochemistry. 1988;  27 1511-5
  • 13 Ruangrungsi N, Prathanturarug S, Lange G L, Organ M G. An N-methyl aristolactam and an oxygenated cyclohexane derivative from Piper ribesioides .  Phytochemistry. 1992;  31 2397-400
  • 14 Rasheed A, Totté J, Herman A G. Eugenol and prostaglandin biosynthesis.  N Engl J Med. 1984;  310 50-1
  • 15 Chia Y C, Chang F R, Teng C M, Wu Y C. Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii .  J Nat Prod. 2000;  63 1160-3
  • 16 Srivastava K C, Malhotra N. Acetyl eugenol, a component of oil of cloves (Syzygium aromaticum L.) inhibits aggregation and alters arachidonic acid metabolism in human blood platelets.  Prostag Leukotr Ess. 1991;  42 73-81
  • 17 Teng C M, Chen C C, Ko F N, Lee L G, Huang T F, Chen Y P, Hsu H Y. Two antiplatelet agents from Magnolia officinalis .  Thromb Res. 1988;  50 757-65
  • 18 Chen J J, Chang Y L, Teng C M, Lin W Y, Chen Y C, Chen I S. A new tetrahydroprotoberberine N-oxide alkaloid and anti-platelet aggregation constituents of Corydalis tashiroi .  Planta Med. 2001;  67 423-7

Prof. Dr. I. S. Chen

College of Pharmacy

Kaohsiung Medical University

Kaohsiung

Taiwan

Republic of China

Fax: +886-7-3210683

Email: m635013@kmu.edu.tw

    >