Environmental and ontogenetic control of accumulation of brachycerine, a bioactive indole alkaloid from Psychotria brachyceras

Journal of Chemical Ecology

Volumn 30, Issue 10, 2004, Pages 2023-2036

  Gregianini, Tatiana Schäffer ^a,b   Porto, Diogo Denardi ^a   Do Nascimento, Naíla Cannes ^a   Fett, Janette Palma ^a   Henriques, Amélia Teresinha ^a   Fett Neto, Arthur Germano ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b Fundacao Estadual de Producao e Pesquisa em Saude   (Brazil)

Author keywords

Developmental control; Herbivory; Jasmonic acid; Monoterpenoid indole alkaloid; Salicylic acid; Seasonal pattern; Wounding

Indexed keywords

CHEMICAL ECOLOGY; HERBIVORY; REPRODUCTIVE BIOLOGY; WOUNDING;

PSYCHOTRIA; TRIXIS;

BRACHYCERINE; CYCLOPENTANE DERIVATIVE; INDOLE ALKALOID; INDOLE DERIVATIVE; JASMONIC ACID; SALICYLIC ACID; TERPENE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; ENVIRONMENT; GERMINATION; MEDICINAL PLANT; METABOLISM; PLANT LEAF; RUBIACEAE; SEASON;

CYCLOPENTANES; ENVIRONMENT; GERMINATION; INDOLE ALKALOIDS; INDOLES; MONOTERPENES; PLANT LEAVES; PLANTS, MEDICINAL; RUBIACEAE; SALICYLIC ACID; SEASONS;

EID: 21644483166     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:JOEC.0000045592.24785.33     Document Type: Article

References (41)

1. BALDWIN, I. T., HALITSCHKE, R., KESSLER, A., and SCHITTKO, U. 2001. Merging molecular and ecological approaches in plant-insect interactions. Curr. Opin. Plant Biol. 4:351-358.
2. BARON, C. and ZAMBRYSKI, P. C. 1995. The plant response in pathogenesis, symbiosis, and wounding: Variations on a common theme? Ann. Rev. Gen. 29:107-129.
3. CONCONI, A., SMERDON, M. J., HOWE, G. A., and RYAN, C. A. 1996. The octadecanoid signalling pathway in plants mediates a response to ultraviolet radiation. Nature 383:826-829.
4. CONTIN, A., VAN DER HEIJDEN, R., LEFEBER, A. W., and VERPOORTE, R. 1998. The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture. FEBS Lett. 434:413-419.
5. DEVOTO, A. and TURNER, J. G. 2003. Regulation of jasmonate-mediated plant responses in Arabidopsis. Ann. Bot. 92:329-337.
6. DILLENBURG, C. R., and PORTO, M. L. 1985. Rubiaceae - Tribo Psychotrieae. Bol. Inst. Biociênc. UFRGS 39:1-76.
7. ELISABETSKY, E., AMADOR, T. A., LEAL, M. B., NUNES, D. S., CARVALHO, A. C. T., and VEROTA, L. 1997. Merging ethnopharmacology with chemotaxonomy: An approach to unveil bioactive natural products. The case of Psychotria alkaloids as potential analgesics. Ciênc. Cul. (J. Braz. Assoc. Adv. Sci.) 49:378-385.
8. FACCHINI, P. J. 2001. Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52:29-66.
9. FARMER, E. E. and RYAN, C. A. 1992. Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors. Plant Cell 4:129-134.
10. FELTON, G. W., KORTH, K. L., BI, J. L., WESLEY, S. V., HUHMAN, D. V., MATHEWS, M. C., MURPHY, J. B., LAMB, C., and DIXON, R. A. 1999. Inverse relationship between systemic resistance of plants to microorganisms and to insect herbivory. Curr. Biol. 9:317-320.
11. FERNANDEZ, J. A., OWEN, T. G., KURZ, W. G. W., and DE LUCA, V. 1989. Immunological detection and quantitation of tryptophan decarboxylase in developing Catharanthus roseus seedlings. Plant Physiol. 91:79-84.
12. FRISCHKNECHT, P. M., BÄTTIG, M., and BAUMANN, T. W. 1987. Effect of drought and wounding stress on indole alkaloid formation in Catharanthus roseus. Phytochemistry 26:707-710.
13. GODOY, H. G. and LOYOLA, V. M. V. 1997. Effect of acetylsalicylic acid on secondary metabolism of Catharanthus roseus tumor suspension cultures. Plant Cell Rep. 16:287-290.
14. GREGIANINI, T. S., SILVEIRA, V. C., PORTO, D. D., KERBER, V. A., HENRIQUES, A. T., and FETT-NETO, A. G. 2003. The alkaloid brachycerine is induced by ultraviolet radiation and is a singlet oxygen quencher. Photochem. Photobiol. 78:470-474.
15. HOLLÓSY, F. 2002. Effects of ultraviolet radiation on plant cells. Micron 33:179-197.
16. KERBER, V. A., GREGIANINI, T. S., PARANHOS, J. T., SCHWAMBACH, J., FARIAS, J., FETT, J. P., FETT-NETO, A. G., ZUANAZZI, J. A. S., QUIRION, J., ELISABETSKY, E., and HENRIQUES, A. T. 2001. Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras. J. Nat. Prod. 64:677-679.
17. KESSLER, A. and BALDWIN, I. T. 2002. Plant responses to insect herbivory: The emerging molecular analysis. Annu. Rev. Plant Biol. 53:299-328.
18. KUTCHAN, T. M. 1995. Alkaloid biosynthesis - The basis for metabolic engineering of medicinal plants. Plant Cell 7:1059-1070.
19. LAUS, G., BRÖSSNER, D., and KEPLINGER, K. 1997. Alkaloids of peruvian Uncaria tomentosa. Phytochemistry 45:855-860.
20. LEÓN, J., YALPANI, N., RASKIN, I., and LAWTON, M. A. 1993. Induction of benzoic acid 2-hydroxylase in virus-inoculated tobacco. Plant Physiol. 103:323-328.
21. LEVIN, D. A. 1976. Alkaloid-bearing plants: An ecogeographic perspective. Am. Nat. 110:261-284.
22. LIU, Z., CARPENTER, S. B., BOURGEOIS, W. J., Yu, Y., CONSTANTIN, R. J., FALCON, M. J., and ADAMS, J. C. 1998. Variations in the secondary metabolite camptothecin in relation to tissue age and season in Camptotheca acuminata. Tree Phys. 18:265-270.
23. MALECK, K. and DIETRICH, R. 1999. Defense on multiple fronts: How do plants cope with diverse enemies? Trends Plant Sci. 4:215-219.
24. McCONN, M., CREELMAN, R. A., BELL, E., MULLET, J. E., and BROWSE, J. 1997. Jasmonate is essential for insect defense in Arabidopsis. Proc. Natl. Acad. Sci. U.S.A. 94:5473-5477.
25. MENKE, F. L. H., PARCHMANN, S., MUELLER, M. J., KIJNE, J. W., and MEMELINK, J. 1999. Involvement of the octadecanoid pathway and protein phosphorylation in fungal elicitor-induced expression of terpenoid indole alkaloid biosynthetic genes in Catharanthus roseus. Plant Physiol. 119:1289-1296.
26. MÉTRAUX, J.-P. 2002. Recent breakthroughs in the study of salicylic acid biosynthesis. Trends Plant Sci. 7:332-334.
27. MURASHIGE, T. and SKOOG, F. 1962. A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol. Plant 15:473-497.
28. OWENS, M. K., LIN, C.-D., TAYLOR, C. A., Jr., and WHISENANT, S. G. 1998. Seasonal patterns of plant flammability and monoterpenoid content in Juniperus ashei. J. Chem. Ecol. 24:2115-2129.
29. PASQUALI, G., GODDIJN, O. J. M., DE WAAL, A., VERPOORTE, R., SCHILPEROORT, R. A., HOGE, J. H. C., and MEMELINK, J. 1992. Coordinated regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors. Plant Mol. Biol. 18:1121-1131.
30. RAMACHANDRA RAO, S. and RAVISHANKAR, G. A. 2002. Plant cell cultures: Chemical factories of secondary metabolites. Biotech. Adv. 20:101-153.
31. RHODES, M. J. C. 1994. Physiological roles for secondary metabolites in plants: Some progress, many outstanding problems. Plant Mol. Biol. 24:1-20.
32. SCHMELZ, E. A., GREBENOK, R. J., GALBRAITH, D. W., and BOWERS, W. S. 1998. Damage-induced accumulation of phytoecdysteroids in spinach: A rapid root response involving the octadecanoic acid pathway. J. Chem. Ecol. 24:339-357.
33. SMITH, L. B. and DOWNS, R. J. 1956. Resumo preliminar das rubiáceas de Santa Catarina. Sellowia 7:13-86.
34. SOKAL, R. R. and ROHLF, F.J. 1981. Biometry: The Principles and Practice of Statistics in Biological Research, 2nd edn. WH Freeman, San Francisco.
35. ST-PIERRE, B, VAZQUEZ-FLOTA, F. A., and DE LUCA, V. 1999. Multicellular compartmentation of Catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate. Plant Cell 11:887-900.
36. THOMMA, B. P. H. J., EGGERMONT, K., PENNINCKX, I. A. M. A., MAUCH-MANI, B., VOGELSANG, R., CAMMUE, B. P. A., and BROEKAERT, W. F. 1998. Separate jasmonate-dependent and salicylate-dependent defense-response pathways in Arabidopsis are essential for resistance to distinct microbial pathogens. Proc. Natal. Acad. Sci. U.S.A. 95: 15107-15111.
37. VAN DER FITS, L. and MEMELINK, J. 2000. ORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism. Science 289:295-297.
38. VESTENA, S., FETT-NETO, A. G., DUARTE, R. C., and FERREIRA, A. G. 2001. Regulation of mimosine accumulation in Leucaena leucocephala seedlings. Plant Sci. 161:597-604.
39. WILLIAMS, W. and HARRISON, J. E. M. 1983. Alkaloid concentration during development in three Lupinus species and the expression of genes for alkaloid biosynthesis in seedlings. Phytochemistry 22:85-90.
40. YUKIMUNE, Y., TABATA, H., HIGASHI, Y., and HARA, Y. 1996. Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nat. Biotech. 14:1129-1132.
41. ZÁRATE, R., DIRKS, C., VAN DER HEIJDEN, R., and VERPOORTE, R. 2001. Terpenoid indole alkaloid profile changes in Catharanthus pusillus during development. Plant Sci. 160:971-977.