Document Type : Research Article-en

Authors

1 Khorasan Razavi Agricultural and Natural Resources Research and Education Center

2 Department of Food Science and Technology, Ferdowsi University of Mashhad, Mashhad, Iran.

3 Department of pharmacognosy

Abstract

Natural materials are complicated compositions; therefore, a rapid screening of the active antioxidants is being challenged in the literature. Different polarity solvents were applied to isolate four fractions (F1, F2, F3 and F4) of methanolic extract of Cuminum cyminum. Their anti-oxidative properties were tested using radical scavenging and FRAP assays. F3 (with IC50=0.006mg/mL and FRAP= 521.95 mmolFe2+/L) was significantly the most active fraction. Guided isolation through bio-autography on TLC using 1, 1- diphenyl- 2 – picryl- hydrazyl radical (DPPH) as a detection reagent led to the isolation of two antioxidant compounds from F3. F3 was injected to a preparative HPLC with the proper mobile phase (acetonitril: methanol/ water) and isolated two main compounds. These compounds were identified as Luteolin 7 glugoside and Apigenin 7 glucoside by means of 1HNMR and 13CNMR and compare them with references.

Keywords

Amarowicz, R., Naczk, M., Shahidi, F. 2000. Antioxidant activity of various fractions of non-tannin phenolics of Canola hulls, Journal of Agricultural and Food Chemistry,48: 2755–2759.
Behera, S., Nagarajan, S., Jagan, S., M Rao, L. J. 2004. Microwave heating and conventional roasting of cumin seeds (Cuminum cyminum L.) and effect on chemical composition of volatiles, Journal of Food Chemistry, 87: 25–29.
Capannesi, C., Palchetti, I., Mascini, M., Parenti, A. 2000. Electrochemical sensor and biosensor for polyphenols detection in olive oils, Food Chemistry, 71: 553–562.
Chauhan, P. S., Satti, N. K., Suri, K. A., Amina, M., Bani, S. 2009. Stimulatory effect of Cuminum cyminum and flavonoid glycoside on Cyclosporine- A and restraint stress induced immune- Supperession in Swiss albino mice, Chemico- Biological Interactions 2009; 185: 66-72.
Gachkar, L., Yadegari, D., Rezaei, M. B., Taghizadeh, M. 2011. Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils, Food Chemistry, 102: 898–904.
Chung, Y., Chien, C., Teng, K., Chou, S. 2006. Antioxidative and mutagenic properties of Zanthoxylum ailanthoides Sieb & zucc, Food Chemistry, 97: 418–425.
Einafshar, S., Purazarang, H., Farhoosh, R., Seyedi, S. M. 2012. Antioxidant activity of the essential oil and methanolic extract of cumin seed (Cuminum cyminum), European Journal of Food Lipid Sciences and Technology, 114: 168-174.
Fisch KM, Bo¨hm V, Wright AD, Ko¨ nig GM. 2003.Antioxidative meroterpenoids from the brown alga Cystoseira crinita, Journal of Natural Products, 66: 968–975.
Gonza´ lez-Lavaut, J. A., Molina-Torres, J. 2006. Flavonoid glycosides from Cuban Erythroxylum species, Biochemical Systematics and Ecology, 34: 539–542.
Guenther, E. 1950. The essential oils. Vol. 4, D. Von Nostrand Company Inc. New York, 615–619.
Howell, J. C. 1986. Food antioxidants: international perspectives welcome and introductory remarks, Food and Chemical Toxicology, 24: 997-1003.
Ito, N., Hirose, M., Fukushima, S., Tsuda, H. 1986. Studies on antioxidants: their carcinogenic and modifying effects on chemical carcinogenesis, Food and Chemical Toxicology, 24: 1071–1082.
Li, H. J., Luo, Y. G., He, Z.H., Zhang, G. L. 2007. Chemical constituents from Lonicera saccata, Chinese Journal of Applied and Environmental Biology, 13:188–191.
Li, X. M., Tian, S. L., Pang, Z. C., Shi, J. Y. 2009. Extraction of Cuminum cyminum essential oil by combination technology of organic solvent with low boiling point and steam distillation, Food Chemistry; 115: 1114–1119.
Nakamura Y, Watanabe S, Miyake N, Kohno H, Osawa T. 2003. Dihydrochalcones: evaluation as novel radical scavenging antioxidants, Journal of Agricultural and Food Chemistry, 51: 3309–3312.
Otsuka, H. 2006. Crystallization in Final stages of purification, In: Methods in Biothechnology 20” Natural products isolation” second Ed. Satyait D. Sarker Zahid Latif, Alexander I.Gray (eds.). Human press, New Jersi, 114-126.
Satti, N. K., Amina, M., Dutti, P., Sharma, B. 2009. A simple and reliable preparative high performance liquid chromatographic technique for isolation of a bioactive flavones diglycoside from and extract of Cuminum cyminum seeds, Acta chromatographica, 21, 499-512.
Shen, J., Liang, J., Peng, S. L., Ding, L. S. 2004. Chemical constituents from Saussurea stella, Natural Product Research and Development. 16: 391–394.
Shobana, S., Akhilender, K. N. 2000. Antioxidant activity of selected Indian spices, Prostaglandins Leukotrienes and Essential Fatty Acids, 62: 107–110.
Shon, M. Y., Kim, T. H., Sung, N. J. 2003. Antioxidants and free radical scavenging activity of Phellinus baumii (Phellinus of Hymenochaetaceae) extracts Food Chemistry, 82: 593–597.
Tasdemir, D., Donmez, A. A., Calis, I., Ruedi, P. 2004. Evaluation of biological activity of Turkish plants. Rapid screening for the antimicrobial, antioxidant, and acetylcholinesterase inhibiting potential by TLC bioautographic method, Pharmaceutical Biology, 42: 374–383.
Valentao, P., Fernandes, E., Carvalho, F., Andrade, P. B. 2002. Antioxidative properties of Cardoon (Cynara cardunculus L.) infusion against superoxide radical, hydroxyl radical, and hypochlorous acid, Journal of Agricultural and Food Chemistry,50: 4989–4993.
Vekiari, S. A., Oreopoulou, V., Tzia, C., 1993. Thomopoulos CD. Oregano Flavonoids as lipid Antioxidants, Journal American Oil Chemistry Society, 70: 483–489.
Winton, A. L., Winton, K. B. 1939. The structure and composition of foods. Vol. 4, Wiley, New York, 420–423.
CAPTCHA Image