New triterpenes from maytenus robusta: Structural elucidation based on NMR experimental data and theoretical calculations

Molecules

Volumn 17, Issue 11, 2012, Pages 13439-13456

  Sousa, Grasiely F ^a   Duarte, Lucienir P ^a   Alcântara, Antônio F C ^a   Silva, Grácia D F ^a   Vieira Filho, Sidney A ^b   Silva, Roqueline R ^a   Oliveira, Djalma M ^c   Takahashi, Jacqueline A ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b FEDERAL UNIVERSITY OF OURO PRETO   (Brazil)

^c UNIVERSIDADE ESTADUAL DO SUDOESTE DA BAHIA   (Brazil)

Author keywords

Acetylcholinesterase inhibitory activity; DFT calculations; Maytenus robusta; NMR; Pentacyclic triterpenes

Indexed keywords

ACETYLCHOLINESTERASE; CHLOROFORM; CHOLINESTERASE INHIBITOR; HEXANE; PLANT EXTRACT; SOLVENT; TRITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; LIQUID LIQUID EXTRACTION; MAYTENUS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF;

ACETYLCHOLINESTERASE; CHLOROFORM; CHOLINESTERASE INHIBITORS; HEXANES; LIQUID-LIQUID EXTRACTION; MAGNETIC RESONANCE SPECTROSCOPY; MAYTENUS; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; SOLVENTS; TRITERPENES;

EID: 84870222337     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171113439     Document Type: Article

References (41)

1. Chin, Y.H.; Balunas, M.J.; Chai, H.B.; Kinghorn, A.D. Drug discovery from natural sources. AAPS J. 2006, 8, E239-E253.
2. Barnes, D.E.; Yaffe, K. The projected effect of risk factor reduction on Alzheimer's disease revalence. Lancet Neurol. 2011, 10, 819-828.
3. Yang, Z.-D.; Duan, D.-Z.; Xue, W.-W.; Yao, X.-J.; Li, S. Steroidal alkaloids from Holarrhena antidysenterica as acetylcholinesterase inhibitors and the investigation for structure-activity relationships. Life Sci. 2012, 90, 929-933.
4. Dumont, M.; Wille, E.; Calingasan, N.Y.; Tampellini, D.; Williams, C.; Gouras, G.K.; Liby, K.; Sporn, M.; Nathan, C.; Flint-Beal, M.; et al. Triterpenoid CDDO-methylamide improves memory and decreases amyloid plaques in a transgenic mouse model of Alzheimer's disease. J. Neurochem. 2009, 109, 502-512.
5. Patil, S.P.; Maki, S.; Khedkar, S.A.; Rigby, A.C.; Chan, C. Withanolide A and Asiatic acidmodulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta clearance. J. Nat. Prod. 2010, 73, 1196-1202.
6. Wilkinson, K.; Boyd, J.D.; Glicksman, M.; Moore, K.J.; El Khoury, J. A high content drug screen identifies ursolic acid as an inhibitor of amyloid beta protein interactions with its receptor CD36. J. Biol. Chem. 2011, 286, 34914-34922.
7. Zhang, X.; Wu, J.; Xia, B.; Rong, W.; Rimbach, G.; Lou, Y. Asiatic acid protects primary neurons against C2-ceramide-induced apoptosis. Eur. J. Pharmacol. 2012, 679, 51-59.
8. Corsino, J.; Silva, D.H.S.; Zanoni, M.V.B.; Bolzani, V.S.; França, S.C.; Pereira, A.M.S.; Furlan, M. Antioxidant flavan-3-ols and flavonol glycosides from Maytenus Aquifolium. Phytother. Res. 2003, 17, 913-916.
9. Yariwake, J.H.; Lanças, F.M.; Cappelaro, E.A.; Vasconcelos, E.C.; Tiberti, L.A.; Pereira, A.M.S.; França, S.C. Seasonal variability of chemical compounds (triterpenes, flavonoids, and polyphenols) from Maytenus aquifolium Mart. (Celastraceae) leaves. Braz. J. Pharmacogn. 2005, 15, 162-168.
10. Ravelo, A.G.; Delgado-Mendes, P.; Herrera, N.; Chaves, H.; Estévez-Braun, A.; Cortes, F.; Castanys, S.; Gamarro, R. New terpenoids from Maytenus aurimacensis as MDR reversal agents in the parasite Leishmania. Bioorg. Med. Chem. 2008, 16, 1425-1430.
11. De Sousa, D.P.; Silva, M.S.; Medeiros, V.M.; Folly, M.A.B.; Tavares, J.F.; Barbosa-Filho, J.M. Alkaloid, flavonoids, and pentacyclic triterpenoids of Maytenus obtusifolia Mart. Biochem. Syst. Ecol. 2008, 36, 500-503.
12. Chabariberi, R.A.O.; Pozzi, A.C.S.; Zeraik, M.L.; Yariwake, J.H. Spectrometric determination of flavonoids from Maytenus (Celastraceae) and Passiflora (Passifloraceae) leaves and comparison with a HPLC-UV method. Braz. J. Pharmacogn. 2009, 19, 860-864.
13. Leite, J.P.V.; Braga, F.C.; Romussi, G.; Persoli, R.M.; Tabach, R.; Carlini, E.A.; Oliveira, A.B. Constituents from Maytenus ilicifolia and bioguided fractionation for gastroprotective activity. J. Braz. Chem. Soc. 2010, 21, 248-357.
14. Niero, R.; Andrade, S.F.; Cechinel Filho, V. A Review of the ethnopharmacology, phytochemistry, and pharmacology of plants of the Maytenus Genus. Curr. Pharm. Des. 2011, 17, 1851-1871.
15. Niero, R.; Moser, R.; Busato, A.C.B.; Yunes, R.A.; Reis, A.; Cechinel-Filho, V.A. Comparative chemical study of Maytenus ilicifolia Rart. Reiss and Maytenus robusta Reiss (Celastraceae). J. Biosci. 2001, 56, 158-161.
16. Niero, R.; Mafra, A.P.; Lenzi, A.C.; Cechinel-Filho, V.; Tisher, CA.; Malheiros, A.; De Sousa, M.M.; Yunes, R.A.; Delle Monache, F. A new triterpene with antinociceptive activity from Maytenus robusta. Nat. Prod. Res. Part B 2006, 20, 1315-1320.
17. De Andrade, S.F.; Lemos, M.; Comunello, E.; Noldin, V.; Delle Monache, F.; Chechinel-Filho, V.; Niero, R. Antiulcerogenic activity of fractions and 3,15-dioxo-21α-hydroxyfriedelane isolated from Maytenus robusta (Celastraceae). Arch. Pharm. Res. 2008, 31, 41-46.
18. Sousa, G.F.; Ferreira, F.L.; Duarte, L.P.; Silva, G.D.F.; Messias, M.C.T.B.; Vieira Filho, S.A. Structural determination of 3β11β- dihydroxyfriedelane from Maytenus robusta (Celastraceae) by 1D and 2D NMR. J. Chem. Res. 2012, 36, 203-205.
19. De Andrade, S.F.; Lemos, M.; Comunello, E.; Noldin, V.F.; Chechinel-Filho, V.; Niero, R. Evaluation of the antiulcerogenic activity of Maytenus robusta (Celastraceae) in different experimental ulcer models. J. Ethnopharmacol. 2007, 113, 252-257.
20. Santos, V.L.; Costa, V.B.M.; Agra, M.F.; Silva, B.A.; Batista, L.M. Pharmacological studies of ethanolic extract of Maytenus rigida Mar. (Celastraceae) in animal models. Braz. J. Pharmacogn. 2007, 17, 336-342.
21. González, A.G.; Alvarenga, N.L.; Estévez-Braun, A.; Ravelo, A.G.; Bazzocchi, I.L. Structure and absolute configuration of triterpene dimers from Maytenus scutioides. Tetrahedron 1996, 52, 9597-9608.
22. Avilla, J.; Teixidó, A.; Velásquez, N.A.; Ferro, E.; Canela, R. Insectidal activity of Maytenus species (Celastraceae) nortriterpene quinone methides against codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae). J. Agric. Food Chem. 2001, 48, 88-92.
23. Shirota, O.; Morita, H.; Takeya, K.; Itokawa, H. Sesquiterpene pyridine alkaloids from Maytenus ilicifolia. Heterocycles 1994, 38, 383-389.
24. González, A.G.; Tincusi, B.M.; Bazzocchi, S.L.; Tokuda, J.; Nishino, H.; Konoshima, T.; Jiménez, J.A.; Ravelo, A.G. Anti-tumor promoting effects of sesquiterpenes from Maytenus cuzcoina (Celastraceae). Bioorg. Med. Chem. 2000, 8, 1773-1778.
25. Madrigal, R.V.; Zilkowski, B.W.; Smith, CR. Structure-activity- relationship among maytansinoides in their effect on the european corn-borer, Ostrinia-Bubilalis (Hubner) (Lipidoptera, Pyralidae). J. Chem. Ecol. 1985, 11, 501-506.
26. Kiem, P.V.; Minh, C.V.; Huong, H.T.; Nam, N.H.; Lee, J.J.; Kim, Y.H. Pentacyclic Triterpenoids from Mallotus apelta. Arch. Pharm. Res. 2004, 27, 1109-1113.
27. David, J.P.; Meira, M.; David, J.M.; Guedes, M.L.S. Triterpenos e Ferrulatos de Alquila de Maprounea guianensis. Quim. Nova 2004, 27, 62-65.
28. Ghosh, A.; Sarkar, A.; Mitra, P.; Banerji, A.; Banerji, J.; Mandal, S.; Das, M. Crystal structure and DFT calculations of 3,4-seco-lup-20(29)-en-3-oic acid isolated from Wrightia tinctoria: Stacking of supramolecular dimmers in the crystal lattice. J. Mol. Struct. 2010, 980, 7-12.
29. Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
30. Rhee, I.K.; Van de Meent, M.; Ingkaninan, K.; Verpoorte, R. Screening for acetylcholinesterase inhibitors from Amaryllidaceae using silica gel thin-layer chromatography in combination with bioactivity staining. J. Chromatogr. A 2001, 915, 217-223.
31. Queiroga, C.L.; Silva, G.F.; Dias, P.C.; Possenti, A.; Carvalho, J.E. Evaluation of the antiulcerogenic activity of friedelan-3β-ol and friedelin isolated from Maytenus ilicifolia (Celastraceae). J. Ethnopharmacol. 2000, 72, 465-468.
32. 13C chemical shift assignments. Magn. Reson. Chem. 2000, 38, 977-980.
33. David, J.M.; Santos, F.A.; Guedes, M.L.S.; David, J.P. Flavonóides e triterpenos de Stigmaphyllom paralias. Quim. Nova 2003, 26, 484-487.
34. Frisch, M.J.; Trucks, GW.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, JR.; Montgomery, J.A., Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; et al. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, USA, 2003.
35. Santos, F.J.L.; Alcântara, A.F.C.; Ferreira-Alves, D.L.; Piló-Veloso, D. Theoretical and experimental NMR studies of the Swern oxidation of methyl 6α,7β-dihydroxyvouacapan-17β-oate. Struct Chem. 2008, 19, 625-631.
36. De Abreu, H.A.; Lagos, I.A.S.; Souza, G.P.; Piló-Veloso, D.; Duarte, H.A.; Alcântara, A.F.C. Antioxidant activity of (+)-bergenin-A phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae). Org. Biomol. Chem. 2008, 6, 2713-2718.
37. Euzébio, F.P.G; Santos, F.J.L.; Piló-Veloso, D.; Alcântara, A.F.C; Ruiz, A.L.G; Carvalho, JE.; Foglio, M.A.; Ferreira-Alves, D.L.; Fátima, A. Synthesis, Antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β- dihydroxyvouacapan-17β-oic acid Mannich base derivatives. Bioorg Med. Chem. 2010, 18, 8172-8177.
38. Souza, G.P.; Konzen, C; Simões, T.R.G; Rodrigues, B.L.; Alcântara, A.F.C; Stumpf, H.O. Structural characterization of a new dioxamic acid derivative by experimental (FT-IR, NMR, and X-ray) analyses and theoretical (HF and DFT) investigations. J. Mol. Struct. 2012, 1016, 13-21.
39. Alcântara, A.F.C.; Piló-Veloso, D.; Almeida, W.B.; Maltha, C.R.A.; Barbosa, L.C.A. Conformational analysis of 8-oxabicyclo[3.2.1]oct-6-en- 3-one derivatives by NMR and theoretical calculations. J. Mol. Struct. 2006, 791, 180-185.
40. Pérez-Rebolledo, A.; Mendes, I.C.; Speziali, N.L.; Bertani, P.; Resende, J.M.; Alcântara, A.F.C.; Beraldo, H. N(4)-Methyl-4- nitroacetophenone thiosemicarbazone and its nickel(II) complex: Experimental and theoretical structural studies. Polyhedron 2007, 26, 1449-1458.
41. 13C-NMR chemical shifts. Struct. Chem. 2012, 23, 703-710.