Chemical Constituents from Wood of Zanthoxylum rigidum Hum. & Bonpl. Ex Willd (Rutaceae) and Antileishmanial Activity
European Journal of Medicinal Plants,
Page 14-20
DOI:
10.9734/ejmp/2021/v32i530390
Abstract
In this study was reported the structural elucidation by means of nuclear magnetic resonance (1D and 2D), FT-IR and mass spectrometry of lupeol (1), a mixture of the steroids campesterol (2), b-sitosterol (3) and stigmasterol (4), sesamin (5), trans-dimethylmatairesinol (6), trans-methylpluviatolide (7), quercetin (8), and d-mannitol (9) isolated from wood of Zanthoxylum rigidum. The lignans 5, 6 and 7 were tested for their ability to inhibit the proliferation of the promastigote forms of Leishmania braziliensis and Leishmania chagasi. Only sesamin (5) and trans-methylpluviatolide (7) showed moderate inhibitory activity with IC50 = 22.4 and 33.6, SI = 3.87 and 2.41 and CC50 = 86.9 and 81.2, for L. braziliensis and L. chagasi, respectively, compared to the positive control (amphotericin B).
Keywords:
- Zanthoxylum rigidum
- antileishmanial
- Leishmania braziliensis
- Leishmania chagasi
- NMR
- MS
How to Cite
Santos, C. H. C. dos, Sousa, M. C., Jr., P. T. de S., Ribeiro, T. A. N., Jacinto, M. J., & Silva, V. C. P. (2021). Chemical Constituents from Wood of Zanthoxylum rigidum Hum. & Bonpl. Ex Willd (Rutaceae) and Antileishmanial Activity. European Journal of Medicinal Plants, 32(5), 14-20. https://doi.org/10.9734/ejmp/2021/v32i530390
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Chase MW, Morton CM, Kallunki JA. Phylogenetic relationships of Rutaceae: A cladistic analysis of the subfamilies using evidence from rbcL and atpB sequence variation. American J Bot. 1999;86(8):1191-1199.
Jullian V, Bourdy G, Georges S, Maurel S, Sauvain M. Validation of use of a traditional antimalarial remedy from French Guiana, Zanthoxylum rhoifolium Lam. J Ethnopharmacol. 2006;106(3):348-352.
Bertani S, Bourdy G, Landau I, Robinson JC, Esterre P, Deharo E. Evaluation of French Guiana traditional antimalarial remedies. J Ethnopharmacol. 2005;98(1-2):45-54.
Gómez Y, Gil K, González E, Farías LM. Actividad antifúngica de extractos orgánicos del árbol Fagara monophylla (Rutaceae) en Venezuela. Rev Biol Trop. 2007;55(3-4):767-775.
Díaz W, Ortega F. Inventario de recursos botánicos útiles y potenciales de la cuenca del Río Morón, estado Carabobo, Venezuela. Ernstia. 2006;16(1):31-67.
Moccelini SK, Silva VC, Ndiaye EA, Sousa Jr PT, Vieira PC. Estudo fitoquímico das cascas das raízes de Zanthoxylum rigidum Humb. & Bonpl. ex Willd (Rutaceae). Quím Nova. 2007;32(1):131-133.
Beirigo PJS, Torquato HFV, Santos CHC, Carvalho MG, Castro RN, Paredes-Gamero EJ, et al. [1-8-NαC]-Zanriorb A1, a proapoptotic orbitide from leaves of Zanthoxylum riedelianum. J Nat Prod. 2016;79(5):1454-1458.
Lee SW, Lim JM, Mohan H, Seralathan KK, Park YJ, Lee JH, et al. Enhanced bioactivity of Zanthoxylum schinifolium fermented extract: Anti-inflammatory, anti-bacterial, and anti-melanogenic activity. J Biosci Bioeng. 2020;129(5):638-645.
Freitas FFBP, Fernandes HB, Piauilino CA, Carvalho KIM, Chaves MH, Soares PMG, et al. Gastroprotective activity of Zanthoxylum rhoifolium Lam. in animal models. J Ethnopharmacol. 2011;137(1): 700-708.
Pott A, Pott VJ. Plantas do Pantanal. Brasília: Embrapa; 1994.
Ribeiro T AN, Silva, LR, Sousa Jr, PT, Castro, RN, Carvalho, MG. A new cyclopeptide and other constituents from the leaves of Zanthoxylum rigidum Humb. Helv. Chim. Acta. 2012; 95(6):935-939.
Chappuis F, Sundar S, Hailu A, Ghalib H, Rijal S, Peeling RW, et al. Visceral leishmaniasis: What are the needs for diagnosis, treatment and control? Nat Rev Microbiol. 2007;5(11):873–882.
Sereno D, Lemesre JL. Use of an enzymatic micromethod to quantify amastigote stage of Leishmania amazonensis in vitro. Parasitol Res. 1997;83(4):401-403.
Al-Nasiry S, Geusens N, Hanssens M, Luyten C, Pijnenborg R. The use of Alamar Blue assay for quantitative analysis of viability, migration and invasion of choriocarcinoma cells. Hum Reprod. 2007;22(5):1304-1309.
Froelich S, Onegi B, Kakooko A, Siems K, Schubert C, Siems KJ. Plants traditionally used against malaria: phytochemical and pharmacological investigation of Momordica foetida. Rev Bras Farmacogn. 2007;17(1):1-7.
Mahato SB, Kundu AP. 13C NMR Spectra of pentacyclic triterpenoids - A compilation and some salient features. Phytochem. 1994;37(6):1517-1575.
Sa FAS, Paula JAM, Santos PA, Oliveira GAR, Liao LM, Paula JR, et al. Phytochemical analysis and antimicrobial activity of Myrcia tomentosa (Aubl.) DC. leaves. Molecules. 2017;22(7):1100-1110.
Hagiwara SY, Takahashi M, Shen Y, Kaihou S, Tomiyma T, Yazawa M, et al. Phytochemical in the edible tamogi-take mushroom (Pleurotus cornucopiae), D-Mannitol, inhibits ACE activity and lowers the blood pressure of spontaneously hypertensive rats. Biosci Biotechnol Biochem. 2005;69(8):1603–1605.
Branco A, Pizzolatti MG. HRGC and HRGC-MS in the analysis of the chemical constituents isolated from hexanic extract of Sebastiania argutidens (Euphorbiaceae). Quím Nova.2002;25(1): 15-19.
Wang X, Lin Y, Geng Y, Li F, Wang D. Preparative separation and purification of sesamin and sesamolin from sesame seeds by high-speed countercurrent chromatography. Cereal Chem. 2009;86(1):23-25.
Heleno VCG, Silva R, Pedersoli S, Albuquerque S, Bastos JK, Silva MLA, et al. Detailed 1H and 13C NMR structural assignment of three biologically active lignan lactones. Spectrochim Acta A. 2006;63(1):234–239.
Correa JE, Ríos CH, Castillo AR, Romero LI, Ortega-Barría E, Coley PD, et al. Minor alkaloids from Guatteria dumetorum with antileishmanial activity. Planta Med. 2006;72(3):270-272.
Rodrigues-Silva D, Nakamura CV, Filho BPD, Ueda-Nakamura T, Cortez DAG. In vitro antileishmanial activity of hydroalcoholic extract, fractions, and compounds isolated from leaves of Piper ovatum Vahl against Leishmania amazonensis. Acta Protozool. 2009;48(1): 73-81.
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