Isolation and identification of antiplatelet aggregatory principles from the leaves of Piper lolot

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 23, 2007, Pages 9436-9442

  Li, Chia Ying ^a   Tsai, Wei Jern ^b   Damu, Amooru Gangaiah ^a   Lee, E Jian ^a   Wu, Tian Shung ^a,b   Nguyen, Xuan Dung ^c   Tran, Dinh Thang ^d   Thanh, Le ^e  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^c VIETNAM NATIONAL UNIVERSITY   (Viet Nam)

^d VINH UNIVERSITY   (Viet Nam)

^e HUE UNIVERSITY   (Viet Nam)

Author keywords

Antiplatelet aggregation; Piper lolot; Piperaceae; Piperlotine

Indexed keywords

ALKALOID; ANTITHROMBOCYTIC AGENT;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; ISOLATION AND PURIFICATION; PIPERACEAE; PLANT LEAF; RABBIT; THROMBOCYTE AGGREGATION;

ALKALOIDS; ANIMALS; PIPER; PLANT LEAVES; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; RABBITS;

ORYCTOLAGUS CUNICULUS; PIPER LOLOT; PIPERACEAE;

EID: 36749028801     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf071963l     Document Type: Article

References (41)

1. Davies, M. J.; Thomas, M. B. Thrombosis and acute coronary lesions in sudden cardiac ischemic death. N. Engl. J. Med. 1984, 310, 1137-1140.
2. Fuster, V. F.; Badimon, J. J.; Chesebro, J. H. Mechanisms of disease: the pathogenesis of coronary artery disease and the acute coronary syndromes. N. Engl. J. Med. 1992, 326, 242-250.
3. Wu, T. S.; Kao, M. S.; Wu, P. L.; Lin, F. W.; Shi, L. S.; Teng, C. M. Antiplatelet principles from the root of Petasites formosanus. Phytochemistry 2000, 52, 901-905.
4. Wu, T. S.; Shi, L. S.; Wang, J. J.; Iou, S. C.; Chang, H. C.; Chen, Y. P.; Kuo, Y. H.; Chang, Y. L.; Teng, C. M. Cytotoxic and antiplatelet aggregation principles of Ruta graveolens. J. Chin. Chem. Soc. 2001, 50, 171-178.
5. Wu, T. S.; Tsang, Z. J.; Wu, P. L.; Lin, F. W.; Li, C. Y.; Teng, C. M.; Lee, K. H. New constituents and antiplatelet aggregation and anti-HIV principles of Artemisia capillaries. Bioorg. Med. Chem. 2001, 9, 77-83.
6. Liou, M. J.; Teng, C. M.; Wu, T. S. Constituents from Rubia ustulata Diels and R. yunnanensis Diels and their antiplatelet aggregation activity. J. Chin. Chem. Soc. 2002, 49, 1025-1030.
7. Shultes, R. E.; Raffauf, R. F. The Healing Forest: Medicinal and Toxic Plants of the Northwest Amazonia; Historical, Ethno- & Economic Botany, Vol. 2; Dioscoride Press: Portland, OR, 1990; pp 362-368.
8. Iwashita, M.; Saito, M.; Yamaguchi, Y.; Takagaki, R.; Nakahata, N. Inhibitory effect of ethanol extract of Piper longum L. on rabbit platelet aggregation through antagonizing thromboxane A2 receptor. Biol. Pharm. Bull. 2007, 30, 1221-1225.
9. Chen, Y. C.; Liao, C. H.; Chen, I. S. Lignans, an amide and anti-platelet activities from Piper philippinum. Phytochemistry 2007, 68, 2101-2111.
10. Tripathi, A. K.; Jain, D. C.; Kumar, S. Secondary metabolites and their biological and medicinal activites of Piper species plants. J. Med. Aromat. Plant Sci. 1996, 18, 302-321.
11. Kiuchi, F.; Nakamura, N.; Tsuda, Y.; Kondo, K.; Yoshimura, H. Studies on crude drugs effective on visceral larva migrans. IV. Isolation and identification of larvicidal principles in pepper. Chem. Pharm. Bull. 1988, 36, 2452-2465.
12. Park, I. K.; Lee, S. G.; Shin, S. C.; Park, J. D.; Ahn, Y. J. Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species. J. Agric. Food Chem. 2002, 50, 1866-1870.
13. Truyen, L. V.; Chau, N. G. Selected Medicinal Plants in Vietnam; Science and Technology Publishing House: Hanoi, Vietnam, 1999; pp 182-184.
14. Parmar, V. S.; Jain, S. C.; Bisht, K. S.; Jain, R.; Taneja, P.; Jha, A.; Tyagi, O. D.; Prasad, A. K.; Wengel, J.; Olsen, C. E.; Boll, P. M. Phytochemistry of the Genus Piper. Phytochemistry 1997, 46, 597-673.
15. Luger, P.; Weber, M.; Dung, N. X.; Luu, V. T.; Rang, D. D.; Tuong, D. T.; Ngoc, P. H. The crystal structure of 3-(4′-methoxyphenyl)propanoyl pyrrole of Piper lolot C. DC from Vietnam. Cryst. Res. Technol. 2002, 37, 627-633.
16. Singh, S. K.; Prasad, A. K.; Olsen, C. E.; Jha, A.; Jain, S. C.; Parmar, V. S.; Wengel, J. Neolignans and alkaloids from Piper argyrophylum. Phytochemistry 1996, 43, 1355-1360.
17. 13C NMR spectroscopic analyses. Phytochemistry 2002, 59, 429-433.
18. Ekundayo, O.; Laakso, I.; Adegbola, R. M.; Oguntimein, B.; Sofowora, A.; Hiltunen, R. Essential oil constituents of Ashanti pepper (Piper guineense) fruits (Berries). J. Agric. Food Chem. 1988, 36, 880-882.
19. Tsai, W. J.; Hsieh, H. T.; Chen, C. C.; Kuo, Y. C.; Chen, C. F. Characterization of the antiplatelet effect of (2 5)-5-methoxy-6-methylflavan-7- ol from Draconis Resina. Eur. J. Pharmacol. 1998, 346, 103-110.
20. Hung, C. C.; Tsai, W. J.; Yang, L. M.; Kuo, Y. H. Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents. Bioorg. Med. Chem. 2005, 13, 1791-1797.
21. Hsu, H. C.; Yang, W. C.; Tsai, W. J.; Chen, C. C.; Huang, H. Y.; Tsai, Y. C. α-Bulnesene, a novel PAF receptor antagonist isolated from Pogostemon cablin. Biochem. Biophys. Res. Commun. 2006, 345, 1033-1038.
22. Ishihara, H.; Hori, K.; Sugihara, H.; Ito, Y. N.; Katsuki, T. Highly diastereo- and enantioselective aziridination of α,β- unsaturated amides with diaziridine and mechanistic consideration on its stereochemistry. Helv. Chim. Acta 2002, 85, 4272-4286.
23. Cerbai, G.; Dipaco, G. F.; Dell'Omodarme, G. Neurosedative and hypotensive activity in a series of acyl derivatives of certain heterocyclic bases. Boll. Chim. Farm. 1962, 101, 211-214.
24. Bruening, C. H.; Darling, C. M.; Magarian, R. A.; Nobles, W. L. Use of N-methyltetrahydrofurfurylamine in the Mannich reaction. J. Pharm. Sci. 1965, 54, 1537-1539.
25. Soloshonok, V. A.; Cai, C.; Hruby, V. J. Rational design of highly diastereoselective, organic base-catalyzed, room-temperature Michael addition reactions. J. Org. Chem. 2000, 65, 6688-6696.
26. Sibi, M. P.; Liu, M. N-Benzylhydroxylamine addition to β-aryl enoates. Enantioselective synthesis of β-aryl-β-amino acid precursors. Org. Lett. 2000, 2, 3393-3396.
27. Priestap, H. A. Seven aristololactams from Aristolochia argentina. Phytochemistry 1985, 24, 849-852.
28. Achari, B.; Chakrabarty, S.; Bandyopadhyay, S.; Pakrashi, S. C. A new 4,5-dioxoaporphine and other constituents of Aristolochia indica. Heterocycles 1982, 19, 1203-1206.
29. Kojima, H.; Sato, N.; Hatano, A.; Ogura, H. Sterol glucosides from Prunella vulgaris. Phytochemistry 1990, 29, 2351-2355.
30. Bohlmann, F.; Abraham, W. R. Neue diterpene aus Helichrysum acutatum. Phytochemistry 1979, 18, 1754-1756.
31. Ishihara, H.; Hori, K.; Sugihara, H.; Ito, Y. N.; Katsuki, T. Highly diastereo- and enantioselective aziridination of alpha, beta-unsaturated amides with diaziridine and mechanistic consideration on its stereochemistry. Helv. Chim. Acta 2002, 85, 4272-4286.
32. Li, C. Y.; Lee, E J.; Wu, T. S. Antityrosinase principles and constituents of the petals of Crocus sativus. J. Nat. Prod. 2004, 67, 437-440.
33. Teresa, J. D. P.; Urones, J. G.; Marcos, I. S.; Núñez, L.; Basabe, P. Diterpenoids and flavonoids from Cistus palinhae. Phytochemistry 1983, 22, 2805-2808.
34. Crosignani, S.; White, P. D.; Lindau, B. Polymer-supported O-alkylisoureas: useful reagents for the O-alkylation of carboxylic acids. J. Org. Chem. 2004, 69, 5897-5905.
35. Yang, D.; Wong, M. K.; Yan, Z. Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ. J. Org. Chem. 2000, 65, 4179-4184.
36. Kai, H.; Baba, M.; Okuyama, T. Two new megastigmanes from the leaves of Cucumis sativus. Chem. Pharm. Bull. 2007, 55, 133-136.
37. Duan, H.; Takaishi, Y.; Momota, H.; Ohmoto, Y.; Taki, T. Immunosuppressive constituents from Saussurea medusa. Phytochemistry 2002, 59, 85-90.
38. Hernandez, L. R.; Riscala, E. C.; de Catalan, C. A. N.; Diaz, J. G.; Herz, W. Sesquiterpene lactones and other constituents of Stevia maimarensis and Synedrellopsis grisebachii. Phytochemistry 1996, 42, 681-684.
39. Lin, C. H.; Li, C. Y.; Kuoh, C. S.; Wu, T. S. Constituents of the leaves of Petasites formosanus and their antioxidative activity. Heterocycles 2003, 60, 1881-1890.
40. Gupta, M. M.; Verma, R. K.; Akhila, A. Oxo acids and branched fatty acid esters from rhizomes of Costus speciosus. Phytochemistry 1986, 25, 1899-1902.
41. Hanahan, D. J. Platelet activating factor: a biologically active phosphoglyceride. Annu. Rev. Biochem. 1986, 55, 483-509.