Characterization of flavonoids and phenolic acids in Myrcia bella cambess. Using FIA-ESI-IT-MSn and HPLC-PAD-ESI-IT-MS combined with NMR

Molecules

Volumn 18, Issue 7, 2013, Pages 8402-8416

  Saldanha, Luiz L ^a   Vilegas, Wagner ^a   Dokkedal, Anne L ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

Brazilian savanna; Flavonoid O glycosides; Medicinal plants; Myrtaceae

Indexed keywords

FLAVONOID; HYDROXYBENZOIC ACID DERIVATIVE; MYRICETIN; PHENOLIC ACID; PLANT EXTRACT; QUERCETIN;

ARTICLE; BRAZIL; CHEMISTRY; DIABETES MELLITUS; ELECTROSPRAY MASS SPECTROMETRY; HERBAL MEDICINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; METABOLISM; MYRTACEAE; NUCLEAR MAGNETIC RESONANCE IMAGING; PLANT LEAF; QUALITY CONTROL; TRADITIONAL MEDICINE;

BRAZIL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIABETES MELLITUS; FLAVONOIDS; HERBAL MEDICINE; HUMANS; HYDROXYBENZOATES; MAGNETIC RESONANCE IMAGING; MEDICINE, TRADITIONAL; MYRTACEAE; PLANT EXTRACTS; PLANT LEAVES; QUALITY CONTROL; QUERCETIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84880796918     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18078402     Document Type: Article

References (35)

1. Calixto, J.B. Efficacy, safety, quality control, marketing and regulatory guidelines for herbal medicines (phytotherapeutic agents). Braz. J. Med. Biol. Res. 2000, 33, 179-189.
2. Mosihuzzaman, M.; Choudhary, M.I. Protocols on safety, efficacy, standardization, and documentation of herbal medicine (IUPAC Technical Report). Pure Appl. Chem. 2008, 80, 2195-2230.
3. Wolfender, J.L. HPLC in natural product analysis: The detection issue. Planta Med. 2009, 75, 719-734.
4. Xing, J.; Xie, C.F.; Lou, H.X. Recent applications of liquid chromatography-mass spectrometry in natural products bioanalysis. J. Pharm. Biomed. Anal. 2007, 44, 368-378.
5. Gouveia, S.C.; Castilho, P.C. Characterization of phenolic compounds in Helichrysum melaleucum by high-performance liquid chromatography with on-line ultraviolet and mass spectrometry detection. Rapid Commun. Mass Spectrom. 2010, 24, 1851-1868.
6. Huang, X.; Liu, Y.; Song, F.R.; Liu, Z.Q.; Liu, S.Y. Studies on principal components and antioxidant activity of different Radix astragali samples using high performance liquid chromatography/electrospray ionization multiple-stage tandem mass spectrometry. Talanta 2009, 78, 1090-1101.
7. Rauter, A.P.; Martins, A.; Lopes, R.; Ferreira, J.; Serralheiro, L.M.; Araújo, M.E.; Borges, C.; Justino, J.; Silva, F.V.; Goulart, M.; et al. Bioactivity studies and chemical profile of the antidiabetic plant Genista tenera. J. Ethnopharmacol. 2009, 122, 384-393.
8. Tiberti, L.A.; Yariwake, J.H.; Ndjoko, K.; Hostettmann, K. Identification of flavonols in leaves of Maytenus ilicifolia and M. aquifolium (Celastraceae) by LC/UV/MS analysis. J. Chromatogr. B 2007, 846, 378-384.
9. Myers, N.; Mittermeier, R.A.; Mittermeier, C.G.; Fonseca, G.A.B.; Kent, J. Biodiversity hotspots for conservation priorities. Nat. Lond. 2000, 403, 853-858.
10. Durigan, G.; Franco, G.A.D.C.; Siqueira, M.F. The Vegetation of Cerrado Remnant in São Paulo State. In Viability of Conservation of Cerrado Remnants São Paulo State; Bitencourt, M.D., Mendonça, R.R., Eds.; Annablume: São Paulo, Brazil, 2004; pp. 29-56.
11. Landrum, L.R.; Kawasaki, M.L. The genera of Myrtaceae in Brazil-An illustrated synoptic treatment and identification keys. Brittonia 1997, 49, 508-536.
12. Carvalho, M.B.; Ishara, K.L.; Maimoni-Rodella, R.C.S. Vascular Flora of a Cerrado sensu stricto remnant in Pratânia, state of São Paulo, southeastern Brazil. Check List: J. Species Lists and Distribution 2010, 6, 350-357.
13. Ishara, K.L.; Déstro, G.F.G.; Maimoni-Rodella, R.C.S.; Yanagizawa, Y.A.N.P. Floristic composition of sensu stricto cerrado remnants in Botucatu, SP. Brazilian J. Botany 2008, 31, 575-586.
14. Hashimoto, G. Illustrade Cyclopedia of Brazilian Medicinal Plants; Aboc-Sha: Kamakura, Japan, 1996.
15. Russo, E.M.K.; Reichelt, A.A.J.; De-sá, J.R.; Furlanetto, R.P.; Moisés, R.C.S.; Kasamatsu, T.S.; Chacra, A.R. Clinical trial of Myrcia uniflora and Bauhinia forficata leaf extracts in normal and diabetic patients. Brazilian J. Med. Biol. Res. 1990, 23, 11-20.
16. Cerqueira, M.D.; Souza-Neta, L.; Passos, M.G.V.M.; Lima, E.O.; Roque, N.F.; Martins, D.; Guedes, M.L.S.; Cruz, F.G. Seasonal variation and antimicrobial activity of Myrcia myrtifolia essential oils. J. Braz. Chem. Soc. 2007, 18, 998-1003.
17. Cole, R.A.; Haber, W.A.; Setzer, W.N. The leaf oil composition of Myrcia splendens from Monteverde, Costa Rica. J. Essent. Oil Bear. Plants 2008, 11, 41-44.
18. Henriques, A.T.; Sobral, M.; Bridi, R.; Vérin, P.; Menut, C.; Lamaty, G.; Bessière, J.M. Essential oils from five southern brazilian species of Myrcia (Myrtaceae). J. Essent. Oil Res. 1997, 9, 13-18.
19. Limberger, R.P.; Sobral, M.; Henriques, A.T.; Menut, C.; Bessière, J. Óleos voláteis de espécies de Myrcia nativas do Rio Grande do Sul. Quim. Nova 2004, 27, 916-919.
20. Reynertson, K.A.; Yang, H.; Jiang, B.; Basile, M.J.; Kennelly, E.J. Quantitative analysis of antiradical phenolic constituents from fourteen edible Myrtaceae fruits. Food Chem. 2008, 109, 883-890.
21. Yoshikawa, M.; Shimada, H.; Nishida, N.; Li, Y.; Toguchida, I.; Yamahara, J.; Matsuda, H. Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): Structures of myrciacitrins I and II and myrciaphenones A and B. Chem. Pharm. Bull. 1998, 46, 113-119.
22. Matsuda, H.; Nishida, N.; Yoshikawa, M. Antidiabetic principles of natural medicines. V. Aldose reductase inhibitors from Myrcia multiflora DC. (2): Structures of myrciacitrins III, IV, and V. Chem. Pharm. Bull. 2002, 50, 429-431.
23. Ferreira, A.C.; Neto, J.C.; da Silva, A.C.; Kuster, R.M.; Carvalho, D.P. Inhibition of thyroid peroxidase by Myrcia uniflora flavonoids. Chem. Res. Toxicol. 2006, 19, 351-355.
24. Pepato, M.T.; Oliveira, J.R.; Kettelhut, I.C.; Migliorini, R.H. Assessment of the antidiabetic activity of Myrcia uniflora extracts in streptozotocin diabetic rats. Diabetes Res. 1993, 22, 49-57.
25. Anvisa 2010. Resolution-RDC n. 14: Registration of herbal drugs. Official Diary of the Union. Available online: http://www.in.gov.br/visualiza/index.jsp? data=05/04/2010&jornal=1&pagina=85&totalArquivos=160 (accessed on 18 April 2013).
26. Ma, Y.L.; Li, Q.M.; van den Heuvel, H.; Claeys, M. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 1997, 11, 1357-1364.
27. Domon, B.; Costello, C.E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj. J. 1998, 5, 397-409.
28. Li, Q.M.; Claeys, M. Characterization and differentiation of diglycosyl flavonoids by positive ion fast atom bombardment and tandem mass spectrometry. Biol. Mass Spectrom. 1994, 23, 406-416.
29. Agrawal, P.K. Carbon 13C- NMR of Flavonoids; Elsevier: New York, NY, USA, 1989.
30. Harborne, J.B. The Flavonoids: Advances in Research since 1986; Chapman & Hall: London, UK, 1994.
31. Andersen, O.M.; Markhan, K.R. Flavonoides: Chemistry, Biochemistry and Applications; Taylor & Francis Group: New York, NY, USA, 2006.
32. Lu, Y.; Foo, L.Y. Identification and quantification of major polyphenols in apple pomace. Food Chem. 1997, 59, 187-194.
33. Chua, L.S.; Latiff, N.A.; Lee, S.Y.; Lee, C.T.; Sarmid, M.R.; Aziz, R.A. Flavonoids and phenolic acids from Labisia pumila (Kacip Fatimah). Food Chem. 2011, 127, 1186-1192.
34. Ablajan, K.; Abliz, Z.; Shang, X.Y.; He, J.M.; Zhang, R.P.; Shi, J.G. Structural characterization of flavonol 3, 7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2006, 41, 352-360.
35. Prista, L.N. Pharmaceutic Tecnology; Calouste Foundation Gulbenkian: Lisboa, Portugal, 1995. Nível Superior (CAPES)