Leishmanicidal Activity of a Quinone Methide Triterpenoid from the roots of Senna spectabilis var. excelsa (Fabaceae)

Juliao Armando Monjane

Abstract


From an extract of the roots of Senna spectabilis var. excelsa (Fabaceae), eight known metabolites including the quinone methide triterpenoid 17-(methoxycarbonyl)-28-nor-isoiguesterin (1) and friedelin (2), a putative biosynthetic precursor of this class of metabolites, were isolated by applying several chromatographic methods. The structures of the isolated metabolites were established by High Resolution NMR and MS analysis, and confirmed by comparison of their experimental spectroscopic and physical data with those previously reported in the literature. The 2D structure and relative configuration of metabolite 1 were initially determined via analysis of NOESY experiment and confirmed by quantum mechanics-based 13C NMR chemical shift calculations. Metabolite 1 showed a potent leishmanicidal activity against Leishmania amazonensis and L. brazilensis, with the IC50 values 9.6 and 6.3 μM, respectively, comparable with the positive control miltefosine (IC50 values 12.5 and 12.0 μM, respectively), a currently used agent for leishmaniosis treatment. The first example of the occurrence of a quinone methide triterpenoid in species belonging to the Fabaceae family and the first leishmanicidal activity of metabolite 1 are reported in this paper.


Keywords


Senna spectabilis (var. excels), Fabaceae, Quinone methide triterpenoids, Natural products, Chromatographic methods, Leishmanicidal activity

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References


Borst P, Quelette M. New mechanisms of drug resistance in parasitic protozoa, Ann. Rev. Microbiol. 49 (1995) 427–460.

Chan-Bacab MJ, Peña-Rodríguez LM. Plant natural products with leishmanicidal activity, Nat. Prod. Rep. 18 (2001) 674–688.

Gallagher R, Marx J, Hines P. Progress in parasitology, Science 264 (1994) 1827.

Berman JD, Lee LS. Activity of Oral Drugs against Leishmania Tropica in Human Macrophages in Vitro, Am. J. Trop. Med. Hyg. 32 (1983) 947–951.

Chawla B, Madhubala R. Drug targets in Leishmania, Am. J. Trop. Med. Hyg. 84 (2010) 1–13.

Dos Santos VAFFM, Leite KM, Da Costa Siqueira M, Regasini LO, Martinez I, Nogueira CT. Galuppo MK, Stolf BS, Pereira MAS, Cicarelli RMB, Furlan M, Graminha MAS. Antiprotozoal activity of quinonemethide triterpenes from Maytenus ilicifolia root barks (Celastraceae), Molecules. 18 (2013) 1053–1062.

Sen R, Chatterjee M. Plant derived therapeutics for the treatment of Leishmaniasis, Phytomedicine. 18 (2011) 1056–1069.

Viegas C, Pivatto M, De Rezende A, Hamerski L, Silva DHS, Da Silva Bolzani V. 7-Hydroxycassine: A new 2,6-dialkylpiperidin-3-ol alkaloid and other constituents isolated from flowers and fruits of Senna spectabilis (Fabaceae), J. Braz. Chem. Soc. 24 (2013) 230–235. doi:10.5935/0103-5053.20130029.

Viegas C, Da V, Bolzani S, Furlan M, Barreiro EJ, Young MCM, Tomazela D, Eberlin MN, Further bioactive piperidine alkaloids from the flowers and green fruits of Cassia spectabilis, J. Nat. Prod. 67 (2004) 908–910.

Viegas C, Silva DHS, Pivatto M, De Rezende A, Castro-gambôa I, Bolzani VS. Lipoperoxidation and Cyclooxygenase Enzyme Inhibitory Piperidine Alkaloids from Cassia spectabilis, Green Fruits, J. Nat. Prod. 70 (2007) 2026–2028.

Karau GM, Nyagah E, Njagi M, King A, Wangai LN. Phytonutrients , Minerals and in vitro Antioxidant Capacity of Leaf and Stem Bark Powders of Senna spectabilis. 2 (2013) 51–59.

Bruschi P, Morganti M, Mancini M, Signorini, MA. Traditional healers and laypeople: A qualitative and quantitative approach to local knowledge on medicinal plants in Muda (Mozambique), J. Ethnopharmacol. 138 (2011) 543–563.

Christofidis I, Welter A, Jadot J. Spectalinine and iso-6-carnavaline, two unprecedented piperidine alkaloids from the seeds of Cassia spectabilis, Tetrahedron. 33 (1977) 3005–3006.

De Albuquerque Melo GM, Silva MCR, Guimarães TP, Pinheiro KM, Da Matta CBB, De Queiroz AC, Pivatto M, Da Silva Bolzani V, Alexandre-Moreira MS, Viegas C.Leishmanicidal activity of the crude extract, fractions and major piperidine alkaloids from the flowers of Senna spectabilis, Phytomedicine. 21 (2014) 277–281.

Muniz G, Melo DA, Campelo M, Silva R, Pereira T, Mantovani K, Barbosa C, Cavalcanti A, De Q, Pivatto M, Bolzani S, Alexandre-Moreira MS, Viegas C.Phytomedicine Leishmanicidal activity of the crude extract , fractions and major piperidine alkaloids from the flowers of Senna spectabilis, Eur. J. Integr. Med. 21 (2014) 277–281.

Corsino J. Biosynthesis of friedelane and quinonemethide triterpenoids is compartmentalized in Maytenus aquifolium and Salacia campestris, Phytochemistry. 55 (2000) 741–748.

Figueiredo JN, Räz B, Séquin U. Novel quinone methides from Salacia kraussii with in vitro antimalarial activity, J. Nat. Prod. 61 (1998) 718–723.

Capusiri ES, Pinell GR, Huallpara JCT, Turba AG. Colorimetric method - XTT: as a tool for high performance evaluation of substances with leishmanicidal activity, Biofabro. 16 (2008) 21–27.

Sousa GF, Duarte LP, Alcântara AFC, Silva GDF, Vieira-Filho SA, Silva RR, Oliveira DM. Takahashi JA. New triterpenes from Maytenus robusta: Structural elucidation based on NMR experimental data and theoretical calculations, Molecules. 17 (2012) 13439–13456.

Yeboah EMO, Majinda RRT, Kadziola A, Muller, A. Dihydro-β-agarofuran sesquiterpenes and pentacyclic triterpenoids from the root bark of Osyris lanceolata, J. Nat. Prod. 73 (2010) 1151–1155.

Abbas M, Disi A, Al-Khalil S. Isolation and identification of anti-ulcer components from Anchusa strigosa root, Jordan J. Pharm. Sci. 2 (2009) 131–139.

Lai JS, Huang JY, Huang KF. Constituents from the Stems of Lantana camara, Chin. Pharm. J. 48 (1996) 451–458.

Al-Musayeib NM, Mohamed GA, Ibrahim SRM, Ross SA. Lupeol-3-O-decanoate, a new triterpene ester from Cadaba farinosa Forssk. growing in Saudi Arabia, Med. Chem. Res. 22 (2013) 5297–5302.

Zhang H, Guo Z, Wu N, Xu W, Han L, Li N, Han Y, Zhang H, Guo Z, Wu N, Xu W, Han L, Li N, Han Y. Two novel naphthalene glucosides and an anthraquinone isolated from Rumex dentatus and their antiproliferation activities in four cell lines, Molecules. 17 (2012) 843–850.

Darmawan A, Kosela S, Kardono LBS, Syah YM. Scopoletin, a coumarin derivative compound isolated from Macaranga gigantifolia Merr, J. Appl. Pharm. Sci. 2 (2012) 175–177.

Thiem DA, Sneden AT, Khan SI,.Tekwani BL. Bisnortriterpenes from Salacia madagascariensis, J. Nat. Prod. 68 (2005) 251–254.




DOI: http://dx.doi.org/10.5281/zenodo.3902297

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