Triterpenes from <i>Cabralea canjerana</i> as <i>in Vitro</i> Inhibitors to Light Reactions of Photosynthesis — Oak Academic Publishing
Research ArticleOpen AccessGoogle Scholar indexed
Triterpenes from <i>Cabralea canjerana</i> as <i>in Vitro</i> Inhibitors to Light Reactions of Photosynthesis
Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, México D. F., México
,
Universidade Federal de Vi?osa (UFV), Rio Paranaíba, Brasil
,
Departamento de Química, Universidade Federal de S?o Carlos (UFSCar), S?o Carlos, Brasil
,
Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, México D. F., México
,
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Departamento de Ciências Exatas e da Terra, Universidade Federal de S?o Paulo (UNIFESP), Diadema, Brasil
1 Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, México D. F., México
2 Universidade Federal de Vi?osa (UFV), Rio Paranaíba, Brasil
3 Departamento de Química, Universidade Federal de S?o Carlos (UFSCar), S?o Carlos, Brasil
4 Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, México D. F., México
5 Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Departamento de Ciências Exatas e da Terra, Universidade Federal de S?o Paulo (UNIFESP), Diadema, Brasil
Aims: Cabraleadiol (1), Ocotilone (2) and Odoratone (3) are three triterpenes isolated from Cabralea canjerana (Vell.) Mart. (Meliaceae). They were chemically characterized, and their effect was tested on the light reaction of photosynthesis. Study Design: Natural products were used as models to find new models for inhibitors of photosynthesis. Place and Duration of Study: Departmento de Química, Universidade Federal de S ã o Carlos and Departmento de Bioquímica, Facultad de Química, Universidad Nacional Autonoma de México, between May 2013 and January 2014. Methodology: The natural products had their effect on the light reaction of photosynthesis studied by pollarography and Chlorophyll a (Chl a ) fluorescence transients. Results: The compounds inhibited ATP synthesis and electron transport rate (basal, phosphorylating and uncoupled). Therefore, they act as Hill reactions inhibitors. Their inhibition site were located in the range of electron flow from OEC complex and between P 680 to Q A of PS II, and inhibited the photosystem II (PS II) by inducing the appearance of a K-band which is an indicative that the photochemical apparatus is failing at the donor side of PS II interacting at the OEC complex and by transforming active reaction centers to “heat sinks” or the formation of silent reaction centers unable to reduce Q A . Conclusion: Furthermore, these triterpenes inhibit PS II and induce the appearance of small G band which is related with the decreased plastoquinone (PQ) pool reduction.
Nugent, J.H.A., Rich, A.M. and Evans, M.C.W. (2001) Photosynthetic Water Oxidation: Towards a Mechanism. Biochimica et Biophysica Acta (BBA)-Bioenergetics, 1503, 138-146. http://dx.doi.org/10.1016/S0005-2728(00)00223-1
Tyystjarvi, E. (2008) Photoinhibition of Photosystem II and Photodamage of the Oxygen Evolving Manganese Cluster. Coordination Chemistry Reviews, 252, 361-376. http://dx.doi.org/10.1016/j.ccr.2007.08.021
Vass, I., Styring, S., Hundal, T., Koivuniemi, A., Aro, E.M. and Andersson, B. (1992) Reversible and Irreversable Intermediates during Photoinhibition of Photosystem II: Stable Reduced QA Species Promote Chlorophyll Triplet Formation. Proceedings of the National Academy of Sciences, 89, 1408-1412. http://dx.doi.org/10.1073/pnas.89.4.1408
Vass, I. and Styring, S. (1993) Characterization of Chlorophyll Triplet Promoting States in Photosystem II Sequentially Induced during Photoinhibition. Biochemistry, 32, 3334-3341. http://dx.doi.org/10.1021/bi00064a016
Good, N.E., Izawa, S. and Hind, G. (1981) Current Topics in Bioenergetics. Academic Press, New York, 75-112.
Torres-Romero, D., King-Diaz, B., Jimenez, I.A., Lotina-Hennsen, B. And Bazzocchi, I.L. (2008) Sesquiterpenes from Celastrus Vulcanicola as Photosynthetic Inhibitors. Journal of Natural Products, 71, 1331-1335. http://dx.doi.org/10.1021/np070647y
Koodkaew, I., Sunohara, Y., Matsuyama, S. and Matsumoto, H. (2012) Isolation of Ambiguine D Isonitrile from Hapalosiphon sp. and characterization of Its Phytotoxic Activity. Plant Growth Regulation, 68, 141-150. http://dx.doi.org/10.1007/s10725-012-9700-8
Menezes-de-Oliveira, D., Aguilar, M.I., King-Díaz, B., Vieira-Filho, A.S., Pains-Duarte, L., Silva, G.D.F. and Lotina-Hennsen, B. (2011) The Triterpenes 3β-Lup-20(29)-en-3-ol and 3β-Lup-20(29)-en-3-yl Acetate and the Carbohydrate 1,2,3,4,5,6-Hexa-O-acetyl-Dulcitol as Photosynthesis Light Reactions Inhibitors. Molecules, 16, 9939-9956. http://dx.doi.org/10.3390/molecules16129939
Macias, F.A., Simonet, A.M. and Esteban, M.D. (1994) Potential Allelopathic Lupane Triterpenes from Bioactive Fractions of Melilotus Messanensis. Phytochemistry, 36, 1369-1379. http://dx.doi.org/10.1016/S0031-9422(00)89726-5
Silva, S.R.S., Silva, G.D.F., Barbosa, L.C.A., Duarte, L.P., King-Diaz, B., Archundia-Camacho, F. and Lotina-Hennsen, B. (2007) Uncoupling and Inhibition Properties of 3,4-Seco-Friedelan-3-Oic Acid Isolated from Maytenus Imbricata. Pesticide Biochemistry and Physiology, 87, 109-114. http://dx.doi.org/10.1016/j.pestbp.2006.06.008
Torres-Romero, D., King-Diaz, B., Strasser, R.J., Jimenez, I.A., Lotina-Hennsen, B. and Bazzocchi, I.L. (2010) Friedelane Triterpenes from Celastrus vulcanicola as Photosynthetic Inhibitors. Journal of Agricultural and Food Chemistry, 58, 10847-10854. http://dx.doi.org/10.1021/jf1022115
Achnine, L., Mata, R., Iglesias-Prieto, R. and Lotina-Hennsen, B. (1998) Impairment of Photosystem II Donor Side by the Natural Product Odoratol. Journal of Agricultural and Food Chemistry, 46, 5313-5317. http://dx.doi.org/10.1021/jf980589+
Cascon, S.C. and Brown Jr., K.S. (1972) Biogenetically Significant Triterpenes in a Species of Meliaceae: Cabralea Polytricha A. Juss. Tetrahedron, 28, 315-323. http://dx.doi.org/10.1016/0040-4020(72)80138-8
Braga, P.A.C., Soares, M.S., Da Silva, M.F.G.F., Vieira, P.C., Fernandes, J.B. and Pinheiro, A.L. (2006) Dammarane Triterpenes from Cabralea canjerana (Vell.) Mart. (Meliaceae): Their Chemosystematic Significance. Biochemical Systematics and Ecology, 34, 282-290. http://dx.doi.org/10.1016/j.bse.2005.10.012
Aalbersberg, W. and Singh, Y. (1991) Tirucallane Triterpenoids from Dysoxylum hainanense. Phytochemistry, 30, 921-926. http://dx.doi.org/10.1016/0031-9422(91)85280-D
Tanaka, O. and Yahara, S. (1978) Dammarane Saponins of Leaves of Panax pseudo-ginseng subsp. Himalaicus. Phytochemistry, 17, 1353-1358. http://dx.doi.org/10.1016/S0031-9422(00)94588-6
Hisham, A., Bai, M.D.A., Fujimoto, Y., Hara, N. and Shimada, H. (1996) Complete 1H and 13C NMR Spectral Assignment of Cabraleadiol, a Dammarane Triterpene from Dysoxylum Malabaricum Bedd. Magnetic Resonance in Chemistry, 34, 146-150. http://dx.doi.org/10.1002/(SICI)1097-458X(199602)34:2 3.0.CO;2-U
Mohamad, K., Sevenet, T., Dumontet, V., Pais, M., Tri, V.M., Hadi, H., Awang, K. and Martin, M. (1999) Dammarane Triterpenes and Pregnane Steroids from Aglaia lawii and A. tomentosa. Phytochemistry, 51, 1031-1037. http://dx.doi.org/10.1016/S0031-9422(99)00053-9
Roux, D., Martin, M.T., Adeline, M.T., Sevenet, T., Hadi, H. and Pais, M. (1998) Foveolins A and B, Dammarane Triterpenes from Aglaia foveolata. Phytochemistry, 49, 1745-1748. http://dx.doi.org/10.1016/S0031-9422(98)00305-7
Veiga, T.A.M., King-Díaz, B., Marques, A.S.F., Sampaio, O.M., Vieira, P.C., da Silva, M.F.G.F. and Lotina-Hennsen, B. (2013) Furoquinoline Alkaloids Isolated from Balfourodendron riedelianum as Photosynthetic Inhibitors in Spinach Chloroplasts. Journal of Photochemistry and Photobiology B: Biology, 120, 36-43. http://dx.doi.org/10.1016/j.jphotobiol.2013.01.006
Morales-Flores, F., Aguilar, M.I., King-Díaz, B. and Lotina-Hennsen, B. (2013) Derivatives of Diterpen Labdane-8α,15-diol as Photosynthetic Inhibitors in Spinach Chloroplasts and Growth Plant Inhibitors. Journal of Photochemistry and Photobiology B: Biology, 125, 42-50. http://dx.doi.org/10.1016/j.jphotobiol.2013.04.010
Mills, J.D., Mitchell, P. and Schurmann, P. (1980) Modulation of Coupling Factor ATPase Activity in Intact Chloroplasts. FEBS Letters, 191, 144-148.
Strain, H.H., Cope, T. and Svec, M.A. (1971) Analytical Procedures for the Isolation, Identification, Estimation and Investigation of the Chlorophylls. Methods in Enzymology, 23, 452-476. http://dx.doi.org/10.1016/S0076-6879(71)23118-9
Allen, J.F. and Holmes, N.G. (1986) Photosynthesis: Energy Transduction: A Practical Approach. IRL Press, Oxford, 103-141.
Dilley, R.A. (1972) Ion Transport (H+, K+, Mg2+ Exchange Phenomena). Methods in Enzymology, 24, 68-74. http://dx.doi.org/10.1016/0076-6879(72)24055-1
Strasser, R.J., Srivastava, A. and Govindjee (1995) Polyphasic Chlorophyll a Fluorescence Transient in Plants and Cyanobacteria. Photochemistry and Photobiology, 66, 32-42. http://dx.doi.org/10.1111/j.1751-1097.1995.tb09240.x
Saha, S., Ouitrakul, R. and Izawa, S. (1971) Electron Transport and Photophosphorylation in Chloroplasts as a Function of the Electron Acceptor. Journal of Biological Chemistry, 246, 3204-3209.
Vernon, L.P. (1969) Photoreduction of 2,6-Dichlorophenolindophenol by Diphenylcarbazide: A Photosystem 2 Reaction Catalyzed by Tris-Washed Chloroplasts and Subchloroplast Fragments. Plant Physiology, 44, 1645-1649. http://dx.doi.org/10.1104/pp.44.11.1645
Rickert, K.W., Sears, J., Beck, W.F. and Brudvig, G.W. (1991) Mechanism of Irreversible Inhibition of O2 Evolution in Thotosystem II by Tris(hydroxymethyl) Aminomethane. Biochemistry, 30, 7888-7896. http://dx.doi.org/10.1021/bi00246a003
Strasser, R.J. (1997) Donor Site Capacity of Photosystem II Probed by Chlorophyll a Transients. Photosynthesis Research, 52, 147-155. http://dx.doi.org/10.1023/A:1005896029778
Lazár, D., Pospísil, P. and Naus, J. (1999) Decrease of Fluorescence Intensity after the K Step in Chlorophyll a Fluorescence Induction Is Suppressed by Electron Acceptors and Donors to Photosystem 2. Photosynthetica, 37, 255-265. http://dx.doi.org/10.1023/A:1007112222952
Strasser, R.J., Tsimilli-Michael, M. and Srivastava, A. (2004) Chlorophyll Fluorescence: A Signature of Photosynthesis. Kluwer Academic Publishers, Dordrecht, Chapter 12, 321.
Veiga, T.A.M., Silva, S.C., Archundia-Camacho, F., Rodrigues Filho, E., Vieira, P.C., Fernandes, J.B., da Silva, M.F.G.F., Muller, M.W. and Lotina-Hennsen, B. (2007) Inhibition of Photophosphorylation and Electron Transport Chain in Thylakoids by Lasiodiplodin, a Natural Product from Botryosphaeria rhodina. Journal of Agricultural and Food Chemistry, 55, 4217-4221. http://dx.doi.org/10.1021/jf070082b
Veiga, T.A.M., González-Vásquez, R., Oiano Neto, J., da Silva, M.F.G.F., King-Díaz, B. and Lotina-Hennsen, B. (2007) Siderin from Toona ciliata (Meliaceae) as Photosystem II Inhibitor on Spinach Thylakoids. Archives of Biochemistry and Biophysics, 465, 38-43. http://dx.doi.org/10.1016/j.abb.2007.05.002