Abstract
Essential oils from inflorescences and roots of Eupatorium adenophorum Spreng (Asteraceae) have been investigated for their antimicrobial, phytotoxic and antioxidant activities. Based on GC–MS, the oil from inflorescences is dominated by sesquiterpenes (55.9 %) with γ-cadinene (18.4 %), γ-muurolene (11.7 %), 3-acetoxyamorpha-4,7(11)-diene-8-one (7.4 %) and bornyl acetate (6.3 %) as the major constituents. The oil obtained from the roots contained both sesquiterpenes (34.3 %) and monoterpenes (32.5 %) in almost equal proportions with E,E-cosmene (19.9 %), γ-muurolene (10.1 %), isothymol (7.5 %), β-cadinene (7.0 %) and α-phellandren-8-ol (5.9 %) as the major constituents. Both oils exhibited significant antifungal activity against five phytopathogenic fungi. The inflorescence oil showed higher antibacterial activity against Klebsiella pneumoniae, while the root oil was more effective against Staphylococcus aureus. The oils strongly inhibited or delayed germination and seedling growth of the weed Phalaris minor in a dose-dependent manner. As evidenced by a DPPH assay, the essential oils also exhibited significant free radical scavenging activity.
Similar content being viewed by others
References
Abbott WS (1925) A method of computing the effectiveness of an insecticide. J Econ Entomol 18:265–267
Abdalla AE, Roozen JP (1999) Effect of plant extracts on the oxidative stability of sunflower oil and emulsion. Food Chem 64:323–329
Adams RP (1995) Identification of essential oil components by gas chromatography-mass spectroscopy. Allured Publishing, Carol Stream
Aggarwal N, Kumar R, Dureja P, Khurana JM (2011) Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives. European J Med Chem 46:4089–4099
Ahluwalia V, Garg N, Kumar B, Walia S, Sati OP (2012) Synthesis, antifungal activity and structure-activity relationships of vanillin oxime-N-O-alkanoates. Nat Prod Commun 7:1635–1638
Akhtar Y, Yeoung YR, Isman MB (2008) Comparative bioactivity of selected extracts from Meliaceae and some commercial botanical insecticides against two noctuid caterpillars Trichoplusia ni and Pseudaletia unipuncta. Phytochem Rev 7:77–88
Albuquerque MR, Silveira ER, De A, Uchôa DE, Lemos TL, Souza EB, Santiago GM, Pessoa OD (2004) Chemical composition and larvicidal activity of the essential oils from Eupatorium betonicaeforme (D.C.) Baker (Asteraceae). J Agric Food Chem 52:6708–6711
Amri I, Gargouri S, Hamrouni L, Hanana M, Fezzani T, Jamoussi B (2012) Chemical composition, phytotoxic and antifungal activities of Pinus pinea essential oil. J Pest Sci 85:199–207
Ansari S, Jain P, Tyagi RP, Joshi BC, Barar SK (1983) Phytochemical and pharmacological studies of the aerial parts of Eupatorium adenophorum. Herba Polon 29:93–96
Aruoma OI (1998) Free radicals, oxidative stress, and antioxidants in human health and disease. J Am Oil Chem Soc 75:199–212
Baldin ELL, Crotti AEM, Wakabayashi KAL, Silva JPGF, Aguiar GP, Souza ES, Veneziani RCS, Groppo M (2013) Plant-derived essential oils affecting settlement and oviposition of Bemisia tabaci (Genn.) biotype B on tomato. J Pest Sci 86:301–308
Bamba D, Bessiere JM, Marion C, Pelissier Y, Fouraste I (1993) Essential oil of Eupatorium odoratum. Planta Med 59:184–185
Bhattarai N, Shrestha G (2009) Antibacterial and antifungal effect of Eupatorium adenophorum Spreng against bacterial and fungal isolates. Nepal J Sci Technol 10:91–95
Cavar S, Maksimovic M, Solic ME, Jerkovic-Mujkic A, Besta R (2008) Chemical composition and antioxidant and antimicrobial activity of two Satureja essential oils. Food Chem 111:648–653
Cheng SS, Lin HY, Chang ST (2005) Chemical composition and antifungal activity of essential oils from different tissues of Japanese Cedar (Cryptomeria japonica). J Agric Food Chem 53:614–619
Cheng L, Ren Q, Liu X, Guo C, Teng Z, Zhang Q (2007) Behavioural responses of Aphis gossypii and Coccinella septempunctata to volatiles from Eupatorium adenophorum and an analysis of chemical components of the volatiles. J Insect Acta Entomol Sinica 50:1194–1199
Clavin ML, Gorzalczany S, Mino J, Kadarian CC, Martino V, Ferraro G, Acevedo C (2000) Antinociceptive effect of some Argentine medicinal species of Eupatorium. Phytother Res 14:275–277
Cristani M, Arrigo M, Mandalari G, Castelli F, Sarpietro MG, Micieli D, Venuti V, Bisignano G, Saija A, Trombetta D (2007) Interaction of four monoterpenes contained in essential oils with model membranes: implications for their antibacterial activity. J Agric Food Chem 55:6300–6308
Daferera DJ, Ziogas BN, Polissiou MG (2000) GC–MS analysis of essential oils from some Greek aromatic plants and their fungitoxicity on Penicillium digitatum. J Agric Food Chem 48:2576–2581
De-Martino L, Formisano C, Mancini E, De Feo V, Piozzi F, Rigano D, Senatore F (2010) Chemical composition and phytotoxic effects of essential oils from four Teucrium species. Nat Prod Commun 5:1969–1976
Ding Z, Guo Y, Ding J (1999) Chemical constituents from flowers of Eupatorium adenophorum. Acta Botanica Yunnanica 21:5055–5068
Douda O, Zouhar M, Mazakova J, Novacova E, Pavela M (2010) Using plant essence as alternative mean for northern root-knot nematode (Meloidogyne hapla) management. J Pest Sci 83:217–221
Ghnaya AB, Hanana M, Amri I, Balti H, Gargouri S, Jamoussi B, Hamrouni L (2013) Chemical composition of Eucalyptus erythrocorys essential oils and evaluation of their herbicidal and antifungal activities. J Pest Sci. doi:10.1007/s10340-013-0501-2
Gurdip S, Pandey SK, Singh G (1999) GC-MS analysis of Eupatorium cannabinum oil from North India. J Med Aromat Plant Sci 21:8–10
Habtemariam S (2001) Antiinflammatory activity of the antirheumatic herbal drug, gravel root (Eupatorium purpureum): further biological activities and constituents. Phytother Res 15:687–690
Haouas D, Cioni PL, Halima-Kamel MB, Flamini G, Hamouda MHB (2012) Chemical composition and bioactivities of three Chrysanthemum essential oils against Tribolium confusum (du Val) (Coleoptera: Tenebrionidae). J Pest Sci 85:367–379
Isman MB (2000) Plant essential oils for pest and disease management. Crop Prot 19:603–608
Isman MB (2004) Plant essential oils as green pesticides for pest and disease management. In: Nelson WM (ed) Agricultural applications in green chemistry. ACS Symposium Series No. 887. American Chemical Society, Washington, DC, pp 41–51
Isman MB (2006) Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annu Rev Entomol 51:45–66
ISTA International Seed Testing Association (1996) International rules for seed testing. Seed Sci Technol 2:1–288
Jiang Z, Akhtar Y, Bradbury R, Zhang X, Isman MB (2009) Comparative toxicity of essential oils of Litsea pungens and Litsea cubeba and blends of their major constituents against the cabbage looper, Trichoplusia ni. J Agric Food Chem 57:4833–4837
Kalemba D, Kunicka A (2003) Antibacterial and antifungal properties of essential oils. Curr Med Chem 10:813–829
King RM, Robinson H (1970) Studies in the Eupatorieae (Compositae). XXXII. A new genus. Neocuatrecasia. Phytol 19:208
Kundu A, Saha S, Ahluwalia V, Walia S (2013) Plant growth inhibitory terpenes from Eupatorium adenophorum leaves. J Appl Bot Food Qual 86:33–36
Kurade NP, Jaitak V, Kaul VK, Sharma OP (2010) Chemical composition and antibacterial activity of essential oils of L. camara, A. houstonianum and E. adenophorum. Pharm Biol 48:539–544
Li Y, Zou H, Nai Z, Li W, Na X, Tang S, Yang Y (2000) Insecticidal activity of different fractions of distilled oil extracted from Eupatorium adenophorum against four species of food grain insects. J Southwest Agric Univ 22:331–332
Maia JGS, Zoghbi MGB, Andrade EHA, da Silva MHL, Luz AIR, da Silva JD (2002) Essential oils composition of Eupatorium species growing wild in the Amazon. Biochem Syst Ecol 30:1071–1077
Mandal SK, Mandal SC, Das AK, Tag H, Sur T (1981) Antipyretic activity of Eupatorium adenophorum leaf extract. Indian J Nat Prod 21:6–8
Nesci A, Montemarani A, Passone MA, Etcheverry M (2011) Insecticidal activity of synthetic antioxidants, natural phytochemicals, and essential oils against an Aspergillus section Flavi vector (Oryzaephilus surinamensis L.) in microcosm. J Pest Sci 84:107–115
Oerke EC (2006) Crop losses to pests. J Agric Sci 144:31–43
Okunade AL, Wiemer DF (1985) Ant-repellent sesquiterpene lactones from Eupatorium quadrangularae. Phytochemistry 24:1199–1201
Padalia RC, Bisht DS, Joshi SC, Mathela CS (2009) Chemical composition of the essential oil from Eupatorium adenophorum Spreng. J Essent Oil Res 21:522–524
Pala-Paul J, Perez-Alonso MJ, Avelanso-Negueruela A, Sanz J (2002) Analysis by gas chromatography-mass spectroscopy of the volatile components of Ageratina adenophorum Spreng., growing in the Canary Islands. J Chromatogr A 947:327–331
Pino JA, Rosado A, Fuentes V (1998) Essential oil of Eupatorium capillifolium (Lam.) from Cuba. J Essent Oil Res 10:79–80
Romagni JG, Allen SN, Dayan FE (2000) Allelopathic effects of volatile cineoles on two weedy plant species. J Chem Ecol 26:303–313
Ruffinengo S, Eguara M, Floris I, Faverin C, Bailac P, Ponzi M (2005) LD50 and repellent effects of essential oils from Argentinean wild plant species on Varroa destructor. J Econom Entomol 98:651–655
Seyran M, Brenneman TB, Stevenson KL (2010) In vitro toxicity of alternative oxidase inhibitors salicylhydroxamic acid and propyl gallate on Fusicladium effusum. J Pest Sci 83:421–427
Sharma KC, Chhetri GKK (1977) Reports on studies on the biological control of Eupatorium adenophorum. Nepal J Agric 12:135–157
Singh HP, Batish DR, Kaur S, Arora K, Kohli RK (2006a) α-pinene inhibits growth and induces oxidative stress in roots. Ann Bot 98:1261–1269
Singh HP, Batish DR, Kaur S, Kohli RK, Arora K (2006b) Phytotoxicity of volatile monoterpene citronellal against some weeds. Z Naturforsch 61:334–340
Trevors JT (1986) A basic programme for estimating LD50 values using the IBM-PC. Bull Environ Contam Toxicol 37:18–26
Tworkoski T (2002) Herbicide effects of essential oils. Weed Sci 50:425–431
Wang P, Kong CH, Zhang CX (2006) Chemical composition and antimicrobial activity of the essential oil from Ambrosia trifida L. Molecule 11:549–555
Weyerstahl P, Marschall H, Seelmann I, Kaul V (1997) Constituents of the flower essential oil of Ageratina adenophora (Spreng) from India. Flavour Fragr J 12:387–396
Yangui T, Sayadi S, Rhouma A, Dhouib A (2010) Potential use of hydroxytyrosol-rich extract from olive mill wastewater as a biological fungicide against Botrytis cinerea in tomato. J Pest Sci 83:437–445
Yong-ming L, Zheng-yue L, Min YE (2008) The chemical compositions and their bioactivity in the different parts of Eupatorium adenophorum Spreng. J Yunnan Agric Univ 23:42–46
Zahid N, Hosni K, Brahim NB, Kallel M, Sebei H (2010) Allelopathic effect of Schinus molle essential oils on wheat germination Acta Physiol Plant 32:1221–1227
Acknowledgments
The authors are thankful to the Head, Department of Chemistry, HNB Garhwal University (A Central University), Srinagar, Uttarakhand, India and Head, Division of Agricultural Chemicals, IARI, New Delhi for providing the necessary facilities. The first author (VA) is thankful to National Innovative Agricultural Project (NAIP), Indian Council of Agricultural Research, New Delhi, India for financial support.
Conflict of interest
The authors declare that there is no conflict of interest.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Communicated by M. B. Isman.
Rights and permissions
About this article
Cite this article
Ahluwalia, V., Sisodia, R., Walia, S. et al. Chemical analysis of essential oils of Eupatorium adenophorum and their antimicrobial, antioxidant and phytotoxic properties. J Pest Sci 87, 341–349 (2014). https://doi.org/10.1007/s10340-013-0542-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10340-013-0542-6