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Identification of phenolic compounds, antioxidant activity and anti-cancer effects of the extract obtained from the shoots of Ornithogalum narbonense L.
Corresponding Author(s) : ć°smail Koyuncu
Cellular and Molecular Biology,
Vol. 64 No. 1: Issue 1
Abstract
This study aimed to examine the anti-cancer and antioxidant properties and identify the phenolic content of methanol extract obtained from the shoots of the Ornithogalum narbonense L. (OR) plant, which is used for folk-medicine and food in the Sanliurfa region of Turkey. The antioxidant activity of the extract was investigated using total phenolics, flavonoids, ABTS and CUPRAC methods. Phenolic component analysis of the plant extract was performed by LC-MS/MS. The anti-cancer property of OR extract was investigated on human colon (DLD-1), endometrium (ECC-1) cancer cells and embryonic kidney (HEK-293) cells. Cytotoxic effects were defined with MTT, apoptotic activity with DNA fragmentation ELISA and AO/EB fluorescent staining, the genotixic effect with the comet assay and the intracellular oxidative status with TAS and TOS methods. As a result of the study, it was determined that OR extract showed an antioxidant effect, and as a result of the content analysis made with LC/MS-MS, phenolic components were determined, the most abundant being cosmosiin, followed by cinnamic acid, p-coumaric acid and Quinic acid. OR extract showed cytotoxic activity on DLD-1 and ECC-1 cancer cells, while the cytotoxic effect on HEK-293 cells was determined to be low. It was determined that through OR extract, by increasing the intracellular amount of free radicals on cancer cells, led to DNA damage, which consequently led to apoptosis of the cancer cells.
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- Dissanayake S, Denny WA, Gamage S, Sarojini V. Recent developments in anticancer drug delivery using cell penetrating and tumor targeting peptides. Journal of Controlled Release. 2017.
- Romualdo GR, Fragoso MF, Borguini RG, de Araújo Santiago MCP, Fernandes AAH, Barbisan LF. Protective effects of spray-dried açaí (Euterpe oleracea Mart) fruit pulp against initiation step of colon carcinogenesis. Food Research International. 2015; 77: 432-440.
- Encalada MA, Rehecho S, Ansorena D, Astiasarán I, Cavero RY, Calvo MI. Antiproliferative effect of phenylethanoid glycosides from Verbena officinalis L. on colon cancer cell lines. LWT-Food Science and Technology. 2015; 63(2): 1016-1022.
- Rao C. Luteinizing hormone is a primary culprit in the endometrial carcinoma development in elderly women. Journal of Reproductive Health and Medicine. 2016; 2: S63-S69.
- Piulats JM, Guerra E, Gil-Martín M et al. Molecular approaches for classifying endometrial carcinoma. Gynecologic oncology. 2017; 145(1): 200-207.
- Suidan RS, He W, Sun CC et al. Impact of body mass index and operative approach on surgical morbidity and costs in women with endometrial carcinoma and hyperplasia. Gynecologic Oncology. 2017; 145(1): 55-60.
- Lei Y, Zhang D, Yu J, Dong H, Zhang J, Yang S. Targeting autophagy in cancer stem cells as an anticancer therapy. Cancer Letters. 2017.
- Letsyo E, Jerz G, Winterhalter P, Beuerle T. Toxic pyrrolizidine alkaloids in herbal medicines commonly used in Ghana. Journal of Ethnopharmacology. 2017; 202: 154-161.
- Gülçin I. Antioxidant activity of food constituents: an overview. Archives of toxicology. 2012; 86(3): 345-391.
- Jia Z, Dumont M-J, Orsat V. Encapsulation of phenolic compounds present in plants using protein matrices. Food Bioscience. 2016; 15: 87-104.
- Soto-Vaca A, Gutierrez A, Losso JN, Xu Z, Finley JW. Evolution of phenolic compounds from color and flavor problems to health benefits. Journal of agricultural and food chemistry. 2012; 60(27): 6658-6677.
- Gulcin I, Beydemir S. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini reviews in medicinal chemistry. 2013; 13(3): 408-430.
- Bursal E, Köksal E, Gülçin ć°, Bilsel G, Gören AC. Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC–MS/MS. Food research international. 2013; 51(1): 66-74.
- Kocak MS, Sarikurkcu C, Cengiz M, Kocak S, Uren MC, Tepe B. Salvia cadmica: Phenolic composition and biological activity. Industrial Crops and Products. 2016; 85: 204-212.
- í–zer Z, Tursun N, í–nen H. Yabancı Otlarla Sağlıklı Yaşam (Gıda ve Tedavi), 5. baskı, 4 Renk Yayın ve Tanıtım Matbaacılık. ISBN; 2004.
- Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food chemistry. 1999; 64(4): 555-559.
- Apak R, Guclu K, Ozyurek M, Karademir SE. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of agricultural and food chemistry. Dec 29 2004; 52(26): 7970-7981.
- Kocyigit A, Koyuncu I, Taskin A, Dikilitas M, Bahadori F, Turkkan B. Antigenotoxic and antioxidant potentials of newly derivatized compound naringenin-oxime relative to naringenin on human mononuclear cells. Drug and chemical toxicology. 2016; 39(1): 66-73.
- Liu K, Liu P-c, Liu R, Wu X. Dual AO/EB staining to detect apoptosis in osteosarcoma cells compared with flow cytometry. Medical science monitor basic research. 2015; 21: 15.
- Erel O. A new automated colorimetric method for measuring total oxidant status. Clinical biochemistry. Dec 2005; 38(12): 1103-1111.
- Erel O. A novel automated direct measurement method for total antioxidant capacity using a new generation, more stable ABTS radical cation. Clinical biochemistry. Apr 2004; 37(4): 277-285.
- Mesicek N, Perpar M. Essential oils from the orpine, Sedum maximum. Farmacevtski Vestnik. 1973; 24: 123-124.
- Orhan I, Deliorman-Orhan D, í–zçelik B. Antiviral activity and cytotoxicity of the lipophilic extracts of various edible plants and their fatty acids. Food chemistry. 2009; 115(2): 701-705.
- Yaylı N, Yaşar A, Yılmaz ć°skender N et al. Chemical constituents and antimicrobial activities of the essential oils from Sedum pallidum var. bithynicum and S. spurium grown in Turkey. Pharmaceutical biology. 2010; 48(2): 191-194.
- Kim S-J, Cho AR, Han J. Antioxidant and antimicrobial activities of leafy green vegetable extracts and their applications to meat product preservation. Food Control. 2013; 29(1): 112-120.
- Ginsburg H, Deharo E. A call for using natural compounds in the development of new antimalarial treatments–an introduction. Malaria Journal. 2011; 10(1): S1.
- Shukla S, Meeran SM, Katiyar SK. Epigenetic regulation by selected dietary phytochemicals in cancer chemoprevention. Cancer letters. 2014; 355(1): 9-17.
- Dias DA, Urban S, Roessner U. A historical overview of natural products in drug discovery. Metabolites. 2012; 2(2): 303-336.
- Işık M, Beydemir Åž, Yılmaz A, Naldan ME, Aslan HE, Gülçin ć°. Oxidative stress and mRNA expression of acetylcholinesterase in the leukocytes of ischemic patients. Biomedicine & Pharmacotherapy. 2017; 87: 561-567.
- Darwiche N, El-Banna S, Gali-Muhtasib H. Cell cycle modulatory and apoptotic effects of plant-derived anticancer drugs in clinical use or development. Expert opinion on drug discovery. 2007; 2(3): 361-379.
- Lee J, Khor TO, Shu L, Su Z-Y, Fuentes F, Kong A-NT. Dietary phytochemicals and cancer prevention: Nrf2 signaling, epigenetics, and cell death mechanisms in blocking cancer initiation and progression. Pharmacology & therapeutics. 2013; 137(2): 153-171.
- Zengin G, Uysal S, Ceylan R, Aktumsek A. Phenolic constituent, antioxidative and tyrosinase inhibitory activity of Ornithogalum narbonense L. from Turkey: a phytochemical study. Industrial Crops and Products. 2015; 70: 1-6.
- Makasci AA, Mammadov R, Dusen O, Isik H. Antimicrobial and antioxidant activities of medicinal plant species Ornithogalum alpigenum stapf. from Turkey. Journal of Medicinal Plants Research. 2010; 4(16): 1637-1642.
- Dastan D, Aliahmadi A. Antioxidant and antibacterial studies on different extracts of Ornithogalum cuspidatum Bertol from Iran. Paper presented at: Biological Forum, 2015.
- Chen R, Li Y, Dong H et al. Optimization of ultrasonic extraction process of polysaccharides from Ornithogalum Caudatum Ait and evaluation of its biological activities. Ultrasonics sonochemistry. Nov 2012; 19(6): 1160-1168.
- González , C G, C R, Ramírez de Molina A. Dietary phytochemicals in cancer prevention and therapy: a complementary approach with promising perspectives. Nutrition reviews.
- ; 71(9): 585-599.
- Lambert JD, Elias RJ. The antioxidant and pro-oxidant activities of green tea polyphenols: a role in cancer prevention. Archives of biochemistry and biophysics. 2010; 501(1): 65-72.
- Araújo JR, Gonçalves P, Martel F. Chemopreventive effect of dietary polyphenols in colorectal cancer cell lines. Nutrition Research. 2011; 31(2): 77-87.
- Feitelson MA, Arzumanyan A, Kulathinal RJ et al. Sustained proliferation in cancer: Mechanisms and novel therapeutic targets. Paper presented at: Seminars in cancer biology, 2015.
References
Dissanayake S, Denny WA, Gamage S, Sarojini V. Recent developments in anticancer drug delivery using cell penetrating and tumor targeting peptides. Journal of Controlled Release. 2017.
Romualdo GR, Fragoso MF, Borguini RG, de Araújo Santiago MCP, Fernandes AAH, Barbisan LF. Protective effects of spray-dried açaí (Euterpe oleracea Mart) fruit pulp against initiation step of colon carcinogenesis. Food Research International. 2015; 77: 432-440.
Encalada MA, Rehecho S, Ansorena D, Astiasarán I, Cavero RY, Calvo MI. Antiproliferative effect of phenylethanoid glycosides from Verbena officinalis L. on colon cancer cell lines. LWT-Food Science and Technology. 2015; 63(2): 1016-1022.
Rao C. Luteinizing hormone is a primary culprit in the endometrial carcinoma development in elderly women. Journal of Reproductive Health and Medicine. 2016; 2: S63-S69.
Piulats JM, Guerra E, Gil-Martín M et al. Molecular approaches for classifying endometrial carcinoma. Gynecologic oncology. 2017; 145(1): 200-207.
Suidan RS, He W, Sun CC et al. Impact of body mass index and operative approach on surgical morbidity and costs in women with endometrial carcinoma and hyperplasia. Gynecologic Oncology. 2017; 145(1): 55-60.
Lei Y, Zhang D, Yu J, Dong H, Zhang J, Yang S. Targeting autophagy in cancer stem cells as an anticancer therapy. Cancer Letters. 2017.
Letsyo E, Jerz G, Winterhalter P, Beuerle T. Toxic pyrrolizidine alkaloids in herbal medicines commonly used in Ghana. Journal of Ethnopharmacology. 2017; 202: 154-161.
Gülçin I. Antioxidant activity of food constituents: an overview. Archives of toxicology. 2012; 86(3): 345-391.
Jia Z, Dumont M-J, Orsat V. Encapsulation of phenolic compounds present in plants using protein matrices. Food Bioscience. 2016; 15: 87-104.
Soto-Vaca A, Gutierrez A, Losso JN, Xu Z, Finley JW. Evolution of phenolic compounds from color and flavor problems to health benefits. Journal of agricultural and food chemistry. 2012; 60(27): 6658-6677.
Gulcin I, Beydemir S. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini reviews in medicinal chemistry. 2013; 13(3): 408-430.
Bursal E, Köksal E, Gülçin ć°, Bilsel G, Gören AC. Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC–MS/MS. Food research international. 2013; 51(1): 66-74.
Kocak MS, Sarikurkcu C, Cengiz M, Kocak S, Uren MC, Tepe B. Salvia cadmica: Phenolic composition and biological activity. Industrial Crops and Products. 2016; 85: 204-212.
í–zer Z, Tursun N, í–nen H. Yabancı Otlarla Sağlıklı Yaşam (Gıda ve Tedavi), 5. baskı, 4 Renk Yayın ve Tanıtım Matbaacılık. ISBN; 2004.
Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food chemistry. 1999; 64(4): 555-559.
Apak R, Guclu K, Ozyurek M, Karademir SE. Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of agricultural and food chemistry. Dec 29 2004; 52(26): 7970-7981.
Kocyigit A, Koyuncu I, Taskin A, Dikilitas M, Bahadori F, Turkkan B. Antigenotoxic and antioxidant potentials of newly derivatized compound naringenin-oxime relative to naringenin on human mononuclear cells. Drug and chemical toxicology. 2016; 39(1): 66-73.
Liu K, Liu P-c, Liu R, Wu X. Dual AO/EB staining to detect apoptosis in osteosarcoma cells compared with flow cytometry. Medical science monitor basic research. 2015; 21: 15.
Erel O. A new automated colorimetric method for measuring total oxidant status. Clinical biochemistry. Dec 2005; 38(12): 1103-1111.
Erel O. A novel automated direct measurement method for total antioxidant capacity using a new generation, more stable ABTS radical cation. Clinical biochemistry. Apr 2004; 37(4): 277-285.
Mesicek N, Perpar M. Essential oils from the orpine, Sedum maximum. Farmacevtski Vestnik. 1973; 24: 123-124.
Orhan I, Deliorman-Orhan D, í–zçelik B. Antiviral activity and cytotoxicity of the lipophilic extracts of various edible plants and their fatty acids. Food chemistry. 2009; 115(2): 701-705.
Yaylı N, Yaşar A, Yılmaz ć°skender N et al. Chemical constituents and antimicrobial activities of the essential oils from Sedum pallidum var. bithynicum and S. spurium grown in Turkey. Pharmaceutical biology. 2010; 48(2): 191-194.
Kim S-J, Cho AR, Han J. Antioxidant and antimicrobial activities of leafy green vegetable extracts and their applications to meat product preservation. Food Control. 2013; 29(1): 112-120.
Ginsburg H, Deharo E. A call for using natural compounds in the development of new antimalarial treatments–an introduction. Malaria Journal. 2011; 10(1): S1.
Shukla S, Meeran SM, Katiyar SK. Epigenetic regulation by selected dietary phytochemicals in cancer chemoprevention. Cancer letters. 2014; 355(1): 9-17.
Dias DA, Urban S, Roessner U. A historical overview of natural products in drug discovery. Metabolites. 2012; 2(2): 303-336.
Işık M, Beydemir Åž, Yılmaz A, Naldan ME, Aslan HE, Gülçin ć°. Oxidative stress and mRNA expression of acetylcholinesterase in the leukocytes of ischemic patients. Biomedicine & Pharmacotherapy. 2017; 87: 561-567.
Darwiche N, El-Banna S, Gali-Muhtasib H. Cell cycle modulatory and apoptotic effects of plant-derived anticancer drugs in clinical use or development. Expert opinion on drug discovery. 2007; 2(3): 361-379.
Lee J, Khor TO, Shu L, Su Z-Y, Fuentes F, Kong A-NT. Dietary phytochemicals and cancer prevention: Nrf2 signaling, epigenetics, and cell death mechanisms in blocking cancer initiation and progression. Pharmacology & therapeutics. 2013; 137(2): 153-171.
Zengin G, Uysal S, Ceylan R, Aktumsek A. Phenolic constituent, antioxidative and tyrosinase inhibitory activity of Ornithogalum narbonense L. from Turkey: a phytochemical study. Industrial Crops and Products. 2015; 70: 1-6.
Makasci AA, Mammadov R, Dusen O, Isik H. Antimicrobial and antioxidant activities of medicinal plant species Ornithogalum alpigenum stapf. from Turkey. Journal of Medicinal Plants Research. 2010; 4(16): 1637-1642.
Dastan D, Aliahmadi A. Antioxidant and antibacterial studies on different extracts of Ornithogalum cuspidatum Bertol from Iran. Paper presented at: Biological Forum, 2015.
Chen R, Li Y, Dong H et al. Optimization of ultrasonic extraction process of polysaccharides from Ornithogalum Caudatum Ait and evaluation of its biological activities. Ultrasonics sonochemistry. Nov 2012; 19(6): 1160-1168.
González , C G, C R, Ramírez de Molina A. Dietary phytochemicals in cancer prevention and therapy: a complementary approach with promising perspectives. Nutrition reviews.
; 71(9): 585-599.
Lambert JD, Elias RJ. The antioxidant and pro-oxidant activities of green tea polyphenols: a role in cancer prevention. Archives of biochemistry and biophysics. 2010; 501(1): 65-72.
Araújo JR, Gonçalves P, Martel F. Chemopreventive effect of dietary polyphenols in colorectal cancer cell lines. Nutrition Research. 2011; 31(2): 77-87.
Feitelson MA, Arzumanyan A, Kulathinal RJ et al. Sustained proliferation in cancer: Mechanisms and novel therapeutic targets. Paper presented at: Seminars in cancer biology, 2015.