Interconverting flavanone glucosides and other phenolic compounds in Lippia salviaefolia Cham. ethanol extracts

Phytochemistry

Volumn 72, Issue 16, 2011, Pages 2052-2061

  Funari, Cristiano Soleo ^a   Passalacqua, Thais Gaban ^a   Rinaldo, Daniel ^a   Napolitano, Assunta ^c   Festa, Michela ^c   Capasso, Anna ^c   Piacente, Sonia ^c   Pizza, Cosimo ^c   Young, Maria Claudia Marx ^b   Durigan, Giselda ^d   Silva, Dulce Helena Siqueira ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b Pós graduação em Biodiversidade Vegetal e Meio Ambiente   (Brazil)

^c UNIVERSITY OF SALERNO   (Italy)

^d Instituto Florestal   (Brazil)

Author keywords

Antioxidant; Cancer cells; Cell growth inhibition; Circular dichroism; Epoxylignan; Flavonoids; Lippia salviaefolia Cham.; Phenylpropanoid glycosides; Reactive oxygen species; Verbenaceae

Indexed keywords

FLAVANONE DERIVATIVE; GLYCOSIDE; PLANT EXTRACT; REACTIVE OXYGEN METABOLITE; SCAVENGER;

APOPTOSIS; ARTICLE; CELL STRAIN HEK293; CHEMISTRY; DRUG EFFECT; FRACTIONATION; HUMAN; ISOLATION AND PURIFICATION; LIPPIA; TUMOR CELL LINE;

APOPTOSIS; CELL LINE, TUMOR; CHEMICAL FRACTIONATION; FLAVANONES; FREE RADICAL SCAVENGERS; GLYCOSIDES; HEK293 CELLS; HUMANS; LIPPIA; PLANT EXTRACTS; REACTIVE OXYGEN SPECIES;

LIPPIA; VERBENACEAE;

EID: 80052928371     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.07.004     Document Type: Article

References (46)

1. T.D. Bernonville, S. Guyot, J. Paulin, M. Gaucher, L. Loufrani, D. Henrion, S. Derbré, D. Guilet, P. Richomme, J.F. Dat, and M. Brisset Dihydrochalcones: implication in resistance to oxidative stress and bioactivities against advanced glycation end-products and vasoconstriction Phytochemistry 71 2010 443 452
2. S. Caccamese, L. Manna, and G. Scivoli Chiral HPLC separation and CD spectra of the C-2 diastereoisomers of naringin in grapefruit during maturation Chirality 15 2003 661 667 (Pubitemid 37158930)
3. S. Caccamese, and R. Chillemi Racemization at C-2 of naringin in pummel (Citrus grandis) with increasing maturity determined by chiral high-performance liquid chromatography J. Chromatogr. A 1217 2010 1089 1093
4. I. ali, M. Hosny, T. Khalifa, and P. Rüedi Phenylpropanoid glycosides from Marrubium alysson Phytochemistry 31 1992 3624 3626
5. C.L. Cardoso, I. Castro-Gamboa, D.H.S. Silva, M. Furlan, R.A. Epifanio, Â.C. Pinto, C.M. Rezende, J.A. Lima, and V.S. Bolzani Indole glucoalkaloids from Chimarrhis turbinata and their evaluation as antioxidant agents and acetylcholinesterase inhibitors J. Nat. Prod. 67 2004 1882 1885 (Pubitemid 39602369)
6. Z. Cheng, J. Moore, and L. Yu High-throughput relative DPPH radical scavenging capacity assay J. Agric. Food Chem. 54 2006 7429 7436 (Pubitemid 44645754)
7. J.W. Clark-Lewis Flavan derivatives. XXI. Nuclear magnetic resonance spectra, configuration, and conformation of flavan derivatives Aust. J. Chem. 21 1968 2059 2075
8. A. Delazar, S. Gibbons, Y. Kumarasamy, L. Nahar, M. Shoeb, and S. Sarker Antioxidant phenylethanoid glycosides from the rhizomes of Eremostachys glabra (Lamiaceae) Biochem. Syst. Ecol. 33 2005 87 90 (Pubitemid 39568607)
9. E. Dozio, M. Ruscica, L. Passafaro, G. Dogliotti, L. Steffani, A. Pagani, G. Demartini, D. Esposti, F. Fraschini, and P. Magni The natural antioxidant alpha-lipoic acid induces p27Kip1-dependent cell cycle arrest and apoptosis in MCF-7 human breast cancer cells Eur. J. Pharmacol. 641 2010 29 34
10. R.O.S. Fontenelle, S.M. Morais, E.H.S. Brito, M.R. Kerntopf, R.S.M. Brilhante, R.A. Cordeiro, A.R. Tomé, M.G.R. Queiroz, N.R.F. Nascimento, J.J.C. Sidrim, and M.F.G. Rocha Chemical composition, toxicological aspects and antifungal activity of essential oil from Lippia sidoides Cham J. Antimicrob. Chemother. 59 2007 934 940 (Pubitemid 47073365)
11. W. Gaffield Circular dichroism, optical rotatory dispersion and absolute configuration of 3-hydroxyflavanones and their glycosides. Determination of aglycone chirality in flavanone glycosides Tetrahedron 26 1970 4093 4108
12. W. Gaffield, R.E. Lundin, B. Gentili, and R.M. Horowitz C-2 stereochemistry of naringin and its relation to taste and biosynthesis in maturing grapefruit Bioorg. Chem. 4 1975 259 269
13. N. Gel-Moreto, R. Streich, and R. Galensa Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice J. Chromatogr. A 925 2001 279 289 (Pubitemid 32680985)
14. X.H. Han, S.S. Hong, J.S. Hwang, M.K. Lee, B.Y. Hwang, and J.S. Ro Monoamine oxidase inhibitory components from Cayratia japonica Arch. Pharm. Res. 30 2007 13 17
15. A. Hermoso, I.A. Jimenez, Z.A. Mamani, I.L. Bazzocchi, J.E. Pinero, A.G. Ravelo, and B. Valladares Antileishmanial activities of dihydrochalcones from Piper elongatum and synthetic related compounds. Structural requirements for activity Bioorg. Med. Chem. 11 2003 3975 3980 (Pubitemid 36970124)
16. K. Hostettmann, E.F. Queiroz, and P.C. Vieira Princípios Ativos de Plantas Superiores 2003 EdUFSCar São Carlos
17. C.D. Hufford, and B.O. Oguntimein Dihydrochalcones from Uvaria angolensis Phytochemistry 19 1980 2036 2038
18. M. Hurabielle, J. Eberle, and M. Paris Flavonoids of Artemisia campestris, ssp. Glutinosa Planta Med. 46 1982 124 125 (Pubitemid 13255347)
19. J.M. Jez, M.E. Bowman, R.A. Dixon, and J.P. Noel Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase Nat. Struct. Mol. Biol. 7 2000 786 791
20. S. Lee, Y.J. Kim, S. Kwon, Y. Lee, S.Y. Choi, J. Park, and H.J. Kwon Inhibitory effects of flavonoids on TNF-alpha-induced IL-8 gene expression in HEK 293 cells BMB Rep. 42 2009 265 270
21. T.L.G. Lemos, F.J. Matos, J.W. Alencar, A.A. Craveiro, A.M. Clark, and J.D. McChesney Antimicrobial activity of essential oils of Brazilian plants Phytother. Res. 4 1990 82 84 (Pubitemid 20221880)
22. Q. Liu, R.A. Dixon, and T.J. Mabry Additional flavonoids from elicitor-treated cell cultures of Cephalocereus senilis Phytochemistry 34 1993 167 170
23. H. Lorenzi, and F.J.A. Matos Plantas Medicinais no Brasil: Nativas e Exóticas Cultivadas 2002 Instituto Plantarum Nova Odessa
24. Y. Lu, and L.Y. Foo Flavonoid and phenolic glycosides from Salvia officinalis Phytochemistry 55 2000 263 267
25. F. Maltese, C. Erkelens, F. Van der Kooy, Y.H. Choi, and R. Verpoorte Identification of natural epimeric flavanone glycosides by NMR spectroscopy Food Chem. 116 2009 575 579
26. C. Marais, W.J. van Rensburg, D. Ferreira, and J.A. Steenkamp (S) and (R)-Eriodictyol-6-C-β-d-glucopyranoside, novel keys to the fermentation of rooibos (Aspalathus linearis) Phytochemistry 55 2000 43 49
27. T. Maraldi, C. Prata, D. Fiorentini, L. Zambonin, L. Landi, and G. Hakim Induction of apoptosis in a human leukemic cell line via reactive oxygen species modulation by antioxidants Free Radic. Biol. Med. 46 2010 244 252
28. R. Masella, R. Di Benedetto, R. Var, C. Filesi, and C. Giovannini Novel mechanisms of natural antioxidant compounds in biological systems: involvement of glutathione and glutathione-related enzymes J. Nutr. Biochem. 16 2005 577 586 (Pubitemid 41338369)
29. C.O. Miles, and L. Main Kinetics and mechanism of the cyclization of 2,6-dihydroxychalcone and derivatives J. Chem. Soc. Perkin Trans. II 1989 1623 1632
30. M. Mizuno, H. Kojima, T. Tanaka, M. Iinuma, R. Kimura, M. Zhi-Da, and H. Murata Phenolic constituents of Coptis japonica VAR. DISSECTA Phytochemistry 26 1987 2071 2074
31. W.B. Mors, C.T. Rizzini, and N.A. Pereira Medicinal Plants of Brazil first ed. 2000 Reference Publications, Inc. Michigan
32. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
33. I. Nicoletti, G. Migliorati, M.C. Pagliacci, F. Grignani, and C. Riccardi A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry J. Immunol. Methods 139 1991 271 279
34. J. Pan, S. Zhang, L. Yan, J. Tai, Q. Xiao, K. Zou, Y. Zhou, and J. Wu Separation of flavanone enantiomers and flavanone glucoside diastereoisomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column J. Chromatogr. A 1185 2008 117 129
35. M.E. Pascual, K. Slowing, M.E. Carretero, and A. Villar Lippia: traditional uses, chemistry and pharmacology: a review J. Ethnopharmacol. 76 2001 201 214 (Pubitemid 32640159)
36. D.E. Pratt, and E.E. Miller Flavonoid antioxidant in Spanish peanuts (Arachia-Hipogoea) J. Am. Oil Chem. Soc. 61 1984 1064 1068
37. D. Rigano, V. Cardile, C. Formisano, M.T. Maldini, S. Piacente, Y. Bevelacqua, A. Russo, and F. Senatore Genista sessilifolia DC. and Genista tinctoria L. inhibit UV light and nitric oxide-induced DNA damage and human melanoma cell growth Chem. Biol. Interact. 15 180 2009 211 219
38. G. Rothe, and G. Valet Flow cytometric analysis of respiratory burst activity in phagocytes with hydroethidine and 2′,7′- dichlorofluorescin J. Leukoc. Biol. 47 1990 440 448 (Pubitemid 20155877)
39. M. Shoeb, M. Jaspars, S.M. MacManus, R.R.T. Majinda, and S.D. Sarker Biochem. Epoxylignans from the seeds of Centaurea cyanus (Asteraceae) Syst. Ecol. 32 2004 1201 1204 (Pubitemid 39444389)
40. D.H.S. Silva, F.C. Pereira, M.V.B. Zanoni, and M. Yoshida Lipophyllic antioxidants from Iryanthera juruensis fruits Phytochemistry 57 2001 437 442 (Pubitemid 32448458)
41. S. Son, and B.A. Lewis Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship J. Agric. Food Chem. 50 2002 468 472 (Pubitemid 34106663)
42. D. Slade, D. Ferreira, and J.P.J. Marais Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids Phytochemistry 66 2005 2177 2215 (Pubitemid 41254096)
43. P. Venturella, A. Bellino, M.L. Marino, and M. Sorrrentino Aurapin, a new dihydroflavonol glycoside and other flavonoids from Acinosalpinus Heterocycles 14 1980 1979 1982
44. L.F. Viccini, P.M.O. Pierre, M.M. Praca, D.C.S. Costa, E.D. Romanel, S.M. Sousa, P.H.P. Peixoto, and F.R.G. Salimena Chromosome numbers in the genus Lippia (Verbenaceae) Plant Syst. Evol. 256 2006 171 178
45. D. Wistuba, O. Trapp, N. Gel-Moreto, R. Galensa, and V. Schurig Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers Anal. Chem. 78 2006 3424 3433
46. 13C NMR data for 10 phenylethanoid glycosides Magn. Reson. Chem. 42 2004 659 662 (Pubitemid 40012901)