2014, Number 3
<< Back Next >>
Rev Cubana Plant Med 2014; 19 (3)
Evaluation of the biological activity of extracts from Crotalaria pallida (streaked rattlepod) seeds using the Drosophila melanogaster model
Peñaloza AGC, Peláez JCA
Language: Spanish
References: 17
Page: 144-153
PDF size: 182.11 Kb.
ABSTRACT
Introduction: the search for metabolites of natural origin with promising biological –particularly insecticidal– activity, is an interesting target for research about natural products.
Objectives: evaluate the bioactivity of extracts of varying polarity from
Crotalaria pallida Aiton seeds using the
Drosophila melanogaster biological model.
Methods: an evaluation was conducted of the bioactivity of extracts of varying polarity from dry
C. pallida seeds by ingestion into the biological model, with the purpose of purifying and determining the chemical structure of the active principle through NMR spectroscopy.
Results: two types of bioactivity were expressed. One caused inhibition of larval stages, evidenced in a smaller number of pupae in treatment controls with respect to non-treatment controls. The dose-response relationship allowed estimation of a CI
50 of 156.47 ppm. The other effect inhibited progress from pupa to adult, reducing the number of adults in the treatment vs. control groups, with an CI
50 of 7.95 ppm. With the use of various NMR assays, it was determined that the alkaloid usaramine was responsible for this biological activity.
Conclusions: the bioactivity of extracts of medium/low polarity permitted the isolation of a metabolite with promising insecticidal activity, manifested in the inhibition of the normal development of the life cycle of
D. melanogaster. The extract does not show any activity on oviposition in the concentration range studied. At low concentrations it inhibits the eclosion of pupae, whereas at high concentrations it affects larval development. Both activities remained when the purified metabolite was tested.
REFERENCES
Flores AiS, Tozzi AMGdA, Trigo JR. Pyrrolizidine alkaloid profiles in Crotalaria species from Brazil: Chemotaxonomic significance. Biochemical Systematics and Ecology. 2009 Oct;37(4):459-69.
Ko HH, Weng JR, Tsao LT, Yen MH, Wang JP, Lin CN. Anti-inflammatory flavonoids and pterocarpanoid from Crotalaria pallida and C. assamica. Bioorganic & Medicinal Chemistry Letters. 2004 Feb 23;14(4):1011-4.
Bernal HY, Universidad Nacional de Colombia. Instituto de Ciencias Naturales - Fondo colombiano de investigaciones científicas. Flora de Colombia: Crotalaria (Fabaceae- Faboideae) 4. Universidad Nacional de Colombia, Facultad de Ciencias; 1986.
Asres K, Sporer F, Wink M. Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species. Biochemical Systematics and Ecology. 2004 Oct;32(10):915-30.
Devendra BN, Srinivas N, Solmon KS. A comparative pharmacological and phytochemical analysis of in vivo & in vitro propagated Crotalaria species. Asian Pacific Journal of Tropical Medicine. 2012 Jan;5(1):37-41.
Wink M, Mohamed GIA. Evolution of chemical defense traits in the Leguminosae: mapping of distribution patterns of secondary metabolites on a molecular phylogeny inferred from nucleotide sequences of the rbcL gene. Biochemical Systematics and Ecology. 2003 Aug;31(8):897-917.
Xia Q, Chou MW, Edgar JA, Doerge DR, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. Cancer Lett. 2006 Jan 8;231(1):138-45.
Pitanga BPS, Silva VDg, Souza CS, Junqueira HA, Fragomeni BON, Nascimento RP, et al. Assessment of neurotoxicity of monocrotaline, an alkaloid extracted from Crotalaria retusa in astrocyte/neuron co-culture system. NeuroToxicology. 2011 Dec;32(6):776-84.
Xia Q, Yan J, Chou MW, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. Toxicology Letters. 2008 May 5;178(2):77-82.
Granados H, Saez J, Saldarriaga N, Moreno ME, Pelaez C, Brun N, et al. In vitro insecticidal activity of the Annona aff. spraguei seeds (Annonaceae) on two biological model of diptera order: Drosophila melanogaster and Aedes aegypti. Afinidad. 2001;57(491):44-8.
Kim SI, Jung JW, Ahn YJ, Restifo LL, Kwon HW. Drosophila as a model system for studying lifespan and neuroprotective activities of plant-derived compounds. Journal of Asia-Pacific Entomology. 2011 Dec;14(4):509-17.
Logie CG, Grue MR, Liddell JR. Proton NMR spectroscopy of pyrrolizidine alkaloids. Phytochemistry. 1994;37(1):43-109.
Mattocks AR. Chemistry and toxicology of pyrrolizidine alkaloids. Academic Press; 1986.
Segall HJ, Dallas JL. 1H NMR Spectroscopy of pyrrolizidine alkaloids. Phytochemistry. 1983;22(5):1271-3.
Marín Loaiza JC, Ernst L, Beuerle T, Theuring C, Céspedes CL, Hartmann T. Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases. Phytochemistry. 2008 Jan;69(1):154-67.
Medina JCM, Gauze GF, Vidotti GJ, Sarragiotto MH, Basso EA, Peixoto JLB. Structural characterization of saturated pyrrolizidine alkaloids from Heliotropium transalpinum var. transalpinum Vell by NMR spectroscopy and theoretical calculations. Tetrahedron Letters. 2009 Jun 3;50(22):2640-2.
Molyneux RJ, Roitman JN, Benson M, Lundin RE. 13C NMR spectroscopy of Pyrrolizidine alkaloids. Phytochemistry. 1982;21(2):439-43.