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http://dx.doi.org/10.9721/KJFST.2017.49.3.242

Anti-proliferative effect of methanolic extracts from Citrus junos seeds and seed oils on HT-29 human colon cancer cells and identification of their major bioactive compounds  

Kim, Kyungeun (Department of Food and Nutrition, and Research Institute of Human Ecology, Seoul National University)
Cho, Hyunnho (Department of Food and Nutrition, and Research Institute of Human Ecology, Seoul National University)
Jung, Hana (Department of Food and Nutrition, and Research Institute of Human Ecology, Seoul National University)
Lee, Hee Jae (Department of Food and Nutrition, and Research Institute of Human Ecology, Seoul National University)
Hwang, Keum Taek (Department of Food and Nutrition, and Research Institute of Human Ecology, Seoul National University)
Publication Information
Korean Journal of Food Science and Technology / v.49, no.3, 2017 , pp. 242-251 More about this Journal
Abstract
The purpose of this study was to investigate the anti-proliferative effect of methanolic extracts from Citrus junos (yuja) seeds and yuja seed oils against HT-29 human colon cancer cells and to identify the key compounds responsible for this effect. Extracts from yuja seeds, yuja seed oil prepared using hexane, and cold-pressed yuja seed oil were prepared using 60% methanol (ES, EHO, and ECO, respectively). The key compounds in the extracts were determined using HPLC-MS. Among the extracts, EHO and ECO inhibited proliferation of HT-29 cells. EHO and ECO were fractionated using preparative LC and the bioactive compounds were determined. Five of the fractions showed a significant anti-proliferative effect and the main compounds in the fractions were isopimpinellin, bergapten, and ichangensin. These compounds showed anti-proliferative effects on HT-29 cells when treated individually, and ichangensin showed the highest anti-proliferative activity. These results suggest that these compounds may be responsible for the anti-cancer effect of EHO and ECO.
Keywords
yuja seed oil; Citrus junos; limonoid; ichangensin; HT-29 cell;
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Times Cited By KSCI : 2  (Citation Analysis)
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1 Poulose SM, Harris ED, Patil BS. Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells. Nutr. Cancer 56: 103-112 (2006)   DOI
2 Chidambara murthy KN, Jayaprakasha G, Kumar V, Rathore KS, Patil BS. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. J. Agr. Food Chem. 59: 2314-2323 (2011)   DOI
3 Miller EG, Porter JL, Binnie WH, Guo IY, Hasegawa S. Further studies on the anticancer activity of citrus limonoids. J. Agr. Food Chem. 52: 4908-4912 (2004)   DOI
4 Dugrand A, Olry A, Duval T, Hehn A, Froelicher Y, Bourgaud F. Coumarin and furanocoumarin quantitation in citrus peel via ultraperformance liquid chromatography coupled with mass spectrometry (UPLC-MS). J. Agr. Food Chem. 61: 10677-10684 (2013)   DOI
5 Frerot E, Decorzant E. Quantification of total furocoumarins in citrus oils by HPLC coupled with UV, fluorescence, and mass detection. J. Agr. Food Chem. 52: 6879-6886 (2004)   DOI
6 Um YR, Kong CS, Lee JI, Kim YA, Nam TJ, Seo Y. Evaluation of chemical constituents from Glehnia littoralis for antiproliferative activity against HT-29 human colon cancer cells. Process Biochem. 45: 114-119 (2010)   DOI
7 Kong CS, Um YR, Lee JI, Kim YA, Yea SS, Seo Y. Constituents isolated from Glehnia littoralis suppress proliferations of human cancer cells and MMP expression in HT1080 cells. Food Chem. 120: 385-394 (2010)   DOI
8 Mira A, Shimizu K. In vitro cytotoxic activities and molecular mechanisms of Angelica shikokiana extract and its isolated compounds. Pharmacogn. Mag. 11: 564-569 (2015)   DOI
9 Lohr C, Raquet N, Schrenk D. Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. Toxicol. In Vitro 24: 558-566 (2010)   DOI
10 Jeong JH, Jung H, Lee SR, Lee HJ, Hwang KT, Kim TY. Antioxidant, anti-proliferative and anti-inflammatory activities of the extracts from black raspberry fruits and wine. Food Chem. 123: 338-344 (2010)   DOI
11 Vikram A, Jesudhasan PR, Jayaprakasha G, Pillai SD, Patil BS. Citrus limonoids interfere with Vibrio harveyi cell-cell signalling and biofilm formation by modulating the response regulator LuxO. Microbiology 157: 99-110 (2011)   DOI
12 Zheng X, Zhang X, Sheng X, Yuan Z, Yang W, Wang Q, Zhang L. Simultaneous characterization and quantitation of 11 coumarins in Radix Angelicae Dahuricae by high performance liquid chromatography with electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal. 51: 599-605 (2010)   DOI
13 Manners GD, Breksa AP. Identifying citrus limonoid aglycones by HPLCEI/MS and HPLCAPCI/MS techniques. Phytochem. Anal. 15: 372-381 (2004)   DOI
14 de Oliveira DM, Lima RMF, Clarencio J, Velozo ES, Amorim IA, da Mota THA, Costa SL, Silva FP, El-Bacha RS. The classical photoactivated drug 8-methoxypsoralen and related compounds are effective without UV light irradiation against glioma cells. Neurochem. Int. 99: 33-41 (2016)   DOI
15 Peroutka R, Schulzova V, Botek P, Hajslova J. Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fruits (Rutaceae). J. Sci. Food Agr. 87: 2152-2163 (2007)   DOI
16 Johnson JA, Webster D, Gray CA. The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. J. Ethnopharmacol. 147: 232-237 (2013)   DOI
17 Jayaprakasha GK, Dandekar DV, Tichy SE, Patil BS. Simultaneous separation and identification of limonoids from citrus using liquid chromatographycollisioninduced dissociation mass spectra. J. Sep. Sci. 34: 2-10 (2011)   DOI
18 Lee YJ, Hwang IG, Joung EM, Kim HY, Park ES, Woo KS, Jeong HS. Physiological activity and antiproliferation effects of Citron seed extracts on cancer cells. J. Korean Soc. Food Sci. Nutr. 38: 1672-1678 (2009)   DOI
19 Shalaby NMM, Abd-alla HI, Ahmed HH, Basoudan N. Protective effect of Citrus sinensis and Citrus aurantifolia against osteoporosis and their phytochemical constituents. J. Med. Plants Res. 5: 579-588 (2011)
20 Gyawali R, Jeon DH, Moon J, Kim H, Song YW, Hyun HB, Jeong D, Cho SK. Chemical composition and antiproliferative activity of supercritical extract of Citrus grandis (L.) Osbeck fruits from Korea. J. Essent. Oil Bear. Pl. 15: 915-925 (2012)   DOI
21 Zhang Y, Xu H, Chen X, Chen C, Wang H, Meng F, Yang H, Huang L. Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry. J. Pharm. Biomed. Anal. 56: 497-504 (2011)   DOI
22 Tsimidou M, Papadopoulos G, Boskou D. Phenolic compounds and stability of virgin olive oil-Part I. Food Chem. 45: 141-144 (1992)   DOI
23 Woo KL, Kim JI, Kim MC, Chang DK. Determination of flavonoid and limonoid compounds in citron (Citrus junos Sieb. et Tanaka) seeds by HPLC and HPLC/MS. J. Korean Soc. Food Sci. Nutr. 35: 353-358 (2006)   DOI
24 Miller EG, Gibbins RP, Taylor SE, Mcintosh JE, Patil BS. Long term screening study on the potential toxicity of limonoids. pp. 82-94. In: Potential Health Benefits of Citrus. Patil BS, Turner ND, Miller EG, Broadbelt JS (eds). ACS Publications, Washington DC, USA (2006)
25 Emerson OH. The bitter principles of citrus fruit. I. Isolation of nomilin, a new bitter principle from the seeds of oranges and lemons. J. Am. Chem. Soc. 70: 545-549 (1948)   DOI
26 Hasegawa S, Bennett RD, Herman Z, Fong CH, Ou P. Limonoid glucosides in citrus. Phytochemistry 28: 1717-1720 (1989)   DOI
27 Herman Z, Fong CH, Ou P, Hasegawa S. Limonoid glucosides in orange juices by HPLC. J. Agr. Food Chem. 38: 1860-1861 (1990)   DOI
28 Ozaki Y, Miyake M, Maeda H, Ifuku Y, Bennett RD, Herman Z, Fong CH, Hasegawa S. Ichangensin glucoside in Citrus junos, Citrus sudachi and Citrus sphaerocarpa. Phytochemistry 30: 2659-2661 (1991)   DOI
29 Herman Z, Fong CH, Hasegawa S. Analysis of limonoids in citrus seeds. pp. 361-375. In: Seed Analysis. Linskens HF, Jackson JF (eds). Springer, Berlin, Germany (1992)
30 Nakagawa H, Duan H, Takaishi Y. Limonoids from Citrus sudachi. Chem. Pharm. Bull. 49: 649-651 (2001)   DOI
31 Hasegawa S, Bennett RD, Verdon CP. Limonoids in citrus seeds: origin and relative concentration. J. Agr. Food Chem. 28: 922-925 (1980)   DOI
32 Hu-hua C, Fumio H. The prospect and current studies on the limonoids in citrus. Acta Bot. Sin. 38: 328-336 (1996)
33 Bray DH, Warhurst DC, Connolly JD, O'neill MJ, Phillipson JD. Plants as sources of antimalarial drugs. Part 7. Activity of some species of Meliaceae plants and their constituent limonoids. Phytother. Res. 4: 29-35 (1990)   DOI
34 Guthrie N, Morley K, Hasegawa S, Manners GD, Vandenberg T. Inhibition of human breast cancer cells by citrus limonoids. pp. 164-174. In: Citrus Limonoids. Berhow MA, Hasegawa S, Manners GD (eds). American Chemical Society, Washington DC, USA (2000)
35 Miller EG, Fanous R, Rivera-hidalgo F, Binnie WH, Hasegawa S, Lam LK. The effects of citrus limonoids on hamster buccal pouch carcinogenesis. Carcinogenesis 10: 1535-1537 (1989)   DOI
36 Tian Q, Miller EG, Ahmad H, Tang L, Patil BS. Differential inhibition of human cancer cell proliferation by citrus limonoids. Nutr. Cancer 40: 180-184 (2001)   DOI
37 Herman Z, Hasegawa S, Fong CH, Ou P. Limonoids in Citrus ichangensis. J. Agr. Food Chem. 37: 850-851 (1989)   DOI