Tenuiflorins A - C: New 2-Phenoxychromones from the Leaves of Mimosa tenuiflora

Abstract

Five 2-phenoxychromones, the new tenuiflorin A [5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenoxy)-6-methoxychromone], tenuiflorin B [5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenoxy)-6-methoxychromone] and tenuiflorin C [5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenoxy)chromone], along with the known 6-demethoxycapillarisin and 6-demethoxy-4′-O-methylcapillarisin were isolated from leaves of Mimosa tenuiflora. Structures of these compounds were established by analysis of their spectroscopic data. A single-crystal diffraction analysis of 6-demethoxy-4′-O-methylcapillarisin was performed in order to confirm the proposed structures.

Mimosa tenuiflora - Leguminosae - 2-phenoxychromones - tenuiflorins A, B and C

References

• 1 Lozoya X, Navarro V, Arnason J T, Kourany E. Experimental evaluation of Mimosa tenuiflora (Willd.) Poir. (Tepescohuite) I. - Screening of the antimicrobial properties of bark extracts.  Archiv Invest Med. 1980;  20 87-93
• 2 Instituto Nacional I ndigenista. Atlas de las plantas de la medicina tradicional mexicana. Vilamar AA, coordinador Vol. III México; 1994: pp 1327-8
• 3 Meckes-Lozoya M, Lozoya X, Gonzalez J L. Propiedades farmacológicas in vitro de algunos extractos de Mimosa tenuiflora (tepescohuite).  Archiv Invest Med. 1990;  21 163-9
• 4 Villarreal M L, Nicasio P, Alonso-Cortes D. Effects of Mimosa tenuiflora bark extracts on WI38 and KB human cells in culture.  Archiv Invest Med. 1991;  22 163-9
• 5 Meckes-Lozoya M, Lozoya X, Gonzalez J L. Efecto producido por la fracción de alcaloides de Mimosa tenuiflora (tepescohuite) sobre el reflejo peristáltico del íleon de cobayo.  Archiv Invest Med. 1990;  21 171-4
• 6 Jiang Y, Beck J P, Italiano L, Haag M, Anton R. Biological effects of the saponins from Mimosa tenuiflora on fibroblast cells in culture.  Planta Medica. 1991;  57 (Suppl. Issue 2) A38
• 7 Jiang Y, Massiot G, Lavaud C, Teulon J M, Guéchot C, Haag-Berrurier M, Anton R. Triterpenoid glycosides from the bark of Mimosa tenuiflora .  Phytochemistry. 1991;  30 2357-60
• 8 Jiang Y, Weniger B, Massiot G, Lavaud C, Anton R. Saponins from the bark of Mimosa tenuiflora .  Planta Medica. 1991;  57 (Suppl. Issue 2) A38-9
• 9 Domínguez X A, García S G, Williams H J, Ortíz C, Scott A I. Kukulkanins A and B, new chalcones from Mimosa tenuefolia .  J Nat Prod. 1989;  52 864-7
• 10 Komiya T, Narusi Y, Oshio H. Studies on ”Inchinko.” II. Studies on the compounds related to capillarisin and flavonoids.  Yakugaku Zasshi. 1976;  96 855-62
• 11 Hashidoko Y, Tahara S, Mizutani J. 2-Phenoxychromones and a structurally related flavone from leaves of Rosa rugosa .  Phytochemistry. 1991;  30 3837-8
• 12 Altomare A, Cascarano G, Giacovazzo C, Guagliardi A, Burla M, Polidore G, Camalli M. SIR92-A program for automatic solution of crystal structures by direct methods.  J Appl Crystallogr. 1994;  27 435
• 13 Sheldrick G M. SHELXS 97, Program of refining of crystal structures. Germany; University of Göttingen 1999
• 14 Kijjoa A, Vieira L M, Pereira J A, Silva A MS, Herz W. Further constituents of Achillea ageratum .  Phytochemistry. 1999;  51 555-8
• 15 Sharon A, Ghirlando R, Gressel J. Isolation, purification, and identification of 2-(p-hydroxyphenoxy)-5,7-dihydroxychromone: A fungal induced phytoalexin from Cassia obtusifolia .  Plant Physiol. 1992;  98 303-8
• 16 Hashidoko Y, Tahara S, Mizutani J. Bisabolane sesquiterpenes and a 2-phenoxychromone from Rosa woodsii leaves.  Phytochemistry. 1992;  31 2148-9
• 17 Huang Y -L, Ou J -C, Chen C -F, Chen C -C. Three new 2-phenoxychromones from the leaves of Epimedium sagitatum .  J Nat Prod. 1993;  56 275-8
• 18 Ibewike J C, Ogundaini A O, Ogungbamila F O, Martin M -T, Gallaard J -F, Bohlin L, Païs M. Piliostigmin, a 2-phenoxychromone, and C-methylflavonols from Piliostigma thonningii .  Phytochemistry. 1996;  43 687-90
• 19 Tanaka H, Hirata M, Etoh H, Shimizu H, Sako M, Murata J, Murata H, Darnaedi D, Fukai T. Eryvarins F and G, two 3-phenoxychromones from the roots of Erythrina variegata .  Phytochemistry. 2003;  62 1243-6