Preussianone, a new flavanone-chromone biflavonoid from garcinia preussii engl.

Molecules

Volumn 17, Issue 5, 2012, Pages 6114-6125

  Messi, Bernadette Biloa ^a,b   Ndjoko Ioset, Karine ^b   Hertlein Amslinger, Barbara ^c   Lannang, Alain Meli ^d   Nkengfack, Augustin E ^a   Wolfender, Jean Luc ^b   Hostettmann, Kurt ^b   Bringmann, Gerhard ^c  

^a UNIVERSITY OF YAOUNDÉ I   (Cameroon)

^b UNIVERSITY OF GENEVA   (Switzerland)

^c UNIVERSITY OF WÜRZBURG   (Germany)

^d UNIVERSITY OF MAROUA   (Cameroon)

Author keywords

Absolute configuration; Antibacterial activity; Garcinia biflavonoids; High temperature NMR

Indexed keywords

ANTIINFECTIVE AGENT; BIFLAVONOID; FLAVANONE DERIVATIVE; PREUSSIANONE;

ARTICLE; BACTERIUM; CHEMISTRY; DRUG EFFECT; GARCINIA; ISOLATION AND PURIFICATION;

ANTI-BACTERIAL AGENTS; BACTERIA; BIFLAVONOIDS; FLAVANONES; GARCINIA;

EID: 84861499993     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17056114     Document Type: Article

References (35)

1. Williams, C.A.; Harborne, J.B. Biflavonoids. In Methods in Plant Biochemistry; Dey, P.M., Harborne, J.B., Eds.; Academic Press: San Diego, CA, USA, 1989; pp. 357-388.
2. Kim, H.; Park, H.; Son, K.; Chang, H.; Kang, S. Biochemical pharmacology of biflavonoids: Implications for anti-inflammatory action. Arch. Pharm. Res. 2008, 31, 265-273.
3. Iwu, M.M.; Igboko, O.A. Biflavonoid constituents of Garcinia kola roots. Fitoterapia 1990, 61, 178-181.
4. Geiger, H.; Quinn, C.; Biflavonoids. In The Flavonoids; Harborne, J.B., Mabry, T.J., Mabry, H., Eds.; Chapman & Hall: London, UK, 1975; pp. 692-742.
5. Geiger, H.; Quinn, C. Biflavonoids. In The Flavonoids; Harborne, J.B., Mabry, T.J., Eds.; Chapman & Hall: London, UK, 1982; pp. 505-534.
6. Ferreira, D.; Slade, D.; Marais, J.P.J. Bi-, Tri-, Tetra-, Penta-, and Hexaflavonoids. In The Flavonoids: Chemistry, Biochemistry and Applications; Øyvind, M.A., Markham, K.R., Eds.; Taylor & Francis: Boca Raton, FL, USA, 2006; pp. 1101-1124.
7. Amellal, M.; Bronner, C.; Briancon, F.; Haag, M.; Anton, R.; Landry, Y. Inhibition of mast-cell histamine-release by flavonoids and biflavonoids. Planta Med. 1985, 51, 16-20.
8. Geiger, H.; Quinn, C. Biflavonoids. In The Flavonoids; Harborne, J.B., Ed.; Chapman & Hall: London, UK, 1988; pp. 99-124.
9. Braide, V.B. Anti-inflammatory effect of Kolaviron, bio-flavonoid extract of Garcinia kola. Fitoterapia 1993, 64, 433-436.
10. Cowan, M.M. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 1999, 12, 564-282.
11. Kaikabo, A.A.; Eloff, J.N. Antibacterial activity of two biflavonoids from Garcinia livingstonei leaves against Mycobacterium smegmatis. J. Ethnopharmacol. 2011, 138, 253-255.
12. Louh, G.N.; Lannang, A.M.; Mbazoa, C.D.; Tangmouo, J.G.; Komguem, J.; Castilho, P.; Ngninzeko, F.N.; Qamar, N.; Lontsi, D.; Choudhary, M.I.; et al. Polyanxanthone A, B and C, three xanthones from the wood trunk of Garcinia polyantha Oliv. Phytochemistry 2008, 69, 1013-1017.
13. Chen, J.-J.; Ting, C.-W.; Hwang, T.-L.; Chen, I.-S. Benzophenone derivatives from the fruits of Garcinia multiflora and their anti-inflammatory activity. J. Nat. Prod. 2009, 72, 253-258.
14. Lin, Y.-M.; Anderson, H.; Flavin, M.T.; Pai, Y.-H.S.; Mata-Greenwood, E.; Pengsuparp, T.; Pezzuto, J.M.; Schinazi, R.F.; Hughes, S.H.; Chen, F.-C. In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora. J. Nat. Prod. 1997, 60, 884-888.
15. Bouquet, A. Féticheurs et Médecines Traditionnelles du Congo (Brazzaville); Office de la Recherche Scientifique et Technique Outre-Mer O.R.S.T.O.M.: Paris, France, 1969; pp. 132-133.
16. Visser, L.E. Plantes Médicinales de la Côte d'Ivoire; Mededelingen Landbouwhogeschool Wageningen: Wageningen, The Netherlands, 1975; p. 54.
17. Cotterill, P.J.; Scheinmann, F.; Stenhouse, I.A. Extractives from Gurriferae 34. Kolaflavanone, a new biflavanone from nuts of Garcinia kola HECKEL-applications of C-13 nuclear magnetic-resonance in elucidation of structures of flavonoids. J. Chem. Soc. Perkin Trans. 1 1978, 1978, 532-539.
18. Jackson, B.; Locksley, H.D.; Scheinmann, F.; Wolstenholme, W.A. Extractives from guttiferae. Part XXII. The isolation and structure of four novel biflavanones from the heartwoods of Garcinia buchananii Baker and Garcinia. eugeniifolia Wall. J. Chem. Soc. C 1971, 1971, 3791-3804.
19. Markham, K.R.; Sheppard, C.; Geiger, H. 13C-NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry 1987, 26, 3335-3337.
20. Chari, V.M.; Ilyas, M.; Wagner, H.; Neszmélyi, A.; Fa-Ching, C.; Li-Kuang, C.; Yu-Chin, L.; Yu-Meei, L. 13C-NMR spectroscopy of biflavanoids. Phytochemistry 1977, 16, 1273-1278.
21. Terashima, K.; Kondo, Y.; Aqil, M.; Waziri, M.; Niwa, M. A study of biflavanones from the stems of Garcinia kola (Guttiferae). Heterocycles 1999, 50, 283-290.
22. Slade, D.; Ferreira, D.; Marais, J.P.J. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry 2005, 66, 2177-2215.
23. Gaffield, W. Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides: Determination of aglycone chirality in flavanone glycosides. Tetrahedron 1970, 26, 4093-4108.
24. Hosoi, S.; Shimizu, E.; Ohno, K.; Yokosawa, R.; Kuninaga, S.; Coskun, M.; Sakushima, A. Structural studies of zoospore attractants from Trachelospermum jasminoides var. pubescens: Taxifolin 3-O-glycosides. Phytochem. Anal. 2006, 17, 20-24.
25. Ansari, W.H.; Rahman, W.; Barraclough, D.; Maynard, R.; Scheinmann, F. Biflavonoids and a flavanone chromone from leaves of Garcinia dulsis (Roxb) Kurz. J. Chem. Soc. Perkin Trans. 1 1976, 1976, 1458-1463.
26. Kumar, V.; Brecht, V.; Frahm, A.W. Conformational analysis of the biflavanoid GB2 and a polyhydroxylated flavanone-chromone of Cratoxylum neriifolium. Planta Med. 2004, 70, 646-651.
27. Duddeck, H.; Snatzke, G.; Yemul, S.S. 13C-NMR and CD of some 3,8''-biflavanoids from Garcinia species and of related flavanone. Phytochemistry 1978, 17, 1369-1973.
28. Crichton, E.G.; Waterman, P.G. Manniflavanone, a new 3,8-linked flavanone dimer from the stem bark of Garcinia mannii. Phytochemistry 1979, 18, 1553-1557.
29. Ferrari, J.; Terreaux, C.; Kurtán, T.; Szikszai-Kiss, A.; Antus, S.; Msonthi, J.D.; Hostettmann, K. Isolation and on-Line LC/CD analysis of 3,8'-linked biflavonoids from Gnidia involucrata. Helv. Chim. Acta 2003, 86, 2768-2778.
30. Ding, Y.; Xing-Cong, L.; Ferreira; D. Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8"-biflavonoid morelloflavone. J. Org. Chem. 2007, 72, 9010-9017.
31. Mbwambo, Z.H.; Kapingu, M.C.; Moshi, M.J.; Machumi, F.; Apers, S.; Cos, P.; Ferreira, D.; Marais, J.P.J.; Vanden Berghe, D.; Maes, L.; et al. Antiparasitic activity of some xanthones and biflavonoids from the root bark of Garcinia livingstonei. J. Nat. Prod. 2006, 69, 369-372.
32. Li, X.-C.; Joshi, A.S.; Tan, B.; ElSohly, H.N.; Walker, L.A.; Zjawiony, J.K.; Ferreira, D. Absolute configuration, conformation, and chiral properties of flavanone-(3 ? 8'')-flavone biflavonoids from Rheedia acuminata. Tetrahedron 2002, 58, 8709-8717.
33. Wiegand, I.; Hilpert, K.; Hancock, R.E.W. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat. Protoc. 2008, 3, 163-175.
34. Eloff, J.N. A Sensitive and quick microplate method to determine the minimal inhibitory concentration of plant extracts for bacteria. Planta Med. 1998, 64, 711-713.
35. Sonnenbichler, J.; Madubunyi, I.; Scheer, H. Stereochemistry of 2-hydroxybiflavanonols from Garcinia kola nuts. Z. Naturforsch. 1987, 42c, 855-857.