GC-MS Analysis of The Chemical Composition of The Hydrodistillate of The Above-Ground Part of Melissa Officinalis L
Keywords:
Melissa Officinalis L., Hydrodistillate, GC-MS, Chemical Composition, Steam Distillation
Abstract
In this paper, a detailed chemical analysis of the hydrodistillate of the above-ground part of the plant Melissa officinalis L. using gas chromatography with mass spectrometry (GC-MS) was carried out. The study showed that the hydrodistillate obtained from the above-ground part of Melissa officinalis contains a rich complex of bioactive compounds including terpenes, flavonoids, phenolic acids and other volatile substances. The major components identified include 1,4-Dioxaspiro[4.5]decane-7-butanoic acid, 6-methyl-, 2-(methylsulfonyloxy)ethyl ester (12.59%) and 2-octadeca-9,12-dienoxyethanol (8.59%). Analysis of the hydrodistillate composition also revealed the presence of compounds such as Dipalmitin, Ethyliso-allocholate and Glycine, N-[(3α,5β)-24-oxo-3-[(trimethylsilyl)oxy]cholan-24-yl]-, methyl ester. These data are important for standardisation and quality control of melissa-based phytopreparations and for the development of new therapeutic and cosmetic products
References
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Mimica-Dukic N., Bozin B., Sokovic M., Simin, N. (2004). Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. Journal of Agricultural and Food Chemistry, 52(9), 2485-2489. https://doi.org/10.1021/jf030698a
Gulluce M., Sahin F., Sokmen M., Ozer H., Daferera D., Sokmen A., Polissiou M. (2007). Antimicrobial and antioxidant properties of the essential oils and methanol extract from Melissa officinalis, Mentha piperita, and Rosmarinus officinalis. Journal of Agricultural and Food Chemistry, 55(25), 9452-9458. https://doi.org/10.1016/j.foodchem.2006.10.061
Edris A.E., Farrag E.S. (2003). Antifungal activity of peppermint and sweet basil essential oils and their major aroma constituents on some plant pathogenic fungi from the vapor phase. Journal of Essential Oil Bearing Plants, 6(3), 23-30. https://doi.org/10.1002/food.200390021
Sadraei H., Asghari G. R., Hajhashemi V., Kolagar A. (2003). Spasmolytic activity of Melissa officinalis L. essential oil on rat ileum contractions. Journal of Ethnopharmacology, 84(2-3), 155-158. https://doi.org/10.1016/S0367-326X(03)00109-6
de Sousa A.C., Alviano D.S., Blank A.F., Alves P.B., Alviano C.S., Gattass C.R. (2004). Melissa officinalis L. essential oil: antitumoral and antioxidant activities. Journal of Pharmacy and Pharmacology, 56(5), 677-681. https://doi.org/10.1211/0022357023321
Bağdat R.B., Coşge B. (2006). The essential oil of lemon balm (Melissa officinalis L.), its components and using fields. Anadolu Tarım Bilimleri Dergisi, 21(1), 116-121. https://doi.org/10.7161/anajas.2006.21.1.116-121
Lopez V., Martin S., Gomez-Serranillos M.P., Carretero M.E., Jager A.K., Calvo M.I. (2009). Neuroprotective and neurological properties of Melissa officinalis. Neurochemical Research, 34(11), 1955-1961. https://doi.org/10.1007/s11064-009-9981-0
Matusinsky P., Zouhar M., Pavela R., Novy P. (2015). Antifungal effect of five essential oils against important pathogenic fungi of cereals. Industrial Crops and Products, 67, 208-215. https://doi.org/10.1016/j.indcrop.2015.01.022
Soares G.A.B.E., Bhattacharya T., Chakrabarti T., Tagde P., Cavalu S. (2021). Exploring pharmacological mechanisms of essential oils on the central nervous system. Plants, 11(1), 21. https://doi.org/10.3390/plants11010021
Aharoni A., Jongsma M.A., Bouwmeester H.J. (2005). Volatile science? Metabolic engineering of terpenoids in plants. Trends in Plant Science, 10(12), 594-602. https://doi.org/10.1016/j.tplants.2005.10.005
Carnat A., Carnat A.P., Fraisse D., Lamaison J.L. (1998). The aromatic and polyphenolic composition of lemon balm (Melissa officinalis L. subsp. officinalis) tea. Phytotherapy Research, 12(3), 157-160. https://doi.org/10.1016/S0031-6865(97)00026-5
Patora J., Klimek B. (2002). Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). Acta Poloniae Pharmaceutica, 59(2), 139-143. https://ptfarm.pl/pub/File/Acta_Poloniae/2002/2/139.pdf
Yosr Z., Hnia C., Rim T., Mohamed B. (2013). Changes in essential oil composition and phenolic fraction in Rosmarinus officinalis L. var. typicus Batt. organs during growth and incidence on the antioxidant activity. Industrial Crops and Products, 43, 412-419. https://doi.org/10.1016/j.indcrop.2012.07.044
Shapoval O.G., Sheremetyeva A.S., Dumova N.A., Mukhamadiev N.Q., Rabbimova G.T., Nazirbekov M.H. (2023). Antimicrobial Activity of Thymus serpyllum L. and Thymus marschallianus Willd. Essential Oils Against Candida albicans. Pharmaceutical Chemistry Journal, 57(9), 1449-1453. https://doi.org/10.1007/s11094-023-03009-6
Shapoval O.G., Sheremet'eva A.S., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Skriningovaja ocenka antibakterial'noj aktivnosti jefirnyh masel Thymus serpyllum L., Thymus marsshallianus Willd. i Pimpinella anisum L. v otnoshenii uropatogenov, vydelennyh ot beremennyh zhenshhin. Vestnik Sankt-Peterburgskogo universiteta. Medicina, 18(2), 167-175. https://doi.org/10.21638/spbu11.2023.205
Shapoval O.G., Sheremet'eva A.S., Durnova N.A., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Antibakterial'naja aktivnost' jefirnyh masel tim'jana polzuchego (Thymus serpyllum L.) i tim'jana Marshalla (Thymus marschallianus Willd.). Razrabotka i registracija lekarstvennyh sredstv, 12(3), 143-150. https://doi.org/10.33380/2305-2066-2023-12-3-143-150
Shapoval O.G., Sheremet'eva A.S., Durnova N.A., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Antimikrobnaja aktivnost' jefirnyh masel Thymus serpyllum L. i Thymus marschallianus Willd. v otnoshenii Candida albicans. Himiko-farmacevticheskij zhurnal, 57(9), 26-31. https://doi.org/10.30906/0023-1134-2023-57-9-26-31
Sheremetyeva A.S., Karavaeva L.V., Durnova N.A., Shapoval O.G., Mukhamadiev N.Q., Rabbimova G.T., Nazirbekov M.H. (2024). Comparative analysis of chemical composition of Thymus serpyllum L. and Thymus marschallianus Willd. essential oils by gas-liquid chromatography with mass spectrometry detection. Problems of Biological Medical and Pharmaceutical Chemistry, 27(2), 49-57. https://doi.org/10.29296/25877313-2024-02-06
Shapoval O., Sheremet'eva A., Durnova N., Muhamadiev N., Rabbimova G., Nazirbekov M. (2022). Sravnitel'naja ocenka antibakterial'noj aktivnosti jefirnyh masel Thymus serpyllum L., Thymus Marshallianus Willd. i Pimpinella Anisum L. v otnoshenii gramotricatel'nyh bakterij–vozbuditelej uroinfekcij u beremennyh zhenshhin. Vestnik biotehnologii i fiziko-himicheskoj biologii imeni JuA Ovchinnikova, 18(3), 63. https://biorosinfo.ru/upload/file/journal_v18_no3.pdf#page=63
Muhamadiev
A.N., Rabbimova G.T., Nurmurodova S.A., Muhamadiev N.K. (2020). Possibilities of using essential oils in obstetric and gynecological practice. Central Asian Journal of Medical and Natural Science, 1(2), 31-43. https://doi.org/10.17605/cajmns.v1i2.46
Kennedy D.O., Scholey A.B., Tildesley N.T.J. (2002). Modulation of mood and cognitive performance following acute administration of single doses of Melissa officinalis (lemon balm). Journal of Psychopharmacology, 16(1), 14-15. https://doi.org/10.1038/sj.npp.1300230
Adams R.P. (2017). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Corporation. http://www.juniperus.org/uploads/2/2/6/3/22639912/bk4frontisbnpreface-contents5thedonline2017.pdf
Chauhan R.S., Kaul M.K., Shahi A.K., Kumar A., Ram G., Tawa A. (2009). Chemical composition of essential oils in wild and cultivated Curcuma longa plants from the North-West Himalaya, India. Journal of Essential Oil Research, 21(6), 530-533. https://doi.org/10.1016/j.indcrop.2008.12.003
Carvalho R.N., Moura L.S., Rosa P.T.V., Meireles M.A.A. (2005). Supercritical fluid extraction from rosemary (Rosmarinus officinalis) essential oil: Kinetic data, extract's global yield, composition, and antioxidant activity. The Journal of Supercritical Fluids, 35(3), 197-204. https://doi.org/10.1016/j.supflu.2005.01.009
Dastmalchi K., Dorman H.J.D., Kosar M., Hiltunen R. (2007). Chemical composition and in vitro antioxidant evaluation of a water-soluble Moldavian balm (Dracocephalum moldavica L.) extract. LWT - Food Science and Technology, 40(2), 239-248. https://doi.org/10.1016/j.lwt.2005.09.019
Saeb K., Gholamrezaee S. (2012). Variation of essential oil composition of Melissa officinalis L. leaves during different stages of plant growth. Asian Pacific Journal of Tropical Biomedicine, 2(2), S547-S549. https://doi.org/10.1016/S2221-1691(12)60271-8
Efremov A.A. (2013). Metod ischerpyvajushhej gidroparodistilljacii pri poluchenii jefirnyh masel dikorastushhih rastenij. Uspehi sovremennogo estestvoznanija, (7), 88-94. https://s.natural-sciences.ru/pdf/2013/2013_07.pdf#page=88
Mukhamadiev N.Q., Sayitkulov S.M., Ergashev I.M., Khafizov K.F., Fayzullaev N.I. (2003). Optimization of separation on the basis of UNIFAC parameters and evaluation of the composition of the stationary phase in gas-liquid chromatography. Chromatographia, 57, 831-833. https://doi.org/10.1007/BF02491773
Novák J. (2021). Quantitative analysis by gas chromatography. In Advances in Chromatography (pp. 1-71). Crc Press. https://doi.org/10.1201/9781003209928
Bakkali F., Averbeck S., Averbeck D., Idaomar M. (2008). Biological effects of essential oils – A review. Food and Chemical Toxicology, 46(2), 446-475. https://doi.org/10.1016/j.fct.2007.09.106
Mimica-Dukic N., Bozin B., Sokovic M., Simin, N. (2004). Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. Journal of Agricultural and Food Chemistry, 52(9), 2485-2489. https://doi.org/10.1021/jf030698a
Gulluce M., Sahin F., Sokmen M., Ozer H., Daferera D., Sokmen A., Polissiou M. (2007). Antimicrobial and antioxidant properties of the essential oils and methanol extract from Melissa officinalis, Mentha piperita, and Rosmarinus officinalis. Journal of Agricultural and Food Chemistry, 55(25), 9452-9458. https://doi.org/10.1016/j.foodchem.2006.10.061
Edris A.E., Farrag E.S. (2003). Antifungal activity of peppermint and sweet basil essential oils and their major aroma constituents on some plant pathogenic fungi from the vapor phase. Journal of Essential Oil Bearing Plants, 6(3), 23-30. https://doi.org/10.1002/food.200390021
Sadraei H., Asghari G. R., Hajhashemi V., Kolagar A. (2003). Spasmolytic activity of Melissa officinalis L. essential oil on rat ileum contractions. Journal of Ethnopharmacology, 84(2-3), 155-158. https://doi.org/10.1016/S0367-326X(03)00109-6
de Sousa A.C., Alviano D.S., Blank A.F., Alves P.B., Alviano C.S., Gattass C.R. (2004). Melissa officinalis L. essential oil: antitumoral and antioxidant activities. Journal of Pharmacy and Pharmacology, 56(5), 677-681. https://doi.org/10.1211/0022357023321
Bağdat R.B., Coşge B. (2006). The essential oil of lemon balm (Melissa officinalis L.), its components and using fields. Anadolu Tarım Bilimleri Dergisi, 21(1), 116-121. https://doi.org/10.7161/anajas.2006.21.1.116-121
Lopez V., Martin S., Gomez-Serranillos M.P., Carretero M.E., Jager A.K., Calvo M.I. (2009). Neuroprotective and neurological properties of Melissa officinalis. Neurochemical Research, 34(11), 1955-1961. https://doi.org/10.1007/s11064-009-9981-0
Matusinsky P., Zouhar M., Pavela R., Novy P. (2015). Antifungal effect of five essential oils against important pathogenic fungi of cereals. Industrial Crops and Products, 67, 208-215. https://doi.org/10.1016/j.indcrop.2015.01.022
Soares G.A.B.E., Bhattacharya T., Chakrabarti T., Tagde P., Cavalu S. (2021). Exploring pharmacological mechanisms of essential oils on the central nervous system. Plants, 11(1), 21. https://doi.org/10.3390/plants11010021
Aharoni A., Jongsma M.A., Bouwmeester H.J. (2005). Volatile science? Metabolic engineering of terpenoids in plants. Trends in Plant Science, 10(12), 594-602. https://doi.org/10.1016/j.tplants.2005.10.005
Carnat A., Carnat A.P., Fraisse D., Lamaison J.L. (1998). The aromatic and polyphenolic composition of lemon balm (Melissa officinalis L. subsp. officinalis) tea. Phytotherapy Research, 12(3), 157-160. https://doi.org/10.1016/S0031-6865(97)00026-5
Patora J., Klimek B. (2002). Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). Acta Poloniae Pharmaceutica, 59(2), 139-143. https://ptfarm.pl/pub/File/Acta_Poloniae/2002/2/139.pdf
Yosr Z., Hnia C., Rim T., Mohamed B. (2013). Changes in essential oil composition and phenolic fraction in Rosmarinus officinalis L. var. typicus Batt. organs during growth and incidence on the antioxidant activity. Industrial Crops and Products, 43, 412-419. https://doi.org/10.1016/j.indcrop.2012.07.044
Shapoval O.G., Sheremetyeva A.S., Dumova N.A., Mukhamadiev N.Q., Rabbimova G.T., Nazirbekov M.H. (2023). Antimicrobial Activity of Thymus serpyllum L. and Thymus marschallianus Willd. Essential Oils Against Candida albicans. Pharmaceutical Chemistry Journal, 57(9), 1449-1453. https://doi.org/10.1007/s11094-023-03009-6
Shapoval O.G., Sheremet'eva A.S., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Skriningovaja ocenka antibakterial'noj aktivnosti jefirnyh masel Thymus serpyllum L., Thymus marsshallianus Willd. i Pimpinella anisum L. v otnoshenii uropatogenov, vydelennyh ot beremennyh zhenshhin. Vestnik Sankt-Peterburgskogo universiteta. Medicina, 18(2), 167-175. https://doi.org/10.21638/spbu11.2023.205
Shapoval O.G., Sheremet'eva A.S., Durnova N.A., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Antibakterial'naja aktivnost' jefirnyh masel tim'jana polzuchego (Thymus serpyllum L.) i tim'jana Marshalla (Thymus marschallianus Willd.). Razrabotka i registracija lekarstvennyh sredstv, 12(3), 143-150. https://doi.org/10.33380/2305-2066-2023-12-3-143-150
Shapoval O.G., Sheremet'eva A.S., Durnova N.A., Muhamadiev N.K., Rabbimova G.T., Nazirbekov M.H. (2023). Antimikrobnaja aktivnost' jefirnyh masel Thymus serpyllum L. i Thymus marschallianus Willd. v otnoshenii Candida albicans. Himiko-farmacevticheskij zhurnal, 57(9), 26-31. https://doi.org/10.30906/0023-1134-2023-57-9-26-31
Sheremetyeva A.S., Karavaeva L.V., Durnova N.A., Shapoval O.G., Mukhamadiev N.Q., Rabbimova G.T., Nazirbekov M.H. (2024). Comparative analysis of chemical composition of Thymus serpyllum L. and Thymus marschallianus Willd. essential oils by gas-liquid chromatography with mass spectrometry detection. Problems of Biological Medical and Pharmaceutical Chemistry, 27(2), 49-57. https://doi.org/10.29296/25877313-2024-02-06
Shapoval O., Sheremet'eva A., Durnova N., Muhamadiev N., Rabbimova G., Nazirbekov M. (2022). Sravnitel'naja ocenka antibakterial'noj aktivnosti jefirnyh masel Thymus serpyllum L., Thymus Marshallianus Willd. i Pimpinella Anisum L. v otnoshenii gramotricatel'nyh bakterij–vozbuditelej uroinfekcij u beremennyh zhenshhin. Vestnik biotehnologii i fiziko-himicheskoj biologii imeni JuA Ovchinnikova, 18(3), 63. https://biorosinfo.ru/upload/file/journal_v18_no3.pdf#page=63
Muhamadiev
A.N., Rabbimova G.T., Nurmurodova S.A., Muhamadiev N.K. (2020). Possibilities of using essential oils in obstetric and gynecological practice. Central Asian Journal of Medical and Natural Science, 1(2), 31-43. https://doi.org/10.17605/cajmns.v1i2.46
Kennedy D.O., Scholey A.B., Tildesley N.T.J. (2002). Modulation of mood and cognitive performance following acute administration of single doses of Melissa officinalis (lemon balm). Journal of Psychopharmacology, 16(1), 14-15. https://doi.org/10.1038/sj.npp.1300230
Adams R.P. (2017). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Corporation. http://www.juniperus.org/uploads/2/2/6/3/22639912/bk4frontisbnpreface-contents5thedonline2017.pdf
Chauhan R.S., Kaul M.K., Shahi A.K., Kumar A., Ram G., Tawa A. (2009). Chemical composition of essential oils in wild and cultivated Curcuma longa plants from the North-West Himalaya, India. Journal of Essential Oil Research, 21(6), 530-533. https://doi.org/10.1016/j.indcrop.2008.12.003
Carvalho R.N., Moura L.S., Rosa P.T.V., Meireles M.A.A. (2005). Supercritical fluid extraction from rosemary (Rosmarinus officinalis) essential oil: Kinetic data, extract's global yield, composition, and antioxidant activity. The Journal of Supercritical Fluids, 35(3), 197-204. https://doi.org/10.1016/j.supflu.2005.01.009
Dastmalchi K., Dorman H.J.D., Kosar M., Hiltunen R. (2007). Chemical composition and in vitro antioxidant evaluation of a water-soluble Moldavian balm (Dracocephalum moldavica L.) extract. LWT - Food Science and Technology, 40(2), 239-248. https://doi.org/10.1016/j.lwt.2005.09.019
Saeb K., Gholamrezaee S. (2012). Variation of essential oil composition of Melissa officinalis L. leaves during different stages of plant growth. Asian Pacific Journal of Tropical Biomedicine, 2(2), S547-S549. https://doi.org/10.1016/S2221-1691(12)60271-8
Efremov A.A. (2013). Metod ischerpyvajushhej gidroparodistilljacii pri poluchenii jefirnyh masel dikorastushhih rastenij. Uspehi sovremennogo estestvoznanija, (7), 88-94. https://s.natural-sciences.ru/pdf/2013/2013_07.pdf#page=88
Mukhamadiev N.Q., Sayitkulov S.M., Ergashev I.M., Khafizov K.F., Fayzullaev N.I. (2003). Optimization of separation on the basis of UNIFAC parameters and evaluation of the composition of the stationary phase in gas-liquid chromatography. Chromatographia, 57, 831-833. https://doi.org/10.1007/BF02491773
Novák J. (2021). Quantitative analysis by gas chromatography. In Advances in Chromatography (pp. 1-71). Crc Press. https://doi.org/10.1201/9781003209928
Published
2024-10-17
How to Cite
Nayimova B.K, Mukhamadiev A.N, & Mukhamadiev N.K. (2024). GC-MS Analysis of The Chemical Composition of The Hydrodistillate of The Above-Ground Part of Melissa Officinalis L. Central Asian Journal of Medical and Natural Science, 5(4), 1025-1031. Retrieved from https://cajmns.centralasianstudies.org/index.php/CAJMNS/article/view/2654
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