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Quantitative analysis of bioactive compounds by LC-MS/MS from Inula graveolens

Year 2023, Volume: 4 Issue: 3, 3 - 10, 28.08.2023

Ramazan Erenler Mehmet Nuri Atalar İlyas Yıldız Esma Nur Geçer Aslı Yıldırım İbrahim Demirtas Mehmet Hakkı Alma

https://doi.org/10.53445/batd.1278048

Abstract

Medicinal plants have been employed commonly in many countries to remedy of various ailments. In this study, Inula graveolens leaves (5.0 g) were extracted with methanol (100 mL) for 24 hours at room temperature. After filtration with Whatman 1 filter pater, the solvent was removed under reduced pressure to yield the crude extract. Quantification of natural products in methanol extract of Inula graveolens was determined by LC-MS/MS. Chlorogenic acid was determined as a chief product (3.5 mg/g extract). Furthermore, salicylic acid (0.055 mg/g extract), caffeic acid (0.054 mg/g extract), protocatechuic acid (0.026 mg/g extract), hesperidin (0.016 mg/g extract), rutin (0.0160 mg/g extract) were found in the methanol extract. Since Inula graveolens contains important bioactive compounds, it has the possibility to be used in pharmaceuticals and food.

Keywords

Inula graveolens LC-MS/MS quantitative analysis bioactive compounds.

References

  • Aksit, H., Çelik, S. M., Sen, Ö., 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.
  • Aydin, A., Erenler, R., Yılmaz, B., & Tekin, Ş. (2016). Antiproliferative effect of Cherry laurel. Journal of the Turkish Chemical Society, Section A: Chemistry, 3(3), 217-228. https://doi.org/10.18596/jotcsa.21204.
  • Bayir, B., Gündüz, H., Usta, T., Şahin, E., Özdemir, Z., Kayır, Ö., Sen, Ö., Akşit, H., Elmastaş, M., & Erenler, R. (2014). Chemical Composition of Essential Oil from Marrubium Vulgare L. Leaves. Journal of New Results in Science, 6(6), 44-50.
  • Del Bo’, C., Bernardi, S., Marino, M., Porrini, M., Tucci, M., Guglielmetti, S., Cherubini, A., Carrieri, B., Kirkup, B., & Kroon, P. (2019). Systematic review on polyphenol intake and health outcomes: is there sufficient evidence to define a health-promoting polyphenol-rich dietary pattern? Nutrients, 11(6), 1355. https://doi.org/10.3390/nu11061355.
  • 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. https://doi.org/10.1016/j.foodchem.2012.07.086.
  • Elmastas, M., Celik, S. M., Genc, N., Aksit, H., Erenler, R., & Gulcin, İ. (2018). Antioxidant activity of an anatolian herbal tea—Origanum minutiflorum: isolation and characterization of its secondary metabolites. International Journal of Food Properties, 21(1), 374-384. https://doi.org/10.1080/10942912.2017.1416399.
  • Elmastas, M., Erenler, R., Isnac, B., Aksit, H., Sen, O., Genc, N., & Demirtas, I. (2016). Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L. Natural Product Research, 30(3), 299-304. https://doi.org/10.1080/14786419.2015.1057583.
  • Elmastas, M., Ozturk, L., Gokce, I., Erenler, R., & Aboul‐Enein, H. Y. (2004). Determination of antioxidant activity of marshmallow flower (Althaea officinalis L.). Analytical Letters, 37(9), 1859-1869. https://doi.org/10.1081/AL-120039431.
  • Erenler, R., Adak, T., Karan, T., Elmastas, M., Yildiz, I., Aksit, H., Topcu, G., & Sanda, M. A. (2017). Chemical Constituents isolated from Origanum solymicum with Antioxidant activities. The Eurasia Proceedings of Science, Technology, Engineering & Mathematics, 1, 139-145.
  • Erenler, R., Carlik, U. E., & Aydin, A. (2023). Antiproliferative activity and cytotoxic effect of essential oil and water extract from origanum Vulgare L. Sigma, 41(1), 202-208. https://10.14744/sigma.2023.00018.
  • Erenler, R., Demirtas, I., Karan, T., Altun, M., & Gul, F. (2017). Inhibitory Effect of 6, 7-dimethoxy-5-hydroxyflavone on Human Cervix Carcinoma in Vitro. International Journal of Secondary Metabolite (IJSM), 4(3, Special Issue 2), 512-516.
  • Erenler, R., Demirtas, I., Karan, T., Gul, F., Kayir, O., & Karakoc, O. C. (2018). Chemical constituents, quantitative analysis and insecticidal activities of plant extract and essential oil from Origanum onites L. Trends in Phytochemical Research, 2(2), 91-96.
  • 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. https://doi.org/10.1080/13880209.2017.1310906.
  • Erenler, R., Pabuccu, K., Yaglioglu, A. S., Demirtas, I., & Gul, F. (2016). Chemical constituents and antiproliferative effects of cultured Mougeotia nummuloides and Spirulina major against cancerous cell lines. Zeitschrift fur Naturforschung - Section C Journal of Biosciences, 71(3-4), 87-92. https://doi.org/10.1515/znc-2016-0010.
  • Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A. S., Elmastas, M., & Telci, İ. (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. https://doi.org/10.1002/jsfa.7155.
  • 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. https://doi.org/10.2174/1386207319666151203002117.
  • Erenler, R., Sen, O., Yildiz, I., & Aydın, A. (2016). Antiproliferative activities of chemical constituents isolated from Thymus praecox subsp. grossheimii (Ronniger) Jalas. Records of Natural Products, 10(6), 766-770.
  • Erenler, R., Telci, İ., Elmastaş, M., Akşit, H., Gül, F., Tüfekçi, A. R., Demirtaş, İ., & Kayir, Ö. (2018). Quantification of flavonoids isolated from Mentha spicata in selected clones of Turkish mint landraces. Turkish Journal of Chemistry, 42(6), 1695-1705. https://doi.org/10.3906/kim-1712-3.
  • Erenler, R., Telci, I., Ulutas, M., Demirtas, I., Gul, F., Elmastas, M., & Kayir, O. (2015). Chemical Constituents, Quantitative Analysis and Antioxidant Activities of Echinacea purpurea (L.) Moench and Echinacea pallida (Nutt.) Nutt. Journal of Food Biochemistry, 39(5), 622-630. https://doi.org/10.1111/jfbc.12168.
  • Erenler, R., Yaman, C., Demirtas, I., & Alma, M. H. (2023). Phytochemical Investigation of Hypericum heterophyllum Flowers: LC-ESI-MS/MS Analysis, Total Phenolic and Flavonoid Contents, Antioxidant Activity. The Natural Products Journal, 13(7), e120123212672. https://doi.org/10.2174/2210315513666230112165545.
  • Erenler, R., Yilmaz, S., Aksit, H., Sen, O., Genc, N., Elmastas, M., & Demirtas, I. (2014). Antioxidant activities of chemical constituents isolated from Echinops orientalis Trauv. Records of Natural Products, 8(1), 32-36.
  • Farah, A., & de Paula Lima, J. (2019). Consumption of Chlorogenic Acids through Coffee and Health Implications. Beverages, 5(1), 11. https://doi.org/10.3390/beverages5010011.
  • Guzel, A., Aksit, H., Elmastas, M., & Erenler, R. (2017). Bioassay-guided isolation and identification of antioxidant flavonoids from Cyclotrichium origanifolium (Labill.) Manden. and Scheng. Pharmacognosy Magazine, 13(50), 316. https://doi.org/10.4103/0973-1296.204556.
  • Haslam, E. (1974). Polyphenol-protein interactions. Biochem J, 139(1), 285-288. https://doi.org/10.1042/bj1390285.
  • Karan, T., Altuner, Z., & Erenler, R. (2017). Growth and Metabolite Production of Chroococcus minutus Under Different Temperature and Light Conditions. Journal of New Results in Science, 6(1), 47-52.
  • Karan, T., Dastan, T., Baral, I., & Altuner, Z. (2016). Effects of Differential Time Applications on Some Cyanobacterial Norharman Production Rates. Cumhuriyet University Faculty of Science, 37(4), 398-404.
  • Karan, T., & Erenler, R. (2017). Screening of norharmane from seven cyanobacteria by high-performance liquid chromatography. Pharmacognosy Magazine, 13(Suppl 3), 723-725. https://doi.org/10.4103/pm.pm_214_17.
  • Karan, T., Erenler, R., & Altuner, Z. (2017). Isolation and Molecular Identification of Some Blue-Green Algae (Cyanobacteria) from Freshwater Sites in Tokat Province of Turkey. Turkish Journal of Agriculture-Food Science and Technology, 5(11), 1371-1378.
  • Karan, T., Yildiz, I., Aydin, A., & Erenler, R. (2018). Inhibition of various cancer cells proliferation of bornyl acetate and essential oil from Inula graveolens (Linnaeus) Desf. Records of Natural Products, 12(3), 273-283.
  • Kaya, G., Karakaya, R., Tilgel, E., Sandikci, M., Yucel, E., Cicek, G., Kayir, O., Aksit, H., Telci, I., & Guzel, A. (2014). Essential Oil Constituents of Thuja orientalis Berries. Journal of New Results in Science, 7(7), 1-6.
  • Sahin Yaglioglu, A., Akdulum, B., Erenler, R., Demirtas, I., Telci, I., & Tekin, S. (2013). Antiproliferative activity of pentadeca-(8E, 13Z) dien-11-yn-2-one and (E)-1,8-pentadecadiene from Echinacea pallida (Nutt.) Nutt. roots. Medicinal Chemistry Research, 22(6), 2946-2953. https://doi.org/10.1007/s00044-012-0297-2.
  • Silinsin, M., & Bursal, E. (2018). UHPLC-MS/MS phenolic profiling and in vitro antioxidant activities of Inula graveolens (L.) Desf. Natural Product Research, 32(12), 1467-1471. https://doi.org/10.1080/14786419.2017.1350673.
  • Topçu, G., Erenler, R., Çakmak, O., Johansson, C. B., Çelik, C., Chai, H.-B., & Pezzuto, J. M. (1999). Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50(7), 1195-1199. https://doi.org/10.1016/S0031-9422(98)00675-X.
  • Türkmen, N., Öz, A., Sönmez, A., Erol, T., Gülümser, D., Yurdakul, B., Kayır, Ö., Elmastas, M., & Erenler, R. (2014). Chemical Composition of Essential Oil from Rosmarinus Officinalis L. Leaves. Journal of New Results in Science, 6(6), 27-31.

Quantitative analysis of bioactive compounds by LC-MS/MS from Inula graveolens

Year 2023, Volume: 4 Issue: 3, 3 - 10, 28.08.2023

Ramazan Erenler Mehmet Nuri Atalar İlyas Yıldız Esma Nur Geçer Aslı Yıldırım İbrahim Demirtas Mehmet Hakkı Alma

https://doi.org/10.53445/batd.1278048

Abstract

Medicinal plants have been employed commonly in many countries to remedy of various ailments. In this study, Inula graveolens leaves (5.0 g) were extracted with methanol (100 mL) for 24 hours at room temperature. After filtration with Whatman 1 filter pater, the solvent was removed under reduced pressure to yield the crude extract. Quantification of natural products in methanol extract of Inula graveolens was determined by LC-MS/MS. Chlorogenic acid was determined as a chief product (3.5 mg/g extract). Furthermore, salicylic acid (0.055 mg/g extract), caffeic acid (0.054 mg/g extract), protocatechuic acid (0.026 mg/g extract), hesperidin (0.016 mg/g extract), rutin (0.0160 mg/g extract) were found in the methanol extract. Since Inula graveolens contains important bioactive compounds, it has the possibility to be used in pharmaceuticals and food.

Keywords

Inula graveolens LC-MS/MS quantitative analysis bioactive compounds

References

  • Aksit, H., Çelik, S. M., Sen, Ö., 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.
  • Aydin, A., Erenler, R., Yılmaz, B., & Tekin, Ş. (2016). Antiproliferative effect of Cherry laurel. Journal of the Turkish Chemical Society, Section A: Chemistry, 3(3), 217-228. https://doi.org/10.18596/jotcsa.21204.
  • Bayir, B., Gündüz, H., Usta, T., Şahin, E., Özdemir, Z., Kayır, Ö., Sen, Ö., Akşit, H., Elmastaş, M., & Erenler, R. (2014). Chemical Composition of Essential Oil from Marrubium Vulgare L. Leaves. Journal of New Results in Science, 6(6), 44-50.
  • Del Bo’, C., Bernardi, S., Marino, M., Porrini, M., Tucci, M., Guglielmetti, S., Cherubini, A., Carrieri, B., Kirkup, B., & Kroon, P. (2019). Systematic review on polyphenol intake and health outcomes: is there sufficient evidence to define a health-promoting polyphenol-rich dietary pattern? Nutrients, 11(6), 1355. https://doi.org/10.3390/nu11061355.
  • 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. https://doi.org/10.1016/j.foodchem.2012.07.086.
  • Elmastas, M., Celik, S. M., Genc, N., Aksit, H., Erenler, R., & Gulcin, İ. (2018). Antioxidant activity of an anatolian herbal tea—Origanum minutiflorum: isolation and characterization of its secondary metabolites. International Journal of Food Properties, 21(1), 374-384. https://doi.org/10.1080/10942912.2017.1416399.
  • Elmastas, M., Erenler, R., Isnac, B., Aksit, H., Sen, O., Genc, N., & Demirtas, I. (2016). Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L. Natural Product Research, 30(3), 299-304. https://doi.org/10.1080/14786419.2015.1057583.
  • Elmastas, M., Ozturk, L., Gokce, I., Erenler, R., & Aboul‐Enein, H. Y. (2004). Determination of antioxidant activity of marshmallow flower (Althaea officinalis L.). Analytical Letters, 37(9), 1859-1869. https://doi.org/10.1081/AL-120039431.
  • Erenler, R., Adak, T., Karan, T., Elmastas, M., Yildiz, I., Aksit, H., Topcu, G., & Sanda, M. A. (2017). Chemical Constituents isolated from Origanum solymicum with Antioxidant activities. The Eurasia Proceedings of Science, Technology, Engineering & Mathematics, 1, 139-145.
  • Erenler, R., Carlik, U. E., & Aydin, A. (2023). Antiproliferative activity and cytotoxic effect of essential oil and water extract from origanum Vulgare L. Sigma, 41(1), 202-208. https://10.14744/sigma.2023.00018.
  • Erenler, R., Demirtas, I., Karan, T., Altun, M., & Gul, F. (2017). Inhibitory Effect of 6, 7-dimethoxy-5-hydroxyflavone on Human Cervix Carcinoma in Vitro. International Journal of Secondary Metabolite (IJSM), 4(3, Special Issue 2), 512-516.
  • Erenler, R., Demirtas, I., Karan, T., Gul, F., Kayir, O., & Karakoc, O. C. (2018). Chemical constituents, quantitative analysis and insecticidal activities of plant extract and essential oil from Origanum onites L. Trends in Phytochemical Research, 2(2), 91-96.
  • 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. https://doi.org/10.1080/13880209.2017.1310906.
  • Erenler, R., Pabuccu, K., Yaglioglu, A. S., Demirtas, I., & Gul, F. (2016). Chemical constituents and antiproliferative effects of cultured Mougeotia nummuloides and Spirulina major against cancerous cell lines. Zeitschrift fur Naturforschung - Section C Journal of Biosciences, 71(3-4), 87-92. https://doi.org/10.1515/znc-2016-0010.
  • Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A. S., Elmastas, M., & Telci, İ. (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. https://doi.org/10.1002/jsfa.7155.
  • 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. https://doi.org/10.2174/1386207319666151203002117.
  • Erenler, R., Sen, O., Yildiz, I., & Aydın, A. (2016). Antiproliferative activities of chemical constituents isolated from Thymus praecox subsp. grossheimii (Ronniger) Jalas. Records of Natural Products, 10(6), 766-770.
  • Erenler, R., Telci, İ., Elmastaş, M., Akşit, H., Gül, F., Tüfekçi, A. R., Demirtaş, İ., & Kayir, Ö. (2018). Quantification of flavonoids isolated from Mentha spicata in selected clones of Turkish mint landraces. Turkish Journal of Chemistry, 42(6), 1695-1705. https://doi.org/10.3906/kim-1712-3.
  • Erenler, R., Telci, I., Ulutas, M., Demirtas, I., Gul, F., Elmastas, M., & Kayir, O. (2015). Chemical Constituents, Quantitative Analysis and Antioxidant Activities of Echinacea purpurea (L.) Moench and Echinacea pallida (Nutt.) Nutt. Journal of Food Biochemistry, 39(5), 622-630. https://doi.org/10.1111/jfbc.12168.
  • Erenler, R., Yaman, C., Demirtas, I., & Alma, M. H. (2023). Phytochemical Investigation of Hypericum heterophyllum Flowers: LC-ESI-MS/MS Analysis, Total Phenolic and Flavonoid Contents, Antioxidant Activity. The Natural Products Journal, 13(7), e120123212672. https://doi.org/10.2174/2210315513666230112165545.
  • Erenler, R., Yilmaz, S., Aksit, H., Sen, O., Genc, N., Elmastas, M., & Demirtas, I. (2014). Antioxidant activities of chemical constituents isolated from Echinops orientalis Trauv. Records of Natural Products, 8(1), 32-36.
  • Farah, A., & de Paula Lima, J. (2019). Consumption of Chlorogenic Acids through Coffee and Health Implications. Beverages, 5(1), 11. https://doi.org/10.3390/beverages5010011.
  • Guzel, A., Aksit, H., Elmastas, M., & Erenler, R. (2017). Bioassay-guided isolation and identification of antioxidant flavonoids from Cyclotrichium origanifolium (Labill.) Manden. and Scheng. Pharmacognosy Magazine, 13(50), 316. https://doi.org/10.4103/0973-1296.204556.
  • Haslam, E. (1974). Polyphenol-protein interactions. Biochem J, 139(1), 285-288. https://doi.org/10.1042/bj1390285.
  • Karan, T., Altuner, Z., & Erenler, R. (2017). Growth and Metabolite Production of Chroococcus minutus Under Different Temperature and Light Conditions. Journal of New Results in Science, 6(1), 47-52.
  • Karan, T., Dastan, T., Baral, I., & Altuner, Z. (2016). Effects of Differential Time Applications on Some Cyanobacterial Norharman Production Rates. Cumhuriyet University Faculty of Science, 37(4), 398-404.
  • Karan, T., & Erenler, R. (2017). Screening of norharmane from seven cyanobacteria by high-performance liquid chromatography. Pharmacognosy Magazine, 13(Suppl 3), 723-725. https://doi.org/10.4103/pm.pm_214_17.
  • Karan, T., Erenler, R., & Altuner, Z. (2017). Isolation and Molecular Identification of Some Blue-Green Algae (Cyanobacteria) from Freshwater Sites in Tokat Province of Turkey. Turkish Journal of Agriculture-Food Science and Technology, 5(11), 1371-1378.
  • Karan, T., Yildiz, I., Aydin, A., & Erenler, R. (2018). Inhibition of various cancer cells proliferation of bornyl acetate and essential oil from Inula graveolens (Linnaeus) Desf. Records of Natural Products, 12(3), 273-283.
  • Kaya, G., Karakaya, R., Tilgel, E., Sandikci, M., Yucel, E., Cicek, G., Kayir, O., Aksit, H., Telci, I., & Guzel, A. (2014). Essential Oil Constituents of Thuja orientalis Berries. Journal of New Results in Science, 7(7), 1-6.
  • Sahin Yaglioglu, A., Akdulum, B., Erenler, R., Demirtas, I., Telci, I., & Tekin, S. (2013). Antiproliferative activity of pentadeca-(8E, 13Z) dien-11-yn-2-one and (E)-1,8-pentadecadiene from Echinacea pallida (Nutt.) Nutt. roots. Medicinal Chemistry Research, 22(6), 2946-2953. https://doi.org/10.1007/s00044-012-0297-2.
  • Silinsin, M., & Bursal, E. (2018). UHPLC-MS/MS phenolic profiling and in vitro antioxidant activities of Inula graveolens (L.) Desf. Natural Product Research, 32(12), 1467-1471. https://doi.org/10.1080/14786419.2017.1350673.
  • Topçu, G., Erenler, R., Çakmak, O., Johansson, C. B., Çelik, C., Chai, H.-B., & Pezzuto, J. M. (1999). Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50(7), 1195-1199. https://doi.org/10.1016/S0031-9422(98)00675-X.
  • Türkmen, N., Öz, A., Sönmez, A., Erol, T., Gülümser, D., Yurdakul, B., Kayır, Ö., Elmastas, M., & Erenler, R. (2014). Chemical Composition of Essential Oil from Rosmarinus Officinalis L. Leaves. Journal of New Results in Science, 6(6), 27-31.
There are 34 citations in total.

Details

Primary Language English
Subjects Organic Chemistry
Journal Section Research Articles
Authors

Ramazan Erenler 0000-0002-0505-3190

Mehmet Nuri Atalar 0000-0003-2993-2605

İlyas Yıldız This is me 0000-0003-1254-1069

Esma Nur Geçer 0000-0002-0095-079X

Aslı Yıldırım 0000-0001-5674-2095

İbrahim Demirtas 0000-0001-8946-647X

Mehmet Hakkı Alma 0000-0001-7011-3965

Publication Date August 28, 2023
Published in Issue Year 2023 Volume: 4 Issue: 3

Cite

APA Erenler, R., Atalar, M. N., Yıldız, İ., Geçer, E. N., et al. (2023). Quantitative analysis of bioactive compounds by LC-MS/MS from Inula graveolens. Bütünleyici Ve Anadolu Tıbbı Dergisi, 4(3), 3-10. https://doi.org/10.53445/batd.1278048
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Bütünleyici ve Anadolu Tıbbı Dergisi

Journal of Integrative and Anatolian Medicine