Planta Med 2011; 77(6): 598-617
DOI: 10.1055/s-0030-1270723
Tropical Diseases
Reviews
© Georg Thieme Verlag KG Stuttgart · New York

Patent Literature on Mosquito Repellent Inventions which Contain Plant Essential Oils – A Review

Adrian Martin Pohlit1 , 3 , Norberto Peporine Lopes3 , Renata Antonaci Gama4 , Wanderli Pedro Tadei2 , Valter Ferreira de Andrade Neto4
  • 1Natural Products Department, National Institute for Amazon Research, Manaus, Brazil
  • 2Health Sciences Department, National Institute for Amazon Research, Manaus, Brazil
  • 3Department of Chemistry and Physics, College of Pharmaceutical Sciences, São Paulo University, Ribeirão Preto, Brazil
  • 4Department of Microbiology and Parasitology, Rio Grande do Norte Federal University, Natal, Brazil
Further Information

Publication History

received July 2, 2010 revised Dec. 28, 2010

accepted January 3, 2011

Publication Date:
15 February 2011 (online)

Abstract

Bites of mosquitoes belonging to the genera Anopheles Meigen, Aedes Meigen, Culex L. and Haemagogus L. are a general nuisance and are responsible for the transmission of important tropical diseases such as malaria, hemorrhagic dengue and yellow fevers and filariasis (elephantiasis). Plants are traditional sources of mosquito repelling essential oils (EOs), glyceridic oils and repellent and synergistic chemicals. A Chemical Abstracts search on mosquito repellent inventions containing plant-derived EOs revealed 144 active patents mostly from Asia. Chinese, Japanese and Korean language patents and those of India (in English) accounted for roughly 3/4 of all patents. Since 1998 patents on EO-containing mosquito repellent inventions have almost doubled about every 4 years. In general, these patents describe repellent compositions for use in topical agents, cosmetic products, incense, fumigants, indoor and outdoor sprays, fibers, textiles among other applications. 67 EOs and 9 glyceridic oils were individually cited in at least 2 patents. Over 1/2 of all patents named just one EO. Citronella [Cymbopogon nardus (L.) Rendle, C.winterianus Jowitt ex Bor] and eucalyptus (Eucalyptus L'Hér. spp.) EOs were each cited in approximately 1/3 of all patents. Camphor [Cinnamomum camphora (L.) J. Presl], cinnamon (Cinnamomum zeylanicum Blume), clove [Syzygium aromaticum (L.) Merr. & L. M. Perry], geranium (Pelargonium graveolens L'Hér.), lavender (Lavandula angustifolia Mill.), lemon [Citrus × limon (L.) Osbeck], lemongrass [Cymbopogon citratus (DC.) Stapf] and peppermint (Mentha × piperita L.) EOs were each cited in > 10 % of patents. Repellent chemicals present in EO compositions or added as pure “natural” ingredients such as geraniol, limonene, p-menthane-3,8-diol, nepetalactone and vanillin were described in approximately 40 % of all patents. About 25 % of EO-containing inventions included or were made to be used with synthetic insect control agents having mosquito repellent properties such as pyrethroids, N,N-diethyl-m-toluamide (DEET), (±)-p-menthane-3,8-diol (PMD) and dialkyl phthalates. Synergistic effects involving one or more EOs and synthetic and/or natural components were claimed in about 10 % of all patents. Scientific literature sources provide evidence for the mosquito repellency of many of the EOs and individual chemical components found in EOs used in patented repellent inventions.

References

  • 1 WHO Media Centre . Malaria. World Health Organization (WHO) Media Centre. Available at. http://www.who.int/mediacentre/factsheets/fs094/en/ Accessed September 26, 2010.
  • 2 WHO Media Centre . Dengue. World Health Organization (WHO) Media Centre. Available at. http://www.who.int/mediacentre/factsheets/fs117/en/ Accessed September 26, 2010
  • 3 Burfield T, Reekie S L. Mosquitoes, malaria and essential oils.  Int J Aromather. 2005;  15 30-41
  • 4 WHO Media Centre . Filariasis. World Health Organization (WHO) Media Centre. Available at. http://www.who.int/topics/filariasis/en/ Accessed September 26, 2010
  • 5 WHO Media Centre . Yellow Fever. World Health Organization (WHO) Media Centre. Avaliable at. http://www.who.int/mediacentre/factsheets/fs100/en/ Accessed September 26, 2010
  • 6 Brown M, Hebert A A. Insect repellents: an overview.  J Am Acad Dermatol. 1997;  36 243-249
  • 7 Nerio L S, Olivero-Verbel J, Stashenko E. Repellent activity of essential oils: a review.  Bioresour Technol. 2010;  101 372-378
  • 8 Batish D R, Singh H P, Kohli R K, Kaur S. Eucalyptus essential oil as a natural pesticide.  For Ecol Manage. 2008;  256 2166-2174
  • 9 EPA. US Environmental Protection Agency .Notice to manufacturers, formulators, producers and registrants of pesticide products on minimum risk pesticides exempted under FIFRA Section 25(b) Pesticide Registration (PR). Notice 2000 – 6, 2000. Labeling Unit, Registration Division (7505C). Washington; Office of Pesticide Programs, EPA 2000 http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_plant-oils.htm Accessed September 26, 2010
  • 10 Bakkali F, Averbeck S, Averbeck D, Zhiri A, Idaomar M. Cytotoxicity and gene induction by some essential oils in the yeast Saccharomyces cerevisiae.  Mutat Res. 2005;  585 1-13
  • 11 SciFinder Scholar. Chemical Abstracts Service – A division of the American Chemical Society. Available at. http://www.cas.org/products/sfacad/index.html Accessed September 28, 2010
  • 12 Tropicos.org. Missouri botanical garden. Available at. http://www.tropicos.org Accessed November 30, 2010
  • 13 Rout P K, Rao Y R, Jena K S, Sahoo D, Mishra B C. Extraction and composition of the essential oil of ambrette (Abelmoschus moschtus) seeds.  J Essent Oil Res. 2004;  16 35-37
  • 14 Rout P K, Barik K C, Jena K S, Sahoo D, Rao Y R. A novel process for the extraction of fragrance components from ambrette (Hibiscus abelmoschus L.) seeds.  Org Proc Res Dev. 2002;  6 401-404
  • 15 Nivinskiene O, Butkiene R, Mockute D. Changes in the chemical composition of essential oil of Angelica archangelica L. roots during storage.  Chemija (Vilnius). 2003;  14 52-56
  • 16 Wu M, Sun X, Dai Y, Guo F, Huang L, Liang Y. Determination of constituents of essential oil from Angelica sinensis by gas chromatography- mass spectrometry.  J Central South Univ Technol. 2005;  12 430-436
  • 17 Arslan N, Gürbüz B, Sarihan E O, Bayrak A, Gümüsçü A. Variation in essential oil content and composition in Turkish anise (Pimpinella anisum L.) populations.  Turkish J Agric For. 2004;  28 173-177
  • 18 Wenqiang G, Shufen L, Ruixiang Y, Yanfeng H. Comparison of composition and antifungal activity of Artemisia argyi Lévl. et Vant inflorescence essential oil extracted by hydrodistillation and supercritical carbon dioxide.  Nat Prod Res. 2006;  20 992-998
  • 19 Zheng X, Deng C, Song G, Hu Y. Comparison of essential oil composition of Artemisia argyi leaves at different collection times by headspace solid-phase microextraction and gas chromatography-mass spectrometry.  Cromatographia. 2004;  59 729-732
  • 20 Inouye S, Uchida K, Abe S. Volatile composition and vapour activity against Trichophyton mentagrophytes of 36 aromatic herbs cultivated in Chichibu district in Japan.  Intl J Aromather. 2006;  16 159-168
  • 21 Viña A, Murillo E. Essential oil composition from twelve varieties of basil (Ocimum spp.) grown in Colombia.  J Braz Chem Soc. 2003;  14 744-749
  • 22 Chalchat J-C, Özcan M M. Comparative essential oil composition of flowers, leaves and stems of basil (Ocimum basilicum L.) used as herb.  Food Chem. 2008;  110 501-503
  • 23 Sangun M K, Aydin E, Timur M, Karadeniz H, Caliskan M, Ozkan A. Comparison of chemical composition of the essential oil of Laurus nobilis L. leaves and fruits from different regions of Hatay, Turkey.  J Environment Biol. 2007;  28 731-733
  • 24 Cosimi S, Rossi E, Cioni P L, Canale A. Bioactivity and qualitative analysis of some essential oils from Mediterranean plants against stored-product pests: evaluation of repellency against Sitophilus zeamais Motschulsky, Cryptolestes ferrugineus (Stephens) and Tenebrio molitor (L.).  J Stored Prod Res. 2009;  45 125-132
  • 25 Wang R, Wang R, Yang B. Extraction of essential oils from five cinnamon leaves and identification of their volatile compound compositions.  Innovative Food Sci Emerg Technol. 2009;  10 289-292
  • 26 Du H, Li H. Antioxidant effect of cassia essential oil on deep-fried beef during the frying process.  Meat Sci. 2008;  78 461-468
  • 27 Gilani A H, Shaha A J, Zubair A, Khalid S, Kiani J, Ahmed A, Rasheed M, Ahmad V U. Chemical composition and mechanisms underlying the spasmolytic and bronchodilatory properties of the essential oil of Nepeta cataria L.  J Ethnopharmacol. 2009;  121 405-411
  • 28 Heuskin S, Godin B, Leroy P, Capella Q, Wathelet J-P, Verheggen F, Haubruge E, Lognay G. Fast gas chromatography characterisation of purified semiochemicals from essential oils of Matricaria chamomilla L. (Asteraceae) and Nepeta cataria L. (Lamiaceae).  J Chromatogr A. 2009;  1216 2768-2775
  • 29 Burfield T. Cedarwood oils. Part 1.  Aromather Times. 2002;  1 14-15
  • 30 Lawrence B M. Progress in essential oils.  Perfumer Flavorist. 2005;  30 56-67
  • 31 Wu L-Y, Gao H-Z, Wang X-L, Ye J-H, Lu J-L, Liang Y-R. Analysis of chemical composition of Chrysanthemum indicum flowers by GC/MS and HPLC.  J Med Plant Res. 2010;  4 421-426
  • 32 Zhu S, Yang Y, Yu H, Ying Y, Zou G. Chemical composition and antimicrobial activity of the essential oils of Chrysanthemum indicum.  J Ethnopharmacol. 2005;  96 151-158
  • 33 Fichi G, Flamini G, Zaralli L J, Perrucci S. Efficacy of an essential oil of Cinnamomum zeylanicum against Psoroptes cuniculi.  Phytomedicine. 2007;  14 227-231
  • 34 Singh G, Maurya S, DeLampasona M P, Catalan C A N. A comparison of chemical, antioxidant and antimicrobial studies of cinnamon leaf and bark volatile oils, oleoresins and their constituents.  Food Chem Toxicol. 2007;  45 1650-1661
  • 35 Nakahara K, Alzoreky N S, Yoshihashi T, Nguyen H T T, Trakoontivakorn G. Chemical composition and antifungal activity of essential oil from Cymbopogon nardus (citronella grass).  Jpn Intl Res Center Agric Sci. 2003;  37 249-252
  • 36 Sethi M L, Taneja S C, Dhar K L, Atal C K. Chemical investigations on the essential oil of Burmese citronella.  Indian Perfumer. 1979;  23 167-171
  • 37 Guan W, Li S, Yan R, Tang S, Quan C. Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other three traditional extraction methods.  Food Chem. 2007;  101 1558-1564
  • 38 Msaada K, Taarit M B, Hosni K, Hammami M, Marzouk B. Regional and maturational effects on essential oils yields and composition of coriander (Coriandrum sativum L.) fruits.  Sci Hortic. 2009;  122 116-124
  • 39 Zheljazkova V D, Pickett K M, Caldwell C D, Pincock J A, Roberts J C, Mapplebeck L. Cultivar and sowing date effects on seed yield and oil composition of coriander in Atlantic Canada.  Indian Crops Prod. 2008;  28 88-94
  • 40 Tapondjou A L, Adler C, Fontem D A, Bouda H, Reichmuth C. Bioactivities of cymol and essential oils of Cupressus sempervirens and Eucalyptus saligna against Sitophilus zeamais Motschulsky and Tribolium confusum du Val.  J Stored Prod Res. 2005;  41 91-102
  • 41 Sacchetti O G, Maietti S, Muzzoli M, Scaglianti M, Manfredini S, Radice M, Bruni R. Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods.  Food Chem. 2005;  91 621-632
  • 42 Bailer J, Aichinger T, Hackl G, de Hueber K, Dachler M. Essential oil content and composition in commercially available dill cultivars in comparison to caraway.  Indian Crops Prod. 2001;  14 229-239
  • 43 Callan N W, Johnson D L, Westcott M P, Welty L E. Herb and oil composition of dill (Anethum graveolens L.): Effects of crop maturity and plant density.  Indian Crops Prod. 2007;  25 282-287
  • 44 Kimbaris A C, Siatis N G, Daferera D J, Tarantilis P A, Pappas C S, Polissiou M G. Comparison of distillation and ultrasound-assisted extraction methods for the isolation of sensitive aroma compounds from garlic (Allium sativum).  Ultrason Sonochem. 2006;  13 54-60
  • 45 Shaath N A, Flores F B, Ositian M, Aal M A- E. The essential oil of Allium sativum L., Liliaceae (garlic). Charalambous G Food flavors: generation, analysis and process influence. Amsterdam; Elsevier Science 1995: 2025-2037
  • 46 Seo S-M, Kim J, Lee S-G, Shin C-H, Shin S-C, Park I-K. Fumigant antitermitic activity of plant essential oils and components from ajowan (Trachyspermum ammi), allspice (Pimenta dioica), caraway (Carum carvi), dill (Anethum graveolens), geranium (Pelargonium graveolens), and litsea (Litsea cubeba) oils against Japanese termite (Reticulitermes speratus Kolbe).  J Agric Food Chem. 2009;  57 6596-6602
  • 47 Singh G, Kapoor I P S, Singh P, de Heluani C S, de Lampasona M P, Catalan C A N. Chemistry, antioxidant and antimicrobial investigations on essential oil and oleoresins of Zingiber officinale.  Food Chem Toxicol. 2008;  46 3295-3302
  • 48 Sakamura F. Changes in volatile constituents of Zingiber officinale rhizomes during storage and cultivation.  Phytochemistry. 1987;  26 2207-2212
  • 49 Chutia M, Deka Bhuyan P, Pathak M G, Sarma T C, Boruah P. Antifungal activity and chemical composition of Citrus reticulata Blanco essential oil against phytopathogens from North East India.  LWT – Food Sci Technol. 2009;  42 777-778
  • 50 Bates R B, Slagel R C. Terpenoids. VI. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils.  Chem Ind. 1962;  1715-1716
  • 51 Yatagai M, Sat T, Takahashi T. Terpenes of leaf oils from Cupressaceae.  Biochem Syst Ecol. 1985;  13 377-385
  • 52 Burfield T. Cedarwood oils – part 2.  Aromather Times. 2003;  1 14-16
  • 53 Nozoe T, Yasue A, Yamane K. On the acidic constituents of the essential oil of Thujopsis dolabrata. Occurrence of α-thujaplicin.  Proc Jpn Acad. 1951;  27 15-17
  • 54 Zhang G, Chen C, Chen Z, Chen R, Lin X. Analysis of principle component and chemistry type of essential oil from Cinnamomum camphora leaf in Fujian province.  Zhiwu Ziyuan Yu Huanjing Xuebao. 2008;  17 24-27
  • 55 Nguyen X D, Trinh D C, Nguyen B T, Pham V K, Leclerco P A. Constituents of the leaf oil of Cinnamomum camphora Nees et Eberm from Hue.  Tap Chi Hoa Hoc. 1994;  32 64-66
  • 56 Kazazi H, Rezaei K, Ghotb-Sharif S J, Emam-Djomeh Z, Yamini Y. Supercriticial fluid extraction of flavors and fragrances from Hyssopus officinalis L. cultivated in Iran.  Food Chem. 2007;  105 805-811
  • 57 Langa E, Cacho J, Palavra A M F, Burillo J, Mainar A M, Urieta J S. The evolution of hyssop oil composition in the supercritical extraction curve.  J Supercrit Fluids. 2009;  49 37-44
  • 58 Chalchat J-C, Adamovic D, Gorunovic M S. Composition of oils of three cultivated forms of Hyssopus officinalis endemic in Yugoslavia: f. albus Alef., f. cyaneus Alef. and f. ruber Mill.  J Essent Oil Res. 2001;  13 419-421
  • 59 Rath C C, Devi S, Dash S K, Mishra R K. Antibacterial potential assessment of jasmine essential oil against E. coli.  Indian J Pharm Sci. 2008;  70 238-241
  • 60 Sandeep, Paarakh P M. Jasminum grandiflorum Linn (Chameli): ethnobotany, phytochemistry and pharmacology – a review.  Pharmacol Online. 2009;  2 586-595
  • 61 Angioni A, Barra A, Russo M T, Coroneo V, Dessi S, Cabras P. Chemical composition of the essential oils of Juniperus from ripe and unripe berries and leaves and their antimicrobial activity.  J Agric Food Chem. 2003;  51 3073-3078
  • 62 Al-Reza S M, Rahman A, Kang S C. Chemical composition and inhibitory effect of essential oil and organic extracts of Cestrum nocturnum L. on food-borne pathogens.  Int J Food Sci Technol. 2009;  44 1176-1182
  • 63 Salehi F A R P, Heydari R, Ebrahimi S N, Haddad P R. Hydrodistillation-headspace solvent microextraction, a new method for analysis of the essential oil components of Lavandula angustifolia Mill.  J Chromatogr A. 2005;  1098 14-18
  • 64 Daferera D J, Ziogas B N, Polissiou M G. GC-MS analysis of essential oils from some Greek aromatic plants and their fungitoxicity on Penicillium digitatum.  J Agric Food Chem. 2000;  48 2576-2581
  • 65 Flamini G, Tebano M, Cioni P L. Volatiles emission patterns of different plant organs and pollen of Citrus limon.  Anal Chim Acta. 2007;  589 120-124
  • 66 El-Zalabani S M, Koheil M M, Meselhy K M, El-Gizawy H A, Sleem A A. Effect of seasonal variation on composition and bioactivities of the essential oil of Eucalyptus citriodora Hook. grown in Egypt.  Egyptian J Biomed Sci. 2007;  24 260-276
  • 67 Brophy J J, Goldsack R J, Punruckvong A, Bean A R, Forster P I, Lepschi B J, Doran J C, Rozefelds A C. Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 7. Leptospermum petersonii, L. liversidgei and allies.  Flav Fragr J. 2000;  15 342-351
  • 68 Patil J R, Jayaprakasha G K, Murthy K N C, Tichy S E, Chetti M B, Patil B S. Apoptosis-mediated proliferation inhibition of human colon cancer cells by volatile principles of Citrus aurantifolia.  Food Chem. 2009;  114 1351-1358
  • 69 Douglas M H, van Klink J W, Smallfield B M, Perry N B, Anderson R E, Johnstone, Weavers R T. Essential oils from New Zealand manuka: triketone and other chemotypes of Leptospermum scoparium.  Phytochemistry. 2004;  65 1255-1264
  • 70 Perry N B, Brennan N J, Van Klink J W, Harris W, Douglas M H, McGimpsey J A, Smallfield B M, Anderson R E. Essential oils from New Zealand manuka and kanuka: chemotaxonomy of Leptospermum.  Phytochemistry. 1997;  44 1485-1494
  • 71 Vági E, Simándi B, Suhajda A, Héthelyi E. Essential oil composition and antimicrobial activity of Origanum majorana L. extracts obtained with ethyl alcohol and supercritical carbon dioxide.  Food Res Int. 2005;  38 51-57
  • 72 Vera R R, Chane-Ming J. Chemical composition of the essential oil of marjoram (Origanum majorana L.) from Reunion Island.  Food Chem. 1999;  66 143-145
  • 73 Lalko J, Api A M. Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay.  Food Chem Toxicol. 2006;  44 739-746
  • 74 Lawrence B M. Progress in essential oils.  Perfumer Flavorist. 2006;  31 54-57
  • 75 Brophy J J, Davies N W, Southwell I A, Stiff I A, Williams L R. Gas chromatographic quality control for oil of melaleuca terpinen-4-ol type (Australian tea tree).  J Agric Food Chem. 1989;  37 1330-1335
  • 76 Marengo E, Baiocchi C, Gennaro M C, Bertolo P L, Lanteri S, Garrone W. Classification of essential mint oils of different geographic origin by applying pattern recognition methods to gas chromatographic data.  Chemometrics Intell Lab Syst. 1991;  11 75-88
  • 77 Tao N-G, Liu Y-J, Zhang M-L. Chemical composition and antimicrobial activities of essential oil from the peel of bingtang sweet orange (Citrus sinensis Osbeck).  Int J Food Sci Technol. 2009;  44 1281-1285
  • 78 Raina V K, Srivastava S K, Aggarwal K K, Syamasundar K V, Khanuja S P S. Essential oil composition of Cymbopogon martinii from different places in India.  Flav Fragr. 2003;  18 312-315
  • 79 Petropoulos S A, Daferera D, Polissiou M G, Passam H C. Effect of nitrogen-application rate on the biomass, concentration, and composition of essential oils in the leaves and roots of three types of parsley.  J Plant Nutr Soil Sci. 2009;  172 210-215
  • 80 Nikiforov A, Jirovetz L, Buchbauer G, Raverdino V. GC-FTIR and GC-MS in odour analysis of essential oils.  Microchim Acta. 2005;  95 193-198
  • 81 Orav A, Stulova I, Kailas T, Müürisepp M. Effect of storage on the essential oil composition of Piper nigrum L. fruits of different ripening states.  J Agric Food Chem. 2004;  52 2582-2586
  • 82 Kapoor I P S, Singh B, Singh G, De Heluani C S, De Lampasona M P, Catalan C A N. Chemistry and in vitro antioxidant activity of volatile oil and oleoresins of black pepper (Piper nigrum).  J Agric Food Chem. 2009;  57 5358-5364
  • 83 Kowalski R, Wawrzykowski J. Essential oils analysis in dried materials and granulates obtained from Thymus vulgaris L., Salvia officinalis L., Mentha piperita L. and Chamomilla recutita L. Essential oil analysis in dried materials and granulates.  Flav Fragr. 2009;  24 31-35
  • 84 Aziz E E, Craker L E. Essential oil constituents of peppermint, pennyroyal, and apple mint grown in a desert agrosystem.  J Herbs Spices Med Plants. 2009;  15 361-367
  • 85 Judzentiene A, Kupcinskiene E. Chemical composition on essential oils from needles of Pinus sylvestris L. grown in northern Lithuania.  J Essent Oil Res. 2008;  20 26-29
  • 86 Ustun O, Sezik E, Kurkcuoglu M, Baser K H C. Study of the essential oil composition of Pinus sylvestris from Turkey.  Chem Nat Comp. 2006;  42 26-31
  • 87 Almasirad A, Amanzadeh Y, Taheri A, Iranshahi M. Composition of a historical rose oil sample (Rosa damascena Mill., Rosaceae).  J Essent Oil Res. 2007;  19 110-112
  • 88 Gillij Y G, Gleiser R M, Zygadlo J A. Mosquito repellent activity of essential oils of aromatic plants growing in Argentina.  Bioresour Technol. 2008;  99 2507-2515
  • 89 Geneva M P, Stancheva I V, Boychinova M M, Mincheva N H, Yonova P A. Effects of foliar fertilization and arbuscular mycorrhizal colonization on Salvia officinalis L. growth, antioxidant capacity, and essential oil composition.  J Sci Food Agric. 2010;  90 696-702
  • 90 Kamatou G P P, Makunga N P, Ramogola W P N, Viljoen A M. South African Salvia species: a review of biological activities and phytochemistry.  J Ethnopharmacol. 2008;  119 664-672
  • 91 Loizzo M R, Menichini F, Tundis R, Bonesi M, Nadjafi F, Saab A M, Frega N G, Menichini F. Comparative chemical composition and antiproliferative activity of aerial parts of Salvia lerifolia Benth. and Salvia acetabulosa L. essential oils against human tumor cell in vitro models.  J Med Food. 2010;  13 62-69
  • 92 Cardile V, Russo A, Formisano C, Rigano D, Senatore F, Arnold N A, Piozzi F. Essential oils of Salvia bracteata and Salvia rubifolia from Lebanon: chemical composition, antimicrobial activity and inhibitory effect on human melanoma cells.  J Ethnopharmacol. 2009;  126 265-272
  • 93 Jones C G, Plummer J A, Barbour E L. Non-destructive sampling of Indian sandalwood (Santalum album L.) for oil content and composition.  J Essent Oil Res. 2007;  19 157-164
  • 94 Lawrence B M. Progress in essential oils.  Perfumer Flavorist. 2005;  30 56-67
  • 95 Kiran U, Patra D D. Influence of natural essential oils and their by-products as nitrification retarders in regulating nitrogen utilization for Japanese mint in sandy loam soils of subtropical central India.  Agric Ecosyst Environ. 2003;  94 237-245
  • 96 Wang Z, Wang L, Li T, Zhou X, Ding L, Yu Y, Yu A, Zhang H. Rapid analysis of the essential oils from dried Illicium verum Hook. f. and Zingiber officinale Rosc. by improved solvent-free microwave extraction with three types of microwave-absorption medium.  Anal Bioanal Chem. 2006;  386 1863-1868
  • 97 Dzamic A, Sokovic M, Ristic M S, Grijic-Jovanovic S, Vukojevic J, Marin P D. Chemical composition and antifungal activity of Illicium verum and Eugenia caryophyllata essential oils.  Chem Nat Comp. 2009;  45 259-261
  • 98 Lawrence B M. Progress in essential oils.  Perfumer Flavorist. 2009;  34 54-58
  • 99 Khodakov G V, Kotikov I V, Pankovetskii V N. Component composition of essential oil from Artemisia abrotanum and A. dracunculus.  Chem Nat Comp. 2009;  45 905-908
  • 100 Argyropoulou C, Daferera D, Tarantilis P A, Fasseas C, Polissiou M. Chemical composition of the essential oil from leaves of Lippia citriodora H. B. K. (Verbenaceae) at two developmental stages.  Biochem Syst Ecol. 2007;  35 831-837
  • 101 Champagnat P, Figueredo G, Chalchat J-C, Carnat A-P. A study on the composition of commercial Vetiveria zizanioldes oils from different geographical origins.  J Essent Oil Res. 2006;  18 416-422
  • 102 Cu J Q, Perineau F, Gaset A. Volatile components of violet leaves.  Phytochemistry. 1992;  31 571-573
  • 103 Tisserand R. Essential oil safety.  Int J Aromather. 1996;  7 28-32
  • 104 Martín C, Moure A, Martín G, Carrillo E, Domínguez H, Parajó J C. Fractional characterisation of jatropha, neem, moringa, trisperma, castor and candlenut seeds as potential feedstocks for biodiesel production in Cuba.  Bioresour Technol. 2010;  34 533-538
  • 105 Bicchi C, Cordero C, Liberto E, Sgorbini B, Rubiolo P. Headspace sampling of the volatile fraction of vegetable matrices.  J Chromatogr A. 2008;  1184 220-233
  • 106 Christie W W. The analysis of evening primrose oil.  Indian Crops Prod. 1999;  10 73-83
  • 107 Jeong J B, Ju S Y, Park J H, Lee J R, Yun K W, Kwon S T, Lim J-H, Chung G Y, Jeong H J. Antioxidant activity in essential oils of Cnidium officinale makino and Ligusticum chuanxiong hort and their inhibitory effects on DNA damage and apoptosis induced by ultraviolet B in mammalian cell.  Cancer Epidemiol. 2009;  33 41-46
  • 108 Nabloussi A, Márquez-Lema M, Fernández-Martínez A, Velasco L. Novel seed oil types of Ethiopian mustard with high levels of polyunsaturated fatty acids.  Indian Crops Prod. 2008;  27 359-363
  • 109 Sidhu O P, Kumar V, Behl H M. Variability in triterpenoids (nimbin and salanin) composition of neem among different provenances of India.  Indian Crops Prod. 2004;  19 69-75
  • 110 Patumi M, d'Andria R, Marsilio V, Fontanazza G, Morelli G, Lanza B. Olive and olive oil quality after intensive monocone olive growing (Olea europaea L., cv. Kalamata) in different irrigation regimes.  Food Chem. 2002;  77 27-34
  • 111 Nitta M, Kobayashi H, Ohnishi-Kameyama M, Nagamine T, Yoshida M. Essential oil variation of cultivated and wild perilla analyzed by GC/MS.  Biochem Syst Ecol. 2006;  34 25-37
  • 112 Longvah T, Deosthale Y G, Kumar P U. Nutritional and short term toxicological evaluation of Perilla seed oil.  Food Chem. 2000;  70 13-16
  • 113 Koezuka Y, Honda G, Tabata M. Genetic control of the chemical composition of volatile oils in Perilla frutescens.  Phytochemistry. 1986;  25 859-863
  • 114 Lee D-S, Lee E-S, Kim H-J, Kim S-O, Kim K. Reversed phase liquid chromatographic determination of triacylglycerol composition in sesame oils and the chemometric detection of adulteration.  Anal Chim Acta. 2001;  429 321-330
  • 115 Ribeiro A P B, Grimaldi R, Gioielli L A, Gonçalves L A G. Zero trans fats from soybean oil and fully hydrogenated soybean oil: physico-chemical properties and food applications.  Food Res Int. 2009;  42 401-410
  • 116 Orban G J, Staton J A. Insect repellent compositions based on essential oils. World Patent 2004010783. 2004
  • 117 He J, Yang X, Wang Y, Li W, Zhao J, Feng J, Zhang X. Plant-derived mosquito repellent synergist. Chinese Patent 101558769. 2009
  • 118 Samson G B. Organic floor wash with disinfectant and mosquito repellent properties. Indian Patent 2007CH00296. 2007
  • 119 Wang Z, Wan T, Zhang J, Liu H, Zhang X, Feng J, Zhang X. Plant-derived synergistic agent for mosquito incense and its preparation process. Chinese Patent 101558770. 2009
  • 120 Inoue S, Hario S, Umibe H. Synergistic insect-repelling microcapsules containing toluamides and isobornyl compounds, for textiles. Japanese Patent 03148203. 1991
  • 121 Peng X. Mosquito-repellent solution containing natural pyrethrin. Chinese Patent 1739353. 2006
  • 122 Bit K C, Rao S R, Sen K. Synergistic insect repellent compositions containing dimethyl phthalate, allyl sulfate, and oils. Indian Patent 2003DE00243. 2007
  • 123 Singh K S P, Kumar T A, Kumar A K, Kumar S M, Kumar S A, Raj B J, Anju Y, Dinesh K, Sudeep T, Anirban P, Umrao B D, Mansoor A, Prakash D O. Slow-vaporizing anti-mosquito synergistic insecticidal herbal formulation comprising essential oil. Indian Patent 2008DE00607. 2010
  • 124 Gilbert B, Teixeira D F, Pereira J F G, Silva Jr I V, Svaiter A, Oliveira Filho A M, Santos C E. Mosquito-repellent fumigant. Brazilian Patent 9800437. 2000
  • 125 Ribas J, Carreno A M. Evaluation of the use of repellent against mosquito bite by military personnel in the Amazon Basin.  An Bras Dermatol. 2010;  85 33-38
  • 126 Erler F, Ulug I, Yalcinkaya B. Repellent activity of five essential oils against Cx. pipiens.  Fitoterapia. 2006;  77 491-494
  • 127 Lin X. Repellent effects of plant essential oils on laboratory animals.  Zhonghua Weisheng Shachong Yaoxie. 2009;  15 430-431
  • 128 Amer A, Mehlhorn H. Repellency effect of forty-one essential oils against Aedes, Anopheles, and Culex mosquitoes.  Parasitol Res. 2006;  99 478-490
  • 129 Onanong N, Usawadee S, Napaporn U, Satit P, Apinan S, Uracha R. In vitro characterization and mosquito (Aedes aegypti) repellent activity of essential-oils-loaded nanoemulsions.  AAPS Pharm Sci Technol. 2009;  10 1234-1242
  • 130 Drapeau J, Froehler C, Touraud D, Kroeckel U, Geier M, Rose A, Kunz W. Repellent studies with Aedes aegypti mosquitoes and human olfactory tests on 19 essential oils from Corsica, France.  Flav Fragr J. 2009;  24 160-169
  • 131 Rudolfs W. Effect of chemicals upon the behavior of mosquitoes.  New Jersey Agric Exp Station Bull. 1930;  2 496-520
  • 132 Yang Y-C, Lee E-H, Lee H-S, Lee D-K, Ahn Y-J. Repellency of aromatic medicinal plant extracts and a steam distillate to Aedes aegypti.  J Am Mosq Control Assoc. 2004;  20 146-149
  • 133 Zhu J, Zeng X, Yanma L T, Qian K, Han Y, Xue S, Tucker B, Schultz G, Coats J, Rowley W, Zhang A. Adult repellency and larvicidal activity of five plant essential oils against mosquitoes.  J Am Mosq Control Assoc. 2006;  22 515-522
  • 134 Zhu J J, Zeng X-P, Berkebile D, Du H-J, Tong Y, Qian K. Efficacy and safety of catnip (Nepeta cataria) as a novel filth fly repellent.  Med Vet Entomol. 2009;  23 209-216
  • 135 Curtis C F, Lines J D, Callaghan A, Hill N, Karimzad M A. The relative efficiency of repellents against mosquito vectors of disease.  Med Vet Entomol. 1987;  1 109-119
  • 136 Prajapati V, Tripathi A K, Aggarwal K K, Khanuja S P S. Insecticidal, repellent and oviposition-deterrent activity of selected essential oils against Anopheles stephensi, Aedes aegypti and Cx. quinquefasciatus.  Bioresour Technol. 2005;  96 1749-1757
  • 137 Gibson A. Mosquito-suppression work in Canada in 1937.  Ann Meet NJ Mosq Exterm Assoc. 1938;  25 176-185
  • 138 Tawatsin A, Wratten S D, Scott R R, Thavara U, Techadamrongsin Y. Repellency of volatile oils from plants against three mosquito vectors.  J Vector Ecol. 2001;  26 76-82
  • 139 Bindra R L, Agarwal K K, Shukla Y N, Agarwal S K, Kumar S. Essential oil formulations as mosquito repellents in floor cleaners.  Indian Perfumer. 2001;  45 269-273
  • 140 Thorsell W, Mikiver A, Malander I, Tunon H. Efficacy of plant extracts and oils as mosquito repellents.  Phytomedicine. 1998;  5 311-323
  • 141 Makhaik M, Naik S N, Tewary D K. Evaluation of anti-mosquito properties of essential oils.  J Sci Indian Res (India). 2005;  64 129-133
  • 142 Yang P, Ma Y. Repellent effect of plant essential oils against Aedes albopictus.  J Vector Ecol. 2005;  30 231-234
  • 143 Moore S J, Lenglet A, Hill N. Field evaluation of three plant-based insect repellents against malaria vectors in Vaca Diez Province, the Bolivian Amazon.  J Am Mosq Control Assoc. 2002;  18 107-110
  • 144 Kim S-I, Chang K-S, Yang Y-C, Kim B-S, Ahn Y-J. Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions.  Pest Manag Sci. 2004;  60 1125-1130
  • 145 Kim D-H, Kim S-I, Chang K-S, Ahn Y-J. Repellent activity of constituents identified in Foeniculum vulgare fruit against Aedes aegypti (Diptera: Culicidae).  J Agric Food Chem. 2002;  50 6993-6996
  • 146 Bhuyan M, Saxena N, Rao K M. Repellent property of oil fraction of garlic, Allium sativum (Linn.).  Indian J Exp Biol. 1974;  12 575-576
  • 147 Qualls W A, Xue R-D. Field evaluation of three botanical repellents against Psorophora ferox, Aedes atlanticus, and Aedes mitchellae.  J Am Mosq Control Assoc. 2009;  25 379-381
  • 148 Osmani Z, Anees I, Naidu M B. Insect repellent creams from essential oils.  Pesticides. 1972;  6 19-21
  • 149 Matsumoto A, Matsumoto T, Yamashita M, Nitsuta I, Kobayashi M, Mesaki J, Kashiwabara T. Harmful insect repellents containing edulan derivatives. Japanese Patent 05221808. 1993
  • 150 Kobayashi A, Mizutani T. Harmful insect-repellent foot bands and method for repelling harmful insects using them. Japanese Patent 2004051564. 2004
  • 151 Kang S-H, Kim M-K, Seo D-K, Noh D-J, Yang J-O, Yoon C, Kim G-H. Comparative repellency of essential oils against Cx. pipiens pallens (Diptera: Culicidae).  J Korean Soc Appl Biol Chem. 2009;  52 353-359
  • 152 Oshaghi M A, Ghalandari R, Vatandoost H, Shayeghi M, Kamalinejad M, Tourabi-Khaledi H, Abolhassani M, Hashemzadeh M. Repellent effect of extracts and essential oils of Citrus limon (Rutaceae) and Melissa officinalis (Labiatae) against main malaria vector, Anopheles stephensi (Diptera: Culicidae).  Iran J Public Health. 2003;  32 47-52
  • 153 Moore S J, Darling S T, Sihuincha M, Padilla N, Devine G J. A low-cost repellent for malaria vectors in the Americas: results of two field trials in Guatemala and Peru.  Malar J. 2007;  6 1-6
  • 154 Maguranyi S K, Webb C E, Mansfield S, Russell R C. Are commercially available essential oils from Australian native plants repellent to mosquitoes?.  J Am Mosq Control Assoc. 2009;  25 292-300
  • 155 Molyneux W M. Mosquito and/or flea control with Leptospermum liversidgei and its essential oil. Canadian Patent 2234476. 1999
  • 157 Tawatsin A, Asavadachanukorn P, Thavara U, Wongsinkongman P, Bansidhi J, Boonruad T, Chavalittumrong P, Soonthornchareonnon N, Komalamisra N, Mulla M S. Repellency of essential oils extracted from plants in Thailand against four mosquito vectors (Diptera : Culicidae) and oviposition deterrent effects against Aedes aegypti (Diptera : Culicidae).  Southeast Asian J Trop Med Pub Health. 2006;  37 915-931
  • 158 Ding D, Sun H. Structural elucidation of an insect repellent in the essential oil of Mentha haplocalyx Briq.  Zhiwu Xuebao. 1983;  25 62-66
  • 159 Dubey V S. An overview of geraniol biosynthesis in palmarosa (Cymbopogon martinii Roxb. var. motia) and its biological and pharmacological properties.  Recent Progr Med Plants. 2006;  11 75-97
  • 160 Trongtokit Y, Rongsriyam Y, Komalamisra N, Apiwathnasorn C. Comparative repellency of 38 essential oils against mosquito bites.  Phytother Res. 2005;  19 303-309
  • 161 Ansari M A, Vasudevan P, Tandon M, Razdan R K. Larvicidal and mosquito repellent action of peppermint (Mentha piperita) oil.  Bioresour Technol. 2000;  71 267-271
  • 162 Tripathi A K, Prajapati V, Ahmad A, Aggarwal K K, Khanuja S P S. Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae).  J Med Entomol. 2004;  41 691-698
  • 163 Pavela R. Larvicidal property of essential oils against Cx. quinquefasciatus Say (Diptera: Culicidae).  Indian Crop Prod. 2009;  30 311-315
  • 164 Omolo M O, Okinyo D, Ndiege I O, Lwande W, Hassanali A. Repellency of essential oils of some Kenyan plants against Anopheles gambiae.  Phytochemistry. 2004;  65 2797-2802
  • 165 Dorfling E A, Mouton I. Insect repellents obtained from Lippia comprising monoterpenes. South African Patent ZA 9505853. 1997
  • 166 Tripathi A K, Prajapati V, Aggarwal K K, Khanuja S P, Kumar S. Repellency and toxicity of oil from Artemisia annua to certain stored-product beetles.  J Econ Entomol. 2000;  93 43-47
  • 167 Das N G, Baruah I, Talukdar P K, Das S C. Evaluation of botanicals as repellents against mosquitoes.  J Vector Borne Dis. 2003;  40 49-53
  • 168 Xue R-D, Alp A, Barnard D R. Laboratory evaluation of toxicity of 16 insect repellents in aerosol sprays to adult mosquitoes.  J Am Mosq Control Assoc. 2003;  19 271-274
  • 169 Vatandoost H, Hanafi-Bojd A A. Laboratory evaluation of 3 repellents against Anopheles stephensi in the Islamic Republic of Iran.  East Mediterr Health J. 2008;  14 260-267
  • 170 Barnard D R, Xue R-D. Laboratory evaluation of mosquito repellents against Aedes albopictus, Cx. nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae).  J Med Entomol. 2004;  41 726-730
  • 171 Sharma V P, Ansari M A, Razdan R K. Mosquito repellent action of neem (Azadirachta indica) oil.  J Am Mosq Control Assoc. 1993;  9 359-360
  • 172 Sharma S K, Dua V K, Sharma V P. Field studies on the mosquito repellent action of neem oil.  Southeast Asian J Trop Med Public Health. 1995;  26 180-182
  • 173 Dua V K, Nagpal B N, Sharma V P. Repellent action of neem cream against mosquitoes.  Indian J Malariol. 1995;  32 47-53
  • 174 Valecha N, Ansari M A, Prabhu S, Razdan R K. Preliminary evaluation of safety aspects of neem oil in kerosene lamp.  Indian J Malariol. 1996;  33 139-143
  • 175 Sharma V P, Ansari M A. Personal protection from mosquitoes (Diptera: Culicidae) by burning neem oil in kerosene.  J Med Entomol. 1994;  31 505-507
  • 176 Mishra A K, Singh N, Sharma V P. Use of neem oil as a mosquito repellent in tribal villages of Mandla District, Madhya Pradesh.  Indian J Malariol. 1995;  32 99-103
  • 177 Fradin M S, Day J F. Comparative efficacy of insect repellents against mosquito bites.  New Engl J Med. 2002;  347 13-18
  • 178 Ritchie S A, Williams C R, Montgomery B L. Field evaluation of new mountain sandalwood mosquito sticks and new mountain sandalwood botanical repellent against mosquitoes in North Queensland, Australia.  J Am Mosq Control Assoc. 2006;  22 158-160
  • 179 Sultana S, Ali M, Ansari S H, Bagri P. The effect of physical factors on chemical composition of the essential oil of Eucalyptus citriodora Hook. leaves.  J Essent Oilbearing Plants. 2008;  11 69-74
  • 180 Noosidum A, Prabaripai A, Chareonviriyaphap T, Chandrapatya A. Excito-repellency properties of essential oils from Melaleuca leucadendron L., Litsea cubeba (Lour.) Persoon, and Litsea salicifolia (Nees) on Aedes aegypti (L.) mosquitoes.  J Vector Ecol. 2008;  33 305-312
  • 181 Choochote W, Chaithong U, Kamsuk K, Jitpakdi A, Tippawangkosol P, Tuetun B, Champakaew D, Pitasawat B. Repellent activity of selected essential oils against Aedes aegypti.  Fitoterapia. 2007;  78 359-364
  • 182 Paluch G, Justingrodnitzky J, Bartholomay L, Coats J. Quantitative structure-activity relationship of botanical sesquiterpenes: spatial and contact repellency to the yellow fever mosquito, Aedes aegypti.  J Agric Food Chem. 2009;  57 7618-7625
  • 183 Hwang Y S, Wu K H, Kumamoto J, Axelrod H, Mulla M S. Isolation and identification of mosquito repellents in Artemisia vulgaris.  J Chem Ecol. 1985;  11 1297-1306
  • 184 Odalo J O, Omolo M O, Malebo H, Angira J, Njeru P M, Ndiege I O, Hassanali A. Repellency of essential oils of some plants from the Kenyan coast against Anopheles gambiae.  Acta Trop. 2005;  95 210-218
  • 185 Chang K-S, Tak J-H, Kim S-I, Lee W-J, Ahn Y-J. Repellency of Cinnamomum cassia bark compounds and cream containing cassia oil to Aedes aegypti (Diptera: Culicidae) under laboratory and indoor conditions.  Pest Manag Sci. 2006;  62 1032-1038
  • 186 Traboulsi A F, El-Haj S, Tueni M, Taoubi K, Nader N A, Mrad A. Repellency and toxicity of aromatic plant extracts against the mosquito Cx. pipiens molestus (Diptera: Culicidae).  Pest Manag Sci. 2005;  61 597-604
  • 187 Beboukian R H, Weldon P J. Spatial inhibitors, deterrents and repellents for mosquitoes and midges. World Patent 2007025197. 2007
  • 188 Sugimoto M. Mosquito repellents of plant origin. Japanese Patent 2004210756. 2004
  • 189 Hao H, Wei J, Dai J, Dui J. Host-seeking and blood-feeding behavior of Aedes albopictus (Diptera: Culicidae) exposed to vapors of geraniol, citral, citronellal, eugenol, or anisaldehyde.  J Med Entomol. 2008;  45 533-539
  • 190 Gu H-J, Cheng S-S, Lin C-Y, Huang C-G, Chen W-J, Chang S-T. Repellency of essential oils of Cryptomeria japonica (Pinaceae) against adults of the mosquitoes Aedes aegypti and Aedes albopictus (Diptera: Culicidae).  J Agric Food Chem. 2009;  57 11127-11133
  • 191 Coats J R, Peterson C J, Zhu J, Baker T C, Nemetz L T. Biorational terpenoid arthropod repellents obtained from plants. US Patent 6524605. 2003
  • 192 Gladkikh S G. Repellents for arthropod carriers of infectious diseases.  Zhurnal Mikrobiologii Epidemiologii i Immunobiologii. 1953;  11 61-65
  • 193 Blagoveshchenskii D I, Bregetova N G, Monchadskii A S. New deterrent substances for protecting man against the attacks of mosquitoes.  Bull Acad Sci USSR, Div Chem Sci (Engl. Transl.). 1943;  40 119-122
  • 194 Cantrell C L, Klun J A, Bryson C T, Kobaisy M, Duke S O. Isolation and identification of mosquito bite deterrent terpenoids from leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) beautyberry.  J Agric Food Chem. 2005;  53 5948-5953
  • 195 Kim S I, Yeon S H, Yoon H S, Ahn Y J. Natural repellent containing essential oils derived from Zanthoxylum armatum and/or Zanthoxylum piperitum. Korean Patent 955344. 2010
  • 196 Kim G H, Kang S H. Mosquito-repellent composition. Korean Patent 756397. 2007
  • 197 Darling S T. Mosquito repellent composition for skin. World Patent 2007082306. 2007
  • 198 Georges P S. Material controllingly releasing a liquid active substance by evaporation and a mosquito repellent bracelet comprising said material. World Patent 2007026082. 2007
  • 199 Thanispong K, Achee N L, Grieco J P, Bangs M J, Suwonkerd W, Prabaripai A, Chauhan K R, Chareonviriyaphap R. A high throughput screening system for determining the three actions of insecticides against Aedes aegypti (Diptera: Culicidae) populations in Thailand.  J Med Entomol. 2010;  47 833-841
  • 200 Hwang Y S, Schultz G W, Mulla M S. Structure-activity relationships of unsaturated fatty acids as mosquito ovipositional repellents.  J Chem Ecol. 1984;  10 145-151
  • 201 Nataraj S. Mosquito repellent comprising natural oils, turmeric powder, and camphor. Indian Patent 2003MA00347. 2005
  • 202 Lee Y I. Natural vegetable essential oil composition having sanitary insect pest exterminating and antibacterial effects and formulation thereof. Korean Patent 2000072252. 2000
  • 203 Gries R, Campbell C, Khaskin G, Avelino N, Gries G. Allyl sulfide compounds, and compositions and methods using said compounds for repelling blood-feeding arthropods. World Patent 2008116321. 2008
  • 204 Hallahan D L, Manzer L E. Preparation of dihydronepetalactone as insect repellent. International Patent 2005034626. 2005
  • 205 Ravid U, Putievsky E, Katzir I, Ikan R. Determination of the enantiomeric composition of terpinen-4-ol in essential oils using a permethylated β-cyclodextrin coated chiral capillary column.  Flav Fragr J. 1992;  7 49-52

Prof. Dr. Valter Ferreira de Andrade Neto

Laboratory of Malaria and Toxoplasmosis Biology
Department of Microbiology and Parasitology
Rio Grande do Norte Federal University (UFRN)

Campus Universitário

Lagoa Nova

CEP 59072-970 Natal – RN

Brazil

Phone: + 55 84 32 15 34 37, ext. 225, 226

Fax: + 55 84 32 11 92 10

Email: aneto@cb.ufrn.br