Subscribe

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

IJPPE > Volume 3 > (+)-Spectaline, a Piperidine Alkaloid from Senna...
< Back to Volume

(+)-Spectaline, a Piperidine Alkaloid from Senna spectabilis DC. Effective in Reducing the In Vitro Infection of Leishmania major

Full Text PDF

Abstract:

Senna spectabilis is known to have antimicrobial, laxative, antiulcerogenic, analgesic, and anti-inflammatory properties in folk medicine. Piperidine alkaloids extracted from various parts of this plant have been shown to have anticonvulsant (iso-6-spectaline), antinociceptive [(-)-spectaline] and lipid peroxidation [(+)-3-O-feruloylcassine, (-)-spectaline and (-)-3-O-acetylspectaline] activities. In our study, the ethyl acetate extract from S. spectabilis exhibited antileishmanial activity via intracellular promastigote assay or leishmanicidal assay and was further fractionated by using bioassay-guided isolation approach. The antiprotozoal principle was isolated from the ethyl acetate portion through solvent fractionation and a few series of chromatographic processes. The isolated active compound 1 was identified as (+)-spectaline on the basis of its spectral analysis (MS, 1D & 2D NMR) with EC50 value of 0.063 ± 0.005 µM for antileishmanial activity and selectivity index of 3.76.

Info:

Periodical:
International Journal of Pharmacology, Phytochemistry and Ethnomedicine (Volume 3)
Pages:
1-8
Citation:
A. Amat Sain et al., "(+)-Spectaline, a Piperidine Alkaloid from Senna spectabilis DC. Effective in Reducing the In Vitro Infection of Leishmania major", International Journal of Pharmacology, Phytochemistry and Ethnomedicine, Vol. 3, pp. 1-8, 2016
Online since:
June 2016
Export:
Distribution:
References:

[1] P. J. Hotez, et al., The global burden of disease study 2010: interpretation and implications for the neglected tropical diseases, PLoS Negl Trop Dis. 8 (2014) e2865.

DOI: https://doi.org/10.1371/journal.pntd.0003135

[2] L. H. Freitas-Junior, et al., Visceral leishmaniasis treatment: What do we have, what do we need and how to deliver it?, Int J Parasitol Drugs Drug Resist. 2 (2012) 11-19.

DOI: https://doi.org/10.1016/j.ijpddr.2012.01.003

[3] J. Alvar, et al., Leishmaniasis worldwide and global estimates of its incidence, PLoS One. 7 (2012) e35671.

[4] D. Pace, Leishmaniasis, J Infect. 69 (2014) 10-18.

[5] S. L. Croft, K. Seifert, and V. Yardley, Current scenario of drug development for leishmaniasis, Indian J Med Res. 123 (2006) 399-410.

[6] J. H. No, Visceral leishmaniasis: Revisiting current treatments and approaches for future discoveries, Acta Trop. 155 (2016) 113-123.

DOI: https://doi.org/10.1016/j.actatropica.2015.12.016

[7] J. Alvar, et al., Case study for a vaccine against leishmaniasis, Vaccine. 31 Suppl 2 (2013) B244-249.

[8] K. Seifert, Structures, targets and recent approaches in anti-leishmanial drug discovery and development, Open Med Chem J. 5 (2011) 31-39.

DOI: https://doi.org/10.2174/1874104501105010031

[9] M. M. Eissa, E. I. Amer, and S. M. El Sawy, Leishmania major: activity of tamoxifen against experimental cutaneous leishmaniasis, Exp Parasitol. 128 (2011) 382-390.

DOI: https://doi.org/10.1016/j.exppara.2011.05.009

[10] T. S. Tiuman, et al., Recent advances in leishmaniasis treatment, Int J Infect Dis. 15 (2011) e525-e532.

[11] A. V. Colares, et al., In Vitro Antileishmanial Activity of Essential Oil of Vanillosmopsis arborea (Asteraceae) Baker, Evid Based Complement Alternat Med. 2013 (2013) 727042.

[12] L. O. Adebayo, Suleman, Dawda and Samson, Abagale Aba, Natural Products in Antileishmanial Drug Discovery: A Review, Journal of Asian Scientific Research. 3 (2013) 157-173.

[13] S. Sundar and J. Chakravarty, Investigational drugs for visceral leishmaniasis, Expert Opin Investig Drugs. 24 (2015) 43-59.

DOI: https://doi.org/10.1517/13543784.2014.954035

[14] N. Krishnan, Ramanathan,S., Sasidharan,S., Murugaiyah,V., Mansor S.M., Antimicrobial Activity Evaluation of Cassia spectabilis Leaf Extracts, Int J Pharm. 6 (2010) 510-514.

DOI: https://doi.org/10.3923/ijp.2010.510.514

[15] A. Torey, et al., Standardization of Cassia spectabilis with Respect to Authenticity, Assay and Chemical Constituent Analysis, Molecules. 15 (2010) 3411-3420.

DOI: https://doi.org/10.3390/molecules15053411

[16] S. L. Jothy, et al., Cassia spectabilis (DC) Irwin et Barn: A Promising Traditional Herb in Health Improvement, Molecules. 17 (2012) 10292-10305.

DOI: https://doi.org/10.3390/molecules170910292

[17] V. Yardley and S. L. Croft, A comparison of the activities of three amphotericin B lipid formulations against experimental visceral and cutaneous leishmaniasis, Int J Antimicrob Agents. 13 (2000) 243-248.

DOI: https://doi.org/10.1016/s0924-8579(99)00133-8

[18] A. Gebre-Hiwot, et al., An in vitro model for screening antileishmanial drugs: the human leukaemia monocyte cell line, THP-1, Acta Trop. 51 (1992) 237-245.

DOI: https://doi.org/10.1016/0001-706x(92)90042-v

[19] G. V. Carbonell, et al., Detection of cytotoxic activity on Vero cells in clinical isolates of Serratia marcescens, Braz J Med Biol Res. 30 (1997) 1291-1298.

DOI: https://doi.org/10.1590/s0100-879x1997001100005

[20] F. Poorrajab, et al., Nitroimidazolyl-1, 3, 4-thiadiazole-based anti-leishmanial agents: synthesis and in vitro biological evaluation, Eur J Med Chem. 44 (2009) 1758-1762.

DOI: https://doi.org/10.1016/j.ejmech.2008.03.039

[21] K. Seifert and S. L. Croft, In vitro and in vivo interactions between miltefosine and other antileishmanial drugs, Antimicrob Agents Chemother. 50 (2006) 73-79.

DOI: https://doi.org/10.1128/aac.50.1.73-79.2006

[22] J. Konowalchuk, J. I. Speirs, and S. Stavric, Vero response to a cytotoxin of Escherichia coli, Infect Immun. 18 (1977) 775-779.

[23] Z. Zahari, et al., Bioassay-guided isolation of a sesquiterpene lactone of deoxyelephantopin from Elephantopus scaber Linn. active on Trypanosome brucei rhodesience, Phytomedicine. 21 (2014) 282-285.

DOI: https://doi.org/10.1016/j.phymed.2013.09.011

[24] U. Veerachari, A.K. Bopaiah, Preliminary phyto-chemical evaluation of the leaf extract of five Cassia Species, J. Chem. Pharm. Res. 3 (2011) 574-583.

[25] E. Chukeatirote, Hanpattanakit,P., Kaprom,A. & Tovaranonte,J., Antimicrobial activity of Senna spectabilis and S. tora, J. Plant Sci. 2 (2007) 123-126.

DOI: https://doi.org/10.3923/jps.2007.123.126

[26] E.N. Bum, G.N. Nkantchoua, N. Njikam, G.S. Taiwe, G.T. Ngoupaye, M.M. Pelanken, Nanga , F. Maidawa, A. Rakotonirina and S.V. Rakotonirina, Anticonvulsant and Sedative Activity of Leaves of Senna spectabilis in Mice, Int J Pharmacol. 6 (2010).

DOI: https://doi.org/10.3923/ijp.2010.123.128

[27] M. J. Chan-Bacab and L. M. Pena-Rodriguez, Plant natural products with leishmanicidal activity, Nat Prod Rep. 18 (2001) 674-688.

[28] G. M. de Albuquerque Melo, et al., Leishmanicidal activity of the crude extract, fractions and major piperidine alkaloids from the flowers of Senna spectabilis, Phytomedicine. 21 (2014) 277-281.

DOI: https://doi.org/10.1016/j.phymed.2013.09.024

[29] J. L. Vennerstrom, et al., Berberine derivatives as antileishmanial drugs, Antimicrob Agents Chemother. 34 (1990) 918-921.

[30] S. L. Croft, Recent developments in the chemotherapy of leishmaniasis, Trends Pharmacol Sci. 9 (1988) 376-381.

[31] C. W. Wright and J. D. Phillipson, Natural products and the development of selective antiprotozoal drugs, Phytother Res. 4 (1990) 127-139.

[32] I. Christofidis, A. Welter, and J. Jadot, Spectaline and iso-6 cassine, two new piperidin 3-ol alkaloids from the leaves of Cassia spectabilis, Tetrahedron. 33 (1977) 977-979.

DOI: https://doi.org/10.1016/0040-4020(77)80211-1

[33] J. L. Siqueira-Neto, et al., An image-based high-content screening assay for compounds targeting intracellular Leishmania donovani amastigotes in human macrophages, PLoS Negl Trop Dis. 6 (2012) e1671.

DOI: https://doi.org/10.1371/journal.pntd.0001671

[34] J. Ei-On, G. P. Jacobs, and L. Weinrauch, Topical chemotherapy of cutaneous Leishmaniasis, Parasitol Today. 4 (1988) 76-81.

DOI: https://doi.org/10.1016/0169-4758(88)90200-1

[35] P. Escobar, et al., Sensitivities of Leishmania species to hexadecylphosphocholine (miltefosine), ET-18-OCH(3) (edelfosine) and amphotericin B, Acta Trop. 81 (2002) 151-157.

DOI: https://doi.org/10.1016/s0001-706x(01)00197-8
Show More Hide