Planta Med 2006; 72(13): 1238-1241
DOI: 10.1055/s-2006-947196
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Effect of Isoquinoline Alkaloids of Different Structural Types on Antiplatelet Aggregation in Vitro

Yi-Chen Chia1 , Fang-Rong Chang2 , Chin-Chung Wu2 , Che-Ming Teng3 , Keh-Shaw Chen1 , Yang-Chang Wu2
  • 1Department of Food Science & Technology, Tajen Institute of Technology, Ping Tung Hsien, Taiwan
  • 2Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 3Pharmacological Institute, College of Medicine, National Taiwan University, Taipei, Taiwan
Further Information

Publication History

Received: December 13, 2005

Accepted: June 1, 2006

Publication Date:
18 September 2006 (online)

Abstract

Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships.

References

  • 1 Wu Y C, Liou Y F, Lu S T, Chen C H, Chang J J, Lee K H. Cytotoxicity of isoquinoline alkaloids and their N-oxides.  Planta Med. 1989;  55 163-5
  • 2 Tzeng C C, Wu Y C, Su T L, Watanabe K A, Lu S T, Chou T C. Inhibitory effects of isoquinoline-type alkaloids on leukemic cell growth and macromolecule biosynthesis.  Kaohsiung J Med Sci. 1990;  6 58-65
  • 3 Tsai I L, Liou Y F, Lu S T. Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities.  Kaohsiung J Med Sci. 1989;  5 132-45
  • 4 Chen K S, Ko F N, Teng C M, Wu Y C. Antiplatelet and vasorelaxing actions of some aporphinoids.  Planta Med. 1996;  62 133-6
  • 5 Chia Y C, Chen K S, Chang Y L, Teng C M, Wu Y C. Antiplatelet actions of aporphinoids from Formosan plants.  Bioorg Med Chem Lett. 1999;  9 3295-300
  • 6 Ukita T, Mizuno D, Tamura T. Studies on the antibacterial properties of berberinium chloride.  Jpn J Exp Med. 1949;  20 103-8
  • 7 Awe W U, Gottingen G. Berberine derivatives. VII. Cleavage of 9-benzyl-16,17-dihydrodesoxypalmatine by iodine or mercuric acetate.  Arch Pharm. 1944;  282 97-100
  • 8 Yang T H, Lu S T. Studies on the alkaloids of Berberidaceous plants XXVI. Alkaloids of Berberis mingetsensis Hayata.  Yakugaku Zasshi. 1960;  80 849-51
  • 9 Sun T T, Loh S H, Kyi Z Y. Synthesis of compound related to corydalis B (tetrahydropalmatine). IV. The synthesis of some acyloxy- and alkoxyberbines.  Yao Xue Xue Bao. 1965;  12 314-8
  • 10 Richter W J, Brochmann-Hanssen E. The structure of discretamine, a tetrahydroprotoberberine alkaloid.  Helv Chim Acta. 1975;  58 209-11
  • 11 Debska W. Separation and determination of the dissociation constants of chelidonine and protopine by paper chromatography.  Nature. 1958;  182 666-7
  • 12 Lu S T, Wang S J, Su T L. Studies on the alkaloids of Formosan Corydalis species. I. Alkaloids of Corydalis campulicarpa Hayata.  Yakugaku Zasshi. 1971;  91 778-81
  • 13 Lu S T, Lan P K. Studies on the alkaloids of Formosa Lauraceous plants. VIII. Alkaloids of Crypyocarya chinensis Hemsl. (1). Structures of the new alkaloids ”crychine” and ”caryachine”.  Yakugaku Zasshi. 1966;  86 177-84
  • 14 Lu S T. Studies on the alkaloids of Formosan Lauraceous plants IX. Alkaloids of Cryptocarya chinensis Hemsl and Cryptocarya konishii Hayata.  Yakugaku Zasshi. 1966;  86 296-9
  • 15 Lu S T, Su T L, Kametani T, Ihara M. Structural elucidation of two new spirobenzylisoquinoline alkaloids, yenhusomine and yenhusomidine.  Heterocycles. 1975;  3 301-5
  • 16 Lu S T, Wu Y C, Leou S P. The oxidation of isoquinoline alkaloids with m-chloroperbenzoic acid.  J Chin Chem Soc. 1987;  34 33-42
  • 17 Tomita M, Yang T H, Lu S T. Studies on the alkaloids of Formosan Lauraceous plants. I. Alkaloids of Machilus kusanoi Hayata. (1). The isolation of L-(-)-N-norarmepavine.  Yakugaku Zasshi. 1963;  83 15-8
  • 18 Lu S T. Studies on the alkaloids of Formosan Lauraceous plants II. Alkaloids of Machilus kusanoi Hayata. (2). The isolation of dl-coclaurine.  Yakugaku Zasshi. 1963;  83 19-21
  • 19 Lu S T, Chen I S. Structure of a new bisbenzylisoquinoline alkaloids, lindoldhamine.  Heterocycles. 1976;  4 1073-6
  • 20 Tomita M, Furukawa H, Lu S T. The constitution of thalicarpine.  Chem Pharm Bull. 1967;  15 959-63
  • 21 Wu Y C, Liou Y F, Lu S T. Antimicrobial activity of isoquinoline alkaloids and their N-oxide derivatives.  Kaohsiung Med Sci. 1988;  4 336-44
  • 22 Yang T H, Lu S T. Studies on the alkaloids of Magnoliaceous plants XXXV. Alkaloids of Magnolia kachirachirai Dandy. (2). The isolation of D-(+)-N-norarmepavine.  Yakugaku Zasshi. 1963;  83 22-5
  • 23 Lu S T, Tsai I L. Hofmann elimination with diazomethane on quaternary benzyltetrahydroisoquinoline related alkaloids.  Heterocycles. 1988;  27 751-68
  • 24 Lu S T, Su T L, Wang E C. Studies on the alkaloids of Formosan Lauraceous plants XVIII. Alkaloids of Neolitsea buisanensis Yamamato et Kamikoti and Neolitsea aurata (Hay.) Koidz.  J Chin Chem Soc. 1975;  22 349-53
  • 25 Lu S T, Wu Y C, Leou S P. Alkaloids of Formosan Fissistigma and Goniothalamus species.  Phytochemistry. 1985;  24 1829-34
  • 26 Vane J R. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs.  Nat New Biol. 1971;  231 232-5

Prof. Dr. Yang-Chang Wu

Graduate Institute of Natural Products

Kaohsiung Medical University

Kaohsiung 807

Taiwan

Republic of China

Phone: +886-7-312-1101-2197

Fax: +886-7-311-4773

Email: yachwu@kmu.edu.tw