Essential Oils from Piper cernuum and Piper regnellii: Antimicrobial Activities and Analysis by GC/MS and ¹³C-NMR

Abstract

The essential oils of Piper cernuum and Piper regnellii leaves were analyzed by gas chromatography-mass spectrometry (GC-MS) and the results were compared to that obtained by means of a program designed to analyse ¹³C-NMR data of complex mixtures. Bicyclogermacrene (21.88 %)/β-caryophyllene (20.69 %) and myrcene (52.60 %)/linalool (15.89 %) were the major constituents in essential oil from leaves of P. cernuum and P. regnellii, respectively. Both essential oils presented growth inhibitory activities against Staphylococcus aureus and Candida albicans.

References

• 1 Cronquist A. An Integrated System of Classification of Flowering Plants. New York; Columbia University 1981
• 2 Sumathykutty M A, Rao J M, Padmakumari K P, Narayanan C S. Essential oil constituents of some Piper species.  Flavour and Fragrance Journal. 1999;  14 279-82
• 3 Torquilho H S, Pinto A C, Godoy R LO, Guimarães E F. Essential oil of Piper permucronatum Yuncker (Piperaceae) from Rio de Janeiro, Brazil.  Journal of Essential Oil Research. 1999;  11 429-30
• 4 Van Genderen M HP, Leclercq P A, Delgado H S, Kanjilal P B, Singh R S. Compositional analysis of the leaf oils of Piper callosum Ruiz & Pav. from Peru and Michelia montana Blume from India.  Spectroscopy. 1999;  14 51-9
• 5 Lima D M, Kaplan M AC, Guimarães E F. Essential oil analysis of two Piper species (Piperaceae).  Anais da Academia Brasileira de Ciências. 1998;  70 751-4
• 6 Martins A P, Salgueiro L, Vila R, Tomi F, Canigueral S, Casanova J et al. Essential oil of two Piper species.  Phytochemistry. 1998;  49 2019-23
• 7 Tirillini B, Velasquez E R, Pellegrino R. Chemical composition and antimicrobial activity of essential oil of Piper angustifolium .  Planta Medica. 1996;  62 372-3
• 8 Zollo P HA, Biyiti L, Tchoumbougnang F, Menut C, Lamaty G, Bouchet P. Aromatic plants of Tropical Central Africa. Part XXXII. Chemical composition and antifungal activity of thirteen essential oils from aromatic plants of Cameroon.  Flavour and Fragrance Journal. 1998;  13 107-14
• 9 Dorman H JD, Deans S G. Antimicrobial agents from plants: antibacterial activtiy of plant volatile oils.  Journal of Applied Microbiology. 2000;  88 308-16
• 10 Alécio A C, Bolzani V S, Kato M J, Furlan M. Antifungal amides from Piper hispidum .  Journal of Natural Products. 1998;  61 637-9
• 11 Navickiene H MD, Alécio A C, Kato M J, Bolzani V S, Young M C, Cavalheiro A J, Furlan M. Antifungal amides from Piper hispidum and Piper tuberculatum .  Phytochemistry. 2000;  56 621-6
• 12 Baldoqui D C, Kato M J, Cavalheiro A J, Bolzani V DS, Young M CM, Furlan M. A chromene and prenylated benzoic acid from Piper aduncum .  Phytochemistry. 1999;  51 899-902
• 13 Martins R C, Sartorelli P, Latorre L R, Kato M F. Phenylpropanoids and tetrahydrofuran lignans from Piper solmsianum .  Phytochemistry. 2000;  57 843-6
• 14 Benevides P JC, Sartorelli P, Kato M J. Phenylpropanoids and neolignans from Piper regnellii .  Phytochemistry. 1999;  52 339-43
• 15 Parmar V S, Jain S C, Bisht K S, Jain R, Taneja P, Jha A et al. Phytochemistry of the genus Piper .  Phytochemistry. 1997;  46 597-673
• 16 Ferreira M JP, Emerenciano V P, Linia G AR, Romoff P, Macari P AT, Rodrigues G V. ¹³C-NMR spectroscopy of monoterpenoids.  Progress in Nuclear Magnetic Resonance Spectroscopy. 1998;  33 153-206
• 17 Bohlmann F, Zdero C, Robinson H, King R M. Naturally-occurring terpene derivatives. 283. Caryophyllene derivatives and a heliangolide from Lychnophora species.  Phytochemistry. 1980;  19 2381-5
• 18 Ulubelen A, Topcu G, Eris C, Sonmez U, Kartal M, Kurucu S et al. Terpenoids from Salvia sclarea .  Phytochemistry. 1994;  36 971-4
• 19 Randriamiharisoa R, Gaydou E M, Faure R. C-13 NMR spectra of five sesquiterpenes isolated from Ylang-Ylang essential oil.  Magnetic Resonance in Chemistry. 1986;  24 275-6
• 20 Farmacopéia Brasileira. 4ed Atheneu São Paulo; 1988: Parte I
• 21 Adams R P. Identification fo essential oils by ion trap mass spectrometry. Academic Press New York; 1995
• 22 Jennings W, Shibamoto T. Qualitative analysis of flavor and fragrance volatiles by glass capillary gas chromatography. Academic Press New York; 1980
• 23 Gastmans J P, Furlan M, Lopes M N, Borges J HG, Emerenciano V P. A Inteligência Artificial aplicada a química de produtos naturais. O Programa SISTEMAT. Parte I - Bases teóricas.  Química Nova. 1990;  13 10-6
• 24 Emerenciano V P, Rodrigues G V, Macari P AT, Vestri S A, Borges J HG, Gastmans J P et al. Applications D'Intelligence Artificielle dans la chimie organique. XVII. Nouvaux programmes du projet SISTEMAT.  Spectroscopy. 1994;  12 91-8