Activity-guided Purification of N-benzyl-N-methyldecan-1-amine from Garlic and Its Antitumor Activity against CT-26 Colorectal Carcinoma in BALB/C Mice
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Seetharaman, Rajasekar
(Department of Horticultural Bioscience, Pusan National University)
Choi, Seong Mi (Department of Horticultural Bioscience, Pusan National University) Guo, Lu (Department of Horticultural Bioscience, Pusan National University) Cui, Zheng Wei (Department of Horticultural Bioscience, Pusan National University) Otgonbayar, Duuriimaa (Department of Horticultural Bioscience, Pusan National University) Park, Ju Ha (Department of Horticultural Bioscience, Pusan National University) Kwon, Young-Seok (Onion and Garlic Lab, Vegetable Research Division, National Institute of Horticultural & Herbal Science) Kwak, Jung Ho (Onion and Garlic Lab, Vegetable Research Division, National Institute of Horticultural & Herbal Science) Kwon, Young Hee (Chungcheongbuk-do Agricultural Research & Extension Services) Min, Ji Hyun (Chungcheongbuk-do Agricultural Research & Extension Services) Kang, Jum Soon (Department of Horticultural Bioscience, Pusan National University) Choi, Young Whan (Department of Horticultural Bioscience, Pusan National University) |
1 | Shen, Y., Shen, Z., Luo, S., Guo, W. and Zhu, Y. Z. 2015. The cardioprotective effects of hydrogen sulfide in heart diseases: From molecular mechanisms to therapeutic potential. Oxid. Med. Cell. Longev. 2015, 925167. http://dx.doi.org/10.1155/2015/925167 DOI |
2 | Sigounas, G., Hooker, J., Anagnostou, A. and Steiner, M. 1997. S-allylmercaptocysteine inhibits cell proliferation and reduces the viability of erythroleukemia, breast, and prostate cancer cell lines. Nutr. Cancer 27, 186-191. DOI |
3 | Snijder, P. M., Frenay, A. R., De Boer, R. A., Pasch, A., Hillebrands, J. L., Leuvenink, H. G. D. and Van Goor, H. 2015. Exogenous administration of thiosulfate, a donor of hydrogen sulfide, attenuates angiotensin II-induced hypertensive heart disease in rats. British J. Pharmacol. 172, 1494-1504. DOI |
4 | Stajner, D., Canadanovic-Brunet, J. and Pavlovic, A. 2004. Allium schoenoprasum L., as a natural antioxidant. Phytother. Res. 18, 522-524. DOI |
5 | Tseng, L. J., Jao, Y. T. and Mo, L. R. 2002. Preoperative staging of colorectal cancer with a balloon-sheathed miniprove. Endoscopy 34, 564-568. DOI |
6 | Vazquez-Prieto, M. A., Gonzalez, R. E., Renna, N. F., Galmarini, C. R. and Miatello, R. M. 2010. Aqueous garlic extracts prevent oxidative stress and vascular remodeling in an experimental model of metabolic syndrome. J. Agric. Food Chem. 58, 6630-6635. DOI |
7 | Williams, J. G. and Smith, J. P. 1993. Alcohol and other drug use among adolescents: Family and peer influences. J. Subst. Abuse 5, 289-294. DOI |
8 | Yang, J. Y., Della-Fera, M. A., Nelson-Dooley, C. and Baile, C. A. 2006. Molecular mechanisms of apoptosis induced by ajoene in 3T3-L1 adipocytes. Obesity (Silver Spring) 14, 388-397. DOI |
9 | Yin, M. C., Hwang, S. W. and Chan, K. C. 2002. Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic. J. Agri. Food Chem. 50, 6143-6147. DOI |
10 | Zhao, L., Wang, Y., Yan, Q., Lv, W., Zhang, Y. and He, S. 2015. Exogenous hydrogen sulfide exhibits anti-cancer effects though p38 MAPK signaling pathway in C6 glioma cells. Biol. Chem. 396, 1247-1253. DOI |
11 | Zong, J. and Martirosyan, D. M. 2018. Anticancer effects of garlic and garlic-derived bioactive compounds and its potential status as functional food. Bioactive Compd. Health Dis. 1, 16-35. DOI |
12 | Block, E., Ahmad, S., Catalfamo, J. L., Jain, M. K. and Apitz-Castro, R. 1986. Antithrombotic organosulfur compounds from garlic-structural, mechanistic, and synthetic studies. J. Am. Chem. Soc. 108, 7045-7055. DOI |
13 | Adams, J. M. and Cory, S. 1998. The Bcl-2 protein family: arbiters of cell survival. Science (New York, NY) 281, 1322-1326. DOI |
14 | Antonsson, B., Montessuit, S., Sanchez, B. and Martinou, J. C. 2001. Bax is present as a high molecular weight oligomer/complex in the mitochondrial membrane of apoptotic cells. J. Biol. Chem. 276, 11615-11623. DOI |
15 | Apitz-Castro, R., Badimon, J. J. and Badimon, L. 1992. Effect of ajoene, the major antiplatelet compound from garlic, on platelet thrombus formation. Thromb. Res. 68, 145-155. DOI |
16 | Arguello-Garcia, R., Medina-Campos, O. N., Perez-Hernandez, N., Pedraza-Chaverri, J. and Ortega-Pierres, G. 2010. Hypochlorous acid scavenging activities of thioallyl compounds from garlic. J. Agri. Food Chem. 58, 11226-11233. DOI |
17 | Ariga, T., Seki, T., Ando, K., Teramoto, S. and Nishimura, H. 1996. Antiplatelet principle found in the essential oil of garlic (Allium sativum) and its inhibition mechanism. In Developments in Food Engineering; Yano, T., Matsuno, R., Nakamura, K., Eds.; Blackie Academic and Professional: Tokyo, Japan, 1994; pp 1056-1058. |
18 | Fogarty, C. E. and Bergmann, A. 2017. Killers creating new life: caspases drive apoptosis-induced proliferation in tissue repair and disease. Cell Death Differ. 24, 1390-1400. DOI |
19 | Dirsch, V. M., Gerbes, A. L. and Vollmar, A. M. 1998. Ajoene, a compound of garlic, induces apoptosis in human promyeloleukemic cells, accompanied by generation of reactive oxygen species and activation of nuclear factor kappaB. Mol. Pharmacol. 53, 402-407. DOI |
20 | Feng, W., Teo, X. Y., Novera, W., Ramanujulu, P. M., Liang, D., Huang, D., Moore, P. K., Deng, L. W. and Dymock, B. W. 2015. Discovery of new H2S-releasing phosphordithioates and 2,3-dihydro-2-phenyl-2-sulfanylenebenzo[d][1, 3,2]oxazaphospholes with improved antiproliferative activity. J. Med. Chem. 58, 6456-6480. DOI |
21 | Ho, C. Y., Cheng, Y. T., Chau, C. F. and Yen, G. C. 2012. Effect of diallyl sulfide on in vitro and in vivo Nrf2-mediated pulmonic antioxidant enzyme expression via activation ERK/p38 signaling pathway. J. Agri. Food Chem. 60, 100-107. DOI |
22 | Gemici, B., Elsheikh, W., Feitosa, K. B., Costa, S. K. P., Muscara, M. N. and Wallace, J. L. 2015. H2S-releasing drugs: Anti-inflammatory, cytoprotective and chemopreventative potential. Nitric Oxide 46, 25-31. DOI |
23 | Guo, W., Cheng, Z. Y. and Zhu, Y. Z. 2013. Hydrogen sulfide and translational medicine. Acta Pharmacologica Sinica 34, 1284-1291. DOI |
24 | Heo, G. J, Oh, D. Y., Yi, S. W. and Shin, G. W. 2016. Antimicrobial activity of Korean garlic extract against fish pathogenic bacteria isolated from cultured Olive Flounder, Paralichthys olivaceus in Korea. J. Prev. Vet. Med. 40, 7-11. DOI |
25 | Nishikawa, T., Yamada, N., Hattori, A., Fukuda, H. and Fujino, T. 2002. Inhibition by ajoene of skin-tumor promotion in mice. Biosci. Biotechnol. Biochem. 66, 2221-2223. DOI |
26 | Jeong, J. W., Park, S., Park, C., Chang, Y. C., Moon, D. O., Kim, S. O., Kim, G. Y., Cha, H. J., Kim, H. S., Choi, Y. W., Kim, W. J., Yoo, Y. H. and Choi, Y. H. 2014. N-benzyl-N-methyldecan-1-amine, a phenylamine derivative isolated from garlic cloves, induces G2/M phase arrest and apoptosis in U937 human leukemia cells. Oncol. Rep. 32, 373-381. DOI |
27 | Kaowinn, S., Kaewpiboon, C., Kim, J. E., Lee, M. R., Hwang, D. Y., Choi, Y. W., Kim, H. W., Park, J. K., Song, K. M., Lee, N. H., Maeng, J. S. and Chung, Y. H. 2018. N-Benzyl-Nmethyl-dodecan-1-amine, a novel compound from garlic, exerts anti-cancer effects on human A549 lung cancer cells overexpressing cancer upregulated gene (CUG). Eur. J. Pharmacol. 841, 19-27. DOI |
28 | Keum, Y., S, Kim, J., Lee, K. H., Park, K. K., Surh, Y. J., Lee, J. M., Lee, S. S., Yoon, J. H., Joo, S. Y., Cha, I. H. and Yook, J. I. 2002. Induction of apoptosis and caspase-3 activation by chemopreventive [6]-paradol and structurally related compounds in KB cells. Cancer Lett. 177, 41-47. DOI |
29 | Kim, D. H. 2009. Risk factors of colorectal cancer. J. Kor. Soc. Coloproctol. 25, 356-362. DOI |
30 | Ledezma, E. and Apitz-Castro, R. 2006. Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent. Rev. Iberoam. Micol. 23, 75-80. DOI |
31 | Nunez, G., Benedict, M. A., Hu, Y. and Inohara, N. 1998. Caspases: the proteases of the apoptotic pathway. Oncogene 17, 3237-3245. DOI |
32 | Ou, H. C., Tzang, B. S., Chang, M. H., Liu, C. T., Liu, H. W., Lii, C. K., Bau, D. T., Chao, P. M. and Kuo, W. W. 2010. Cardiac contractile dysfunction and apoptosis in streptozotocin- induced diabetic rats are ameliorated by garlic oil supplementation. J. Agric. Food Chem. 58, 10347-10355. DOI |
33 | Schafer, G. and Kaschula, C. H. 2014. The immunomodulation and anti-inflammatory effects of garlic organosulfur compounds in cancer chemoprevention. Anticancer Agents Med. Chem. 14, 233-240. DOI |
34 | Parvu, M., Parvu, A. E., Rosca-Casian, O., Vlase, L. and Groza, G. 2010. Antifungal activity of Allium obliquum. J. Med. Plants Res. 4, 138-141. |
35 | Rivlin, R. S. 2001. Historical perspective on the use of garlic. J. Nutr. 131, 951S-954S. DOI |
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