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Individual sampling approach to study the chemodiversity of volatile and semivolatile compounds of Mentha longifolia L. growing wild in Jiloca basin, Spain

Research Paper | October 1, 2015

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Juan Antonio Llorens-Molina, David García-Rellán, Sandra Vacas, Alejandro Bonet

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Int. J. Biosci.7( 4), 166-176, October 2015

DOI: http://dx.doi.org/10.12692/ijb/7.4.166-176


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Volatile and semivolatile composition of 47 individuals of Mentha longifolia L. collected from five locations in Jiloca basin (Teruel, Spain) was investigated to give insight into sources of chemical variability. It was determined by Simultaneous Distillation Extraction using a Likens-Nickerson apparatus and subsequent analysis by GC/MS and GC/FID. The statistical analysis of results allowed to identify four chemotypes: (a) pulegone (63.94 %) + isomenthone (16.67 %); (b) piperitone oxide (15.53 %) + piperitenone oxide (50.32 %); (c) α-terpineol acetate (39.81 %) + carvone acetate (33.84 %) and (d): (Z)-sabinenhydrate (41.15 %) + 1-terpinen-4-ol (13.99 %). The last two chemotypes have never been reported so far. As the sampling locations were selected with similar environmental conditions, the co-occurrence of different chemotypes in the same population turned out to be very noticeable. These results support the advisability of individual sampling instead of mixing material from randomly selected individuals, in order to identify and make available selected chemotypes for their propagation. It may be particularly useful for applied purposes based on relationships between chemical composition and biological activity.


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Individual sampling approach to study the chemodiversity of volatile and semivolatile compounds of Mentha longifolia L. growing wild in Jiloca basin, Spain

Adams RP. 2007. Identification of  essential  oil components by gas chromatography/mass spectrometry. Allured Publishing Corporation, Illinois, USA.

Ahmad I, Ahmad MSA, Ashraf M, Hussain M, Ashraf MY. 2011. Seasonal variation in some medicinal and biochemical ingredients in Mentha longifolia (l.) Huds. Pakistan Journal of Botany 43, 69-77.

Asekun OT, Grierson DS, Afolayan AJ. 2007. Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. Capensis. Food Chemistry 101(3), 995-998. http://dx.doi.org/10.1016/j.foodchem.2006.02052

Baser KHC, Kürkçüoglu M, Tarimcilar G, Kaynak G. 1999. Essential oils of Mentha species from Northern Turkey. Journal of Essential Oil Research 11(5), 579-588. http://dx.doi.org/10.1080/10412905.1999.9701218

Benzo M, Gilardoni G, Gandini C, Caccialanza G, Vidari G, Abdo S, Layedra P. 2007. Determination of the threshold odor concentration of main odorants in essential oils using gas chromatography-olfactometry incremental dilution technique, Journal of Chromatography. A 1150(1-2), 131-135. http://dx.doi.org/10.1016/j.chroma.2007.02031

Bertoli A, Leonardi M, Krzyzanowska J, Oleszek W, Pistelli L. 2011. Mentha longifolia in vitro cultures as safe source of flavouring ingredients. Acta Biochimica Polonica 58(4), 581-587.

Bhatia SP, Letizia CS, Api AM. 2008. Fragrance material review on 4-thujanol. Food and Chemical Toxicology 46(11), 295-296. http://dx.doi.org/10.1016/j.fct.2008.06024

Campo  E, Ferreira  V, Escudero  A,  Cacho  J. 2005. Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data. Journal of Agricultural and Food Chemistry 53(14), 5682-5690. http://dx.doi.org/10.1021/jf0478.70a

Chaintreau  A.  2001.  Simultaneous  distillation–extraction: from birth to maturity—review. Flavour and Fragrance Journal 16, 136-148.

De-sheng D, Han-dong S. 1983. Structural Determination of a Repellent Principle in the Essential Oil of Mentha haplocalyx, (植物学报(英文版), Briq. 1, 9. Web source: http://en.cnki.com.cn/Article_en/CJFDTOTAL-ZWXB198301009.htm

Dudai N, Segey D, Haykin-Frenkel D, Eshel A. 2005. Genetic Variation of Phenolic Compounds Content, Essential Oil Composition and Anti Oxidative Activity in Israel-Grown Mentha longifolia L. In: I International Symposium on Natural Preservatives in Food Systems, Princeton, USA, March 30-31, 2005, 709, 69-78. http://dx.doi.org/10.17660/ActaHortic.2006.7098

Duke SO. 2003. Ecophysiological aspects of allelopathy. Planta 217(4), 529-539.

Džamić AM, Soković MD, Ristić MS, Novaković M, Grujić-Jovanović S, Tešević V, Marin PD. 2010. Antifungal and antioxidant activity of Mentha longifolia (L.) Hudson (Lamiaceae) essential  oil.  Botanica  Serbica  34(1),  57-61.  Web access: http://botanicaserbica.bio.bg.ac.rs/arhiva/pdf/2010.34.1.509_full.pdf

Fleisher A, Fleisher Z. 1998. Volatile extracts of Mentha longifolia growing in Israel. Aromatic Plants of the Holy Land and the Sinai. Part XIII. Journal of Essential Oil Research 10, 647-648. http://dx.doi.org/10.1080/10412905.1998.9700997

Franzios G, Mirotsou M, Hatziapostolou E, Kral J, Scouras ZG, Mavragani-Tsipidou P. 1997. Insecticidal and genotoxic activities of mint essential oils. Journal of Agricultural and Food Chemistry 45(7), 2690-2694. http://dx.doi.org/10.1021/jf960.685f

Gulluce M, Sahin  F, Sokmen M, Ozer H, Daferera D, Sokmen A, Ozkan H. 2007. Antimicrobial and antioxidant properties of the essential oils  and  methanol  extract  from Mentha longifolia L. ssp. longifolia. Food Chemistry 103(4), 1449-1456. http://dx.doi.org/10.1016/j.foodchem.2006.10061

Hafedh H, Fethi BA, Mejdi S, Emira N, Amina B. 2010. Effect of Mentha longifolia L. ssp longifolia essential oil on the morphology of four pathogenic bacteria visualized by atomic force microscopy. African Journal of Microbiology Research 4(11), 1122-1127.

Hajlaoui H, Snoussi M, Jannet HB, Mighri Z, Bakhrouf A. 2008. Comparison of chemical composition and antimicrobial activities of Mentha longifolia L. ssp. longifolia essential oil from two Tunisian localities (Gabes and Sidi Bouzid). Annals of Microbiology 58(3), 513-520.

Hajlaoui H, Trabelsi N, Noumi E, Snoussi M, Fallah H, Ksouri R, Bakhrouf A. 2009. Biological activities of the essential oils and methanol extract of tow cultivated mint species (Mentha longifolia and Mentha pulegium) used in the Tunisian folkloric medicine. World Journal of Microbiology and Biotechnology 25(12), 2227-2238. http://dx.doi.org/10.1007/s11274-009-0130.3

Hussain A, Anwar F, Nigam PS, Ashraf M, Gilani AH. 2010. Seasonal variation in content, chemical composition and antimicrobial and cytotoxic activities of essential oils from four Mentha species. Journal of the Science of Food and Agriculture 90(11), 1827-1836. http://dx.doi.org/10.1002/jsfa.40.21

Iqbal T, Hussain A I, Chatha SAS, Naqvi SAR, Bokhari TH. 2013. Antioxidant activity and volatile and phenolic profiles of essential oil and different extracts of wild mint (Mentha longifolia) from the Pakistani  Flora.  Journal  of  Analytical  Methods  in Chemistry 2013, 1-6. http://dx.doi.org/10.1155/2013/5364.90

Jamzad M, Jamzad Z, Mokhber F, Ziareh S, Yari M. 2013. Variation in essential oil composition of Mentha longifolia var. chlorodichtya Rech. f. and Ziziphora clinopodiodes Lam. growing in different habitats. Journal of Medicinal Plants Research 7(22), 1618-1623. Web access: http://www.academicjournals.org/article/article1380793489Jamzad%20et%20al.pdf

Kokkini S, Papageorgiou VP. 1988. Constituents of essential oils from Mentha longifolia growing wild in Greece. Planta Medica 54(1), 59-60.

Koliopoulos G, Pitarokili D, Kioulos E, Michaelakis A, Tzakou O. 2010. Chemical composition and larvicidal evaluation of Mentha, Salvia, and Melissa essential oils against the West Nile virus mosquito Culex pipiens. Parasitology Research 107(2), 327-335. http://dx.doi.org/10.1007/s00436-010-1865.3

Kordali S, Cakir A, Sutay S. 2007. Inhibitory effects of monoterpenes on seed germination and seedling growth. Z Naturforsch C 62(3/4), 207. http://dx.doi.org/10.1515/znc-2007-3.409

Lawrence BM. 2006. Oil Composition of the Other Mentha Species and Hybrids, B. M. Lawrence, in Mint: The genus Mentha. Florida, USA: CRC Press.

Liendo D, Biurrun I, Campos JA, Herrera M, Loidi J, García-Mijangos I. 2013. Invasion patterns in riparian habitats: The role of anthropogenic pressure in temperate streams. Plant Biosystems – An International Journal Dealing with all Aspects of Plant Biology 149(2), 289-297. http://dx.doi.org/10.1080/11263504.2013.82243.4

Llorens-Molina JA, Vacas S, López S, Rivero CF, García-Rellán D, Boira H. 2012. Diurnal and environmental variations in essential oil composition of Mentha suaveolens L. and Mentha longifolia L. populations from the Eastern Iberian Peninsula. Proceedings of International Symposium on Essential Oils, 5 to 8 September 2012, Lisbon (Portugal), 108.

Llorens-Molina JA, Vacas S, García D, Verdeguer M. 2014. Individual Monitoring to Study Organ and Diurnal Variations in Mentha longifolia L. Natural Volatiles & Essential Oils 1(1), 73-79.

Maffei M. 1988. A chemotype of Mentha longifolia (L.) Hudson particularly rich in piperitenone oxide. Flavour and Fragrance Journal 3(1), 23-26. http://dx.doi.org/10.1002/ffj.2730030105

Mastelic J, Jerkovic I. 2002. Free and glycosidically bound volatiles of Mentha longifolia growing in Croatia. Chemistry of Natural Compounds 38(6), 561-564. http://dx.doi.org/10.1023/A:1022634704232

Mimica-Dukić N, Bozin B, Soković M, Mihajlović B, Matavulj M. 2003. Antimicrobial and antioxidant activities of three Mentha species essential oils. Planta Medica 69(5), 413-419. http://dx.doi.org/10.1055/s-2003-39704

Mkaddem M, Bouajila J, Ennajar M, Lebrihi A, Mathieu F, Romdhane M. 2009. Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils. Journal of Food Science 74(7), 358-363. http://dx.doi.org/10.1111/j.1750-3841.2009.012.72.x

Mondello L. 2012. HS-SPME-GCxGC-MS analysis of Yerba Mate (Ilex paraguariensis) in Shimadzu GC-GC application compendium of comprehensive 2D GC, Vol. 1-5, Shimadzu Corp. 2012, 1-29.

Monfared A, Nabid MR, Rustaiyan A. 2002. Composition of a carvone chemotype of Mentha longifolia L. Huds. from Iran. Journal of Essential Oil Research 14(1), 51-52. http://dx.doi.org/10.1080/10412905.2002.9699761

Moradalizadeh M, Khodashenas M, Amirseifadini L, Ganjehkaviri M. 2014. Identification of chemical compounds in essential oils from stems, leaves and flowers of Mentha longifolia Var. kermanensis by GC/MS. International Journal of Biosciences 4(6), 117-121. http://dx.doi.org/10.12692/ijb/4.6.117-121

Nikšić H, Bešović EK, Makarević E, Durić K. 2012. Chemical composition, antimicrobial and antioxidant properties of Mentha longifolia (L.) Huds. essential oil. Journal of Health Sciences 2(3), 192-200. http://dx.doi.org/10.17532/jhsci.2012.3.8

Pajohi MR, Tajik H, Farshid AA, Basti AA, Hadian M. 2011. Effects of Mentha longifolia L. essential oil and nisin alone and in combination on Bacillus cereus and Bacillus subtilis in a food model and bacterial ultrastructural changes. Foodborne Pathogens and Disease 8(2), 283-290.

Raya MD, Utrilla MP, Navarro MC, Jimenez J. 1990. CNS activity of Mentha rotundifolia and Mentha longifolia essential oil in mice and rats. Phytotherapy Research 4(6), 232-234. http://dx.doi.org/10.1002/ptr.26500406.06

Saeidi Z, Saeidi KA, Salehi A, Jouneghani RS, Amirshekari H, Taghipour A. 2012. Essential oil content and composition of Mentha longifolia (L.) Hudson grown wild in Iran. Journal of Medicinal Plants Research 6(29), 4522-4525. http://dx.doi.org/10.5897/JMPR11.933

Segev D, Nitzan N, Chaimovitsh D, Eshel A, Dudai N. 2012. Chemical and Morphological Diversity in Wild Populations of Mentha longifolia in Israel. Chemistry & Biodiversity 9(3), 577-588. http://dx.doi.org/10.1002/cbdv.2011001.08

Sharopov FS, Sulaimonova VA, Setzer WN. 2012. Essential oil composition of Mentha longifolia from wild populations growing in Tajikistan. Journal of Medicinally Active Plants 1(2), 6.

Singh HP, Batish DR, Mittal S, Dogra KS, Yadav S, Kohli RK. 2008. Constituents of leaf essential oil of Mentha longifolia from India. Chemistry of Natural Compounds 44(4), 528-529. http://dx.doi.org/10.1007/s10600-008-9124-x

Slavkovska V, Couladis M, Bojovic S, Tzakou O, Pavlovic M, Lakusic B, Jancic R. 2005. Essential oil and its systematic significance in species of Micromeria Bentham from Serbia Montenegro, Plant Systematics and Evolution 255(1-2), 1-15. http://dx.doi.org/10.1007/s00606-005-0303.y

Stanisavljević D, Đorđević S, Milenković M, Lazić M, Veličković D, Ranđelović N, Zlatković B. 2014. Antimicrobial and Antioxidant Activity of the Essential Oils Obtained from Mentha longifolia L. Hudson, Dried by Three Different Techniques. Records of Natural Products 8(1), 61-65.

Tripathi AK, Prajapati V, Ahmad A, Aggarwal KK, Khanuja SP. 2004. Piperitenone oxide as toxic, repellent, and reproduction retardant toward malarial vector Anopheles stephensi (Diptera: Anophelinae). Journal of Medical Entomology 41(4), 691-698. http://dx.doi.org/10.1603/0022-2585-41.4691

Viljoen AM, Petkar S, Van Vuuren SF, Figueiredo AC, Pedro LG, Barroso JG. 2006. The Chemo-Geographical Variation in Essential Oil Composition and the Antimicrobial Properties of “Wild Mint”: Mentha longifolia subsp. Polyadena (Lamiaceae) in Southern Africa. Journal of Essential Oil Research 18, 60-65.

Young GP, Bush JK. 2009.  Assessment  of  the allelopathic   potential   of   Juniperus   ashei   on germination and growth of Bouteloua curtipendula. Journal of Chemical Ecology 35(1), 74-80. http://dx.doi.org/10.1007/s10886-008-9585.1