Cytotoxic Chalcones and Flavonoids from the Leaves of Muntingia calabura

Abstract

Two new dihydrochalcones, 2′,4′-dihydroxy-3′-methoxydihydrochalcone, (-)-3′-methoxy-2′,4′,β-trihydroxydihydrochalcone, a new flavanone, (2S)-(-)-5′-hydroxy-7,3′,4′-trimethoxyflavanone, and a new flavonol derivative, muntingone, along with sixteen known compounds, were isolated from the leaves of Muntingia calabura. The structures of these new compounds were determined using spectral analyses including extensive 2D NMR data. Among the isolates, (2S)-5′-hydroxy-7,3′,4′-trimethoxyflavanone, 4′-hydroxy-7-methoxyflavanone, 2′,4′-dihydroxychalcone, and 2′,4′-dihydroxy-3′-methoxychalcone exhibited cytotoxicity (IC₅₀ values < 4 μg/mL) against P-388 and/or HT-29 cell lines in vitro.

References

• 1 Liu T S, Lo H C. Tiliaceae in Flora of Taiwan. 2nd edn. Editorial Committee of the Flora of Taiwan Taipei, Taiwan; 1993 Vol 3: pp 730-2
• 2 Chen J J, Lin R W, Duh C Y, Huang H Y, Chen I S. Flavones and cytotoxic constituents from the stem bark of Muntingia calabura .  J Chin Chem Soc. 2004;  51 665-70
• 3 Kaneda N, Pezzuto J M, Soejarto D D, Kinghorn A D, Farnsworth N R, Santisuk T, Tuchinda P, Udchachon J, Reutrakul V. Plant anticancer agents, XL VIII. New cytotoxic flavonoids from Muntingia calabura roots.  J Nat Prod. 1991;  54 196-206
• 4 Nshimo C M, Pezzuto J M, Kinghorn A D, Farnsworth N R. Cytotoxic constituents of Muntingia calabura leaves and stems collected in Thailand.  Int J Pharmacog. 1993;  31 77-81
• 5 Su B N, Park E J, Vigo J S, Graham J G, Cabieses F, Fong H HS, Pezzuto J M, Kinghorn A D. Activity-guided isolation of the chemical constituents of Muntingia calabura using a quinone reductase induction assay.  Phytochemistry. 2003;  63 335-41
• 6 Jain A C, Mehta A. A new synthesis of homoisoflavanones (3-benzyl-4-chromanones).  Tetrahedron. 1985;  41 5933-7
• 7 Achenbach H, Stöcker M, Constenla M A. Flavonoid and other constituents of Bauhinia manca .  Phytochemistry. 1988;  27 1835-41
• 8 Economides C, Adam K P. Lipophilic flavonoids from the fern Woodsia scopulina .  Phytochemistry. 1998;  49 859-62
• 9 Thusoo A, Raina N, Minhaj N, Ahmed S R, Zaman A. Crystalline constituents from Daphne oleoides .  Indian J Chem Sect B. 1981;  20 937-8
• 10 Parmar V S, Gupta S, Sinha R, Sharma S K. Synthesis of some commonly occurring 2-phenyl-4H-1-benzopyran-4-ones: revised structures for three natural products.  Indian J Chem Sect B. 1993;  32 244-56
• 11 Mesquita A AL, de B Correa D, de Padua A P, Guedes M LO, Gottlieb O R. Flavonoids from four Compositae species.  Phytochemistry. 1986;  25 1255-6
• 12 Kurkin V A, Sentsov M F, Zapesochnaya G G, Braslavskii V B, Tolkachev N O. Flavonoids of the buds of Populus laurifolia .  Chem Nat Compd. 1994;  30 778-80
• 13 Proksch M, Proksch P, Weissenboeck G, Rodriguez E. Flavonoids from the leaf resin of Adenostoma sparsifolium .  Phytochemistry. 1982;  21 1835-6
• 14 Urzúa A, Mendoza L, Tojo E, Rial M E. Acylated flavonoids from Pseudognaphalium species.  J Nat Prod. 1999;  62 381-2
• 15 Fukai T, Nomura T. NMR spectra of isoprenoid substituted phenols. Part 5. Proton NMR chemical shift of the flavonol 5-hydroxy proton as a characterization of 6- or 8-isoprenoid substitution.  Heterocycles. 1992;  34 1213-25
• 16 Lee J M, Tseng T H, Lee Y J. An efficient synthesis of neoflavonoid antioxidants based on montmorillonite K-10 catalysis. Synthesis 2001: 2247-54
• 17 Tanrisever N, Fronczek F R, Fischer N H, Williamson G B. Ceratiolin and other flavonoids from Ceratiola ericoides .  Phytochemistry. 1987;  26 175-9
• 18 Ramadan M A, Kamel M S, Ohtani K, Kasai R, Yamasaki K. Minor phenolics from Crinum bulbispermum bulbs.  Phytochemistry. 2000;  54 891-6
• 19 Furlong J JP, Nudelman N S. Mechanism of cyclization of substituted 2′-hydroxychalcones to flavanones.  J Chem Soc Perkin Trans. 1985;  2 633-40
• 20 Chen J J, Duh C Y, Huang H Y, Chen I S. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia .  Planta Med. 2003;  69 542-6