Browse > Article

Isolation of the Anti-tumor Promoters from Citrus Peels  

Yoon, Chang-Hoon (Department of Food Science and Nutrition, Jeju National University)
Jwa, Seung-Mi (Department of Food Science and Nutrition, Jeju National University)
Publication Information
Applied Biological Chemistry / v.49, no.1, 2006 , pp. 25-29 More about this Journal
Abstract
This study was carried out to isolate the possible anti-tumor promoters from the citrus peel (Citrus natsudaidai Hayata). We fractionated the cold-pressed oil of citrus peel by column chromatography, HPLC and TLC. The analysis on column chromate-graphy yielded seven peaks $(F-I{\sim}F-VII)$, all of which showed single spot on TLC analysis ($R_f$ for $F-I{\sim}VIII$; 0.31, 0.13, 0.13, 0.78, 0.79, 0.69 and 0.84). Among the seven fractions, three fractions (F-I, -II and F-IV) were re-analyzed on HPLC, also showing single peak except for one fraction (F-IV) which was divided two peaks. The retention times $(R_f)$ of F-I and F-II was 3 min. and 2.5 min., respectively, but these of two peaks from F-IV were 2 min. and 4.5 min., respectively. Since the area of the latter peak (4.5 min.) was very smaller than that of the former one (2 min.), it is considered that the latter one did not appear on TLC analysis. The inhibitory effect on tumor promoter 12-O-tetradecanoylphorbol-13-acetate(TPA)-induced Epstein-Barr virus activation in Raji cells was tested for the seven fraction obtained. It decreased in order of F-VI (82.3+1.3%) > F-I (80.4+1.6%) > F-II (77.2+0.9%) > F-III (75.0+1.2%) > F-IV (74.1=1.0%) > F-V (71.0+1.1%) > F-VII (70.2+1.2%). These results imply that some constiuents contained in citrus peels have the inhibitory activity of TPA-induced tumor promotion.
Keywords
citrus peels; Raji cells; anti-tumor promoters;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Sumida, T (2000) The physiological functions of fruit juices. Food Industry Shokuhin Kogyo. 43, 27-34
2 Son, H. S., Kim, H. S., Kwon T. B. and Ju, J. S. (1992) Isolation, purification and hypotensive effect of bioflavonoids in citrus sinensis. J. Korean Soc. Food Nutr. 21, 136-142
3 Kakiuchi, N., Senaraten, L. R., Hung, S. L., Yang, X. W., Hattori, M., Pilapitiya, U. and Namba, T. (1991) Effects of constituents of Beli(Aegle marmelos) on spontaneous beating and calcium-paradox of myocardinal cells. Planta Med. 57, 43-46   DOI   ScienceOn
4 Murakami, A., Kuki, W., Takahashi, Y., Yonei H., Nakamura Y., Ohto, Y., Ohigashi H. and Koshimizu, K. (1997) Auraptene, a citrus coumarin, inhibits 12-0-tetradecanoyl-phorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes. Jpn, J. Cancer Res 88, 443-452
5 Nomura, D. (1950) Coumarin derivatives of Citrus aurantinum natsudaidai. J. Japan. Chem. 4, 561-565
6 Feuer, G., Kellen, J. A. and Kovacs, K. (1976) Suppression of 7, 12-dimethylbenz[${\alpha}$]anthracene-induced by coumarin in the rat. Oncology. 33, 35-39   DOI   ScienceOn
7 Stanley, W. L. and Jurd, L. (1971) Citrus coumarins. J. Agri. Food Chem. 19, 1106-1110   DOI
8 Nakatani N., Yamada Y. and Fuwa H. (1987) 7-Geranyloxy coumarin from juice oil of Hassaku (Citrus hassaku) and antimicrobial effects of related coumarins. Agric. Biol. Chem. 51, 419-423
9 Fischer, J. F. and Trama, L. A. (1979) High-performance liquid chromatographic determination of some coumarins and psolarens found in citrus peel oils. J. Agri. Food Chem. 27, 1334-1339   DOI
10 Wattenberg, L. W., Lam, K. K. T. and Fladmoe, A. V. (1979) Inhibition of chemical carcinogen-induced neoplasia by coumarins and ${\alpha}$-angelicalactone. Cancer Res. 93, 1651-1654
11 Chen, I. S., Lin, Y. C., Tsai, I. L., Teng, C. M., Ko, F. N., Oshikawa, T. and Ishii, H. (1995) Coumarins and anti-platelet aggregation constituents from Zanthoxylum schinifolium. Phytochemistry 39, 1091-1097   DOI   ScienceOn
12 Berenblum, I. (1941) The cocarcinogenic action of croton resin. Cancer Res. 1, 44-48
13 Kirchner, J. G. (1961) Oils in peel, juice sac and seed. In The Orange, ed. Sinclair, W., Univ, of California Press, Riverside
14 Yamada, Y., Nakatani, N. and Fuwa, H. (1987) Spasmolytic activity of geranyloxycoumarin-related compounds. Agric. Biol. Chem. 51, 1711-1713
15 Shaw, P. E., (1977) Essential oils. In Citrus Science and Tech., Vol. 1, eds. Nagy, S., Shaw, P. E. and Veldhuis, M. K., AVl, Westport, Connecticut
16 Komatsu, S. and Tanaka, S. (1930) Studies on the constituents of orange oil. J. Chem. Soc. Jpn. 51, 478-491
17 Feuer G. and Kellen, J. A., (1974) Inhibition and enhancement of mammary tumorigenesis by 7,12-dimethylbenz[${\alpha}$]anthracene in the female Sprague Dawley. Int. J. Clin. Pharmacol. 9, 62-69
18 Tanaka T., Kawabata K., Kakumoto M., Hara A., Murakami A., Kuki W., Takahashi Y., Yonei H., Maeda M., Ota T., Odashima S., Yamane T., Koshimizu K. and Ohigashi H. (1998) Citrus auraptene exerts dose-dependent chemopreventive activity in rat large bowel tumorigenesis: The inhibition correlates with suppression of cell proliferation and lipid peroxidation and with induction of phase II drug-metabolizing enzymes, Cancer Res. 58, 2550-2556
19 Miller, E. G., Fanous, R., Rivera-Hidalgo, F., Binnie, W. H., Hasegawa, S. and Lam, L.K.T. (1989) The effect of citrus limonoids on hamster buccal pauch. Carcinogenesis. 10, 1535-1537   DOI
20 Itoh, Y., Yanase, S., Fujita, T., Harayama, T. and Imanaka, H. (1981) A short-term in vitro assay for promoter substances using human lymphoblastoid cells latenly infected with Epstein Barr virus. Cancer Lett. 13, 29-37   DOI   ScienceOn
21 Wolford, R. W., Kesterson, J. W. and Attaway, J. W. (1971) Physicochemical properties of citrus oils from Florida, J. Agric. Food Chem. 19, 1097-1105   DOI
22 Nishino, H., Okuyama, T., Tanaka, T., Shibata, S., Tokuda, H., Tahayasu, J., Hasegawa, T., Nishino, A., Uema, H. and Iwashima, A. (1990) Sudies on the anti-tumor-promoting activity of naturally occurring substances, IV. Pd-II[(+) anomalin, (+) praeruptorin B], seselin-type coumarin, inhibits the promotion of skin tumor formation by 12-O-tetradecanoylphorbol-13-acetate in 7,12-dimethylbenz[d]anthracene-initiated mice. Carcinogenesis 11, 1557-1561   DOI   ScienceOn
23 Murakami, A., Ohigashi, H., and Koshimizu, K (1999) Chemoprevention: Insight into biological mechanism and promising food factors. Food Rev. Int. 15, 335-395   DOI
24 Hunter, G. L. K. and Brogden, W. B. Jr. (1966) Analysis of cold-pressed range oil paraffin waxes. Phytochemistry 5, 807-809   DOI   ScienceOn