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CHEMICAL CONSTITUENTS ISOLATED FROM ORİGANUM SOLYMICUM WITH ANTIOXIDANT ACTIVITITES

Yıl 2017, Sayı: 1, 139 - 145, 09.11.2017

Öz

Origanum genus includes 43 species and 18 hybrids. Sixteen
species are endemic for Turkey. Due to the spicy fragrance,
Origanum has been widely used in
food products as flavoring agents.
These species are well known for their essential oils
which have been applied
in food and cosmetic industries. Origanum Solymicum P.H. Davis was collected from Kemer,
Antalya. The aerial part of plant materials were dried and powdered then
boiled in water. After filtration, water phase was partitioned with ethyl acetate and n-butanol sequentially. After
removal of the solvent by rotary evaporator, the chromatographic methods were
applied for ethyl acetate extract to isolate the bioactive compounds.
3,4-dihdroxy benzoic acid (protocatechuic acid) (1), 3,4-dihydroxy benzaldehyde (protocatechuic
aldehyde) (2), 2-O-ß-D-
glycopyronozyl-4,6-dihydroxyacetophenone
(myrciaphenone) (3), caffeic
acid (4), rosmarinic acid (5), lithospermic acid B (6) were isolated by
chromatographic techniques (column
chromatography, preparative HPLC) and spectroscopic methods (1D, 2D NMR,
LC-TOF/MS) were used for elucidation of isolated compounds. All isolated
natural products revealed the outstanding activities on antioxidant assays
including DPPHfree radical scavenging, ABTS•+ radical
cation scavenging, and reducing power (FRAP).

Kaynakça

  • Abu-Lafi, S., Odeh, I., Dewik, H., Qabajah, M., Hanuš, L., & Dembitsky, V. (2008). Thymol and carvacrol production from leaves of wild Palestinian Majorana syriaca. Bioresource Technology, 99(9), 3914-3918. Aksit, H., Celik, S. M., Sen, O., Erenler, R., Demirtas, I., Telci, I., & Elmastas, M. (2014). Complete Isolation and Characterization of Polar Portion of Mentha dumetorum Water Extract. Records of Natural Products, 8(3), 277-280. Awaad, A. S., El-Meligy, R., Qenawy, S., Atta, A., & Soliman, G. A. (2011). Anti-inflammatory, antinociceptive and antipyretic effects of some desert plants. Journal of Saudi Chemical Society, 15(4), 367-373. Ayinde, B. A., Onwukaeme, D. N., & Omogbai, E. (2007). Isolation and characterization of two phenolic compounds from the stem bark of Musanga cecropioides R. Brown (Moraceae). Acta Poloniae Pharmaceutica, 64(2), 183-185. Ban, J. Y., Jeon, S.-Y., Bae, K., Song, K.-S., & Seong, Y. H. (2006). Catechin and epicatechin from Smilacis chinae rhizome protect cultured rat cortical neurons against amyloid β protein (25–35)-induced neurotoxicity through inhibition of cytosolic calcium elevation. Life sciences, 79(24), 2251-2259. Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature(26), 1199-1200. Bower, A. M., Hernandez, L. M. R., Berhow, M. A., & de Mejia, E. G. (2014). Bioactive Compounds from Culinary Herbs Inhibit a Molecular Target for Type 2 Diabetes Management, Dipeptidyl Peptidase IV. Journal of Agricultural and Food Chemistry, 62(26), 6147-6158. Busatta, C., Vidal, R., Popiolski, A., Mossi, A., Dariva, C., Rodrigues, M., Cansian, R. (2008). Application of Origanum majorana L. essential oil as an antimicrobial agent in sausage. Food Microbiology, 25(1), 207-211. Cerveny, L., Kovarova, L., & Marhoul, A. (1996). The synthesis of 3,4-dihydroxy-benzaldehyde. Chimica Oggi-Chemistry Today, 14(5), 37-40. Cragg, G. M., Newman, D. J., & Snader, K. M. (1997). Natural products in drug discovery and development. Journal of Natural Products, 60(1), 52-60. Demirtas, I., Erenler, R., Elmastas, M., & Goktasoglu, A. (2013). Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chemistry, 136(1), 34-40. Duman, H., Aytaç, Z., Ekici, M., Karavelioğulları, F., Dönmez, A., & Duran, A. (1995). Three new species (Labiatae) from Turkey. Flora Mediterranea, 5, 221-228. Erdemli, H. K., Akyol, S., Armutcu, F., Gulec, M. A., Canbal, M., & Akyol, O. (2016). Melatonin and caffeic acid phenethyl ester in the regulation of mitochondrial function and apoptosis: The basis for future medical approaches. Life Sci, 148, 305-312. Erenler, R., Meral, B., Sen, O., Elmastas, M., Aydin, A., Eminagaoglu, O., & Topcu, G. (2017). Bioassay-guided isolation, identification of compounds from Origanum rotundifolium and investigation of their antiproliferative and antioxidant activities. Pharmaceutical Biology, 55(1), 1646-1653. Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A. S., Elmastas, M., & Telci, I. (2016). Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities. Journal of the Science of Food and Agriculture, 96(3), 822-836. Erenler, R., Sen, O., Yaglioglu, A. S., & Demirtas, I. (2016). Bioactivity-guided isolation of antiproliferative sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis. Combinatorial chemistry & high throughput screening, 19(1), 66-72. Erenler, R., Sen, O., Yildiz, I., & Aydin, A. (2016). Antiproliferative activities of chemical constituents isolated from Thymus praecox subsp grossheimii (Ronniger) Jalas. Records of Natural Products, 10(6), 766-770. Ietswaart, J. H., & Ietswaart, J. (1980). A taxonomic revision of the genus Origanum (Labiatae) (Vol. 4): Leiden University Press The Hague. Karaman, M., Bogavac, M., Radovanović, B., Sudji, J., Tešanović, K., & Janjušević, L. (2017). Origanum vulgare essential oil affects pathogens causing vaginal infections. Journal of applied microbiology, 122(5), 1177-1185. Makhmoor, T., & Choudhary, M. I. (2010). Radical scavenging potential of compounds isolated from Vitex agnus-castus. Turkish Journal of Chemistry, 34(1), 119-126. Murata, T., Oyama, K., Fujiyama, M., Oobayashi, B., Umehara, K., Miyase, T., & Yoshizaki, F. (2013). Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon. Fitoterapia, 91, 51-59. Oke Altuntas, F., & Demirtas, I. (2017). Real-Time Cell Analysis of the Cytotoxicity of Origanum acutidens Essential Oil on HT-29 and HeLa Cell Lines. Turkish Journal of Pharmaceutical Sciences, 14(1). Orhan, I. E., Ozcelik, B., Kan, Y., & Kartal, M. (2011). Inhibitory Effects of Various Essential Oils and Individual Components against Extended‐Spectrum Beta‐Lactamase (ESBL) Produced by Klebsiella pneumoniae and Their Chemical Compositions. Journal of Food Science, 76(8). Oyaizu, M. (1986). Studies on products of browing reaction antioxidative activities of products browing reaction prepared from glucosamine. Japanese Journal of Nutrition, 44, 307-315. Petersen, M., & Simmonds, M. S. (2003). Rosmarinic acid. Phytochemistry, 62(2), 121-125. Quiroga, P. R., Grosso, N. R., Lante, A., Lomolino, G., Zygadlo, J. A., & Nepote, V. (2013). Chemical composition, antioxidant activity and anti-lipase activity of Origanum vulgare and Lippia turbinata essential oils. International Journal of Food Science and Technology, 48(3), 642-649. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237. Ren, D., Han, B., Xin, Z., Ma, S., Liu, W., & Yi, L. (2017). Combined application of chromatographic techniques for the separation of phenolic compounds from Stenoloma chusanum Ching. Journal of Separation Science, 40(5), 1076-1082. Semaming, Y., Pannengpetch, P., Chattipakorn, S. C., & Chattipakorn, N. (2015). Pharmacological properties of protocatechuic acid and its potential roles as complementary medicine. Evidence-Based Complementary and Alternative Medicine, 2015, 1-11. Singleton, V. L., & Slinkard, K. (1977). Total phenol analysis: Automation and comparison with manual methods. American Journal of Enology and Viticulture, 28, 49-55. Soliman, A. M., Desouky, S., Marzouk, M., & Sayed, A. A. (2016). Origanum majorana Attenuates Nephrotoxicity of Cisplatin Anticancer Drug through Ameliorating Oxidative Stress. Nutrients, 8(5), 264. Tepe, B., Cakir, A., & Sihoglu Tepe, A. (2016). Medicinal uses, phytochemistry, and pharmacology of Origanum onites (L.): A Review. Chemistry & Biodiversity, 13(5), 504-520. Topcu, G., Erenler, R., Cakmak, O., Johansson, C. B., Celik, C., Chai, H. B., & Pezzuto, J. M. (1999). Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50(7), 1195-1199. Walker, J. F., Santos, P. d. S., Schmidt, C. A., Bittencourt, T. C. C. d., & Guimarães, A. G. (2016). Antimicrobial Activity of Marjoram (Origanum Majorana) Essential Oil Against the Multidrug‐Resistant Salmonella Enterica Serovar Schwarzengrund Inoculated in Vegetables from Organic Farming. Journal of Food Safety, 36(4), 489-496. Waller, S. B., Cleff, M. B., Serra, E. F., Silva, A. L., dos Reis Gomes, A., de Mello, J. R. B., Meireles, M. C. A. (2017). Plants from Lamiaceae family as source of antifungal molecules in humane and veterinary medicine. Microbial Pathogenesis. Yazdanparast, R., & Shahriyary, L. (2008). Comparative effects of Artemisia dracunculus, Satureja hortensis and Origanum majorana on inhibition of blood platelet adhesion, aggregation and secretion. Vascular pharmacology, 48(1), 32-37. Yılmaz, H., Çarıkçı, S., Kılıç, T., Dirmenci, T., Arabacı, T., & Gören, A. C. (2017). Screening of Chemical Composition, Antioxidant and Anticholinesterase Activity of Section Brevifilamentum of Origanum (L.) Species. Department of Biology Educations, Balıkesir. Zhang, H., Shao, Q., Wang, W., Zhang, J., Zhang, Z., Liu, Y., & Yang, Y. (2017). Characterization of Compounds with Tumor–Cell Proliferation Inhibition Activity from Mushroom (Phellinus baumii) Mycelia Produced by Solid-State Fermentation. Molecules, 22(5), 698.
Yıl 2017, Sayı: 1, 139 - 145, 09.11.2017

Öz

Kaynakça

  • Abu-Lafi, S., Odeh, I., Dewik, H., Qabajah, M., Hanuš, L., & Dembitsky, V. (2008). Thymol and carvacrol production from leaves of wild Palestinian Majorana syriaca. Bioresource Technology, 99(9), 3914-3918. Aksit, H., Celik, S. M., Sen, O., Erenler, R., Demirtas, I., Telci, I., & Elmastas, M. (2014). Complete Isolation and Characterization of Polar Portion of Mentha dumetorum Water Extract. Records of Natural Products, 8(3), 277-280. Awaad, A. S., El-Meligy, R., Qenawy, S., Atta, A., & Soliman, G. A. (2011). Anti-inflammatory, antinociceptive and antipyretic effects of some desert plants. Journal of Saudi Chemical Society, 15(4), 367-373. Ayinde, B. A., Onwukaeme, D. N., & Omogbai, E. (2007). Isolation and characterization of two phenolic compounds from the stem bark of Musanga cecropioides R. Brown (Moraceae). Acta Poloniae Pharmaceutica, 64(2), 183-185. Ban, J. Y., Jeon, S.-Y., Bae, K., Song, K.-S., & Seong, Y. H. (2006). Catechin and epicatechin from Smilacis chinae rhizome protect cultured rat cortical neurons against amyloid β protein (25–35)-induced neurotoxicity through inhibition of cytosolic calcium elevation. Life sciences, 79(24), 2251-2259. Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature(26), 1199-1200. Bower, A. M., Hernandez, L. M. R., Berhow, M. A., & de Mejia, E. G. (2014). Bioactive Compounds from Culinary Herbs Inhibit a Molecular Target for Type 2 Diabetes Management, Dipeptidyl Peptidase IV. Journal of Agricultural and Food Chemistry, 62(26), 6147-6158. Busatta, C., Vidal, R., Popiolski, A., Mossi, A., Dariva, C., Rodrigues, M., Cansian, R. (2008). Application of Origanum majorana L. essential oil as an antimicrobial agent in sausage. Food Microbiology, 25(1), 207-211. Cerveny, L., Kovarova, L., & Marhoul, A. (1996). The synthesis of 3,4-dihydroxy-benzaldehyde. Chimica Oggi-Chemistry Today, 14(5), 37-40. Cragg, G. M., Newman, D. J., & Snader, K. M. (1997). Natural products in drug discovery and development. Journal of Natural Products, 60(1), 52-60. Demirtas, I., Erenler, R., Elmastas, M., & Goktasoglu, A. (2013). Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chemistry, 136(1), 34-40. Duman, H., Aytaç, Z., Ekici, M., Karavelioğulları, F., Dönmez, A., & Duran, A. (1995). Three new species (Labiatae) from Turkey. Flora Mediterranea, 5, 221-228. Erdemli, H. K., Akyol, S., Armutcu, F., Gulec, M. A., Canbal, M., & Akyol, O. (2016). Melatonin and caffeic acid phenethyl ester in the regulation of mitochondrial function and apoptosis: The basis for future medical approaches. Life Sci, 148, 305-312. Erenler, R., Meral, B., Sen, O., Elmastas, M., Aydin, A., Eminagaoglu, O., & Topcu, G. (2017). Bioassay-guided isolation, identification of compounds from Origanum rotundifolium and investigation of their antiproliferative and antioxidant activities. Pharmaceutical Biology, 55(1), 1646-1653. Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A. S., Elmastas, M., & Telci, I. (2016). Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities. Journal of the Science of Food and Agriculture, 96(3), 822-836. Erenler, R., Sen, O., Yaglioglu, A. S., & Demirtas, I. (2016). Bioactivity-guided isolation of antiproliferative sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis. Combinatorial chemistry & high throughput screening, 19(1), 66-72. Erenler, R., Sen, O., Yildiz, I., & Aydin, A. (2016). Antiproliferative activities of chemical constituents isolated from Thymus praecox subsp grossheimii (Ronniger) Jalas. Records of Natural Products, 10(6), 766-770. Ietswaart, J. H., & Ietswaart, J. (1980). A taxonomic revision of the genus Origanum (Labiatae) (Vol. 4): Leiden University Press The Hague. Karaman, M., Bogavac, M., Radovanović, B., Sudji, J., Tešanović, K., & Janjušević, L. (2017). Origanum vulgare essential oil affects pathogens causing vaginal infections. Journal of applied microbiology, 122(5), 1177-1185. Makhmoor, T., & Choudhary, M. I. (2010). Radical scavenging potential of compounds isolated from Vitex agnus-castus. Turkish Journal of Chemistry, 34(1), 119-126. Murata, T., Oyama, K., Fujiyama, M., Oobayashi, B., Umehara, K., Miyase, T., & Yoshizaki, F. (2013). Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon. Fitoterapia, 91, 51-59. Oke Altuntas, F., & Demirtas, I. (2017). Real-Time Cell Analysis of the Cytotoxicity of Origanum acutidens Essential Oil on HT-29 and HeLa Cell Lines. Turkish Journal of Pharmaceutical Sciences, 14(1). Orhan, I. E., Ozcelik, B., Kan, Y., & Kartal, M. (2011). Inhibitory Effects of Various Essential Oils and Individual Components against Extended‐Spectrum Beta‐Lactamase (ESBL) Produced by Klebsiella pneumoniae and Their Chemical Compositions. Journal of Food Science, 76(8). Oyaizu, M. (1986). Studies on products of browing reaction antioxidative activities of products browing reaction prepared from glucosamine. Japanese Journal of Nutrition, 44, 307-315. Petersen, M., & Simmonds, M. S. (2003). Rosmarinic acid. Phytochemistry, 62(2), 121-125. Quiroga, P. R., Grosso, N. R., Lante, A., Lomolino, G., Zygadlo, J. A., & Nepote, V. (2013). Chemical composition, antioxidant activity and anti-lipase activity of Origanum vulgare and Lippia turbinata essential oils. International Journal of Food Science and Technology, 48(3), 642-649. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237. Ren, D., Han, B., Xin, Z., Ma, S., Liu, W., & Yi, L. (2017). Combined application of chromatographic techniques for the separation of phenolic compounds from Stenoloma chusanum Ching. Journal of Separation Science, 40(5), 1076-1082. Semaming, Y., Pannengpetch, P., Chattipakorn, S. C., & Chattipakorn, N. (2015). Pharmacological properties of protocatechuic acid and its potential roles as complementary medicine. Evidence-Based Complementary and Alternative Medicine, 2015, 1-11. Singleton, V. L., & Slinkard, K. (1977). Total phenol analysis: Automation and comparison with manual methods. American Journal of Enology and Viticulture, 28, 49-55. Soliman, A. M., Desouky, S., Marzouk, M., & Sayed, A. A. (2016). Origanum majorana Attenuates Nephrotoxicity of Cisplatin Anticancer Drug through Ameliorating Oxidative Stress. Nutrients, 8(5), 264. Tepe, B., Cakir, A., & Sihoglu Tepe, A. (2016). Medicinal uses, phytochemistry, and pharmacology of Origanum onites (L.): A Review. Chemistry & Biodiversity, 13(5), 504-520. Topcu, G., Erenler, R., Cakmak, O., Johansson, C. B., Celik, C., Chai, H. B., & Pezzuto, J. M. (1999). Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50(7), 1195-1199. Walker, J. F., Santos, P. d. S., Schmidt, C. A., Bittencourt, T. C. C. d., & Guimarães, A. G. (2016). Antimicrobial Activity of Marjoram (Origanum Majorana) Essential Oil Against the Multidrug‐Resistant Salmonella Enterica Serovar Schwarzengrund Inoculated in Vegetables from Organic Farming. Journal of Food Safety, 36(4), 489-496. Waller, S. B., Cleff, M. B., Serra, E. F., Silva, A. L., dos Reis Gomes, A., de Mello, J. R. B., Meireles, M. C. A. (2017). Plants from Lamiaceae family as source of antifungal molecules in humane and veterinary medicine. Microbial Pathogenesis. Yazdanparast, R., & Shahriyary, L. (2008). Comparative effects of Artemisia dracunculus, Satureja hortensis and Origanum majorana on inhibition of blood platelet adhesion, aggregation and secretion. Vascular pharmacology, 48(1), 32-37. Yılmaz, H., Çarıkçı, S., Kılıç, T., Dirmenci, T., Arabacı, T., & Gören, A. C. (2017). Screening of Chemical Composition, Antioxidant and Anticholinesterase Activity of Section Brevifilamentum of Origanum (L.) Species. Department of Biology Educations, Balıkesir. Zhang, H., Shao, Q., Wang, W., Zhang, J., Zhang, Z., Liu, Y., & Yang, Y. (2017). Characterization of Compounds with Tumor–Cell Proliferation Inhibition Activity from Mushroom (Phellinus baumii) Mycelia Produced by Solid-State Fermentation. Molecules, 22(5), 698.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Konular Mühendislik
Bölüm Makaleler
Yazarlar

Ramazan Erenler

Tugba Adak

Tunay Karan

Mahfuz Elmastas

İlyas Yildiz

Huseyin Aksit

Gulacti Topcu

Murat Aydin Sanda

Yayımlanma Tarihi 9 Kasım 2017
Yayımlandığı Sayı Yıl 2017Sayı: 1

Kaynak Göster

APA Erenler, R., Adak, T., Karan, T., Elmastas, M., vd. (2017). CHEMICAL CONSTITUENTS ISOLATED FROM ORİGANUM SOLYMICUM WITH ANTIOXIDANT ACTIVITITES. The Eurasia Proceedings of Science Technology Engineering and Mathematics(1), 139-145.