Copaifera langsdorffii supercritical fluid extraction: Chemical and functional characterization by LC/MS and in vitro assays

Journal of Supercritical Fluids

Volumn 100, Issue , 2015, Pages 86-96

  Costa, Ana R M ^a,b   Freitas, Luís A P ^a   Mendiola, J ^b   Ibanez E ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b INSTITUTE OF FOOD SCIENCE RESEARCH CIAL   (Spain)

Author keywords

Antioxidant activity; Copaifera langsdorffii; Flavonoids; Kaurenoic acid; Quercitrin; Response surface methodology; Supercritical fluid extraction

Indexed keywords

ANTIOXIDANTS; ASSAYS; BIOACTIVITY; CARBON DIOXIDE; CHEMICAL COMPOUNDS; EFFLUENT TREATMENT; ETHANOL; EXTRACTION; FLAVONOIDS; ORGANIC SOLVENTS; SUPERCRITICAL FLUIDS; SURFACE PROPERTIES;

ANTI-OXIDANT ACTIVITIES; CHEMICAL CHARACTERIZATION; COPAIFERA LANGSDORFFII; EXTRACTION TEMPERATURES; FUNCTIONAL CHARACTERIZATION; QUERCITRIN; RESPONSE SURFACE METHODOLOGY; SUPERCRITICAL FLUID EXTRACTION (SFE);

SUPERCRITICAL FLUID EXTRACTION;

EID: 84924721139     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2015.02.028     Document Type: Article

References (64)

1. V.F. Veiga, and A.C. Pinto The Copaifera L. genus Quimica Nova 25 2002 273 286
2. V.F. Veiga, A.C. Pinto, and M.A.M. Maciel Medicinal plants: safe cure? Quimica Nova 28 2005 519 528
3. V. Cascon Copaíba - Copaifera spp J.C.T. Carvalho, Fitoterápicos antiinflamatórios: aspectos químicos, farmacológicos e aplicações terapêuticas 2004 Tecmedd Ribeirão Preto 221 256
4. L.A.F. Paiva, L.A. Gurgel, E.T. De Sousa, E.R. Silveira, R.M. Silva, F.A. Santos, and V.S.N. Rao Protective effect of Copaifera langsdorffii oleo-resin against acetic acid-induced colitis in rats J. Ethnopharmacology 93 2004 51 56
5. L.A.F. Paiva, L.A. Gurgel, R.M. Silva, A.R. Tome, N.V. Gramosa, E.R. Silveira, F.A. Santos, and V.S.N. Rao Anti-inflammatory effect of kaurenoic acid, a diterpene from Copaifera langsdorffii on acetic acid-induced colitis in rats Vascular Pharmacology 39 2002 303 307
6. J.P.B. Sousa, N.P.D. Nanayakkara, A.A. Berretta, and J.K. Bastos Leishmanicidal and antimalarial activities of crude extracts from aerial parts of Copaifera langsdorffii and isolation of secondary metabolites J. Pharmacy Research 5 2012 4103 4107
7. 2 supercritical fluid extraction: isotherms of global yield, kinetics data, antioxidant activity and neuroprotective effects J. Supercritical Fluids 98 2015 167 171
8. J.K. Bastos, A.R.F. Brunharoto, C. Brunharoto-Júnior, and L.P.F. Brunharoto Process of Obtain and Uses of the Extracts, Fractions and Isolated Substances from Copaifera Species in the Treatment of Urinary Lithiasis in Human Beings and Animals 2005 Instituto Nacional de Propriedade Intelectual Brasil
9. R.B. de Oliveira, E.B. Coelho, M.R. Rodrigues, A.R.M. Costa-Machado, J.P.B. de Sousa, A.A. Berretta, and J.K. Bastos Effect of the Copaifera langsdorffii Desf. leaf extract on the ethylene glycol-induced nephrolithiasis in rats Evidence-Based Complementary and Alternative Medicine 2013 10.1155/2013/131372
10. A.P.S. Brancalion, R.B. Oliveira, J.P.B. Sousa, M. Groppo, A.A. Berretta, M.E. Barros, M.A. Boim, and J.K. Bastos Effect of hydroalcoholic extract from Copaifera langsdorffii leaves on urolithiasis induced in rats Urological Research 40 2012 475 481
11. J.H. Langenheim, C.L. Convis, C.A. Macedo, and W.H. Stubblebine Hymenaea and Copaifera leaf sesquiterpenes in relation to lepidopteran herbivory in southeastern Brazil Biochemical Systematics and Ecology 14 1986 41 49
12. C.A. Macedo, and J.H. Langenheim A further investigation of leaf sesquiterpene variation in relation to herbivory in 2 Brazilian populations of Copaifera langsdorfii Biochemical Systematics and Ecology 17 1989 207 216
13. C.A. Macedo, and J.H. Langenheim Microlepidopteran herbivory in relation to leaf sesquiterpenes in Copaifera langsdorfii adult trees and their seedling progeny in a Brazilian woodland Biochemical Systematics and Ecology 17 1989 217 224
14. J.P.B. Sousa, A.P.S. Brancalion, M.G. Junior, and J.K. Bastos A validated chromatographic method for the determination of flavonoids in Copaifera langsdorffii by HPLC Natural Product Communications 7 2012 25 29
15. th November 2014. Available from: 〈http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=87225407〉.
16. S. Kim, H. Kim, S. Choi, K. Park, H. Choi, and M. Lee Anti-oxidative and inhibitory activities on nitric oxide (NO) and prostaglandin E2 (COX-2) production of flavonoids from seeds of Prunus tomentosa Thunberg Archives of Pharmacal Research 31 2008 424 428
17. G.H. Xu, I.J. Ryoo, Y.H. Kim, S.J. Choo, and I.D. Yoo Free radical scavenging and antielastase activities of flavonoids from the fruits of Thuja orientalis Archives of Pharmacal Research 32 2009 275 282
18. W. Li, and D.K.J. Lin Optimal foldover plans for two-level fractional factorial designs Technometrics 45 2003 142 149
19. B.S. Min, S.Y. Lee, J.H. Kim, J.K. Lee, T.J. Kim, D.H. Kim, Y.H. Kim, H. Joung, H.K. Lee, N. Nakamura, H. Miyashiro, and M. Hattori Anti-complement activity of constituents from the stem-bark of Juglans mandshurica Biological & Pharmaceutical Bulletin 26 2003 1042 1044
20. E.K. Kwon, D.Y. Lee, H. Lee, D.O. Kim, N.I. Baek, Y.E. Kim, and H.Y. Kim Flavonoids from the buds of Rosa damascena inhibit the activity of 3-hydroxy-3-methylglutaryl-coenzyme a reductase and angiotensin I-converting enzyme J. Agricultural and Food Chemistry 58 2010 882 886
21. H.S. Rho, S.M. Ahn, B.C. Lee, M.K. Kim, A.K. Ghimeray, C.W. Jin, and D.H. Cho Changes in flavonoid content and tyrosinase inhibitory activity in kenaf leaf extract after far-infrared treatment Bioorganic & Medicinal Chemistry Letters 20 2010 7534 7536
22. L.O. Regasini, J.C.R. Vellosa, D.H.S. Silva, M. Furlan, O.M.M. Oliveira, N.M. Khalil, I.L. Brunetti, M.C.M. Young, E.J. Barreiro, and V.S. Bolzani Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors Phytochemistry 69 2008 1739 1744
23. Motta Desenvolvimento e validação de método analítico por CLAE-UV-DAD para quantificação e análise sazonal de derivados galoilquínicos nas folhas de Copaifera langsdorffii 2014 Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo Ribeirão Preto 160
24. Kaurenoic acid, National Center for Biotechnology Information, PubChem Compound Database, Accessed in 19 November 2014. Available from: 〈http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=14036〉.
25. E.P. Padla, L.T. Solis, and C.Y. Ragasa Antibacterial and antifungal properties of ent-kaurenoic acid from Smallanthus sonchifolius Chinese J. Natural Medicines 10 2012 408 414
26. R.J. Choi, E.M. Shin, H.A. Jung, J.S. Choi, and Y.S. Kim Inhibitory effects of kaurenoic acid from Aralia continentalis on LPS-induced inflammatory response in RAW264.7 macrophages Phytomedicine 18 2011 677 682
27. C.R. Tirapelli, S.R. Ambrosio, F.B. da Costa, S.T. Coutinho, D.C.R. de Oliveira, and A.M. de Oliveira Analysis of the mechanisms underlying the vasorelaxant action of kaurenoic acid in the isolated rat aorta European J. Pharmacology 492 2004 233 241
28. N. Balekar, T. Nakpheng, N.G. Katkam, and T. Srichana Wound healing activity of ent-kaura-9(11), 16-dien-19-oic acid isolated from Wedelia trilobata (L.) leaves Phytomedicine 19 2012 1178 1184
29. F. Gelmini, G. Beretta, C. Anselmi, M. Centini, P. Magni, M. Ruscica, A. Cavalchini, and R.M. Facino GC-MS profiling of the phytochemical constituents of the oleoresin from Copaifera langsdorffii Desf. and a preliminary in vivo evaluation of its antipsoriatic effect European J. Pharmacology 440 2013 170 178
30. B.C. Cavalcanti, D.P. Bezerra, H.I.F. Magalhães, M.O. Moraes, M.A.S. Lima, E.R. Silveira, C.A.G. Câmara, V.S. Rao, C. Pessoa, and L.V. Costa-Lotufo Kauren-19-oic acid induces DNA damage followed by apoptosis in human leukemia cells J. Applied Toxicology 29 2009 560 568
31. L.V. Costa-Lotufo, G.M.A. Cunha, P.A.M. Farias, G.S.B. Viana, K.M.A. Cunha, C. Pessoa, M.O. Moraes, E.R. Silveira, N.V. Gramosa, and V.S.N. Rao The cytotoxic and embryotoxic effects of kaurenoic acid, a diterpene isolated from Copaifera langsdorffii oleo-resin Toxicon 40 2002 1231 1234
32. d.M.N. Gomes, d.M.C. Rezende, S.P. Fontes, A.M.C. Hovell, R.G. Landgraf, M.E. Matheus, A.D.C. Pinto, and P.D. Fernandes Antineoplasic activity of Copaifera multijuga oil and fractions against ascitic and solid Ehrlich tumor J. Ethnopharmacology 119 2008 179 184
33. S.R.M. Lima, V.F. Veiga, H.B. Christo, A.C. Pinto, and P.D. Fernandes In vivo and in vitro studies on the anticancer activity of Copaifera multijuga Hayne and its fractions Phytotherapy Research 17 2003 1048 1053
34. M.O. Moraes, M.C. Fonteles, M.E.A. Moraes, M.I.L. Machado, and F.J.A. Matos Screening for anticancer activity of plants from the Northeast of Brazil Fitoterapia 68 1997 235
35. A. Ohsaki, L.T. Yan, S. Ito, H. Edatsugi, D. Iwata, and Y. Komoda The isolation and in-vivo potent antitumor-activity of clerodane diterpenoid from the oleoresin of the Brazilian medicinal plant, Copaifera-langsdorfii Desfon Bioorganic & Medicinal Chemistry Letters 4 1994 2889 2892
36. C.D. Souza, and J.M. Felfili Uso de plantas medicinais na região de Alto Paraíso de Goiás Acta Botanica Brasilica 20 2006 7
37. M. Contini, S. Baccelloni, R. Massantini, and G. Anelli Extraction of natural antioxidants from hazelnut (Corylus avellana L.) shell and skin wastes by long maceration at room temperature Food Chemistry 110 2008 659 669
38. ANVISA. Agência Nacional de Vigilância Sanitária. Fundação Oswaldo Cruz Brazilian Pharmacopoeia 2010 ANVISA. Agência Nacional de Vigilância Sanitária. Fundação Oswaldo Cruz Brasília, DF
39. M. Herrero, A. Cifuentes, and E. Ibañez Sub- and supercritical fluid extraction of functional ingredients from different natural sources: plants, food-by-products, algae and microalgae: a review Food Chemistry 98 2006 136 148
40. T. Anaelle, E. Serrano Leon, V. Laurent, I. Elena, J.A. Mendiola, C. Stéphane, K. Nelly, L.B. Stéphane, M. Luc, and S.-P. Valérie Green improved processes to extract bioactive phenolic compounds from brown macroalgae using Sargassum muticum as model Talanta 104 2013 44 52
41. B. Beňová, M. Adam, P. Pavlíková, and J. Fischer Supercritical fluid extraction of piceid, resveratrol and emodin from Japanese knotweed J. Supercritical Fluids 51 2010 325 330
42. J.H.Y. Vilegas, E. de Marchi, and F.M. Lancas Extraction of low-polarity compounds (with emphasis on coumarin and kaurenoic acid) from Mikania glomerata ('guaco') leaves Phytochemical Analysis 8 1997 266 270
43. 2) using Box-Behnken experimental design J. Supercritical Fluids 81 2013 112 118
44. P.H. List, and P.C. Schmidt Phytopharmaceutical Technology 1989 Heyden & Son Limited London
45. A.R.D. Costa, F.S. Marquiafavel, M.M.D.L.L. Vaz, B.A. Rocha, P.C.P. Bueno, P.L.M. Amaral, H.D. Barud, and A. Ap Berreta-Silva Quercetin-PVP K25 solid dispersions: preparation, thermal characterization and antioxidant activity J. Thermal Analysis and Calorimetry 104 2011 273 278
46. L.E. Dowd Spectrophotometric determination of quercetin Analytical Chemistry 31 1959 1184 1187
47. T.L. Miron, M. Plaza, G. Bahrim, E. Ibañez, and M. Herrero Chemical composition of bioactive pressurized extracts of Romanian aromatic plants J. Chromatography A 1218 2011 4918 4927
48. ICH Validation of analytical procedures: text and methodology Q2(R1) International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use 2005
49. th May, 2003, Guia para validação de métodos analíticos e bioanalíticos, Brasília, DF, Brasil.
50. A.R.M. Costa-Machado Obtenção de produtos a partir das folhas de Copaifera langsdorffii Desf.: otimização da extração e secagem em spray dryer utilizando planejamentos experimentais, in:Departamento de Ciências Farmacêuticas 2011 Universidade de São Paulo Ribeirão Preto 115
51. J.P. de Sousa, M.F. Leite, R.F. Jorge, D.O. Resende, A.A. da Silva Filho, N.A. Furtado, A.E. Soares, A.C. Spadaro, P.M. de Magalhaes, and J.K. Bastos Seasonality role on the phenolics from cultivated Baccharis dracunculifolia Evidence-Based Complementary and Alternative Medicine 2011 10.1093/ecam/nep077
52. A. Kazan, H. Koyu, I.C. Turu, and O. Yesil-Celiktas Supercritical fluid extraction of Prunus persica leaves and utilization possibilities as a source of phenolic compounds J. Supercritical Fluids 92 2014 55 59
53. W. Kukula-Koch, N. Aligiannis, M. Halabalaki, A.-L. Skaltsounis, K. Glowniak, and E. Kalpoutzakis Influence of extraction procedures on phenolic content and antioxidant activity of Cretan barberry herb Food Chemistry 138 2013 406 413
54. M. Herrero, M. Plaza, A. Cifuentes, and E. Ibáñez Green processes for the extraction of bioactives from Rosemary: chemical and functional characterization via ultra-performance liquid chromatography-tandem mass spectrometry and in-vitro assays J. Chromatography A 1217 2010 2512 2520
55. S.V. Siqueira, d.S.M. Falcão-Silva, d.F. Agra, C.J.P. Dariva, d. Siqueira-Júnior, and M.J.V. Fonseca Biological activities of Solanum paludosum Moric. extracts obtained by maceration and supercritical fluid extraction J. Supercritical Fluids 58 2011 391 397
56. G. Box, S. Hunter, and W.G. Hunter Statistics for Experimenters: An Introduction to Design, Data Analysis, and Model Building second ed. 2005 John Wiley & Sons, Inc. New Jersey, NJ
57. th November 2014. Available from: 〈http://dnp.chemnetbase.com/AAA00.entry?parentCHNumber=BDZ39&exno=BDZ39〉.
58. th November, 2014. Available from: 〈http://phenol-explorer.eu/compounds/413〉.
59. C.A. RiceEvans, N.J. Miller, and G. Paganga Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biology and Medicine 20 1996 933 956
60. J. Galvez, J.P. Delacruz, A. Zarzuelo, F.S. Demedina, J. Jimenez, and F.S. Delacuesta Oral-administration of quercitrin modifies intestinal oxidative status in rats General Pharmacology 25 1994 1237 1243
61. P. Rodriguez, F. Gonzalez-Mujica, J. Bermudez, and M. Hasegawa Inhibition of glucose intestinal absorption by kaempferol 3-O-alpha-rhamnoside purified from Bauhinia megalandra leaves Fitoterapia 81 2010 1220 1223
62. R. Batista, P.A. García, M.A. Castro, J.M. Miguel del Corral, N.L. Speziali, F. de, P. Varotti, R.C. de Paula, L.F.A. García-Fernández, s. Francesch, A. San Feliciano, and A.B. de Oliveira Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives European J. Medicinal Chemistry 62 2013 168 176
63. R. Batista, J.L. Humberto, E.A. Chiari, and d.B. de Oliveira Synthesis and trypanocidal activity of ent-kaurane glycosides Bioorganic & Medicinal Chemistry 15 2007 381 391
64. C.O. Rezende Jr., C. Rigotto, W. Caneschi, C.A.M. Rezende, M. Le Hyaric, M.R.C. Couri, C.M.O. Simões, and M.V. de Almeida Anti-HSV-1 and antioxidant activities of dicaffeoyl and digalloyl esters of quinic acid Biomedicine & Preventive Nutrition 4 2014 35 38