Chemical Composition and Biological Activity of Essential Oils from Different Species of Piper from Panama^[*]

Abstract

The chemical composition of leaf essential oils from 11 species of Piper from Panama was analyzed by a combination GC-FID and GC-MS procedures. Six of them had sesquiterpene hydrocarbons as major constituents, three were characterized by monoterpene hydrocarbons, one by a diterpene, and one by a phenylpropanoid, dillapiole. The main components identified in each species were: cembratrienol (25.4 %) in Piper augustum; β-pinene (26.6 %) in Piper corrugatum; α-pinene (19.4 %) in Piper curtispicum; trans-β-farnesene (63.7 %) in Piper darienense; p-cymene (43.9 %) in Piper grande; dillapiole (57.7 %) in Piper hispidum; linalool (14.5 %), α-phellandrene (13.8 %), and limonene (12.2 %) in Piper jacquemontianum; β-caryophyllene (45.2 %) in Piper longispicum; linalool (16.5 %), α-phellandrene (11.8 %), limonene (11.4 %), and p-cymene (9.0 %) in Piper multiplinervium; β-selinene (19.0 %), β-elemene (16.1 %), and α-selinene (15.5 %) in Piper reticulatum; and germacrene D (19.7 %) in Piper trigonum. The essential oils of P. hispidum and P. longispicum at a concentration of 250 µg/mL showed larvicidal activity against Aedes aegypti, while the oils from P. curtispicum, P. multiplinervium, P. reticulatum, and P. trigonum were inactive (LC₁₀₀ ≥ 500 µg/mL). The essential oils of P. grande, P. jacquemontianum, and P. multiplinervium showed no significant antifungal activity (MIC > 250 µg/mL) against several yeasts and filamentous fungal strains.

Key words

Piper - Piperaceae - essential oil - cembratrienol - larvicidal - Panama

^* Dedicated to Professor Dr. Dr. h. c. mult. Kurt Hostettmann in recognition of his outstanding contribution to natural product research.

• References

• 1 Stöhr J, Xiao PG, Bauer R. Constituents of Chinese Piper species and their inhibitory activity on prostaglandin and leukotriene biosynthesis in vitro . J Ethnopharmacol 2001; 75: 133-139
• 2 Valadeau C, Castillo JA, Sauvain M, Lores AF, Bourdy G. The rainbow hurts my skin: medicinal concepts and plants uses among the Yanesha (Amuesha), an Amazonian Peruvian ethnic group. J Ethnopharmacol 2010; 127: 175-192
• 3 Raju G, Maridass M. Evaluation of antimicrobial potential of Piper (L.) species. Nat Pharm Technol 2011; 1: 19-22
• 4 Lopes JJ, Marx C, Ingrassia R, Picarda JN, Pereira P, Ferraz Ade B. Neurobehavioral and toxicological activities of two potentially CNS-acting medicinal plants Piper genus. Exp Toxicol Pathol 2012; 64: 9-14
• 5 Correa M, Galdames C, Staff M. Catálogo de las Plantas vasculares de Panamá. Panamá: Editora Novo Art, S.A.; 2004
• 6 Prasad AK, Kumar V, Arya P, Kumar S, Dabur R, Singh N, Chhillar AK, Sharma GL, Gosh B, Wengel J, Olsen CE, Parmar VS. Investigations toward new lead compounds from medicinally important plants. Pure Appl Chem 2005; 77: 25-40
• 7 Wade DE. The ethnomedicine of the Waorani of Amazonian Ecuador. J Ethnopharmacol 1983; 9: 273-297
• 8 Rodríguez N, Rodríguez M, Calderón AI, San Feliciano A, Solís PN, Gupta MP. Anesthetic activity of pipercallosine isolated from Piper darienense . Rev Latinoamer Quim 2006; 33: 115-119
• 9 Otero R, Fonnegra R, Jiménez SL, Núñez V, Evans N, Alzate SP, García ME, Saldarriaga M, Valle GD, Osorio RG, Díaz A, Valderrama R, Duque A, Velez HN. Snakebites and ethnobotany in the northwest region of Colombia: Part I: traditional use of plants. J Ethnopharmacol 2000; 71: 493-504
• 10 Otero R, Núñez V, Barona J, Fonnegra R, Jiménez SL, Osorio RG, Saldarriaga M, Díaz A. Snakebites and ethnobotany in the northwest region of Colombia. Part III: neutralization of the haemorrhagic effect of Bothrops atrox venom. J Ethnopharmacol 2000; 73: 233-241
• 11 Schultes RE. De plantis toxicariis e mundo novo tropicale commentationes. XII. Notes on biodynamic piperaceous plants. Rhodora 1975; 77: 165-170
• 12 Martínez MA. Medicinal plants used in a Totonac community of the Sierra Norte de Puebla: Tuzamapan de Galeana, Puebla, Mexico. J Ethnopharmacol 1984; 11: 203-221
• 13 Da Silva JKR, Pinto LC, Burbano RMR, Montenegro RC, Guimarães EF, Andrade EHA, Maia JGS. Essential oils of Amazon Piper species and their cytotoxic, antifungal, antioxidant and anti-cholinesterase activities. Ind Crops Prod 2014; 58: 55-60
• 14 Barrett B. Medicinal plants of Nicaraguaʼs Atlantic coast. Econ Bot 1994; 48: 8-20
• 15 Coe FG, Anderson GJ. Ethnobotany of the Garifuna of Eastern Nicaragua. Econ Bot 1996; 50: 71-107
• 16 Coe FG, Anderson GJ. Screening of medicinal plants used by the Garifuna of Eastern Nicaragua for bioactive compounds. J Ethnopharmacol 1996; 53: 29-50
• 17 Gupta MP, Correa M, Solís PN, Jones A, Galdames C, Guionneau-Sinclair F. Medicinal plant inventory of Kuna Indians: Part I. J Ethnopharmacol 1993; 40: 77-109
• 18 Ruegg T, Calderón AI, Queiroz EF, Solís PN, Marston A, Rivas F, Ortega-Barría E, Hostettmann K, Gupta MP. 3-Farnesyl-2-hydroxybenzoic acid is a new anti-Helicobacter pylori compound from Piper multiplinervium . J Ethnopharmacol 2006; 103: 461-467
• 19 Assis A, Brito V, Bittencourt M, Silva L, Oliveira F, Oliveira R. Essential oils composition of four Piper species from Brazil. J Essent Oil Res 2013; 25: 203-209
• 20 Tangarife-Castaño V, Correa-Royero JB, Roa-Linares VC, Pino-Benitez N, Betancur-Galvis LA, Durán DC, Stashenko EE, Mesa-Arango AC. Anti-dermatophyte, anti-Fusarium and cytotoxic activity of essential oils and plant extracts of Piper genus. J Essent Oil Res 2014; 26: 221-227
• 21 Houël E, Gonzalez G, Bessière JM, Odonne G, Eparvier V, Deharo E, Stien D. Therapeutic switching: from antidermatophytic essential oils to new leishmanicidal products. Mem Inst Oswaldo Cruz 2015; 110: 106-113
• 22 Caballero-Gallardo K, Olivero-Verbel J, Pino-Benítez N, Stashenko EE. Chemical composition and bioactivity of Piper auritum and P. multiplinervium essential oils against the red flour beetle, Tribolium castaneum (Herbst). B Latinoam Caribe PL 2014; 13: 10-19
• 23 Cicció JF. Essential oil from the leaves of Piper augustum from “Alberto M. Brenes” biological preserve, Costa Rica. J Essent Oil Res 2005; 17: 251-253
• 24 Pino JA, Marbot R, Bello A, Urquiola A. Composition of the essential oil of Piper hispidum Sw. from Cuba. J Essent Oil Res 2004; 16: 459-460
• 25 Pino Benitez N, Meléndez León EM, Stashenko EE. Essential oil composition from two species of Piperaceae family grown in Colombia. J Chromatogr Sci 2009; 47: 804-807
• 26 Facundo VA, Pollli AR, Rodrigues RV, Militão JSLT, Stabelli RG, Cardoso CT. Fixed and volatile chemical constituents from stems and fruits of Piper tuberculatum Jacq. and from roots of P. hispidum H.B.K. Acta Amazon 2008; 38: 743-748
• 27 Cruz SM, Cáceres A, Álvarez LE, Apel MA, Henriques AT. Chemical diversity of essential oils of 15 Piper species from Guatemala. Acta Hortic 2012; 964: 39-46
• 28 Cruz SM, Cáceres A, Álvarez L, Morales J, Apel MA, Henriques AT, Salamanca E, Giménez A, Vásquez Y, Gupta MP. Chemical composition of essential oils of Piper jacquemontianum and Piper variabile from Guatemala and bioactivity of the dichloromethane and methanol extracts. Rev Bras Farmacogn 2011; 21: 587-593
• 29 Luz AIR, Zoghbi MGB, Maia JGS. The essential oils of Piper reticulatum L. and P. crassinervium H.B.K. Acta Amazon 2003; 33: 341-344
• 30 European Directorate for the Quality of Medicines & Healthcare (EDQM). European Pharmacopeia, 5th edition. Strasbourg: Council of Europe; 2005
• 31 Mc Lafferty FW. Wiley registry of mass spectral data, 4th edition. New York: John Wiley & Sons; 1993
• 32 Adams RP. Identification of essential oils by gas chromatography/mass spectroscopy. Carol Stream, IL: Allured; 1995
• 33 Vila R, Iglesias J, Cañigueral S, Gupta MP. Constituents and biological activity of the essential oil of Eugenia acapulcensis Steud. J Essent Oil Res 2004; 16: 384-386
• 34 Vila R, Santana AI, Pérez-Rosés R, Valderrama A, Castelli MV, Mendonca S, Zacchino S, Gupta MP, Cañigueral S. Composition and biological activity of the essential oil from leaves of Plinia cerrocampanensis, a new source of α-bisabolol. Bioresour Technol 2010; 101: 2510-2514