13C-NMR Data from Coumarins from Moraceae Family

DOI: 10.4236/ajac.2015.611081   PDF   HTML   XML   2,556 Downloads   3,259 Views   Citations


Species from Moraceae family stand out in popular medicine and phytotherapy, have been for example used as expectorants, bronchodilators, anthelmintics and treatment of skin diseases, such as vitiligo, due to the presence of compounds with proven biological activity, as the coumarins. Coumarins are lactones with 1,2-benzopyrone basic structure, and are widely distributed in the plant kingdom, both in free form, and in glycosylated form. This work reports a literature review, describing the data of 13C NMR from 53 coumarins isolated from the family Moraceae, and data comparison between genera who presented photochemical studies, in order to contribute to the chemotaxonomy of this family.

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Luz, R. , Vieira, I. , Braz-Filho, R. and Moreira, V. (2015) 13C-NMR Data from Coumarins from Moraceae Family. American Journal of Analytical Chemistry, 6, 851-866. doi: 10.4236/ajac.2015.611081.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Barooso, G.M., Peixoto, A.L., Ichaso, C.L.F., Guimaraes, E.F. and Costa, C.G. (2002) Sistemática de angiospermas do Brasil. 2nd Edition, Universidade Federal de Vicosa, Vicosa.
[2] Romaniuc Neto, S., Carauta, J.P.P., Vianna Filho, M.D.M., Pereira, R.A.S., da S. Ribeiro, J.E.L., Machado, A.F.P., dos Santos, A., Pelissari, G. and Pederneiras, L.C. (2015) Moraceae in List of Species of Flora of Brazil.
[3] Castro, R.M. (2006) Flora da Bahia—Moraceae. Master’sThesis, Universidade Estadual de Feira de Santana, Feira de Santana.
[4] Monteiro, V. (1999) Estudo fitoquímico de Brosimum gaudichaudii Trécul (Moraceae). Master’sThesis, Universidade Estadual do Norte Fluminense Darcy Ribeiro: Campos dos Goytacazes.
[5] Pio-Correa, M. and Pena, L.A. (1984) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Vol. 2-3, Ministério da Agricultura, Instituto Brasileiro de Desenvolvimento Florestal, Rio de Janeiro.
[6] Chang, M.A., Yang, Y. C., Kuo, Y.C., Kuo, Y.H., Chang, C., Chen, C.M. and Lee, T.H. (2005) Furocoumarin Glycosides from the Leaves of Ficus ruficaulis Merr. Var. antaoensis. Journal of Natural Products, 68, 11-13.
[7] Diaz, M.G., Arruda, A.C., Arruda, M.S.P. and Muller, A.H. (1997) Methoxyflavones from Ficus máxima. Phyto-chemistry, 45, 1697-1699.
[8] Hayasida, W., Sousa, A.S., Lima, M.P., Nascimento, C.C. and Ferreira, A.G. (2008) Proposta de aproveitamento em resíduos de paurainha (Brosimum rubescens) descartados pelo setor madeireiro. Acta Amazonica, 38, 749-752.
[9] Pozetti, G.L. (2005) Brosimum gaudichaudii Trecul (Moraceae): Da planta ao medicamento. Revista de Ciências Farmacêuticas Básica e Aplicada, 26, 159-166.
[10] Dewick, P.M. (2009) Medicinal Natural Products: A Biosynthetic Approach. 3rd Edition, John Wiley & Sons, New York.
[11] Sardari, S., Nishibe, S. and Danesstalab, M. (2000) Coumarins, the Bioactive Structures Antifungal Property. Studies in Natural Products Chemistry, 23, 335-393.
[12] Ribeiro, C.V.C. and Kaplan, M.A.C. (2002) Evolutionary Tendency of Coumarin-Bearing Families in Angiospermae. Química Nova, 25, 533-538.
[13] Monteiro, V., Mathias, L.M., Vieira, I.J.C., Schripsema, J. and Braz-Filho, R. (2002) Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii. Journal of the Brazilian Chemistry Society, 13, 281-287.
[14] Lourenco, M.V. (2001) Estudo comparativo dos constituintes químicos de Brosimum gaudichaudii Trécul e do medicamento “V”. PhD Thesis, Universidade Estadual Paulista, Araraquara.
[15] Vouffo, B., Hussain, H., Eyong, K.O., Dongo, E., Folefoc, G.N., Nkengfack, A.E. and Krohn, K. (2008) Chemical Constituents of Dorstenia picta and Newbouldia laevis. Biochemical Systematics and Ecology, 36, 730-732.
[16] Lazreg-Aref, H., Mars, M., Fekih, A., Aouni, M. and Said, K. (2012) Chemical Composition and Antibacterial Activity of a Hexane Extract of Tunisian Caprifig Latex from the Unripe Fruit of Ficus carica. Pharmaceutical Biology, 50, 407-412.
[17] Chan, K.K., Giannini, D.D., Cain, A.H., Roberts, J.D., Porter, W. and Trager, W. (1977) Carbon-13 Nuclear Magnetic Resonance Studies of Coumarin and Related Compounds. Tetrahedron, 33, 899-906.
[18] Poumale, H.M., Amadou, D., Shiono, Y., Kapche, G.D.W.F. and Ngadjui, B.T. (2011) Chemical Constituents of Dorstenia convexa. Asian Journal of Chemistry, 23, 525-527.
[19] Vilegas, W. and Pozetti, G.L. (1993) Coumarins from Brosimum gaudichaudii. Journal of Natural Products, 56, 416-417.
[20] Chiang, C.C., Cheng, M.J., Peng, C.F., Huang, H.Y. and Chen, I.S. (2010) A Novel Dimeric Coumarin Analog and Antimycobacterial Constituents from Fatoua pilosa. Chemistry and Biodiversity, 7, 1728-1736.
[21] Wang, Y., Liang, H., Zhang, Q., Cheng, W. and Yi, S. (2014) Phytochemical and Chemotaxonomic Study on Ficus tsiangii. Biochemical Systematics and Ecology, 57, 210-215.
[22] Zolek, T., Paradowska, K. and Wawer, I. (2003) 13C MAS NMR and GIAO-CHF Calculations of Coumarins. Solid State Nuclear Magnetic Resonance, 23, 77-87.
[23] Dudek-Makuch, M. and Matlawska, I. (2013) Coumarins in Horse Chestnut Flowers: Isolation and Quantification by UPLC Method. Acta Poloniae Pharmaceutica—Drug Research, 70, 517-522.
[24] Shults, E.E., Petrova, T.N., Shakirov, M.M., Chernyak, E.I., Pokrovskiy, L.M., Nekhoroshev, S.A. and Tolstikov, G.A. (2003) Coumarin Compounds from Roots of Peucedanum (Peucedanum morisonii Bess.). Chemistry of Sustainable Development, 11, 649-654.
[25] Prabowo, W.C., Wirasutisna, K.R. and Insanu, M. (2013) Isolation and Characterization of 3-Acetylaleuritolic Acid and Scopoletin from Stem Bark of Aleurites moluccana (L. Willd). International Journal of Pharmacy and Pharmaceutical Sciences, 5, 851-853.
[26] Oh, H., Ko, E.K., Jun, J.Y., Oh, M.H., Park, S.U., Kang, K.H., Lee, H.S. and Kim, Y.C. (2002) Hepatoprotective and Free Radical Scavenging Activities of Prenylflavonoids, Coumarin, and Stilbene from Morus alba. Planta Medica, 68, 932-934.
[27] Yue, M., Li, Y. and Shi, Y.P. (2007) Determination of Six Bioactive Components of Saussurea katochaete by Capillary Electrophoresis. Biomedical Chromatography, 21, 376-381.
[28] Naressia, M.A., Ribeiroa, M.A. dos S., Bersani-Amadob, C.A., Zamunerb, M.L.M., da Costa, W.F., Tanaka, C.M.A. and Sarragiottoa, M.H. (2012) Chemical Composition, Anti-Inflammatory, Molluscicidal and Free-Radical Scavenging Activities of the Leaves of Ficus radicans “Variegata” (Moraceae). Natural Product Research, 26, 323-330.
[29] Boeck, F., Blazejak, M. and Anneser, M.R. and Hintermann, L. (2012) Cyclization of Ortho-Hydroxycinnamates to Coumarins under Mild Conditions: A Nucleophilic Organocatalysis Approach. Beilstein Journal of Organic Chemistry, 8, 1630-1636.
[30] Li, L.Q., Li, J., Huang, Y., Wu., Q., Deng, S.P., Su, X.J., Yang, R.Y., Huang, J.G., Chen, Z.Z. and Li, S. (2012) Lignans from the Heartwood of Streblus asper and Their Inhibiting Activities to Hepatitis B Virus. Fitoterapia, 83, 303-309.
[31] Ragasa, C.Y., Ng, V.A.S., Reyes, M.M. De L., Mandia, E.H. and Shen, C.C. (2014) Triterpenes and a Coumarin Derivative from Kibatalia gitingensis (Elm.) Woodson. Der Pharma Chemica, 6, 360-364.
[32] Gao, W., Li, Q., Chen, J., Wang, Z. and Hua, C. (2013) Total Synthesis of 3,4-Unsubstituted Coumarins. Molecules, 18, 15613-15623.
[33] Parveen, M., Ali, A., Malla, A.M., Silva, P.S.P. and Silva, M.R. (2011) A Halogenated Coumarin from Ficus krishnae. Chemical Papers, 65, 735-738.
[34] Patre, R.E., Shet, J.B., Parameswaran, P.S. and Tilve, S.G. (2009) Cascade Wittig Reaction-Double Claisen and Cope Rearrangements: One-Pot Synthesis of Diprenylated Coumarins Gravelliferone, Balsamiferone, and 6,8-Diprenylum-belliferone. Tetrahedron Letters, 50, 6488-6490.
[35] Yn, W., Chen, H., Wang, T. and Cai, M. (1997) A New Coumarin Compound with Anticancer Activity. Chinese Traditional and Herbal Drugs, 28, 3-4.
[36] Rivière, C., Krisa, S., Péchamat, L., Nassra, M., Delaunay, J.C., Marchal, A., Badoc, A., Waffo-Téguo, P. and Mérillon, J.M. (2014) Polyphenols from the Stems of Morus alba and Their Inhibitory Activity against Nitric Oxide Production by Lipopolysaccharide-Activated Microglia. Fitoterapia, 97, 253-260.
[37] Heinke, R., Franke, K., Porzel, A., Wessjohann, L.A., Ali, N.A.A. and Schimidt, J. (2011) Furanocoumarins from Dorstenia foetida. Phytochemistry, 72, 929-934.
[38] Chiang, C.C., Cheng, M.J., Huang, H.Y., Chang, H.S., Wang, C.J. and Vhen, I.S. (2010) Prenyl Coumarins from Fatoua pilosa. Journal of Natural Products, 73, 1718-1722.
[39] Juan, E.A., Rideout, J.A. and Ragasa, C.Y. (1997) Bioactive Furanocoumarin Derivatives from Ficus pumila (Moraceae). Philippine Journal of Science, 126, 143-153.
[40] Santana, L.L.B., Silva, C.V., Almeida, L.C., Costa, T.A.C. and Velozo, E.S. (2011) Extraction with Supercritical Fluid and Comparison of Chemical Composition from Adults and Young Leaves of Zanthoxylum tingoassuiba. Brazilian Journal of Pharmaceutical Science, 21, 564-567.
[41] Chang, M.S., Yang, Y.C., Kuo, Y.C., Kuo, Y.H., Chang, C., Chen, C.M. and Lee, T.H. (2005) Furocoumarin Glycosides from the Leaves of Ficus ruficaulis Merr. var. antaoensis. Journal of Natural Products, 68, 11-13.
[42] El-Khrisy, E.A.M., Khattab, A.A. and Abu-Mustafa, E.A. (1980) Constituents of Local Plants. Part XXVIII. Constituents of Ficusas prima, F. hispida and F. carica. Fitoterapia, 51, 269-272.
[43] Marrelli, M., Menichini, F., Statti, G.A., Bonesi, M., Duez, P., Menichini, F. and Conforti, F. (2012) Changes in the Phenolic and Lipophilic Composition, in the Enzyme Inhibition and Antiproliferative Activity of Ficus carica L. Cultivar Dottato Fruits during Maturation. Food and Chemical Toxicology, 50, 726-733.
[44] Elgamal, M.H.A., Elewa, N.H., Elkhrisy, E.A.M. and Duddeck, H. (1979) 13C NMR Chemical Shifts and Carbon-Proton Coupling Constants of Some Furocoumarins and Furochromones. Phytochemistry, 18, 139-143.
[45] Lemmich, J. and Shabana, M. (1984) Coumarin Sulphates of Seseli libanotis. Phytochemistry, 23, 863-865.
[46] Vieira, I.J.C., Mathias, L., Monteiro, V. de F.F., Braz-Filho, R. and Rodrigues-Filho, E. (1999) A New Coumarln from Brosimum Gaudichaudii Trecul. Natural Products Letters, 13, 47-52.
[47] Nizamutdinova, I.T., Jeong, J.J., Xu, G.H., Lee, S.H., Kang, S.S., Kim, Y.S., Chang, K.C. and Kim, H.J. (2008) Hesperidin, Hesperidin Methyl Chalone and Phellopterin from Poncirus trifoliata (Rutaceae) Differentially Regulate the Expression of Adhesion Molecules in Tumor Necrosis Factor-α-Stimulated Human Umbilical Vein Endothelial Cells. International Immunopharmacology, 8, 670-678.
[48] Liu, R., Li, A., Sun, A. and Kong, L. (2004) Preparative Isolation and Purification of Psoralen and Isopsoralen from Psoralea corylifolia by High-Speed Counter-Current Chromatography. Journal of Chromatography A, 1057, 225-228.
[49] Souri, E., Farsam, H., Sarkheil, P. and Ebadi, F. (2004) Antioxidant Activity of Some Furocoumarins Isolated from Heracleum persicum. Pharmaceutical Biology, 42, 396-399.
[50] Oliveira, L.S. dos S. (2014) Chemical Constituents of Conchocarpus cyrtanthus (Rutaceae). Master’s Thesis, Universidade Estadual do Norte Fluminense Darcy Ribeiro, Campos dos Goytacazes.
[51] Elgamal, M.H.A., Shalaby, N.M.M., Duddeck, H. and Hiegemann, M. (1993) Coumarins and Coumarin Glucosides from the Fruits of Ammi majus. Phytochemistry, 34, 819-823.

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