Share This Article:

Chemistry and Biological Activity of Condamineeae Tribe: A Chemotaxonomic Contribution of Rubiaceae Family

Full-Text HTML XML Download Download as PDF (Size:528KB) PP. 2612-2631
DOI: 10.4236/ajps.2015.616264    2,921 Downloads   3,215 Views  

ABSTRACT

This study is a review of the Condamineeae tribe, through the acquisition of data from phytochemical studies and evaluation of genera activities that constitute the tribe, in order to contribute to chemotaxonomic classification of this tribe in the Rubiaceae family. This review also states the scarcity of phytochemical investigations of several genera and consequently a lot of species of family.

Cite this paper

F. Moreira, V. , Vieira, I. and Braz-Filho, R. (2015) Chemistry and Biological Activity of Condamineeae Tribe: A Chemotaxonomic Contribution of Rubiaceae Family. American Journal of Plant Sciences, 6, 2612-2631. doi: 10.4236/ajps.2015.616264.

References

[1] Robbrecht, E. and Manen, J. (2006) The Major Evolutionary Lineages of the Coffee Family (Rubiaceae, Angiosperms). Combined Analysis (nDNA and cpDNA) to Infer the Position of Coptosapelta and Luculia, and Supertree Construction Based on rbcL, rps16, trnL-trnF and atpB-rbcL Data. A New Classification in Two Subfamilies, Cinchonoideae and Rubioideae. Systematics and Geography of Plants, 76, 85-146.
[2] Bremer, B., Jansen, R.K., Oxelman, B., Backlund, M., Lantz, H. and Kim, K.J. (1999) More Characters and More Taxa for a Robust Phylogeny—Case Study from the Coffee Family (Rubiaceae). Systematic Biology, 48, 413-435.
http://dx.doi.org/10.1080/106351599260085
[3] Rova, J.H.E., Delprete, P.G., Andersson, L. and Albert, V.A. (2002) A trnL-F cpDNA Sequence Study of the Condamineeae-Rondeletieae-Sipaneeae Complex with Implications on the Phylogeny of the Rubiaceae. American Journal of Botany, 89, 145-159.
http://dx.doi.org/10.3732/ajb.89.1.145
[4] Judd, W.S., Campbell, C.S., Kellogg, E.A. and Stevens, P.F. (2007) Plant Systematics: A Phylogenetic Approach. 3rd Edition, Sinauer Associates, Inc., Sunderland.
[5] Delprete, P.G. (1999) Rondeletieae (Rubiaceae)—Part I (Rustia, Tresanthera, Condaminea, Picardaea, Pogonopus, Chimarrhis, Dioicodendron, Molopanthera, Dolichodelphys, and Parachimarrhis). Flora Neotropica Monograph, Vol. 77, 1-226.
[6] Barbosa, M.R. Simira in List of Species of Flora of Brazil. Botanical Garden of Rio de Janeiro. Accessed 30 March 2014.
http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB14287
[7] Cardoso, C.L., Silva, D.H.S., Young, M.C.M., Castro-Gamboa, I. and da Silva Bolzani, V. (2008) Indole Monoterpene Alkaloids from Chimarrhis turbinata DC Prodr.: A Contribution to the Chemotaxonomic Studies of the Rubiaceae Family. Brazilian Journal of Pharmacognosy, 18, 26-29.
http://dx.doi.org/10.1590/s0102-695x2008000100007
[8] Bolzani, V.S., Yong, M.C.M., Furlan, M., Cavalheiro, A.J., Araujo, A.R., Silva, D.H.S. and Lopes, M.N. (2001) Secondary Metabolites from Brazilian Rubiaceae Plant Species: Chemotaxonomical and Biological Significance. Recent Research Developments in Phytochemistry, 5, 19-31.
[9] Bremer, B. and Eriksson, O. (2009) Time Tree of Rubiaceae: Phylogeny and Dating the Family, Subfamily, and Tribes. International Journal of Plant Science, 170, 766-793.
http://dx.doi.org/10.1086/599077
[10] Bremer, B. (2009) A Review of Molecular Phylogenetic Studies of Rubiaceae. Annals of the Missouri Botanical Garden, 96, 4-26.
http://dx.doi.org/10.3417/2006197
[11] Kainulainen, K., Persson, C., Eriksson, T. and Bremer, B. (2010) Molecular Systematics and Morphological Character Evolution of the Condamineeae (Rubiaceae). American Journal of Botany, 97, 1961-1981.
http://dx.doi.org/10.3732/ajb.1000090
[12] Razafimandimbison, S.G. and Bremer, B. (2001) Tribal Delimitation of Nuclease (Cinchonoideae, Rubiaceae): Inference from Molecular and Morphological Data. Systematics and Geography of Plants, 71, 515-538.
http://dx.doi.org/10.2307/3668697
[13] Fay, M.F., Bremer, B., Prance, G.T., van der Bank, M., Bridson, D. and Chase, M.W. (2000) Plastid rbcL Sequence Data Show Dialypetalanthus to Be a Member of Rubiaceae. Kew Bulletin, 55, 853-864.
http://dx.doi.org/10.2307/4113630
[14] Moreira, V.F., Vieira, I.J.C. and Braz-Filho, R. (2014) Chemical Constituents and Biological Activities of Simira Genus: A Contribution to the Chemotaxonomic of Rubiaceae Family. The Natural Products Journal, 4, 290-298.
http://dx.doi.org/10.2174/2210315505666141211225600
[15] Soto-Sobenis, A., Castillo, B., Delgado, A., González, A. and Montenegro R. (2001) Alkaloid Screening of Herbarium Samples of Rubiaceae from Panama. Pharmaceutical Biology, 39, 161-169.
http://dx.doi.org/10.1076/phbi.39.3.161.5925
[16] Slish, D.F., Arvigo, R. and Balick, M.J. (2004) Alseis yucatanensis: A Natural Product from Belize That Exhibits Multiple Mechanisms of Vasorelaxation. Journal of Ethnopharmacology, 92, 297-302.
http://dx.doi.org/10.1016/j.jep.2004.03.003
[17] Slish, D.F., Ueda, H., Arvigo, R. and Balick, M.J. (1999) Ethnobotany in the Search for Vasoactive Herbal Medicines. Journal of Ethnopharmacology, 66, 159-165.
http://dx.doi.org/10.1016/S0378-8741(98)00225-6
[18] Cosenza, G.P., Somavilla, N.S., Fagg, C.W. and Brandão, M.G.L. (2013) Bitter Plants Used as Substitute of Cinchona spp. (Quina) in Brazilian Traditional Medicine. Journal of Ethnopharmacology, 149, 790-796.
http://dx.doi.org/10.1016/j.jep.2013.08.004
[19] Weeks, R.A., Dobberstein, R.H. and Farnsworth, N.R. (1977) Isolation of Paeonol from Bathysa meridionalis. Lloydia, 40, 515-516.
[20] Rangel, L.P., de Abreu, L.F., de Andrade, A.R., Leitão, S.G., Leitão, G.G. and Ferreira-Pereira, A. (2008) Effect of Different Extracts from the Brazilian Atlantic Forest on the Pdr5p ATPase Activity. Brazilian Journal of Pharmacognosy, 18, 30-36.
http://dx.doi.org/10.1590/s0102-695x2008000100008
[21] Gontijo, D.C., Nunes, L.G., Souza, C.J.A., Fietto, L.G. and Leite, J.P.V. (2012) Evaluation of the Genotoxic Potential of Ethanolic Extracts of Stem Bark and Leaves of Bathysa cuspidata (A.St.-Hil.) Hook. Revista de Ciências Farma- cêuticas Básica e Aplicada, 33, 355-359.
[22] Novaes, R.D., Gonçalves, R.V., Marques, D.C.S., Cupertino, M.C., Peluzio, M.C.G., Neves, C.A., Leite, J.P.V. and Maldonado, I.R.S.C. (2012) Effect of Bark Extract of Bathysa cuspidata on Hepatic Oxidative Damage and Blood Glucose Kinetics in Rats Exposed to Paraquat. Toxicologic Pathology, 40, 62-70.
http://dx.doi.org/10.1177/0192623311425059
[23] Calderón, A.I., Simithy, J., Quaggio, G., Espinosa, A., López-Pérez, J.L. and Gupta, M.P. (2009) Triterpenes from Warszewiczia coccinea (Rubiaceae) as Inhibitors of Acetylcholinesterase. Natural Product Communications, 4, 1323-1326.
[24] de Castro Miguel, E., Gomes, V.M., de Oliveira, M.A. and da Cunha, M. (2006) Colleters in Bathysa nicholsonii K. Schum. (Rubiaceae): Ultrastructure, Secretion Protein Composition, and Antifungal Activity. Plant Biology, 8, 715-722.
http://dx.doi.org/10.1055/s-2006-924174
[25] Fonseca, T.L., Von Groll, A., Leitão, G.G., Scaini, C.J., Ramos, D.F. and Silva, P.E.A. (2008) Antimycobacterial Vegetal Extracts against Mycobacterium fortuitum and Mycobacterium malmoense. Vittalle, 20, 65-71.
[26] Carvalho, D.D.C., Alves, E., Camargos, R.B., Oliveira, D.F., Scolforo, J.R.S., de Carvalho, D.A. and Batista, T.R.S. (2011) Plant Extracts to Control Alternaria alternata in Murcott Tangor Fruits. Revista Iberoamericana de Micología, 28, 173-178.
http://dx.doi.org/10.1016/j.riam.2011.05.001
[27] Novaes, R.D., Gonçalves, R.V., Cupertino, M.C., Marques, D.C.S., Rosa, D.D., Peluzio, M.C.G., Neves, C.A. and Leite, J.P.V. (2012) Bark Extract of Bathysa cuspidata Attenuates Extra-Pulmonary Acute Lung Injury Induced by Paraquat and Reduces Mortality in Rats. International Journal of Experimental Pathology, 93, 225-233.
http://dx.doi.org/10.1111/j.1365-2613.2012.00808.x
[28] Gonçalves, R.V., Novaes, R.D., Leite, J.P.V., Vilela, E.F., Cupertino, M.C., Nunes, L.G. and Matta, S.L.P. (2012) Hepatoprotective Effect of Bathysa cuspidata in a Murine Model of Severe Toxic Liver Injury. International Journal of Experimental Pathology, 93, 370-376.
http://dx.doi.org/10.1111/j.1365-2613.2012.00835.x
[29] Gonçalves, R.V., Novaes, R.D., Cupertino, M.C., Araújo, B.M., Vilela, E.F., Machado, A.T., Leite, J.P.V. and Matta, S.L.P. (2014) Bathysa cuspidata Extract Modulates the Morphological Reorganization of the Scar Tissue and Accelerates Skin Wound Healing in Rats: A Time-Dependent Study. Cells Tissues Organs, 199, 266-277.
http://dx.doi.org/10.1159/000365504
[30] Schultes, R.E. (1985) De Plantis Toxicariis e Mundo Novo Tropicale Commentationes XXXIV: Biodynamic Rubiaceous Plants of the Northwest Amazon. Journal of Ethnopharmacology, 14, 105-124.
http://dx.doi.org/10.1016/0378-8741(85)90082-0
[31] Saenz, R., Nassar, J.A. and Maryssia, C. (1965) Phytochemical Screening of Costa Rican Plants: Alkaloid Analysis II. Revista de Biologia Tropical, 13, 207-212.
[32] Zuleta, L.M.C., Cavalheiro, A.J., Silva, D.H.S., Furlan, M., Young, M.C.M., Albuquerque, S., Castro-Gamboa, I. and da Silva Bolzani, V. (2003) seco-Iridoids from Calycophyllum spruceanum (Rubiaceae). Phytochemistry, 64, 549-553.
http://dx.doi.org/10.1016/S0031-9422(03)00153-5
[33] Portillo, A., Vila, R., Freixa, B., Adzet, T. and Cañigueral, S. (2001) Antifungal Activity of Paraguayan Plants Used in Traditional Medicine. Journal of Ethnopharmacology, 76, 93-98.
http://dx.doi.org/10.1016/S0378-8741(01)00214-8
[34] Odonne, G., Bourdy, G., Castillo, D., Estevez, Y., Lancha-Tangoa, A., Alban-Castillo, J., Deharo, E., Rojas, R., Stien, D. and Sauvain, M. (2009) Ta’ta’, Huayani: Perception of Leishmaniasis and Evaluation of Medicinal Plants Used by the Chayahuita in Peru. Part II. Journal of Ethnopharmacology, 126, 149-158.
http://dx.doi.org/10.1016/j.jep.2009.07.015
[35] Deharo, E., Bourdy, G., Quenevo, C., Muñoz, V., Ruiz, G. and Sauvain, M. (2001) A Search for Natural Bioactive Compounds in Bolivia through a Multidisciplinary Approach. Part V. Evaluation of the Antimalarial Activity of Plants Used by the Tacana Indians. Journal of Ethnopharmacology, 77, 91-98.
http://dx.doi.org/10.1016/S0378-8741(01)00270-7
[36] Graham, J.G., Pendland, S.L., Prause, J.L., Danzinger, L.H., Vigo, J.S., Cabieses, F. and Farnsworth, N.R. (2003) Antimycobacterial Evaluation of Peruvian Plants. Phytomedicine, 10, 528-535.
http://dx.doi.org/10.1078/094471103322331502
[37] Wen, L., Haddad, M., Fernandez, I., Espinoza, G., Ruiz, C., Neyra, E., Bustamante, B. and Rojas, R. (2011) Antifungal Activity of Four Plants Used in Peruvian Traditional Medicine: Isolation of the Active Principle of Psidium acutangulum. Revista de la Sociedad Quimica del Peru, 77, 199-204.
[38] Jovel, E.M., Cabanillas, J. and Towers, G.H.N. (1996) An Ethnobotanical Study of the Traditional Medicine of the Mestizo People of Suni Mirano, Loreto, Perú. Journal of Ethnopharmacology, 53, 149-156.
http://dx.doi.org/10.1016/0378-8741(96)01437-7
[39] Polesna, L., Polesny, Z., Clavo, M.Z., Hansson, A. and Kokoska, L. (2011) Ethnopharmacological Inventory of Plants Used in Coronel Portillo Province of Ucayali Department, Peru. Pharmaceutical Biology, 49, 125-136.
http://dx.doi.org/10.3109/13880209.2010.504927
[40] Castillo, D., Arevalo, J., Herrera, F., Ruiz, C., Rojas, R., Rengifo, E., Vaisberg, A., Lockb, O., Lemesre, J.L., Gornitzka, H. and Sauvain, M. (2007) Spirolactone Iridoids Might Be Responsible for the Antileishmanial Activity of a Peruvian Traditional Remedy Made with Himatanthus sucuuba (Apocynaceae). Journal of Ethnopharmacology, 112, 410-414.
http://dx.doi.org/10.1016/j.jep.2007.03.025
[41] Cardoso, C.L., Silva, D.H.S., Tomazela, D.M., Verli, H., Young, M.C.M., Furlan, M., Eberlin, M.N. and da Silva Bolzani, V. (2003) Turbinatine, a Potential Key Intermediate in the Biosynthesis of Corynanthean-Type Indole Alkaloids. Journal of Natural Products, 66, 1017-1021.
http://dx.doi.org/10.1021/np020547m
[42] Cardoso, C.L., Castro-Gamboa, I., Silva, D.H.S., Furlan, M., Epifanio, R.D.A., da Cunha Pinto, A., de Rezende, C.M., Lima, J.A. and da Silva Bolzani, V. (2004) Indole Glucoalkaloids from Chimarrhis turbinata and Their Evaluation as Antioxidant Agents and Acetylcholinesterase Inhibitors. Journal of Natural Products, 67, 1882-1885.
http://dx.doi.org/10.1021/np049863m
[43] Cardoso, C.L., Silva, D.H.S., Castro-Gamboa, I. and da Silva Bolzani, V. (2005) New Biflavonoid and Other Flavonoids from the Leaves of Chimarrhis turbinate and Their Antioxidant Activities. Journal of the Brazilian Chemical Society, 16, 1353-1359.
http://dx.doi.org/10.1590/S0103-50532005000800008
[44] Cardoso, C.L., da Silva Bolzani, V., Silva, D.H.S., Ishii, H., Berova, N. and Nakanishi, K. (2006) The Absolute Configuration of 1-(3’,4’-Dihydroxycinnamoyl)Cyclopentane-2,3-diol from the Amazonian Tree Chimarrhis turbinate. Journal of Natural Products, 69, 1046-1050.
http://dx.doi.org/10.1021/np050522y
[45] Cardoso, C.L., Castro-Gamboa, I., Bergamini, G.M., Cavalheiro, A.J., Silva, D.H.S., Lopes, M.N., Araujo, A.R., Furlan, M., Verli, H. and da Silva Bolzani, V. (2011) An Unprecedented Neolignan Skeleton from Chimarrhis turbinata. Journal of Natural Products, 74, 487-491.
http://dx.doi.org/10.1021/np1007476
[46] Bertani, S., Bourdy, G., Landau, I., Robinson, J.C., Esterre, P. and Deharo, E. (2005) Evaluation of French Guiana Traditional Antimalarial Remedies. Journal of Ethnopharmacology, 98, 45-54.
http://dx.doi.org/10.1016/j.jep.2004.12.020
[47] Gunatilaka, A.A.L., Samaranayake, G. and Kingston, D.G.I. (1992) Bioactive Ergost-5-ene-3ß,7a-diol Derivatives from Pseudobersama mossambicensis. Journal Natural Products, 55, 1648-1654.
http://dx.doi.org/10.1021/np50089a014
[48] Sanz-Biset, J. and Cañigueral, S. (2011) Plant Use in the Medicinal Practices Known as “Strict Diets” in Chazuta Valley (Peruvian Amazon). Journal of Ethnopharmacology, 137, 271-288.
http://dx.doi.org/10.1016/j.jep.2011.05.021
[49] Moraes, F., Hahn, M.G. and Braga, M.R. (2001) Comparative Analysis of Leaf Cell-Wall Polysaccharides of Dialypetalanthus fuscescens and Bathysa meridionalis: Evidence of Biochemical Similarities between Dialypetalanthaceae and Rubiaceae-Cinchonoideae. Revista Brasileira de Botanica, 24, 289-294.
http://dx.doi.org/10.1590/S0100-84042001000300007
[50] Aldana, J., Téllez, N. and Gamboa, F. (2013) Antimicrobial Activity of Fractions and Subfractions of Elaegia utilis against Microoganisms of Importance in Dental Caries. Acta Odontológica Latinoamericana, 26, 104-111.
[51] Quiros, D.I., Emmen, D.A., Dominguez, E., Heller, M.V., Coley, P.D. and Kursar, T.A. (2006) A Rapid, Efficient Method for the Bioassay of Extracts, Fractions and Compounds for Activity against Tropical Aphids. International Journal of Pest Management, 52, 333-342.
http://dx.doi.org/10.1080/09670870600847525
[52] Ma, Z.W. and He, G.F. (1989) Chemical Constituents of Emmenopterys henryi Oliv. Native to China. Acta Botanica Sinica, 31, 620-625.
[53] Wu, X.D., He, J., Li, X.Y., Dong, L.B., Gong, X., Gao, X., Song, L.D., Li Y., Peng, L.Y. and Zhao, Q.S. (2013) Triterpenoids and Steroids with Cytotoxic Activity from Emmenopterys henryi. Planta Medica, 79, 1356-1361.
http://dx.doi.org/10.1055/s-0033-1350645
[54] Liu, T.X., Xu, H.H. and Luo, W.C. (2006) Opportunities and Potentials of Botanical Extracts and Products for Management of Insect Pests in Cruciferous Vegetables. Naturally Occurring Bioactive Compounds, 8, 171-197.
http://dx.doi.org/10.1016/S1572-557X(06)03008-X
[55] Odonne, G., Valadeau, C., Alban-Castillo, J., Stien, D., Sauvain, M. and Bourdy, G. (2013) Medical Ethnobotany of the Chayahuita of the Paranapura Basin (Peruvian Amazon). Journal of Ethnopharmacology, 146, 127-153.
http://dx.doi.org/10.1016/j.jep.2012.12.014
[56] Li, X.C., Jacob, M.R., ElSohly, H.N., Nagle, D.G., Smillie, T.J., Walker, L.A. and Clark, A.M. (2003) Acetylenic Acids Inhibiting Azole-Resistant Candida albicans from Pentagonia gigantifolia. Journal of Natural Products, 66, 1132- 1135.
http://dx.doi.org/10.1021/np030196r
[57] Delprete, P.G. (1996) Systematics, Typification, Distribution, and Reproductive Biology of Pinckneya bracteata (Rubiaceae). Plant Systematics and Evolution, 201, 243-261.
http://dx.doi.org/10.1007/BF00989065
[58] Ito, A., Lee, Y.H., Chai, H.B., Gupta, M.P., Farnsworth, N.R., Cordell, G.A., Pezzuto, J.M. and Kinghorn, A.D. (1999) 1’,2’,3’,4’-Tetradehydrotubulosine, a Cytotoxic Alkaloid from Pogonopus speciosus. Journal of Natural Products, 62, 1346-1348.
http://dx.doi.org/10.1021/np990255u
[59] Sauvain, M., Moretti, C., Bravo, J.A., Callapa, J., Muñoz, V., Ruiz, E., Richard, B. and Le Men-Olivier, L. (1996) Antimalarial Activity of Alkaloids from Pogonopus tubulosus. Phytotherapy Research, 10, 198-201.
http://dx.doi.org/10.1002/(SICI)1099-1573(199605)10:3<198::AID-PTR798>3.0.CO;2-Z
[60] Perdomo, R.T. (2011) Evaluation of the Antiproliferative Activity and Inhibition of Topoisomerases by Extracts, Pure and Semi-Synthetic Substances Obtained from Natural Products. Doutorate Degree Thesis, Federal University of Mato Grosso do Sul, Campo Grande.
[61] Desjardins, R.E., Canfield, C.J., Haynes, J.D. and Chulay, J.D. (1979) Quantitative Assessment of Antimalarial Activity in Vitro by a Semi-Automated Microdilution Technique. Antimicrobial Agents and Chemotherapy, 16, 710-718.
http://dx.doi.org/10.1128/AAC.16.6.710
[62] Frederich, M., Tits, M. and Angenot, L. (2008) Potential Antimalarial Activity of Indole Alkaloids. Royal Society of Tropical Medicine and Hygiene, 102, 11-19.
http://dx.doi.org/10.1016/j.trstmh.2007.10.002
[63] Vieira, R.C., Delprete, P.G., Leitão, G.G. and Leitão, S.G. (2001) Anatomical and Chemical Analyses of Leaf Secretory Cavities of Rustia formosa (Rubiaceae). American Journal of Botany, 88, 2151-2156.
http://dx.doi.org/10.2307/3558376
[64] Li, X.C., Jacob, M.R., Khan, S.I., Ashfaq, M.K., Babu, K.S., Agarwal, A.K., ElSohly, H.N., Manly, S.P. and Clark, A.M. (2008) Potent in Vitro Antifungal Activities of Naturally Occurring Acetylenic Acids. Antimicrobial Agents and Chemotherapy, 52, 2442-2448.
http://dx.doi.org/10.1128/AAC.01297-07
[65] Loustalot, A.J. and Pagan, C. (1949) Local “Fever” Plants Tested for Presence of Alkaloids. El Crisol, 3, 3-5.
[66] Mohammed, M.J. and Seaforth, C.E. (1981) Extractives of Warszewiczia coccinea Klotzch. Revista Latinoamericana de Quimica, 12, 72-73.
[67] Estevez, Y., Castillo, D., Pisango, M.T., Arevalo, J., Rojas, R., Alban, J., Deharo, E. and Bourdy, G. (2007) Sauvain, M. Evaluation of the leishmanicidal Activity of Plants Used by Peruvian Chayahuita Ethnic Group. Journal of Ethnopharmacology, 114, 254-259.
http://dx.doi.org/10.1016/j.jep.2007.08.007
[68] Valadeau, C., Pabon, A., Deharo, E., Albán-Castillo, J., Estevez, Y., Lores, F.A., Rojas, R., Gamboa, D., Sauvain, M., Castillo, D. and Bourdy, G. (2009) Medicinal Plants from the Yanesha (Peru): Evaluation of the Leishmanicidal and Antimalarial Activity of Selected Extracts. Journal of Ethnopharmacology, 123, 413-422.
http://dx.doi.org/10.1016/j.jep.2009.03.041
[69] Cunha, A.P. (2005) Farmacognosia e fitoquímica. Fundação Calouste Gulbenkian, Lisboa, 403-412.

  
comments powered by Disqus

Copyright © 2017 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.