Abstract
The n-hexane, ethyl acetate, methanol, and acetone extracts of Piper cubeba Linn. and P. retrofractum Vahl. (Piperaceae) were evaluated in vitro against promastigotes of Leishmania donovani, and all exhibited significant in vitro activity at 100 μg/ml. Two lignans, cubebin and hinokinin, were isolated from the hexane extract of P. cubeba; and one bis-epoxy lignan, (−)-sesamin, and two amides, pellitorine and piplartine, were isolated from the hexane and methanol extracts of P. retrofractum. Cubebin and piplartine showed significant antileishmanial activity in vitro at 100 μM and were further tested in vivo in a hamster model of visceral leishmaniasis. Piplartine showed activity at 30 mg/kg dose. This is the first report of antileishmanial activity of these two plants and their isolated constituents.
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References
Chan-Bacab MJ, Peña-Rodríguez LM (2001) Plant natural products with leishmanicidal activity. Nat Prod Rep 18:674–688
Carvalho PB, Ferreira EI (2001) Leishmaniasis phytotherapy. Nature’s leadership against an ancient disease. Fitoterapia 72:599–618
Kapil A (1993) Piperine: a potent inhibitor of Leishmania donovani promastigotes in vitro. Planta Med 59:474
Veerareddy PR, Vobalabonia V, Nahid A (2004) Formulation and evaluation of oil-in-water emulsions of piperine in visceral leishmaniasis. Pharmazie 59:194–197
Raay B, Medda S, Mukhopadhyay S, Basu MK (1999) Targeting of piperine intercalated in mannose-coated liposomes in experimental leishmaniasis. Indian J Biochem Biophys 36:248–251
Verma NK, Dey CS (2004) Possible mechanism of Miltefosine-mediated death of Leishmania donovani. Antimicrob Agents Chemother 48:3010–3015
Prasad V, Kaur J, Dey CS (2000) Arsenite resistant Leishmania donovani promastigotes express an enhanced membrane P-type adenosine triphosphatase activity that is sensitive to verapamil treatment. Parasitol Res 86:661–664
Ghosh AK, Bhattacharya FK, Ghosh DK (1985) Leishmania donovani: amastigote inhibition and mode of action of berberine. Exp Parasitol 60:404–413
Koul SK, Taneja SC, Dhar KL, Atal CK (1983) Lignans of Piper clusii. Phytochemistry 22:999–1000
Rehnburg N, Magnusson G (1988) Total synthesis of the lignans (−)- and(+)- Burseran, (−)-Cubebin and (−)-Hinokinin by diastereoselective conjugate addition of benzylanions to 2-(R)- and (S)-benzyloxy-2,5-dihydro-4-(3,4)-methylenedioxy benzoylfuran. Tetrahedron Lett 29:3599–3602
Rehnburg N, Magnusson G (1990) General conjugate addition method for synthesis of enantiomerically pure lignans. Total synthesis of (−)- and (+)-Burseran, (−)-Dehydro cubebin, (−)-Trichostin, (−)-Cubebin, (−)-5′′-methoxyhinokinin and (−)-Hinokinin. J Org Chem 55:4340–4349
Atal CK, Girothra RN, Dhar KL (1966) Occurrence of sesamin in Piper longum Linn. Indian J Chem 4:252
Lin RW, Tsai IL, Duh CY, Lee KH, Chen IS (2004) New lignans and cytotoxic constituents of Wilkstroemia lanceolata. Planta Med 70:234–238
Chen LC, Kang IJ, Wang HM (1999) Ene reaction with pummerer-type reaction intermediate of α-(methylthio)isobutyl acetamide: a new synthesis of pellitorine. J Chin Chem Soc 46:963–966
Saadali B, Boriky D, Blaghen M, Vanhaelen M, Talbi M (2001) Alkamides from Artemisia dracunculus. Phytochemistry 58:1083–1086
Duh CY, Wu YC, Wang SK (1990) Cytotoxic pyridone alkaloids from Piper aborescens. Phytochemistry 29:2689–2691
Acknowledgments
We express our sincere thanks to Prof. P. Ramarao, director, NIPER, for continuous support for this work. HSB is thankful to NIPER for fellowship. Technical assistance from Mr. Rakesh Kumar and Mr. K.S. Singh is gratefully acknowledged. GS is thankful to CSIR, New Delhi for fellowship.
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NIPER Communication No. 395.
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Bodiwala, H.S., Singh, G., Singh, R. et al. Antileishmanial amides and lignans from Piper cubeba and Piper retrofractum . J Nat Med 61, 418–421 (2007). https://doi.org/10.1007/s11418-007-0159-2
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DOI: https://doi.org/10.1007/s11418-007-0159-2