Flavonoids from Mimosa xanthocentra (Leguminosae: Mimosoideae) and molecular modeling studies for isovitexin-2″-O-α-l-rhamnopyranoside rotamers

Phytochemistry Letters

Volumn 5, Issue 3, 2012, Pages 427-431

  Camargo, Luiza Maria De Magalhães ^a   Férézou, Jean Pierre ^b   Tinoco, Luzineide Wanderley ^a   Kaiser, Carlos Roland ^a   Costa, Sônia Soares ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

C Glycosylflavone; Flavonoid; Mimosa xanthocentra; MM2 calculations; NMR; Rotamerism

Indexed keywords

ACETIC ACID ETHYL ESTER; AVICULARINE; BUTANOL; FLAVONOID; ISOVITEXIN 2'' O ALPHA LEVO RHAMNOPYRANOSIDE; MIMOSA XANTHOCENTRA EXTRACT; PLANT EXTRACT; REYNOUTRIN; UNCLASSIFIED DRUG; VITEXIN 2'' O ALPHA LEVO RHAMNOPYRANOSIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; HYDROGEN BOND; LEGUME; MIMOSA XANTHOCENTRA; MOLECULAR MODEL; PHYTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SOLVENT EXTRACTION; STEREOISOMERISM;

BLASTOCEROS DICHOTOMUS; FABACEAE; MIMOSA; MIMOSOIDEAE; OZOTOCEROS BEZOARTICUS;

EID: 84865041374     PISSN: 18743900     EISSN: 18767486     Source Type: Journal    
DOI: 10.1016/j.phytol.2012.03.015     Document Type: Article

References (38)

1. R.B. An, H.C. Kim, and Y.H. Tian Free radical scavenging and hepatoprotective constituents from the leaves of Juglans sinensis Arch. Pharm. Res. 28 2005 529 533
2. X. Bu, P.J. Skrdla, and P.G. Dormer Separation of triphenyl atropisomers of a pharmaceutical compound on a novel mixed mode stationary phase: a case study involving dynamic chromatography, dynamic NMR and molecular modeling J. Chromatogr. A 1217 2010 7255 7264
3. E.N. Bum, D.L. Dawack, and M. Schmutz Anticonvulsant activity of Mimosa pudica decoction Fitoterapia 75 2004 309 314 (Pubitemid 38670559)
4. G. Cheng, Y. Bai, and Y. Zhao Flavonoids from Ziziphus jujuba Mill var. spinosa Tetrahedron 56 2000 8915 8920
5. S.S. Costa, D.B. Oliveira, and A.M. Manço Plants composing the diet of marsh and pampas deer in the Brazilian Pantanal Wetland and their ethnomedicinal properties J. Biol. Sci. 6 2006 840 846 (Pubitemid 46242305)
6. S.S. Dhillion, and S.L. Camargo-Ricalde The cultural and ecological roles of Mimosa species in the Tehuacán-Cuicatlán Valley, México Econ. Bot. 59 2005 390 394 (Pubitemid 43107924)
7. A.J. Dick, P.R. Redden, and A.C. DeMarco Flavonoid glycoside of Spartan apple peel J. Agric. Food Chem. 35 1987 529 531
8. B. Dinda, B. Ghosh, and S. Arima Steroids and terpenoids from Mimosa pudica roots J. Indian Chem. Soc. 83 2006 1044 1046 (Pubitemid 44759421)
9. X.A. Dominguez, S.G. Garcia, and H.J. Williams Kukulkanins A and B, new chalcones from Mimosa tenuefolia J. Nat. Prod. 52 1989 864 867
10. A.R. Dos Santos, A.C. Pinheiro, and A.C.R. Sodero Atropoisomerismo: o efeito da quiralidade axial em substâncias bioativas Química Nova 30 2007 125 135
11. V.M.S. Gil, and C.F.G.C. Geraldes Ressonância Magnética Nuclear. Fundamentos, métodos e aplicações 2nd ed. 2002 Fundação Calouste Gulbenkian Lisboa
12. P.W. Grosvenor, P.K. Gothard, and N.C. McWilliam Medicinal plants from Riau Province, Sumatra, Indonesia. Part 1: uses J. Ethnopharmacol. 45 1995 75 95
13. J.B. Harborne, and T.J. Mabry The Flavonoids: Advances in Research 1982 Chapman and Hall London
14. T.A. Heard, and W. Pettit Review and analysis of the surveys for natural enemies of Mimosa pigra: what does it tell us about surveys for broadly distributed hosts? Biol. Control 34 2005 247 254 (Pubitemid 41161136)
15. B.K. Hoffmann, H. Lotter, and O. Seligmann Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis Planta Med. 58 1992 544 548 (Pubitemid 23074546)
16. N. Hussain, M.H. Modan, and S.G. Shabbir Antimicrobial principles in Mimosa hamata J. Nat. Prod. 42 1979 525 527 (Pubitemid 10185394)
17. T. Iwashina Flavonoid function and activity to plants and other organisms Biol. Sci. Space 17 2003 24 44
18. M. Jay Naturally occurring C-glycosylflavonoids J.B. Harborne, The Flavonoids. Advances in Research Since 1986 1994 Chapman & Hall Florida 441 497
19. H.E. Khadem, and Y.S. Mohammed Constituents of the leaves of Psidium guaijava L. Part II: quercetin, avicularin and guaijaverin J. Chem. Soc. 1958 3320 3323
20. M.Y. Kim, Y.C. Kim, and S.K. Chung Identification and in vitro biological activities of flavonoids in garlic and shoot: inhibition of soybean lipoxygenase and hyaluronidase activities and scavenging of free radicals J. Sci. Food Agric. 85 2004 633 640
21. L.F. Kirk, M.V. Moller, and J. Christensen A 5-deoxyflavonol derivative in Mimosa pudica Biochem. Syst. Ecol. 31 2003 103 105 (Pubitemid 36093221)
22. M. Larionova, I. Spengler, and C. Nogueiras A C-glycosylflavone from Piper ossanum, a compound conformationnally controlled by CH/π and other weak intramolecular interactions J. Nat. Prod. 73 2010 1623 1627
23. K.P. Latté, D. Ferreira, and M.S. Venkatraman O-Galloyl-C- glycosylflavones from Pelargonium reniforme Phytochemistry 59 2002 419 424 (Pubitemid 34202560)
24. 1H) NMR studies on spinosin Magn. Reson. Chem. 38 2000 771 774
25. A. Lobstein, B. Weniger, and B.H. Um 4"-Hydroxymaysin and cassiaoccidentalin B, two unusual C-glycosyflavones from Mimosa pudica Biochem. Syst. Ecol. 30 2002 375 377 (Pubitemid 34263221)
26. N.H. Martin, N.W. Allen, and K.D. Moore A proton NMR shielding model for the face of a benzene ring J. Mol. Struct. (Theochem) 454 1998 161 166 (Pubitemid 128411944)
27. W.B. Mors, C.T. Rizzini, and N.A. Pereira Medicinal Plants of Brazil 2000 Algonac Michigan
28. M. Naczk, and F. Shahidit Phenolics in cereals, fruits and vegetables: occurrence, extraction and analysis J. Pharm. Biomed. Anal. 41 2006 1523 1542 (Pubitemid 44247468)
29. P. Ninfali, M. Bacchioccam, and A. Antonelli Characterization and biological activity of the main flavonoids from Swiss Chard (Beta vulgaris subspecies cycla) Phytomedicine 14 2007 216 221 (Pubitemid 46157100)
30. R. Norbæk, K. Brandt, and T. Kondo Identification of flavone C-glycosides including a new flavonoid chromophore from Barley leaves (Hordeum vulgare L.) by improved NMR techniques J. Agric. Food Chem. 48 2000 1703 1707 (Pubitemid 30331512)
31. A. Ohsaki, R. Yokoyama, and H. Miyatake Two diterpene rhamnosides, mimosaside B and C, from Mimosa hostilis Chem. Pharm. Bull. 54 2006 1728 1729 (Pubitemid 44901210)
32. S. Rayyan, T. Fossen, and H.S. Nateland Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug 'Crataegi folium cum flore' (Howthorn) Phytochem. Anal. 16 2005 334 341 (Pubitemid 41388237)
33. M. Shimizu, T. Ito, and S. Terashima Inhibition of lens aldose reductase by flavonoids Phytochemistry 23 1984 1885 1888
34. R. Song, A. Robert, and J. Bernadou Illustrating atropisomerism in the porphyrin series using NMR spectroscopy Analusis 27 1999 464 467
35. Y. Wang, S.Y. Zhang, and X.F. Ma Potent inhibition of fatty acid synthase by parasitic loranthus [Taxillus chinensis (DC.) Danser] and its constituent avicularin J. Enzyme Inhib. Med. Chem. 21 2006 87 93 (Pubitemid 43884207)
36. X. Yan, B.T. Murph, and G.B. Hammond Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium macrocarpon) J. Agric. Food Chem. 50 2002 5844 5849 (Pubitemid 35155303)
37. K. Yuan, J.L. Lu, and M.W. Yin Chemical constituents of C-glycosylflavones from Mimosa pudica Yao Xue Xue Bao 41 2006 435 438 (Pubitemid 44022668)
38. K. Yuan, A. Jia, and J.L. Lu Structural identification of new C-glycosylflavones from Mimosa pudica Chin. J. Anal. Chem. 35 2007 739 742