Determination of Phytochemical Profile of Allium tuncelianum and Evaluation of Its Antiproliferative Effect on Various Human Cell Lines

In this study, Allium tuncelianum, one of the endemic garlic speciesgrowing in Anatolia, was investigated for its phytochemical content.LC-MS/MS, HPLC, GC-MS, GC-FID and ICP-OES techniques wereused for this purpose. Major phenolic components of Alliumtuncelianum were found to be malic acid (3322.6 µg/g), kainic acid(626.8 µg/g), cinnamic acid (69.15 µg/g), fumaric acid (13.02 µg/g) andcatechin (3933.3 µg/g). The main components of volatile oil, on theother hand, were detected as diallyl disulfide (28.30%), diallyltrisulfide (30.90%) and allyl methyl trisulfide (9.44%). The fatty acidcomposition of the plant was revealed as oleic acid (27.19%), linoleicacid (19.46%) and elaidic acid (3%) whereas high content of potassium(4207± 67 mg/kg), calcium (518± 35 mg/kg) and magnesium (376 ± 20mg/kg) was determined as the minerals. Moreover, cytotoxic effects ofethanol/water and hexane/chloroform extracts of the plant wereevaluated in prostate, colon, cervical and breast cancer cell lines andcytotoxicity of both extracts were detected for all the cell lines studied.Therefore, we conclude that Allium tuncelianum may be a newphytotherapy agent with its rich phytochemical content andanticancer activity.

Allium tuncelianum' un Fitokimyasal Profilinin Belirlenmesi ve Çeşitli İnsan Hücre Hatlarında Antiproliferatif Etkilerinin Değerlendirilmesi

Bu çalışmada, Anadoluda yetişen endemik sarımsak türlerinden biri olan Tunceli Dağ Sarımsağı (Allium tuncelianum) incelenmiştir. Fitokimyasal içeriği belirlemek için LC-MS / MS, HPLC, GC-MS, GCFID ve ICP-OES teknikleri kullanılmıştır. Allium tuncelianum'un başlıca fenolik bileşenleri; malik asit (3322,6 µg / g), kainik asit (626.8 µg / g), sinamik asit (69.15 µg / g), fumarik asit (13.02 µg / g) ve kateşin (3933.3 µg / g) olduğu belirlendi. Uçucu yağın ana bileşenleri, dialil disülfit (% 28.30), dialil trisülfit (% 30.90) ve allil metil trisülfit (% 9.44) idi. Yağ asidi bileşimi; oleik asit (% 27.19), linoleik asit (% 19.46) ve elaidik asit (% 3) iken, mineral içeriğindeki major elementler; potasyum (4207 ± 67 mg / kg), kalsiyum (518 ± 35 mg / kg) ve magnezyum (376 ± 20) mg / kg) olarak belirlenmiştir. Prostat, kolon, servikal ve meme kanseri hücre dizilerinde sitotoksik etki de incelenmiştir. Kolon, Meme, Servikal ve Prostat kanseri hücre hatlarında sitotoksik etki tespit edildi. Bu sonuçlar göstermektedir ki; Allium tuncelianum, zengin fitokimyasal içeriği ve antikanser aktivitesi ile yeni bir fitoterapi ajanı olabilir.

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Banerjee SK, Mukherjee PK, Maulik SK 2003. Garlic as an Antioxidant: The Good, the Bad and the Ugly. Phytotherapy Research, 17(2): 97-106.

Cai Y, Luo Q, Sun M, Corke H 2004. Antioxidant Activity and Phenolic Compounds of 112 Traditional Chinese Medicinal Plants Associated with Anticancer. Life Sciences, 74(17): 2157-84.

Çelik SE, Özyürek M, Güçlü K, Apak R 2010. Determination of Antioxidants by a Novel On-Line HPLC-Cupric Reducing Antioxidant Capacity (CUPRAC) Assay with Post-Column Detection. Analytica Chimica Acta, 674(1): 79-88.

Chekki RZ, Snoussi A, Hamrouni I, Bouzouita N 2014. Chemical Composition, Antibacterial and Antioxidant Activities of Tunisian Garlic (Allium Sativum) Essential Oil and Ethanol Extract. Mediterranean Journal of Chemistry, 3(4): 947-56.

Emen S, Çeken B, Kizil G, Kizil M 2009. DNA Damage Protecting Activity and in Vitro Antioxidant Potential of the Methanol Extract of Cyclotrichium Niveum. Pharmaceutical Biology, 47(3): 219-29.

Ertas, A, Boga M, Yilmaz MA, Yesil Y, Tel G, Temel H, Hasimi N, Gazioglu I, Ozturk M, Ugurlu P 2015. A Detailed Study on the Chemical and Biological Profiles of Essential Oil and Methanol Extract of Thymus Nummularius (Anzer Tea): Rosmarinic Acid. Industrial Crops and Products. 1(67): 336-45.

Farag MA, Ali SE, Hodaya RH, El-Seedi HR, Sultani HN, Laub A, FE Tarek, Abou-Zaid F, Wessjohann LA 2017. Phytochemical Profiles and Antimicrobial Activities of Allium Cepa Red Cv. and A. Sativum Subjected to Different Drying Methods: A Comparative MS-Based Metabolomics. Molecules, 8(22)5: 761

Fratianni F, Ombra MN, Cozzolino A, Riccardi R, Spigno P, Tremonte P, Coppola R, Nazzaro F 2016. Phenolic Constituents, Antioxidant, Antimicrobial and Anti-Proliferative Activities of Different Endemic Italian Varieties of Garlic (Allium Sativum L.). Journal of Functional Foods, 1(21): 240-48.

Gercek YC, Akman G, Morgil H,Calıkan M, Oz GC 2017. Organosulfur compounds of Allium Tuncelianum (Kollmann) Ozhatay, B. Mathew & Şiraneci extracts by SPME/GC-MS and determining their cytotoxic effect on HeLa cells. International Journal of Advances in Science Engineering and Technology. 5(2):53-58.

Hayaloglu AA, Demir N 2016. Phenolic compounds, volatiles, and sensory characteristics of twelve sweet cherry (Prunus avium L.) cultivars grown in Turkey. Journal of food science. 81(1): 7-18.

Huang WY, Cai YZ, Zhang Y 2009. Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutrition and cancer. 62(1): 1-20.

Islam MS, Kusumato Y, Abdulla Al-Mamun M 2011. Cytotoxicity and cancer (HeLa) cell killing efficiancy aqueous garlic (Allium sativum) extract. Journal of Scientific Research. 3(2):375-382.

Izol E 2016. Determination of Heavy Metals And Seconder Metabolites of Some Allium (Wild Garlic) Species By ICP-MS and LCMS/ MS Investigation of Their Biological Activities. DÜ Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 129 s.

Jirovetz L, Jäger W, Koch HP, Remberg G 1992. Investigations of volatile constituents of the essential oil of Egyptian garlic (Allium sativum L.) by means of GC-MS and GC-FTIR. Zeitschrift für Lebensmittel-Untersuchung und Forschung. 194(4): 363-5.

Kilic A, Koyuncu I, Durgun M, Ozaslan I, Kaya IH, Gönel A 2018. Synthesis and Characterization of the Hemi‐Salen Ligands and Their Triboron Complexes: Spectroscopy and Examination of Anticancer Properties. Chemistry & biodiversity. 15(1): 17-42.

Kokten K, Bakoglu A, Kocak A, Bagci E, Akcura M, Kaplan M 2011. Chemical composition of the seeds of some Medicago species. Chemistry of Natural Compounds. 47(4): 619.

Lachowicz S, Kolniak‐Ostek J, Oszmiański J, Wiśniewski R 2017. Comparison of phenolic content and antioxidant capacity of bear garlic (Allium ursinum L.) in different maturity stages. Journal of food processing and preservation. 41(1): e12921.

Lee SN, Kim NS, Lee DS 2003. Comparative study of extraction techniques for determination of garlic flavor components by gas chromatography–mass spectrometry. Analytical and bioanalytical chemistry. 377(4): 749-56.

Li H, Wang SW, Zhang BL, Xie YH, Yang Q, Cao W, Wang JB 2011. Simultaneous quantitative determination of 9 active components in traditional Chinese medicinal preparation ShuangDan oral liquid by RP-HPLC coupled with photodiode array detection. Journal of pharmaceutical and biomedical analysis. 56(4): 820-4.

Lu HF, Sue CC, Yu CS, Chen SC, Chen GW, Chung JG 2004. Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells. Food and chemical toxicology. 42(10): 1543-52.

Menendez JA, Vellon L, Colomer R, Lupu R 2005. Oleic acid, the main monounsaturated fatty acid of olive oil, suppresses her-2/neu (erb b-2) expression and synergistically enhances the growth inhibitory effects of trastuzumab (herceptin™) in breast cancer cells with her-2/neu oncogene amplification. Annals of oncology. 16(3): 359-71.

Narendhirakannan RT, Rajeswari K 2010. In vitro antioxidant properties of three varieties of Allium sativum L. extracts. Journal of Chemistry. 7(1): 573-9.

Oommen S, Anto RJ, Srinivas G, Karunagaran D 2004. Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells. European journal of pharmacology. 485(1-3): 97-103.

Özhatay N, Mathew B 1995. New taxa and notes on the genus Allium (Alliaceae) in Turkey and Arabia. Kew Bulletin. 1: 723-31.

Özhatay, N. 2002. Diversity of bulbous monocots in Turkey with special reference chromosome numbers. Pure Appl. Chem. 74(4):547-555

Ozkaya A, Ciftci H, Yilmaz O, Zafer Tel A, Cil E, Cevrimli BS 2012. Vitamin, trace element, and fatty acid levels of Vitex agnus-castus L., Juniperus oxycedrus L., and Papaver somniferum L. plant seeds. Journal of Chemistry. 2013(43): 4

Pandey M, Debnath M, Gupta S, Chikara SK 2011. Phytomedicine: An ancient approach turning into future potential source of therapeutics. Journal of Pharmacognosy and phytotherapy. 3(1):113-7.

Prakash E, Saxena AK, Gupta DK 2016. Cytotoxic activities of ethanolic extract of Allium sativum against colon cancer cell lines. International Journal of Innovative Research in Science, Engineering and Technology. 5(3):3041-3045.

Sarneckis CJ, Dambergs RG, Jones P, Mercurio M, Herderich MJ, Smith PA 2006. Quantification of condensed tannins by precipitation with methyl cellulose: development and validation of an optimised tool for grape and wine analysis. Australian Journal of Grape and Wine Research. 12(1): 39-49.

Singh A, Shukla Y 1998. Antitumour activity of diallyl sulfide on polycyclic aromatic hydrocarbon-induced mouse skin carcinogenesis. Cancer letters. 131(2): 209-14.

Soares ME, Carvalho F, de Lourdes Bastos M 2001. Determination of amphetamine and its metabolite p‐hydroxyamphetamine in rat urine by reversed‐ phase high‐performance liquid chromatography after dabsyl derivatization. Biomedical Chromatography. 15(7): 452-6.

Mosmann T 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of immunological methods. 65(1-2):55-63.

Yildirim I, Kutlu T, Takim K 2015. Comparison of antioxidant activity of Rheum ribes fruits and seed methanolic extracts against protein oxidation and lipid peroxidation. Pakistan J. Biol. Sci. 18(5): 232- 9.

Tsiaganis MC, Laskari K, Melissari E 2006. Fatty acid composition of Allium species lipids. Journal of Food Composition and Analysis. 19(6-7): 620-7.

Vlase L, Parvu M, Parvu E, Toiu A 2013. Chemical constituents of three Allium species from Romania. Molecules. 18(1): 114-27.

Waheed A, Jaffar M, Masud K 2003. Comparative study of selected essential and non-essential metals in various canned and raw foodstuffs consumed in Pakistan. Nutrition & Food Science. 33(6): 261-7.

Yanmaz R, Yazar E, Kantoglu KY, Alper A 2010. In vitro plant regeneration and bulblet formation of Tunceli garlic (Allium tuncelianum (Kollman) Özhatay, Matthew, Siraneci) by shoot and root culture. Journal of Food, Agriculture & Environment. 8(3&4): 572-6.

Yılmaz MA 2015. Determining the Metabolic Profile of Some Achillea. DÜ Fen Bil. Ens., Kimya ABD, Doktora Tezi, 314 s.

Yünlü S 2011. Determination of Phenolic Compounds in Onion (Allium Cepa) and Garlic (Allium Sativum) By HPLC Method. SDÜ. Fen Bil. Ens., Kimya ABD, Yüksek Lisans Tezi, 101 s.