Monoamine oxidase inhibition by monoterpene indole alkaloids and fractions obtained from Psychotria suterella and Psychotria laciniata

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 3, 2013, Pages 611-618

  Dos Santos Passos, Carolina ^a   Soldi, Tatiane Cristina ^a   Torres Abib, Renata ^a   Anders Apel, Miriam ^a   Simões Pires, Cláudia ^b   Marcourt, Laurence ^b   Gottfried, Carmem ^a   Henriques, Amélia Teresinha ^a  

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

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

MAO A; MAO B; Monoterpene indole alkaloids; Psychotria laciniata; Psychotria suterella; Rubiaceae

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CLORGYLINE; INDOLE ALKALOID; ISOVALLESIACHOTAMINE; LYALOSIDE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; PARGYLINE; PLANT EXTRACT; PSYCHOTRIA LACINIATA EXTRACT; PSYCHOTRIA SUTERELLA EXTRACT; STRICTOSAMIDE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; VALLESIACHOTAMINE;

ANIMAL TISSUE; ARTICLE; BRAIN MITOCHONDRION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ASSAY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; MALE; MEDICINAL PLANT; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSYCHOTRIA; PSYCHOTRIA LACINIATA; PSYCHOTRIA SUTERELLA; RAT; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG IDENTIFICATION; ENZYMATIC ASSAY; ENZYME ACTIVITY; IC50; NEOTROPICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIMALS; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; INHIBITORY CONCENTRATION 50; MALE; MITOCHONDRIA; MONOAMINE OXIDASE INHIBITORS; PLANT EXTRACTS; PSYCHOTRIA; RATS; RATS, WISTAR; SECOLOGANIN TRYPTAMINE ALKALOIDS;

PSYCHOTRIA; RATTUS; RUBIACEAE;

EID: 84875407617     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2012.666536     Document Type: Article

References (39)

1. Lopes S, Von Poser GL, Kerber VA, Farias FM, Konrath EL, Moreno P, et al. Taxonomic significance of alkaloids and iridoid glucosides in the tribe Psychotrieae (Rubiacea). Biochem Syst Ecol 2004;32:1187-1195.
2. Pasquali G, Porto DD, Fett-Neto AG. Metabolic engineering of cell cultures versus whole plant complexity in production of bioactive monoterpene indole alkaloids: Recent progress related to old dilemma. J Biosci Bioeng 2006;101:287-296.
3. Porto DD, Henriques AT, Fett-Neto AG. Bioactive alkaloids from South American Psychotria and related species. Open Bioact Compound J 2009;2:29-36.
4. De Santos LV, Fett-Neto AG, Kerber VA, Elisabetsky E, Quirion JC, Henriques AT. Indole monoterpene alkaloids from the leaves of Psychotria suterella Müll. Arg. (Rubiaceae). Biochem Syst Ecol 2001;29:1185-1187.
5. Kerber VA, Gregianini TS, Paranhos JT, Schwambach J, Farias FM, Fett JP, et al. Brachycerine, a novel monoterpene indole alkaloid from Psychotria brachyceras. J Nat Prod 2001;64:677-679.
6. Henriques AT, Lopes SO, Paranhos JT, Gregianini TS, Von Poser GL, Fett-Neto AG et al. N,beta-D-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa. Phytochemistry 2004;65:449-454.
7. Simões-Pires CA, Farias FM, Marston A, Queiroz EF, Chaves CG, Henriques AT, et al. Indole monoterpenes with antichemotactic activity from Psychotria myriantha. Nat Prod Commun 2006;1: 1101-1106.
8. Kerber VA, Passos CS, Verli H, Fett-Neto AG, Quirion JP, Henriques AT. Psychollatine, a glucosidic monoterpene indole alkaloid from Psychotria umbellata. J Nat Prod 2008;71:697-700.
9. Farias FM, Konrath EL, Zuanazzi JAS, Henriques AT. Strictosamide from Psychotria nuda (Cham. et Schltdl) Wawra (Rubiaceae). Biochem Syst Ecol 2008;36:919-920.
10. Paul JH, Maxwell AR, Reynolds WF. Novel bis(monoterpenoid) indole alkaloids from Psychotria bahiensis. J Nat Prod 2003;66: 752-754.
11. Pimenta AAT, Braz-Filho R, Delprete PG, Souza EB, Silveira ER, Lima MAS. Unusual monoterpene indole alkaloids from Psychotria stachyoides Benth. Biochem Syst Ecol 2010;38:846-849.
12. Pimenta AT, Braz-Filho R, Delprete PG, de Souza EB, Silveira ER, Lima MA. Structure elucidation and NMR assignments of two unusual monoterpene indole alkaloids from Psychotria stachyoides. Magn Reson Chem 2010;48:734-737.
13. Faria EO, Kato L, De Oliveira CMA, Carvalho BG, Silva CC, Sales LS, et al. Quaternary ?-carboline alkaloids from Psychotria prunifolia (Kunth) Steyerm. Phytochem Lett 2010;3:113-116.
14. Both FL, Kerber VA, Henriques AT, Elisabetsky E. Analgesic properties of umbellatine from Psychotria umbellata. Pharm Biol 2002;40:336-341.
15. Both FL, Meneghini L, Kerber VA, Henriques AT, Elisabetsky E. Psychopharmacological profile of the alkaloid psychollatine as a 5HT2A/C serotonin modulator. J Nat Prod 2005;68:374-380.
16. Both FL, Meneghini L, Kerber VA, Henriques AT, Elisabetsky E. Role of glutamate and dopamine receptors in the psychopharmacological profile of the indole alkaloid psychollatine. J Nat Prod 2006;69:342-345.
17. Reanmongkol W, Subhadhirasakul S, Kongsang J, Tanchong M, Kitti J. Analgesic and Antipyretic Activities of n-Butanol Alkaloids Extracted from the Stem Bark Hunteria Zeylanica and its Major Constituent, Strictosidinic Acid, in Mice. Pharm Biol 2000;38:68-73.
18. Farias FM, Passos CS, Arbo MD, Zuanazzi JA, Steffen VM, Henriques AT. Monoamine levels in rat striatum after acute intraperitoneal injection of strictosidinic acid isolated from Psychotria myriantha Mull. Arg. (Rubiaceae). Phytomedicine 2010;17:289-291.
19. Soto-Otero R, Méndez-Alvarez E, Hermida-Ameijeiras A, Sánchez-Sellero I, Cruz-Landeira A, Lamas ML. Inhibition of brain monoamine oxidase activity by the generation of hydroxyl radicals: Potential implications in relation to oxidative stress. Life Sci 2001;69:879-889.
20. Ma J, Yoshimura M, Yamashita E, Nakagawa A, Ito A, Tsukihara T. Structure of rat monoamine oxidase A and its specific recognitions for substrates and inhibitors. J Mol Biol 2004;338:103-114.
21. Youdim MB, Edmondson D, Tipton KF. The therapeutic potential of monoamine oxidase inhibitors. Nat Rev Neurosci 2006;7:295-309.
22. Youdim MB, Bakhle YS. Monoamine oxidase: Isoforms and inhibitors in Parkinson's disease and depressive illness. Br J Pharmacol 2006;147 Suppl 1:S287-S296.
23. Herraiz T. Identification and occurrence of beta-carboline alkaloids in raisins and inhibition of monoamine oxidase (MAO). J Agric Food Chem 2007;55:8534-8540.
24. Wang YH, Samoylenko V, Tekwani BL, Khan IA, Miller LS, Chaurasiya ND et al. Composition, standardization and chemical profiling of Banisteriopsis caapi, a plant for the treatment of neurodegenerative disorders relevant to Parkinson's disease. J Ethnopharmacol 2010;128:662-671.
25. Valverde J, Tamayo G, Hesse M. ?-Carboline monoterpenoid glucosides from Palicourea adusta. Phytochemistry 1999;52:6.
26. Peterson GL. A simplification of the protein assay method of Lowry et al. which is more generally applicable. Anal Biochem 1977;83:346-356.
27. van Diermen D, Marston A, Bravo J, Reist M, Carrupt PA, Hostettmann K. Monoamine oxidase inhibition by Rhodiola rosea L. roots. J Ethnopharmacol 2009;122:397-401.
28. Copeland R. (2005). Evaluation on enzyme inhibitors in drug discovery: A guide for medicinal chemists and pharmacologists. New York: Wiley, 111-140.
29. Djerassi C, Monteiro HJ, Walser A, Durham LJ. Alkaloid studies. LVI. The constitution of vallesiachotamine. J Am Chem Soc 1966;88:1792-1798.
30. Taylor C. Psychotria in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro 2010 [online]. Available at: Http://floradobrasil.jbrj.gov.br/2010/FB014153. Accessed on 27 April 2009.
31. Waterman PG, Zhong S. Vallesiachotamine and isovallesiachotamine from the seeds of Strychnos tricalysioides. Planta Med 1982;44:696-700.
32. van Beek TA, Verpoorte R, Baerheim Svendsen A. Alkaloids from Tabernaemontana psorocarpa. Planta Med 1983;47:83-86.
33. Vencato I, Da Silva FM, De Oliveira CMA, Kato L, Tanaka CMA, Da Silva CC, Sabino Jr. Vallesiachotamine. Acta Crystallogr E 2006;62:o429-o431.
34. Cardoso CL, Siqueira Silva DH, Tomazela DM, Verli H, Young MC, Furlan M et al. Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids. J Nat Prod 2003;66:1017-1021.
35. Herraiz T, Chaparro C. Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by beta-carboline alkaloids occurring in foods and plants. J Chromatogr A 2006; 1120:237-243.
36. Samoylenko V, Rahman MM, Tekwani BL, Tripathi LM, Wang YH, Khan SI et al. Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease. J Ethnopharmacol 2010;127:357-367.
37. Buckholtz NS, Boggan WO. Monoamine oxidase inhibition in brain and liver produced by beta-carbolines: Structure-activity relationships and substrate specificity. Biochem Pharmacol 1977;26:1991-1996.
38. Dreiseitel A, Korte G, Schreier P, Oehme A, Locher S, Domani M et al. Berry anthocyanins and their aglycons inhibit monoamine oxidases A and B. Pharmacol Res 2009;59:306-311.
39. Han XH, Hong SS, Hwang JS, Lee MK, Hwang BY, Ro JS. Monoamine oxidase inhibitory components from Cayratia japonica. Arch Pharm Res 2007;30:13-17.