TLC-GC/MS Method for identifying and selecting valuable essential Oil Chemotypes from Wild Populations of Mentha longifolia L.
Year 2017,
Volume: 4 Issue: 4, 49 - 61, 29.12.2017
Juan Antonio Llorens-molina
,
Vicente Castell
Sandra Vacas
Mercedes Verdeguer
Abstract
Wild populations of aromatic plants can be
considered resources of natural biodiversity for selecting valuable genotypes
in order to obtain well-characterized cultivars with defined essential oil (EO)
profiles suitable for different purposes due to their biological activity.
Often, their high intrapopulational variability requires preliminary screenings
based on a significant number of individuals and, therefore, simple and fast
methods to identify EO profiles are required. For this purpose, a TLC-GC/MS method
has been proposed in order to identify chemotypes occurring in a selected wild
population. Stolons of 50 individuals of Mentha longifolia L were planted and
bred in greenhouse conditions before growing in experimental plots. Individual
sampling and extraction of leaves were performed to determinate TLC individual
profiles. They were validated by preparative TLC and GC/MS analysis of
discriminant spots. Fresh material belonging to each defined TLC profile was
collected in full flowering stage and subjected to SDE extraction and GC/MS
analysis. Five chemotypes were characterized: A (piperitone and piperitenone
oxides); B (piperitone oxide + pulegone); C (α- terpineol acetate + carvone
acetate); D ((E) – dihydrocarvone)
and E (pulegone + isomenthone + menthol). This TLC method was applied to
individuals coming from another population. All of them could be clearly
identified as belonging to chemotype E, which was afterwards confirmed by GC/MS
analysis.
References
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- Asekun, O.T., Grierson, D. S. & Afolayan, A. J. (2007). Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. capensis. Food Chemistry, 101, 995-998.
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- Bertoli, A., Leonardi, M., Krzyzanowska, J., Oleszek, W. and Pistelli, L. (2011). Mentha longifolia in vitro cultures as safe source of flavouring ingredients. Acta Biochimica Polonica, 58(4), 581-587.
- Chaintreau, A. (2001). Simultaneous distillation–extraction: From birth to maturity—review. Flavour and Fragrance Journal, 16, 136-148.
- Delpit, B., Lamy, J., Holland, J. C., Chalchat, J.C. & Garry, L. P. (2000). Clonal selection of sabinene hydrate- rich thyme (Thymus vulgaris). yield and chemical composition of essential oils. Journal of Essential Oil Research 12 (3), 387-391.
- Dias, D. D., Urban, S. & Roessner, U. (2012). A Historical Overview of Natural Products in Drug Discovery, Metabolites, 2(2), 303-336.
- Džamić, A. M., Soković, M. D., Ristić, M. S., Novaković, M., Grujić-Jovanović, S., Tešević, V. & Marin, P. D. (2010). Antifungal and antioxidant activity of Mentha longifolia (L.) Hudson (Lamiaceae) essential oil. Botanica Serbica, 34(1), 57-61.
- Figueiredo, A. C., Barroso, J. G., Pedro, L. G. & Scheffer J. J. (2008). Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour Fragrance Journal, 23(4), 213-226.
- 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.
- Franz, C. M. (2010). Essential Oils Research: Past, present and future. Flavour and Fragrance Journal, 25(3), 112-113.
- Goliaris, A. H., Chatzopoulou, P. S. & Katsiotis, S. T. (2003). Production of new Greek oregano clones and analysis of their essential oils. Journal of herbs, spices & medicinal plants, 10(1), 29-35.
- Gudi, G., Krämer, K. & Krüger, H. (2014). Discrimination of fennel chemotypes applying IR and Raman spectroscopy: Discovery of a new γ-asarone chemotype. Journal of Agricultural and Food Chemistry, 62, 3537-3547.
- 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 two cultivated mint species (Mentha longifolia and Mentha pulegium) used in the Tunisian folkloric medicine. World Journal of Microbiology and Biotechnology, 25(12), 2227-2238.
- Harvey, A. L., Edrada-Ebel, R. & Quinn, R. J. (2015). The re-emergence of natural products for drug discovery in the genomics era. Nature Reviews Drug Discovery. 14(2), 111-129.
- 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, 1827-1836.
- 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, 1618-1623.
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- Kokkini, S.; Karousou, R. & Lanaras, T. (1995) Essential oils of spearmint (carvone-rich) plants from the island of Crete (Greece). Biochemical Systematics and Ecology, 23(4), 425-430.
- 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, 327-335.
- Lawrence, B. M. (2006). Oil Composition of the Other Mentha Species and Hybrids, in B. M. Lawrence, Mint: The genus Mentha, 325-346, Florida, USA, CRC Press.
- Llorens-Molina, J. A., Rellán, D. G., Vacas, S. & Sanfeliu, A. B. (2015). Individual sampling approach to study the chemodiversity of volatile and semivolatile compounds of Mentha longifolia L. growing wild in Jiloca basin (Spain). International Journal of Biosciences, 7(4), 166-176.
- Maffei, M. (1988). A chemotype of Mentha longifolia (L.) Hudson particularly rich in piperitenone oxide. Flavour and Fragrance Journal, 3(1), 23-26.
- Mastelic, J. & Jerkovic, I. (2002). Free and glycosidically bound volatiles of Mentha longifolia growing in Croatia. Chemistry of Natural Compounds, 38, 561-564.
- Matovic, M. & Lavadinovic, V. (1999). Essential Oil composition of Mentha longifolia (L) Huds. from the Mountain Zlatar in Yugoslavia, Journal of Essential Oils Bearing Plants, 2(2) 78-81.
- 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.
- 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.
- 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.
- Mulas, M., Francesconi, A. H. D., Bicchi, C., Perinu, B., & Vais, E. D. (2001). Plant characters and essential oil composition of new selections of rosemary (Rosmarinus officinalis L.). International Conference on Medicinal and Aromatic Plants. Possibilities and Limitations of Medicinal and Aromatic Plant, ISHS Acta Horticulturae, DOI: 10.17660/ActaHortic.2002.576.24
- Newman, D. J. & Cragg, G. M. (2007). Natural Products as Sources of New Drugs over the Last 25 Years, Journal of Natural Products, 70, 461-477.
- Oyedeji, A. O. & Afolayan, A. J. (2006). Chemical Composition and Antibacterial activity of the essential oil isolated from South African Mentha Longifolia (L.) L. subsp. capensis (Thunb.) Briq., Journal of Essential Oil Research, 18, 57-60.
- Pothier, J., Galand, N., El Ouali, M., Viel, C. (2001). Comparison of planar chromatographic methods (TLC, OPLC, AMD) applied to essential oils of wild thyme and seven chemotypes of thyme. Il Farmaco, 56 (5), 505- 511.
- Rahimmalek, M.,Tabatabaei, B. E. S., Arzani, A. & Etemadi, N. (2009). Essential oil variation among and within six Achillea species transferred from different ecological regions in Iran to the field conditions. Industrial Crops and Products, 29(2), 348-355.
- Robinson C.J. (2006). A new essential oil – Agonis fragrans: chemotype selection and evaluation. A report for the Rural Industries Research and Development Corporation. Kingston (Australia), RIRDC.
- Rufino, E. R., Siqueira, W. J., Marques, M. O. M., Colombo, C. A., Filho, J. A. A. & Martins, A. L. M. (2012). Selection of new clones of linalool chemotype from genetic recombination in Lippia alba. Bragantia, 71(2), 155-164.
- Saeidi, Z., Saeidi, K. A., Salehi, A., Jouneghani, R. S., 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, 4522-4525.
- Schulz, H.; Schrader, B.; Quilitzsch, R.; Pfeffer, S. & Krüger, H. (2003). Rapid classification of basil chemotypes by Various vibrational spectroscopy methods. Journal of Agricultural and Food Chemistry, 51, 2475-2481.
- 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.
- Sharopov, F. S., Sulaimonova, V. A. & Setzer, W. N. (2012). Essential oil composition of Mentha longifolia from wild populations growing in Tajikistan. Journal of Medicinally Active Plants, 1(2), 6.
- Singh, H. P., Batish, D. R., Mittal, S., Dogra, K. S., Yadav, S. & Kohli, R. K. (2008). Constituents of leaf essential oil of Mentha longifolia from India. Chemistry of Natural Compounds, 44(4), 528-529.
- Turgut, K., Tutuncu, B., Ozyigit, Y. & Ucar, E. (2016). Clone Selection for High Quality Types of Oregano (Boiss.) 6th International Symposium Breeding Research on Medicinal and Aromatic Plants, BREEDMAP 6, Quedlinburg, Germany, Julius-Kühn-Archiv, 453, 164.
- Vouillamoz, J. F., Schaller, M. & Carron, C. A. (2009). Discrimination des chémotypes de thym vulgaire avec le 'nez électronique' SMart Nose®. Revue suisse de viticulture, arboriculture, horticulture, 41(6), 345.
- Wagner, H. & Bladt, S. (2002). Plant Drug Analysis: A Thin Layer Chromatography Atlas. New York, US, Springer Science & Business Media.
- Zuzarte, M., Dinis, A. M., Salgueiro, L. & Canhoto, J. (2015). A Rapid and Efficient Protocol for Clonal Propagation of Phenolic-Rich. Journal of Agricultural Science, 7 (3), 8.
Year 2017,
Volume: 4 Issue: 4, 49 - 61, 29.12.2017
Juan Antonio Llorens-molina
,
Vicente Castell
Sandra Vacas
Mercedes Verdeguer
References
- Abedi, R., Golparvar, A. R. & Hadipanah, A. (2015). Identification of the essential oils composition from four ecotypes of Mentha longifolia (L.) Huds. growing wild in Isfahan province, Iran. Journal of Bioscience and Biotechnology, 4(2), 117-121.
- Adams, R. P. (2007). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Illinois, USA, Allured Publishing Corporation.
- Asekun, O.T., Grierson, D. S. & Afolayan, A. J. (2007). Effects of drying methods on the quality and quantity of the essential oil of Mentha longifolia L. subsp. capensis. Food Chemistry, 101, 995-998.
- Baser, K. H. C., Kürkçüoglu, M., Tarimcilar, G. & Kaynak, G. (1999). Essential oils of Mentha species from Northern Turkey. Journal of Essential Oil Research, 11(5), 579-588.
- Bertoli, A., Leonardi, M., Krzyzanowska, J., Oleszek, W. and Pistelli, L. (2011). Mentha longifolia in vitro cultures as safe source of flavouring ingredients. Acta Biochimica Polonica, 58(4), 581-587.
- Chaintreau, A. (2001). Simultaneous distillation–extraction: From birth to maturity—review. Flavour and Fragrance Journal, 16, 136-148.
- Delpit, B., Lamy, J., Holland, J. C., Chalchat, J.C. & Garry, L. P. (2000). Clonal selection of sabinene hydrate- rich thyme (Thymus vulgaris). yield and chemical composition of essential oils. Journal of Essential Oil Research 12 (3), 387-391.
- Dias, D. D., Urban, S. & Roessner, U. (2012). A Historical Overview of Natural Products in Drug Discovery, Metabolites, 2(2), 303-336.
- Džamić, A. M., Soković, M. D., Ristić, M. S., Novaković, M., Grujić-Jovanović, S., Tešević, V. & Marin, P. D. (2010). Antifungal and antioxidant activity of Mentha longifolia (L.) Hudson (Lamiaceae) essential oil. Botanica Serbica, 34(1), 57-61.
- Figueiredo, A. C., Barroso, J. G., Pedro, L. G. & Scheffer J. J. (2008). Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour Fragrance Journal, 23(4), 213-226.
- 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.
- Franz, C. M. (2010). Essential Oils Research: Past, present and future. Flavour and Fragrance Journal, 25(3), 112-113.
- Goliaris, A. H., Chatzopoulou, P. S. & Katsiotis, S. T. (2003). Production of new Greek oregano clones and analysis of their essential oils. Journal of herbs, spices & medicinal plants, 10(1), 29-35.
- Gudi, G., Krämer, K. & Krüger, H. (2014). Discrimination of fennel chemotypes applying IR and Raman spectroscopy: Discovery of a new γ-asarone chemotype. Journal of Agricultural and Food Chemistry, 62, 3537-3547.
- 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 two cultivated mint species (Mentha longifolia and Mentha pulegium) used in the Tunisian folkloric medicine. World Journal of Microbiology and Biotechnology, 25(12), 2227-2238.
- Harvey, A. L., Edrada-Ebel, R. & Quinn, R. J. (2015). The re-emergence of natural products for drug discovery in the genomics era. Nature Reviews Drug Discovery. 14(2), 111-129.
- 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, 1827-1836.
- 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, 1618-1623.
- Kokkini, S. & Papageorgiou, V. P. (1988). Constituents of essential oils from Mentha longifolia growing wild in Greece. Planta Medica, 54(1), 59-60.
- Kokkini, S.; Karousou, R. & Lanaras, T. (1995) Essential oils of spearmint (carvone-rich) plants from the island of Crete (Greece). Biochemical Systematics and Ecology, 23(4), 425-430.
- 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, 327-335.
- Lawrence, B. M. (2006). Oil Composition of the Other Mentha Species and Hybrids, in B. M. Lawrence, Mint: The genus Mentha, 325-346, Florida, USA, CRC Press.
- Llorens-Molina, J. A., Rellán, D. G., Vacas, S. & Sanfeliu, A. B. (2015). Individual sampling approach to study the chemodiversity of volatile and semivolatile compounds of Mentha longifolia L. growing wild in Jiloca basin (Spain). International Journal of Biosciences, 7(4), 166-176.
- Maffei, M. (1988). A chemotype of Mentha longifolia (L.) Hudson particularly rich in piperitenone oxide. Flavour and Fragrance Journal, 3(1), 23-26.
- Mastelic, J. & Jerkovic, I. (2002). Free and glycosidically bound volatiles of Mentha longifolia growing in Croatia. Chemistry of Natural Compounds, 38, 561-564.
- Matovic, M. & Lavadinovic, V. (1999). Essential Oil composition of Mentha longifolia (L) Huds. from the Mountain Zlatar in Yugoslavia, Journal of Essential Oils Bearing Plants, 2(2) 78-81.
- 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.
- 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.
- 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.
- Mulas, M., Francesconi, A. H. D., Bicchi, C., Perinu, B., & Vais, E. D. (2001). Plant characters and essential oil composition of new selections of rosemary (Rosmarinus officinalis L.). International Conference on Medicinal and Aromatic Plants. Possibilities and Limitations of Medicinal and Aromatic Plant, ISHS Acta Horticulturae, DOI: 10.17660/ActaHortic.2002.576.24
- Newman, D. J. & Cragg, G. M. (2007). Natural Products as Sources of New Drugs over the Last 25 Years, Journal of Natural Products, 70, 461-477.
- Oyedeji, A. O. & Afolayan, A. J. (2006). Chemical Composition and Antibacterial activity of the essential oil isolated from South African Mentha Longifolia (L.) L. subsp. capensis (Thunb.) Briq., Journal of Essential Oil Research, 18, 57-60.
- Pothier, J., Galand, N., El Ouali, M., Viel, C. (2001). Comparison of planar chromatographic methods (TLC, OPLC, AMD) applied to essential oils of wild thyme and seven chemotypes of thyme. Il Farmaco, 56 (5), 505- 511.
- Rahimmalek, M.,Tabatabaei, B. E. S., Arzani, A. & Etemadi, N. (2009). Essential oil variation among and within six Achillea species transferred from different ecological regions in Iran to the field conditions. Industrial Crops and Products, 29(2), 348-355.
- Robinson C.J. (2006). A new essential oil – Agonis fragrans: chemotype selection and evaluation. A report for the Rural Industries Research and Development Corporation. Kingston (Australia), RIRDC.
- Rufino, E. R., Siqueira, W. J., Marques, M. O. M., Colombo, C. A., Filho, J. A. A. & Martins, A. L. M. (2012). Selection of new clones of linalool chemotype from genetic recombination in Lippia alba. Bragantia, 71(2), 155-164.
- Saeidi, Z., Saeidi, K. A., Salehi, A., Jouneghani, R. S., 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, 4522-4525.
- Schulz, H.; Schrader, B.; Quilitzsch, R.; Pfeffer, S. & Krüger, H. (2003). Rapid classification of basil chemotypes by Various vibrational spectroscopy methods. Journal of Agricultural and Food Chemistry, 51, 2475-2481.
- 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.
- Sharopov, F. S., Sulaimonova, V. A. & Setzer, W. N. (2012). Essential oil composition of Mentha longifolia from wild populations growing in Tajikistan. Journal of Medicinally Active Plants, 1(2), 6.
- Singh, H. P., Batish, D. R., Mittal, S., Dogra, K. S., Yadav, S. & Kohli, R. K. (2008). Constituents of leaf essential oil of Mentha longifolia from India. Chemistry of Natural Compounds, 44(4), 528-529.
- Turgut, K., Tutuncu, B., Ozyigit, Y. & Ucar, E. (2016). Clone Selection for High Quality Types of Oregano (Boiss.) 6th International Symposium Breeding Research on Medicinal and Aromatic Plants, BREEDMAP 6, Quedlinburg, Germany, Julius-Kühn-Archiv, 453, 164.
- Vouillamoz, J. F., Schaller, M. & Carron, C. A. (2009). Discrimination des chémotypes de thym vulgaire avec le 'nez électronique' SMart Nose®. Revue suisse de viticulture, arboriculture, horticulture, 41(6), 345.
- Wagner, H. & Bladt, S. (2002). Plant Drug Analysis: A Thin Layer Chromatography Atlas. New York, US, Springer Science & Business Media.
- Zuzarte, M., Dinis, A. M., Salgueiro, L. & Canhoto, J. (2015). A Rapid and Efficient Protocol for Clonal Propagation of Phenolic-Rich. Journal of Agricultural Science, 7 (3), 8.