Advertisement

Phytochemistry Reviews

, 7:65 | Cite as

A review of Piper spp. (Piperaceae) phytochemistry, insecticidal activity and mode of action

  • Ian M. Scott
  • Helen R. Jensen
  • Bernard J. R. Philogène
  • John T. Arnason
Original Paper

Abstract

The tropical plant family Piperaceae has provided many past and present civilizations with a source of diverse medicines and food grade spice. The secondary plant compounds that produce these desired qualities function also as chemical defenses for many species in the genus Piper. The compounds with the greatest insecticidal activity are the piperamides. Many studies have shown the effectiveness of Piper spp. extracts for the control of stored products pests and recently studies from our laboratory group have tested the extracts of Piper. nigrum, P. guineense and P. tuberculatum against insect pests of the home and garden. These results and those from investigations that examined the biochemical and molecular modes of action of the piperamides singly or in combination will be the focus of this review. The conclusions of our current work with Piperaceae are that Piper extracts offer a unique and useful source of biopesticide material for controlling small-scale insect out-breaks and reducing the likelihood of resistance development when applied as a synergist with other botanical insecticides such as pyrethrum.

Keywords

Enzyme inhibition Gene expression Insecticidal activity Piperaceae Piperamides 

Abbreviations

Kdr

Knock-down resistance

MDP

Methylenedioxyphenyl

PBO

Piperonyl butoxide

PSMO

Polysubstrate monooxygenase

Notes

Acknowledgements

We thank F. Duval and J. Livesey for technical and analytical support (Biology Department, University of Ottawa); T. Durst and E. Puniani for piperamide synthesis (Chemistry Department, University of Ottawa) and L. Poveda and P. Sánchez-Vindas for Piper collection and identification (Universidad Nacional, Heredia 3000, Costa Rica). Funding was provided by the Ontario Ministry of Science and Technology, Ontario Graduate Scholarship (OGS), the Fonds québécois de recherche sur la nature et les technologies (FQRNT), Whitmire Micro-Gen, Canadian Organic Growers and Natural Sciences and Engineering Research Council (NSERC) Canada.

References

  1. Arnason JT, Durst T, Philogène BJR (2002) Prospection d’insecticides phytochimiques de plantes tempérées et tropicales communes ou rares. In: Regnault-Roger C, Philogène BJR, Vincent C (eds) Biopesticides d’origine végétale. Editions TEC and DOC, Paris pp 37–51Google Scholar
  2. Baier AH, Webster BD (1992) Control of Acanthoscelides obtectus Say (Coleoptera: Bruchidae) in Phaseolus vulgaris L. seed stored on small farms-1. Evaluation of damage. J Stored Prod Res 28:289–293CrossRefGoogle Scholar
  3. Bernard CB, Arnason JT, Philogène BJR, Lam J, Waddell T (1989) Effects of lignans and other secondary metabolites of the Asteraceae on the PSMO activity of the European corn borer, Ostrinia nubilalis. Phytochemistry 28:1371–1378CrossRefGoogle Scholar
  4. Bhardwaj RK, Glaesser H, Becquemont L, Klotz U, Gupta SK, Fromm MF (2002) Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther 302:645–650PubMedCrossRefGoogle Scholar
  5. Bourbonnais-Spear N, Awad R, Maquin P, Cal V, Sánchez-Vindas P, Poveda L, Arnason JT (2005) Plant use by the Q’Eqchi’ Maya of Belize in ethnopsychiatry and neurological pathology. Econ Bot 59:326–336CrossRefGoogle Scholar
  6. Budzinski JW, Foster BC, Vandenhoek S, Arnason JT (2000) An in vitro evaluation of human cytochrome P450 3A4 inhibition by selected commercial herbal extracts and tinctures. Phytomedicine 7:273–282PubMedGoogle Scholar
  7. Burger W (1971) Flora Costaricensis. Fieldiana Botany 35Google Scholar
  8. Dalvi RR, Dalvi PS (1991) Differences in the effects of piperine and piperonyl butoxide on hepatic drug-metabolizing enzyme system in rats. Drug Chem Toxicol 14:219–229Google Scholar
  9. de Paula VF, de A Barbosa LC, Demuner AJ, Piló-Veloso D, Picanço MC (2000) Synthesis and insecticidal activity of new amide derivatives of piperine. Pest Manage Sci 56:168–174CrossRefGoogle Scholar
  10. Dev S, Koul O (1997) Insecticides of Natural Origin. Hardwood Academic Publishers, Amsterdam, Netherlands p 365Google Scholar
  11. Devasahayam S, Abdulla Koya KM (1994) Field evaluation of insecticides for the control of scale (Lepidosaphes piperis Gr.) on black pepper (Piper nigrum L.). J Entomol Res 18:213–215Google Scholar
  12. Dyer LA, Palmer ADN (eds) (2004) Piper: a model genus for studies of phytochemistry, ecology and evolution. Kluwer Academic/Plenum Publishers, New York p 228Google Scholar
  13. Elliott M, Farnham AW, Janes NF, Johnson DM, Pulman DA, Sawicki RM (1986) Insecticidal amides with selective potency against a resistant (super-kdr) strain of houseflies (Musca domestica L.). Agric Biol Chem 50:1347–1349Google Scholar
  14. EPA (2006) Regulating biopesticides. United States Environmental Protection Agency. http://www.epa.gov/pesticides/biopesticides/Google Scholar
  15. Evans PH, Bowers WS, Funk EJ (1984) Identification of fungicidal and nematocidal components in the leaves of Piper betle (Piperaceae). J Agric Food Chem 32:1254–1256CrossRefGoogle Scholar
  16. Gbewonyo WSK, Candy DJ, Anderson M (1993) Structure-activity relationships of insecticidal amides from Piper guineense root. Pestic Sci 37:57–66CrossRefGoogle Scholar
  17. Gersdorff WA, Piquett PG (1957) Comparative effects of piperettine in pyrethrum and allethrin mixtures as house fly sprays. J Econ Entomol 50:164–166Google Scholar
  18. Hodgson E, Levi PE (1998) Interactions of piperonyl butoxide with cytochrome P450. In: Jones DG (ed) Piperonyl Butoxide: the insecticide synergist Academic Press, San Diego CA, pp 41–53Google Scholar
  19. Isman MB (1994) Botanical insecticides. Pestic Outlook 5:26–30Google Scholar
  20. Iwu MM (ed) (1993) Handbook of African medicinal plants. CRC Press, Boca Raton, FL, p 435Google Scholar
  21. Jensen HR, Scott IM, Sims S, Trudeau VL, Arnason JT (2006a) Gene expression profiles of Drosophila melanogaster exposed to an insecticidal extract of Piper nigrum. J Agric Food Chem 54:1289–1295CrossRefGoogle Scholar
  22. Jensen HR, Scott IM, Sims S, Trudeau VL, Arnason JT (2006b) The effect of a synergistic concentration of a P. nigrum extract used in conjunction with pyrethrum upon gene expression in Drosophila melanogaster. Insect Mol Biol 15:329–339CrossRefGoogle Scholar
  23. Kéïta SM, Vincent C, Schmidt JP, Ramaswamy S, Bélanger A (2000) Effect of various essential oils on Callosobruchus maculatus (F.) (Coleoptera: Bruchidae). J Stored Prod Res 36:355–364PubMedCrossRefGoogle Scholar
  24. Lee S-E, Park B-S, Kim M-K, Choi W-S, Kim H-T, Cho K-Y, Lee S-G, Lee H-S (2001) Fungicidal activity of pipernonaline, a piperidine alkaloid derived from long pepper, Piper longum L., against phytopathogenic fungi. Crop Prot 20:523–528CrossRefGoogle Scholar
  25. Lees G, Burt PE (1988) Neurotoxic actions of a lipid amide on the cockroach nerve cord and on locust somata maintained in short-term culture: a novel preparation for the study of Na+ channel pharmacology. Pesticid Sci 24:189–191Google Scholar
  26. Lydon J, Duke SO (1989) The potential of pesticides from plants. Herbs Spices Med Plants 4:1–41Google Scholar
  27. MacKinnon S, Chauret D, Wang M, Mata R, Pereda-Miranda R, Jiminez A, Bernard CB, Krishnamurty HG, Poveda LJ, Sanchez-Vindas PE, Arnason JT, Durst T (1997) Botanicals from the Piperaceae and Meliaceae of the American Neotropics: phytochemistry. In: Hedin PA, Hollingworth RM, Masler EP, Miyamoto J, Thompson DG (eds) Phytochemicals for pest control American Chemical Society, Washington, DC, pp 49–57Google Scholar
  28. Maitra S, Dombrowski SM, Waters LC, Ganguly R (1996) Three second chromosome-linked clustered Cyp6 genes show differential constitutive and barbital-induced expression in DDT-resistant and susceptible strains of Drosophila melanogaster. Gene 180:165–171PubMedCrossRefGoogle Scholar
  29. Mbata GN, Oji OA, Nwana IE (1995) Insecticidal action of preparation from the brown pepper, Piper guineense Schum, seeds to Callosobruchus maculatus (Fabricius). Discov Innov 7:139–142Google Scholar
  30. McFerren MA, Cardova D, Rodriguez E, Rauh JJ (2002) In vitro neuropharmacological evaluation of piperovatine, an isobutylamide from Piper piscatorum (Piperaceae). J Ethnopharmacol 83:201–207PubMedCrossRefGoogle Scholar
  31. Miyakado M, Nakayama I, Yoshioka H, Nakatani N (1979) The Piperaceae amides I : Structure of pipercide, a new insecticidal amide from Piper nigrum L. Agric Biol Chem 43:1609–1611Google Scholar
  32. Miyakado M, Nakayama I, Yoshioka H (1980) Insecticidal joint action of pipercide and co- occurring compounds isolated from Piper nigrum L. Agric Biol Chem 44:1701–1703Google Scholar
  33. Miyakado M, Nakayama I, Ohno N (1989) Insecticidal unsaturated isobutylamides. From natural products to agrochemical leads. In: Insecticides of plant origin. Amer Chem Soc Symp Ser 387, Washington, DC, pp 173–187Google Scholar
  34. National Research council (2000) The future role of pesticides in U.S. agriculture. Committee on the future role of pesticides in U.S. agriculture, board on agriculture and natural resources and board on environmental studies and toxicology, Commission on Life Sciences, National Academy of Sciences, Washington, DC, p 301Google Scholar
  35. Okorie TG, Ogunro OF (1992) Effects of extracts and suspensions of the black pepper Piper guineense on the immature stages of Aedes agypti (Linn) (Diptera: Culicidae) and associated aquatic organisms. Discov Innov 4:59–63Google Scholar
  36. Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE, Boll PM (1997) Phytochemistry of the genus Piper. Phytochemistry 46:597–673CrossRefGoogle Scholar
  37. Parmar VS, Jain SC, Gupta S, Talwar S, Rajwanshi VK, Kumar R, Azim A, Malhotra S, Kumar N, Jain R, Sharma NK, Tyagi OD, Lawrie SJ, Errington W, Howarth OW, Olsen CE, Singh SK, Wengel J (1998) Polyphenols and alkaloids from Piper species. Phytochemistry 49:1069–1078CrossRefGoogle Scholar
  38. Perakis C, Louli V, Magoulas K (2005) Supercritical fluid extraction of black pepper oil. J Food Eng 71:386–393CrossRefGoogle Scholar
  39. Petersen RA, Zangerl AR, Berenbaum MR, Schuler MA (2001) Expression of CYP6B1 and CYP6B3 cytochrome P450 monooxygenases and furanocoumarin metabolism in different tissues of Papillio polyxenes (Lepidoptera: Papilionidae). Insect Biochem Mol Biol 31:679–690PubMedCrossRefGoogle Scholar
  40. PMRA (2006) Update on reduced-risk pesticides in Canada. Pest Management Regulatory Agency, Health Canada, http://www.pmra-arla.gc.ca/english/pdf/nafta/naftajr/nafta-jr-pest-e.pdfGoogle Scholar
  41. Ranjith AM, Pillalay VS, Sasikumaran S, Mammootty KP (1991) Record of Pterolophia griseovaria Breuning as a pest on pepper (Piper nigrum L.). Entomon 16:323–325Google Scholar
  42. Raut SK, Bhattacharya SS (1999) Pests and diseases of betelvine (Piper betle) and their natural enemies in India. Exp Appl Acarol 23:319–325CrossRefGoogle Scholar
  43. Reen RK, Singh J (1991) In vitro and in vivo inhibition of pulmunary cytochrome P450 activities by piperine, a major ingredient of Piper species. Indian J Exp Biol 29:568–573PubMedGoogle Scholar
  44. Regnault-Roger C, Philogène BJR, Vincent C (eds) (2002) Biopesticides d’origine végétale. Editions TEC and DOC, Paris, p 337Google Scholar
  45. Santhosh-Babu PB (1994) Some aspects of biology of Longitarsus nigripennis mots. (Coleoptera: Chrysomelidae), a serious pest on black pepper, Piper nigrum L. Entomon 19:159–161 Google Scholar
  46. Scott IM, Gagnon N, Lesage L, Philogène BJR, Arnason JT (2005a) Efficacy of botanical insecticides from Piper spp. (Piperaceae) extracts for control of European chafer (Coleoptera Scarabaeidae). J Econ Entomol 98:845–855Google Scholar
  47. Scott IM, Helson BV, Strunz GM, Finlay H, Sánchez-Vindas PE, Poveda L, Lyons BL, Philogène BJR, Arnason JT (2007) Efficacy of Piper Extracts (Piperaceae) for control of insect defoliators of forest and ornamental trees. Can Entomol (Revised and resubmitted Dec. 4 2006)Google Scholar
  48. Scott IM, Jensen H, Nicol R, Lesage L, Bradbury R, Sánchez-Vindas P, Poveda L, Arnason JT, Philogène BJR (2004) Efficacy of Piper (Piperaceae) extracts for control of common home and garden insect pests. J Econ Entomol 97:1390–1403PubMedCrossRefGoogle Scholar
  49. Scott IM, Jensen H, Scott JG, Isman MB, Arnason JT, Philogène BJR (2003) Botanical insecticides for controlling agricultural pests: piperamides and the Colorado potato beetle Leptinotarsa decemlineata Say (Coleoptera: Chrysomelidae). Arch Insect Biochem Physiol 54:212–225PubMedCrossRefGoogle Scholar
  50. Scott IM, Puniani E, Durst T, Phelps D, Merali S, Assabgui RA, Sánchez-Vindas P, Poveda L, Philogène BJR, Arnason JT (2002) Insecticidal activity of Piper tuberculatum Jacq. extracts synergistic interaction of piperamides. Agric For Entomol 4:137–144CrossRefGoogle Scholar
  51. Scott IM, Puniani E, Jensen H, Livesey JF, Poveda L, Sánchez-Vindas P, Durst T, Arnason JT (2005b) Analysis of Piperaceae germplasm by HPLC and LCMS: A method for isolating and identifying unsaturated amides from Piper spp extracts. J Agric Food Chem 53:1907–1913CrossRefGoogle Scholar
  52. Semler U, Gross GG (1988) Distribution of piperine in vegetative parts of Piper nigrum. Phytochemistry 27:1566–1567CrossRefGoogle Scholar
  53. Shultes RE, Raffauf RF (1990) The healing forest. Medicinal and toxic plants of the northwest Amazonia. Dudley TR (ed) Historical, ethno- and economic botany series, vol 2. Dioscorides Press, Portland, OR, p 484Google Scholar
  54. Sighamony S, Anees I, Chanrakala T, Osmani Z (1986) Efficacy of certain indigenous plant products as grain protectants against Sitophilus oryzae (L.) and Rhyzopertha dominica (F.). J Stored Prod Res 22:21–23CrossRefGoogle Scholar
  55. Simpson BB, Ogorzaly MO (1995) Economic Botany: plants in our world. Simpson BB, Ogorzaly MO (eds) 2nd edn. McGraw-Hill Inc., New York, p 742Google Scholar
  56. Singh G, Marimuthu P, Catalan C, deLampasona MP (2004) Chemical, antoxidant and antifungal activities of volatile oil of black pepper and its acetone extract. J Sci Food Agric 84:1878–1884CrossRefGoogle Scholar
  57. Singh A, Rao AR (1993) Evaluation of the modulatory influence of black pepper (Piper nigrum, L.) on the hepatic detoxication system. Cancer Lett 72:5–9PubMedCrossRefGoogle Scholar
  58. Singh J, Reen RK (1994) Modulation of constitutive, benz[a]anthracene- and phenobarbital-inducible cytochromes P450 activities in rat hepatoma H4IIEC3/G- cells by piperine. Curr Sci 66:365–369Google Scholar
  59. Supreme Court of Canada (2001) 114957 Canada Ltée (Spraytech, Société d’arrosage) and Service des Espaces Verts Ltée v. Town of Hudson (Respondent)) http://www.lexum.umontreal.ca/csc-scc/en/pub/2001/vol2/html/2001scr2_0241.htmlGoogle Scholar
  60. Tripathi AK, Jain DC, Kumar S (1996) Secondary metabolites and their biological and medicinal activities of Piper species plants. J Med Aromat Plant Sci 18:302–321Google Scholar

Copyright information

© Springer Science+Business Media B.V. 2007

Authors and Affiliations

  • Ian M. Scott
    • 1
    • 2
  • Helen R. Jensen
    • 1
  • Bernard J. R. Philogène
    • 1
  • John T. Arnason
    • 1
  1. 1.Biology DepartmentUniversity of OttawaOttawaCanada
  2. 2.Entomology DepartmentCornell UniversityIthacaUSA

Personalised recommendations