Pyrone and Unusually Furanone-substituted Flavones from the Leaves of Hoslundia opposita

Abstract

Two new unusual 6-furanoflavones, hoslunfuranine (5) and 5-O-methylhoslunfuranine (6), were isolated from the leaves of Hoslundia opposita Vahl.. Four known methylpyranoflavonic analogues [hosloppin (1), hoslundin (2), 5-O-methylhoslundin (3), oppositin (4)], all specific of the species, were also obtained. Their structures were established on the basis of their spectroscopic data. In vitro cytotoxic, trypanocidal, and leishmanicidal activities of compounds 1 and 3 to 6 were evaluated. Compounds 4 and 6 exhibited leishmanicidal potential in the micromolar range.

Key words

antiparasitic activity - cytotoxicity - furanoflavones - Hoslundia opposita Vahl. - Lamiaceae

• References

• 1 Tonzibo ZF, Ahibo CA, Chalachat JC, Nʼguessan YT. Chemical composition of essential oils of Hoslundia opposita Vahl. from Ivory Coast. Flav Fragr J 2006; 21: 789-791
• 2 Avedoun MA, Adéoti BS, Setondji J, Tchoumbougnang F, Kuiaté JR, Amvam Zollo PH, Menut C, Lamaty G, Bessière JM. Essential oil of Hoslundia opposita Vahl. growing in Benin and Cameroon. Flav Fragr J 1999; 14: 319-321
• 3 Achenbach H, Waibel R, Nkunya MH, Weenent H. Antimalarial compounds from Hoslundia opposita . Phytochemistry 1992; 31: 3781-3784
• 4 Ngadjui BT, Ayafor JF, Sondengam BL, Rycroft DS, Tillequin F. Hoslundin, hoslundal, and hoslunddiol: three new flavonoids from the twigs of Hoslundia opposita (Lamiaceae). Tetrahedron 1991; 47: 3555-3564
• 5 Ngadjui BT, Ayafor JF, Sondengam BL, Connolly JD, Rycroft DS, Tillequin F. Oppositin and 5-O-methylhoslundin, pyrone-substituted flavonoids of Hoslundia opposita . Phytochemistry 1993; 32: 1313-1315
• 6 Mujovo FS, Hussein AA, Meyer JJM, Fourie B, Muthivhi T, Lall N. Bioactive compounds from Lippia javanica and Hoslundia opposita . Nat Prod Res 2008; 22: 1047-1054
• 7 Ngadjui BT, Tsopmo A, Ayafor JF, Connolly JD, Tamboué H. Hosloppin, a new pyrone-substituted flavonoid from Hoslundia opposita . J Nat Prod 1995; 58: 109-111
• 8 Perry NB, Benn MH, Foster LM, Routledge A, Weavers RT. The glycosidic precursor of (Z)-5-ethylidene-2(5H)-furanone in Halocarpus biformis juvenile foliage. Phytochemistry 1996; 42: 453-459
• 9 Hollenbeak KH, Kuehne ME. The isolation and structure determination of the fern glycoside osmundalin and the synthesis of its aglycone osmundalactone. Tetrahedron 1974; 30: 2307-2316
• 10 Numata A, Hokimoto K, Takemura T, Katsuno T, Yamamoto K. Plant constituents biologically active to insects. V. Antifeedants for the larvae of the yellow butterfly, Eurema hecabe mandarina, in Osmunda japonica . Chem Pharm Bull 1984; 32: 2815-2820
• 11 Loiseau PM, Lubert P, Wolf JG. Contribution of dithiol ligands to in vitro and in vivo trypanocidal activities of dithiaarsanes and investigation of ligand exchange in an aqueous solution. Antimicrob Agents Chemother 2000; 44: 2954-2961
• 12 Desrivot J, Waikedre J, Cabalion P, Herrenknecht C, Bories C, Hocquemiller R, Fournet A. Antiparasitic activity of some New Caledonian medicinal plants. J Ethnopharmacol 2007; 112: 7-12
• 13 Tempête C, Werner GH, Favre F, Roja A, Langlois N. In vitro cytostatic activity of 9-demethoxyporothramycin B. Eur J Med Chem 1995; 30: 647-650