Glycosidically Bound Volatile Compounds of Satureja Montana L., S. cuneifo-lia Ten., S. subspicata Vis. and Endemic S. visianii Šilic
ABSTRACT
In this paper, the glycoconjugated volatile compounds of four Croatian Satureja species (Satureja montana L., S. cuneifolia Ten., S. subspicata Vis. and endemic S. visianii Silic) were investigated. Content and composition of these compounds were examined depending on the stage of plant development. GC and GC–MS analysis of volatile aglycones revealed twenty-one compounds. Thymoquinone, geraniol and carvacrol were detected in all vegetative phases of the investigated plants. Other quantitatively important aglycones were eugenol and thymol of S. montana, phenyl ethyl alcohol, benzene acetaldehyde, borneol, α-terpineol, thymol and eugenol of S. cuneifolia, phenyl ethyl alcohol, benzene acet-aldehyde, terpinen-4-ol, α-terpineol and β-ionone of S. subspicata and camphor, thymol and 8a-acetoxylemolol of S. visianii. Moderate similarity in the chemical composition of essential oils and volatile aglycones of investigated plant species indicate that many biologically active compounds are glycosylated and accumulate as non-volatile glycosides.
In this paper, the glycoconjugated volatile compounds of four Croatian Satureja species (Satureja montana L., S. cuneifolia Ten., S. subspicata Vis. and endemic S. visianii Silic) were investigated. Content and composition of these compounds were examined depending on the stage of plant development. GC and GC–MS analysis of volatile aglycones revealed twenty-one compounds. Thymoquinone, geraniol and carvacrol were detected in all vegetative phases of the investigated plants. Other quantitatively important aglycones were eugenol and thymol of S. montana, phenyl ethyl alcohol, benzene acetaldehyde, borneol, α-terpineol, thymol and eugenol of S. cuneifolia, phenyl ethyl alcohol, benzene acet-aldehyde, terpinen-4-ol, α-terpineol and β-ionone of S. subspicata and camphor, thymol and 8a-acetoxylemolol of S. visianii. Moderate similarity in the chemical composition of essential oils and volatile aglycones of investigated plant species indicate that many biologically active compounds are glycosylated and accumulate as non-volatile glycosides.
KEYWORDS
Satureja montana, S. cuneifolia, S. subspicata, S. visianii, Glicosydically Bound Volatiles, Free Aglycones
Satureja montana, S. cuneifolia, S. subspicata, S. visianii, Glicosydically Bound Volatiles, Free Aglycones
Cite this paper
Dunkić, V. , Radovanović, I. , Bezić, N. and Vuko, E. (2015) Glycosidically Bound Volatile Compounds of Satureja Montana L., S. cuneifo-lia Ten., S. subspicata Vis. and Endemic S. visianii Šilic. Advances in Biological Chemistry, 5, 235-238. doi: 10.4236/abc.2015.57020.
Dunkić, V. , Radovanović, I. , Bezić, N. and Vuko, E. (2015) Glycosidically Bound Volatile Compounds of Satureja Montana L., S. cuneifo-lia Ten., S. subspicata Vis. and Endemic S. visianii Šilic. Advances in Biological Chemistry, 5, 235-238. doi: 10.4236/abc.2015.57020.
References
[1] Silic, C. (1979) Monografija rodova Satureja L., Calamintha Miller, Micromeria Bentham, Acinos Miller i Clinopodium L. u flori Jugoslavije. Zemaljski muzej BiH, Sarajevo. [2] Bezic, N., Samanic, I., Dunkic, V., Besendorfer, V. and Puizina, J. (2009) Essential Oil Composition and Internal Transcribed Spacer (ITS) Sequence Variability of Four South-Croatian Satureja Species (Lamiaceae). Molecules, 14, 925-938.
http://dx.doi.org/10.3390/molecules14030925 [3] Dunkic, V., Kremer, D., Dragojevic Müler, I., Stabentheinerd, E., Kuzmic, S., Jurisic Grubesic, R., Vujic, L., Kosalec, I., Randic, M., Srecec, S. and Bezic, N. (2012) Chemotaxonomic and Micromorphological Traits of Satureja montana L. and S. subspicata Vis. (Lamiaceae). Chemistry and Biodiversity, 9, 2825-2842.
http://dx.doi.org/10.1002/cbdv.201100376 [4] Cavar, S., Maksimovic, M., Solic, M.E., Jerkovic-Mujkic, A. and Besta, R. (2008) Chemical Composition and Antioxidant and Antimicrobial Activity of Two Satureja Essential Oils. Food Chemisty, 111, 648-653.
http://dx.doi.org/10.1016/j.foodchem.2008.04.033 [5] Milos, M., Radonic, A., Bezic, N. and Dunkic, V. (2001) Localities and Seasonal Variations in the Chemical Composition of Essential Oils of Satureja montana L. and S. cuneifolia Ten. Flavour and Fragrance Journal, 16, 157-160.
http://dx.doi.org/10.1002/ffj.965 [6] Angelini, L.G., Carpanese, G., Cioni, P.L., Morelli, I., Macchia, M. and Flamini, G. (2003) Essential Oils from Mediterranean Lamiaceae as Weed Germination Inhibitors. Journal of Agricultural and Food Chemistry, 51, 6158-6164.
http://dx.doi.org/10.1021/jf0210728 [7] Skocibusic, M., Bezic, N. and Dunkic, V. (2006) Phytochemical Composition and Antimicrobial Activities of the Essential Oils from Satureja subspicata Vis. Growing in Croatia. Food Chemistry, 96, 20-28.
http://dx.doi.org/10.1016/j.foodchem.2005.01.051 [8] Ciani, M., Menghini, L., Mariani, F., Pagiotti, R., Menghini, A. and Fatichenti, F. (2000) Antimicrobial Properties of Essential Oil of Satureja montana L. on Patho-Genic and Spoilage Yeasts. Biotechnology Letters, 22, 1007-1010.
http://dx.doi.org/10.1023/A:1005649506369 [9] Mastelic, J. and Jerkovic, I. (2003) Gas Chromatography-Mass Spectrometry Analysis of Free and Glycoconjugated Aroma Compounds of Seasonally Collected Satureja montana L. Food Chemistry, 80, 135-140.
http://dx.doi.org/10.1016/S0308-8146(02)00346-1 [10] Radonic, A. and Milos, M. (2003) Chemical Composition and Antioxidant Test of Free and Glycosidically Bound Volatile Compounds of Savory (Satureja montana L. Subsp. Montana) from Croatia. Nahrung/Food, 47, 236-237.
http://dx.doi.org/10.1002/food.200390055 [11] Mahmoud, S.S. and Croteau, R.B. (2002) Strategies for Transgenic Manipulation of Monoterpene Biosynthesis in Plants. Trends in Plant Science, 7, 366-373.
http://dx.doi.org/10.1016/S1360-1385(02)02303-8 [12] Wink, M. (2003) Evolution of Secondary Metabolites from an Ecological and Molecular Phylogenetic Perspective. Phytochemistry, 64, 3-19.
http://dx.doi.org/10.1016/S0031-9422(03)00300-5 [13] Adams, R.P. (2007) Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. 4th Edition, Allured Publishing, Carol Stream. [14] Stahl-Biskup, E., Intert, F., Holthuijzen, J., Stengele, M. and Schulz, G. (1993) Glycosidically Bound Volatiles. A Review. 1986-1991. Flavour and Fragrance Journal, 8, 61-80.
http://dx.doi.org/10.1002/ffj.2730080202 [15] Milos, M., Mastelic, J. and Jerkovic, I. (2000) Chemical Composition and Glycosidically Bound Volatile Compounds from Oregano (Origanum vulgare L. spp. hirtum). Food Chemistry, 71, 79-83.
http://dx.doi.org/10.1016/S0308-8146(00)00144-8
[1] Silic, C. (1979) Monografija rodova Satureja L., Calamintha Miller, Micromeria Bentham, Acinos Miller i Clinopodium L. u flori Jugoslavije. Zemaljski muzej BiH, Sarajevo. [2] Bezic, N., Samanic, I., Dunkic, V., Besendorfer, V. and Puizina, J. (2009) Essential Oil Composition and Internal Transcribed Spacer (ITS) Sequence Variability of Four South-Croatian Satureja Species (Lamiaceae). Molecules, 14, 925-938.
http://dx.doi.org/10.3390/molecules14030925 [3] Dunkic, V., Kremer, D., Dragojevic Müler, I., Stabentheinerd, E., Kuzmic, S., Jurisic Grubesic, R., Vujic, L., Kosalec, I., Randic, M., Srecec, S. and Bezic, N. (2012) Chemotaxonomic and Micromorphological Traits of Satureja montana L. and S. subspicata Vis. (Lamiaceae). Chemistry and Biodiversity, 9, 2825-2842.
http://dx.doi.org/10.1002/cbdv.201100376 [4] Cavar, S., Maksimovic, M., Solic, M.E., Jerkovic-Mujkic, A. and Besta, R. (2008) Chemical Composition and Antioxidant and Antimicrobial Activity of Two Satureja Essential Oils. Food Chemisty, 111, 648-653.
http://dx.doi.org/10.1016/j.foodchem.2008.04.033 [5] Milos, M., Radonic, A., Bezic, N. and Dunkic, V. (2001) Localities and Seasonal Variations in the Chemical Composition of Essential Oils of Satureja montana L. and S. cuneifolia Ten. Flavour and Fragrance Journal, 16, 157-160.
http://dx.doi.org/10.1002/ffj.965 [6] Angelini, L.G., Carpanese, G., Cioni, P.L., Morelli, I., Macchia, M. and Flamini, G. (2003) Essential Oils from Mediterranean Lamiaceae as Weed Germination Inhibitors. Journal of Agricultural and Food Chemistry, 51, 6158-6164.
http://dx.doi.org/10.1021/jf0210728 [7] Skocibusic, M., Bezic, N. and Dunkic, V. (2006) Phytochemical Composition and Antimicrobial Activities of the Essential Oils from Satureja subspicata Vis. Growing in Croatia. Food Chemistry, 96, 20-28.
http://dx.doi.org/10.1016/j.foodchem.2005.01.051 [8] Ciani, M., Menghini, L., Mariani, F., Pagiotti, R., Menghini, A. and Fatichenti, F. (2000) Antimicrobial Properties of Essential Oil of Satureja montana L. on Patho-Genic and Spoilage Yeasts. Biotechnology Letters, 22, 1007-1010.
http://dx.doi.org/10.1023/A:1005649506369 [9] Mastelic, J. and Jerkovic, I. (2003) Gas Chromatography-Mass Spectrometry Analysis of Free and Glycoconjugated Aroma Compounds of Seasonally Collected Satureja montana L. Food Chemistry, 80, 135-140.
http://dx.doi.org/10.1016/S0308-8146(02)00346-1 [10] Radonic, A. and Milos, M. (2003) Chemical Composition and Antioxidant Test of Free and Glycosidically Bound Volatile Compounds of Savory (Satureja montana L. Subsp. Montana) from Croatia. Nahrung/Food, 47, 236-237.
http://dx.doi.org/10.1002/food.200390055 [11] Mahmoud, S.S. and Croteau, R.B. (2002) Strategies for Transgenic Manipulation of Monoterpene Biosynthesis in Plants. Trends in Plant Science, 7, 366-373.
http://dx.doi.org/10.1016/S1360-1385(02)02303-8 [12] Wink, M. (2003) Evolution of Secondary Metabolites from an Ecological and Molecular Phylogenetic Perspective. Phytochemistry, 64, 3-19.
http://dx.doi.org/10.1016/S0031-9422(03)00300-5 [13] Adams, R.P. (2007) Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. 4th Edition, Allured Publishing, Carol Stream. [14] Stahl-Biskup, E., Intert, F., Holthuijzen, J., Stengele, M. and Schulz, G. (1993) Glycosidically Bound Volatiles. A Review. 1986-1991. Flavour and Fragrance Journal, 8, 61-80.
http://dx.doi.org/10.1002/ffj.2730080202 [15] Milos, M., Mastelic, J. and Jerkovic, I. (2000) Chemical Composition and Glycosidically Bound Volatile Compounds from Oregano (Origanum vulgare L. spp. hirtum). Food Chemistry, 71, 79-83.
http://dx.doi.org/10.1016/S0308-8146(00)00144-8