Skip to content
Publicly Available Published by De Gruyter January 1, 2009

Chemistry and evolution of the Piperaceae

  • Massuo J. Kato and Maysa Furlan

Abstract

The chemistry of members of the family Piperaceae is of great interest owing to the variety of biological properties displayed. A survey of structural diversity and bioactivity reveals that groups of species specialize in the production of amides, phenylpropanoids, lignans and neolignans, benzoic acids and chromenes, alkaloids, polyketides, and a plethora of compounds of mixed biosynthetic origin. Bioassays against Cladosporium cladosporioides and C. sphaerospermun have resulted in the characterization of various amides, prenylated phenolic compounds, and polyketides as potential classes of antifungal agents. Studies on the developmental process in seedlings of Piper solmsianum have shown that phenylpropanoid are produced instead of the tetrahydrofuran lignans found in adult plants. In suspension cultures of P. cernuum and P. crassinervium, phenylethylamines and alkamides predominate, whereas in the adult plants prenylpropanoids and prenylated benzoic acids are the respective major compound classes. Knowledge of the chemistry, bioactivity, and ecology of Piperaceae species provides preliminary clues for an overall interpretation of the possible role and occurrence of major classes of compounds.


Conference

International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 25th, Kyoto, Japan, 2006-07-23–2006-07-28


References

1. T. G. Yuncker. Hoehnea 2, 19 (1972).Search in Google Scholar

2. T. G. Yuncker. Hoehnea 3, 29 (1973).Search in Google Scholar

3. T. G. Yuncker. Hoehnea 4, 71 (1974).Search in Google Scholar

4. doi:10.1016/S0031-9422(97)00328-2, V. S. Parmar, S. C. Jain, K. S. Bisht, R. Jain, P. Taneja, J. A. Tyagi, O. D. Prasad, A. K. Wengel, J. C. E. Olsen, P. M. Boll. Phytochemistry 46, 597 (1997).Search in Google Scholar

5. doi:10.1086/382803, M. A. Jaramillo, P. S. Manos, E. A. Zimmer. Int. J. Plant Sci. 165, 403 (2004).Search in Google Scholar

6. doi:10.1023/A:1026290022642, S. B. Mikich, G. V. Bianconi, B. H. L. N. S. Maia, S. D. Teixeira. J. Chem. Ecol. 29, 2379 (2003).Search in Google Scholar

7. doi:10.1017/S0266467400001383, H. M. Rogers, A. E. Hartemink. J. Trop. Ecol. 16, 243 (2006).Search in Google Scholar

8. doi:10.1055/s-2005-873060, S. Wanke, M.-S. Samain, L. Vanderschaeve, G. Mathieu, P. Goetghebeur, C. Neinhuis. Plant Biol. 8, 93 (2006).Search in Google Scholar

9. L. A. Dyer, A. D. N. Palmer. Piper. A Model Genus for Studies of Evolution, Chemical Ecology, and Trophic Interactions, Kluwer Academic/Plenum (2004).10.1007/978-0-387-30599-8Search in Google Scholar

10. doi:10.1016/S0031-9422(99)00132-6, D. C. Baldoqui, M. J. Kato, A. J. Cavalheiro, V. S. Bolzani, M. C. M. Young, M. Furlan. Phytochemistry 51, 899 (1999).Search in Google Scholar

11. doi:10.1021/np030530j, J. G. L. Lago, C. S. Ramos, D. C. C. Casanova, A. A. Morandim, D. Bergamo, A. J. Cavalheiro, V. S. Bolzani, M. Furlan, E. F. Guimaraes, M. C. M. Young, M. J. Kato. J. Nat. Prod. 67, 1783 (2004).Search in Google Scholar

12. doi:10.1016/0031-9422(93)85442-T, S. Jensen, J. Hansen, P. M. Boll. Phytochemistry 33, 523 (1993).Search in Google Scholar

13. doi:10.1016/S0031-9422(99)00177-6, P. J. C. Benevides, P. Sartorelli, M. J. Kato. Phytochemistry 52, 339 (1999).Search in Google Scholar

14. doi:10.1016/S0031-9422(00)00295-8, R. C. C. Martins, P. Sartorelli, L. R. Latorre, M. J. Kato. Phytochemistry 7, 843 (2000).Search in Google Scholar

15. doi:10.1016/S0031-9422(98)00208-8, V. S. Parmar, S. C. Jain, S. Gupta, S. Talwar, V. K. Rajwanshi, R. Kumar, A. Azim, S. Malhotra, N. Kumar, R. Jain, N. K. Sharma, O. D. Tyagi, S. J. Lawrie, W. Errington, O. W. Howarth, C. E. Olsen, S. K. S. J. Wengel. Phytochemistry 49, 1069 (1998).Search in Google Scholar

16. doi:10.1016/S0031-9422(97)01050-9, T. Tanaka, F. Asai, M. Linuma. Phytochemistry 49, 229 (1998).Search in Google Scholar

17. doi:10.1016/j.phytochem.2005.01.003, K. J. M. Salazar, G. E. D. Paredes, L. R. Lluncor, M. C. M. Young, M. J. Kato. Phytochemistry 66, 573 (2005).Search in Google Scholar

18. doi:10.1016/j.phytochem.2006.08.007, R. O. S. Kitamura, P. Romoff, M. C. M. Young, M. J. Kato, J. H. G. Lago. Phytochemistry 67, 2398 (2006).Search in Google Scholar

19. doi:10.1021/np050417o, N. Li, J.-L. Wu, T. Hasegawa, J. I. Sakai, L. Y. Wang, S. Kakuta, Y. Furuya, A. Tomida, T. Tsuruo, M. Ando. J. Nat. Prod. 69, 234 (2006).Search in Google Scholar

20. doi:10.1021/np0600447, J.-L. Wu, N. Li, T. Hasegawa, J. Sakai, T. Mitsui, H. Ogura, T. Kataoka, S. Oka, M. Kiuchi, A.Tomida, T. Turuo, M. Li, W. Tang, M. Ando. J. Nat. Prod. 69, 790 (2006).Search in Google Scholar

21. doi:10.1021/np9703656, A. C. Alecio, V. S. Bolzani, M. J. Kato, M. Furlan. J. Nat. Prod. 61, 637 (1998).Search in Google Scholar

22. doi:10.1016/S0031-9422(00)00226-0, H. M. D. Navickiene, A. C. Alecio, M. J. Kato, V. S. Bolzani, M. C. M. Young, A. J. Cavalheiro, M. Furlan. Phytochemistry 55, 621 (2000).Search in Google Scholar

23. doi:10.1016/S0031-9422(01)00431-9, R. V. Silva, H. M. D. Navickiene, M. J. Kato, V. S. Bolzani, C. I. Meda, M. C. M. Young, M.Furlan. Phytochemistry 59, 521 (2002).Search in Google Scholar

24. doi:10.1002/arch.10118, I. M. Scott, H. Jensen, J. G. Scott, M. B. Isman, J. T. Arnason, B. J. R. Philogene. Arch. Insect Biochem. Physiol. 54, 212 (2003).Search in Google Scholar

25. doi:10.1023/A:1026310001958, L. A. Dyer, C. D. Dodson, J. O. Stireman, M. A. Tobler, A. M. Smilanich, R. M. Fincher, D. K. Letourneau. J. Chem. Ecol. 29, 2499 (2003).Search in Google Scholar

26. doi:10.1016/S0261-2194(00)00172-1, S.-E. Lee, B.-S. Park, M.-K. Kim, W.-S. Choi, H.-T. Kim, K.-Y. Cho, S.-G. Lee, H.-S. Lee. Crop Prot. 20, 523 (2001).Search in Google Scholar

27. doi:10.1021/jf011708f, Y.-C. Yang, S.-G. Lee, H.-K. Lee, M.-K. Kim, S.-H. Lee, H.-S. Lee. J. Agric. Food Chem. 50, 3765 (2002).Search in Google Scholar

28. doi:10.1007/BF02033462, C. B. Bernard, H. G. Krishnamurty, D. Chauret, T. Durst, B. J. R. Philogene, P. Sanchezvindas, C. Hasbun, L. Poveda, L. Sanroman, J. T. Arnason. J. Chem. Ecol. 21, 801 (1995).Search in Google Scholar

29. doi:10.1021/np010410g, A. Lopes, D. S. Ming, G. H. N. Towers. J. Nat. Prod. 65, 62 (2002).Search in Google Scholar

30. doi:10.1055/s-2006-959758, J. Orjala, C. A. Erdelmeier, A. D. Wright, T. Rali, O. Sticher. Planta Med. 59, 546 (1993).Search in Google Scholar

31. doi:10.1016/S0031-9422(98)00197-6, C. Terreaux, M. P. Gupta, K. Hostettmann. Phytochemistry 49, 461 (1998).Search in Google Scholar

32. doi:10.1590/S0103-50532005000800018, D. C. B. Bergamo, M. J. Kato, V. S. Bolzani, M. Furlan. J. Braz. Chem. Soc. 16, 1406 (2005).Search in Google Scholar

33. doi:10.1016/S0031-9422(03)00299-1, A. P. Danelutte, J. H. G. Lago, M. C. M. Young, M. J. Kato. Phytochemistry 64, 555 (2003).Search in Google Scholar

34. doi:10.1016/S0040-4039(01)86615-6, B. M. Howard, K. Clarkson, R. C. Bernstein. Tetrahedron Lett. 46, 4449 (1979).Search in Google Scholar

35. doi:10.1016/S0040-4039(00)74359-0, M. Fadli, J. M. Aracil, G. Jeanty, B. Banaigs, C. Francisco, S. Moreau. Tetrahedron Lett. 32, 2477 (1991).Search in Google Scholar

36. W. E. G. Muller, A. Maidhof, R. K. Zahn, H. C. Schoroder, M. J. Gasic, D. Heidemann, A. Bernd, B. Kurelec, E. Eich, G. Seibert. Cancer Res. 45, 4822 (1985).Search in Google Scholar

37. doi:10.1016/0742-8413(85)90130-6, W. E. G. Muller, R. K. Zhan, M. J. Gasic, N. Dogovic, A. Maidhof, C. Becker, B. Diehl-Seifert, E. Eich. Comp. Biochem. Physiol. C 80, 47 (1985).Search in Google Scholar

38. doi:10.1002/ptr.2650050202, R. De Pasquale, C. Circosta, F. Occhiuto, S. De Rosa, S. De Stefano. Phytother. Res. 5, 49 (1991).Search in Google Scholar

39. doi:10.1016/0891-5849(91)90188-9, N. Cotele, S. Moreau, J. S. Bernier, J. P. Catteau, J. P. Henichart. Free Radical Biol. Med. 11, 63 (1991).Search in Google Scholar

40. doi:10.1016/j.phytochem.2006.03.001, L. F. Yamaguchi, J. H. G. Lago, T. M. Tanizaki, P. Di Mascio, M. J. Kato. Phytochemistry 67, 1838 (2006).Search in Google Scholar

41. doi:10.1016/j.ijpharm.2005.07.006, V. V. Silva, C. D. Ropke, R. L. de Almeida, D. V. Miranda, C. Z. Kera, D. P. Rivelli, T. C. H. Sawada, S. B. M. Barros. Int. J. Pharm. 303, 125 (2005).Search in Google Scholar

42. doi:10.1002/pca.843, A. A. Morandim, D. C. B. Bergamo, M. J. Kato, A. J. Cavalheiro, V. S. Bolzani, M. Furlan. Phytochem. Anal. 16, 282 (2005).Search in Google Scholar

43. doi:10.1021/np050417o, N. Li, J.-L. Wu, T. Hasegawa, J.-I. Sakai, L.-Y. Wang, S. Kakuta, Y. Furuya, A. Tomida, T. Tsuruo, M. Ando. J. Nat. Prod. 69, 234 (2006).Search in Google Scholar

44. doi:10.1021/np0600447, J.-L. Wu, N. Li, T. Hasegawa, J.-I. Sakai, T. Mitsui, H. Ogura, T. Kataoka, S. Oka, M. Kiuchi, A.Tomida, T. Turuo, M. Li, W. Tang, M. Ando. J. Nat. Prod. 69, 790 (2006).Search in Google Scholar

45. doi:10.1021/np050283e, J.-L. Wu, N. Li, T. Hasegawa, J.-I. Sakai, S. Kakuta, W. Tang, S. Oka, M. Kiuchi, H. Ogura, T.Kataoka, A. Tomida, T. Tsuruo, M. Ando. J. Nat. Prod. 68, 1656 (2005).Search in Google Scholar

46. doi:10.1016/S0031-9422(03)00356-X, R. C. Martins, J. H. G. Lago, M. J. Kato. Phytochemistry 64, 667 (2003).Search in Google Scholar

47. K. Nihei, K. Konno, L. S. C. Bernardes, N. P. Lopes, S. Albuquerque, I. Carvalho, M. T. Pupo, R. C. C. Martins, M. J. Kato. Arkivoc (vi) 112 (2004).10.3998/ark.5550190.0005.615Search in Google Scholar

48. doi:10.1016/j.bmc.2006.07.006, L. S. C. Bernardes, M. J. Kato, S. Albuquerque, I. Carvalho. Bioorg. Med. Chem. 14, 7075 (2006).Search in Google Scholar

49. doi:10.1002/pca.716, H. M. D. Navickiene, M. J. Kato, V. S. Bolzani, M. Furlan. Phytochem. Anal. 14, 281 (2002).Search in Google Scholar

50. doi:10.1016/S0031-9422(99)00177-6, P. J. C. Benevides, P. Sartorelli, M. J. Kato. Phytochemistry 52, 339 (1999).Search in Google Scholar

51. doi:10.1016/S0168-9452(01)00512-X, P. Sartorelli, P. J. C. Benevides, R. E. Ellensohn, M. V. A. F. Rocha, P. R. H. Moreno, M. J. Kato. Plant Sci. 161, 1083 (2001).Search in Google Scholar

52. doi:10.1590/S0103-50532005000800022, A. P. Danelutte, M. B. Costantin, G. E. Delgado, R. Braz-Filho, M. J. Kato. J. Braz. Chem. Soc. 16, 1425 (2005).Search in Google Scholar

53. doi:10.1016/S0031-9422(00)00050-9, P. J. Facchini, K. L. Huber-Allanach, L. W. Tari. Phytochemistry 54, 121 (2000).Search in Google Scholar

54. doi:10.1021/np0401260, R. Mata, I. Morales, O. Perez, I. Rivero-Cruz, L. Acevedo, I. Enriquez-Mendoza, R. Bye, S.Franzblau, B. Timmermann. J. Nat. Prod. 67, 1961 (2004).Search in Google Scholar

55. doi:10.1016/S0031-9422(96)00502-X, S. K. Singh, A. K. Prasad, C. E. Olsen, A. Jha, S. C. Jain, V. S. Parmar, J. Wengel. Phytochemistry 43, 1355 (1996).Search in Google Scholar

56. doi:10.1016/S0031-9422(00)83890-X, J. M. Barbosa-Filho, M. Yoshida, O. R. Gottlieb, R. D. S. B. C. Barbosa, A. M. Giesbrecht, M.C.M. Young. Phytochemistry 26, 2615 (1987).Search in Google Scholar

57. doi:10.1104/pp.104.050294, G. Guillet, V. de Luca. Plant Physiol. 137, 692 (2005).Search in Google Scholar

58. doi:10.1016/S0031-9422(00)95143-4, O. Borg-Olivier, B. Monties. Phytochemistry 32, 601 (1993).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2007-01-01

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 14.5.2024 from https://www.degruyter.com/document/doi/10.1351/pac200779040529/html
Scroll to top button