New Flavonoids from Boldoa purpurascens Cav.

Abstract

Phytochemical analysis of the leaves of Boldoa purpurascens Cav. led to isolation of four flavone glycosides, three of which are new compounds. Their structures have been determined by mass spectrometry and by 1 D and 2 D NMR analysis, i. e., 4′,5-dihydroxy-6,7-methylenedioxyflavonol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (1), 4′,5-dihydroxy-6,7-methylenedioxyflavonol 3-O-β-D-xylopyranoside (2), and 4′,5-dihydroxy-6,7-methylenedioxyflavonol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3). The known compound was 4′,5-dihydroxy-6,7-methylenedioxyflavonol 3-O-β-D-glucopyranoside (4). The aglycone 4′,5-dihydroxy-6,7-methylenedioxyflavonol is known as gomphrenol. Compounds 1 and 2 failed to show antifungal activity when tested against three different strains of fungi, i. e., Fusarium culmorum, Botrytis cinerea, and Aspergillus flavus.

Key words

Boldoa purpurascens - Nyctaginaceae - flavonoid glycosides - gomphrenol glycosides - antifungal activity

References

• 1 Roig J T. Medicinal plants from Cuba. Botanic Dictionary of Cuban Common Names, 3rd edition. Editorial Science and Technic 1988: 225-6
• 2 Gonzalez D MM, Cuéllar A C, Cabrera K, Hernandez P. Evaluation of the diuretic effect of aqueous extract of Boldoa purpurascens.  Rev Cub Farm, special edition. 2001;  35 174-6
• 3 Lopez Abraham A M, Rojas Hernandez N M, Jimenez Misas C A. Extractos de plantas que crecen en Cuba con potenciales antitumorales. Parte III.  Rev Cub Farm. 1980;  14 35-42
• 4 Jimenez Misas C A, Rojas Hernandez N M, Lopez Abraham A M. Resultados comparativos de la actividad biologica de extractos de plantas que crecen en Cuba. III.  Rev Cub Farm. 1980;  14 301-10
• 5 Krauze-Baranowska M, Wiwart M. Antifungal activity of biflavones from Taxus baccata and Ginkgo biloba.  . 2003;  58 65-9
• 6 Magalhães A F, Tozzi A M, Magalhães E G, Sannomiya M, Soriano Medel P, Perez M A. Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity.  An Acad Bras Cienc. 2007;  79 51-67
• 7 Pal M, Joshi H, Kapoor V P, Pushpangadan P, Chaurasia L. Antifungal activity of wogonin.  Phytother Res. 2003;  17 1215-6
• 8 Brouwer M, Lievens B, Van Hemelrijck W, Van den Ackerveken G, Cammue B P, Thomma B P. Quantification of disease progression of several microbial pathogens on Arabidopsis thaliana using real-time fluorescence PCR.  FEMS Microbiol Lett. 2003;  228 241-8
• 9 Kanda H, Ito H. Isolation of a flavonoid and its glycoside as blood platelet aggregation inhibitor. Jpn Kokai Tokkyo Koho 1988: JP63203682 A
• 10 Kohda H, Niwa A, Nakamoto Y, Takeda O. Flavonoid glycosides from Polygonum tinctorium.  Chem Pharm Bull. 1990;  38 523-4
• 11 Thevissen K, Kristensen H H, Thomma B P, Cammue B P, François I E. Therapeutic potential of antifungal plant and insect defensins.  Drug Discov Today. 2007;  12 966-71
• 12 Terras F R, Schoofs H M, De Bolle M F, Van Leuven F, Rees S B, Vanderleyden J. et al . Analysis of two novel classes of plant antifungal proteins from radish (Raphanus sativus L.) seeds.  J Biol Chem. 1992;  267 5301-9
• 13 Niassy B, Um B H, Lobstein A, Weniger B, Koné M, Anton R. Flavonoïdes de Tephrosia deflexa et Tephrosia albifoliolis.  C R Acad Sci II. 2004;  7 993-6
• 14 Bouillant M L, Redolfi P, Cantisani A, Chopin J. Gomphrenol, a new methylenedioxyflavonol from leaves of Gomphrene globosa.  Phytochemistry. 1978;  17 2138-40
• 15 Pretsch E, Bühlmann P, Affolter C. Structure determination of organic compounds. Tables of spectral data, 3rd completely revised and enlarged English edition. Berlin; Springer Verlag 2000