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Volumn 47, Issue 8, 1999, Pages 3151-3157

Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation

Author keywords

Chemopreventive agent; Citrus limon; Coumarin; Epstein Barr virus; Nitric oxide; Psoralen; Superoxide

Indexed keywords

5 GERANYLOXY 7 METHOXYCOUMARIN; 5 GERANYLOXYPSOLAREN; 8 GERANYLOXYPSOLAREN; ANTINEOPLASTIC AGENT; ANTIOXIDANT; COUMARIN DERIVATIVE; LIPOPOLYSACCHARIDE; NITRIC OXIDE; PHORBOL 13 ACETATE 12 MYRISTATE; PLANT EXTRACT; PSORALEN; RADICAL; RECOMBINANT GAMMA INTERFERON; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG;

EID: 0032847060     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980999y     Document Type: Article
Times cited : (76)

References (42)
  • 1
    • 0016685233 scopus 로고
    • Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test
    • Ames, B. N. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutat. Res. 1995, 31, 347-364.
    • (1995) Mutat. Res. , vol.31 , pp. 347-364
    • Ames, B.N.1
  • 2
    • 0017381552 scopus 로고
    • Carbon-13 magnetic resonance spectroscopy of coumarins. Carbon-13-proton long-range couplings
    • Chang, C.; Floss, H. G.; Steck, W. Carbon-13 magnetic resonance spectroscopy of coumarins. Carbon-13-proton long-range couplings. J. Org. Chem. 1977, 42, 1337-1340.
    • (1977) J. Org. Chem. , vol.42 , pp. 1337-1340
    • Chang, C.1    Floss, H.G.2    Steck, W.3
  • 4
    • 0025756918 scopus 로고
    • Enzymatic mechanisms of Superoxide production
    • Cross, A. R.; Jones, O. T. G. Enzymatic mechanisms of Superoxide production. Biochim. Biophys. Acta 1991, 1057, 281-298.
    • (1991) Biochim. Biophys. Acta , vol.1057 , pp. 281-298
    • Cross, A.R.1    Jones, O.T.G.2
  • 5
    • 0005424513 scopus 로고
    • Coumarins of Citrus marcroptera
    • Dreyer, D. L.; Huey, P. F. Coumarins of Citrus marcroptera. Phytochemistry 1973, 12, 3011-3013.
    • (1973) Phytochemistry , vol.12 , pp. 3011-3013
    • Dreyer, D.L.1    Huey, P.F.2
  • 6
    • 0029586719 scopus 로고
    • Inhibition of mutagenesis of 2-amino-methylimidazo[4,5-F]quinoline (IQ) by coumarins and furanocoumarins, chromoanoes, and furanochromanones
    • Edenharder, R.; Speth, C.; Decker, M.; Kolodziej, H.; Kayser, O.; Platt, K. L. Inhibition of mutagenesis of 2-amino-methylimidazo[4,5-F]quinoline (IQ) by coumarins and furanocoumarins, chromoanoes, and furanochromanones. Mutat. Res. 1995, 345, 57-71.
    • (1995) Mutat. Res. , vol.345 , pp. 57-71
    • Edenharder, R.1    Speth, C.2    Decker, M.3    Kolodziej, H.4    Kayser, O.5    Platt, K.L.6
  • 7
    • 0018538424 scopus 로고
    • High-performance liquid chromatographic determination of some coumarins and psoralens found in citrus peel oils
    • Fisher, J. F.; Trama, L. A. High-performance liquid chromatographic determination of some coumarins and psoralens found in citrus peel oils. J. Agric. Food Chem. 1979, 27, 1334-1337.
    • (1979) J. Agric. Food Chem. , vol.27 , pp. 1334-1337
    • Fisher, J.F.1    Trama, L.A.2
  • 8
    • 0001550314 scopus 로고
    • Coumarins in the Rutaceae
    • Gray, A. I.; Waterman, P. G. Coumarins in the Rutaceae. Phytochemistry 1978, 17, 845-864.
    • (1978) Phytochemistry , vol.17 , pp. 845-864
    • Gray, A.I.1    Waterman, P.G.2
  • 11
    • 0021875487 scopus 로고
    • Furocoumarines dans les finies essentielles identification et dosage du 5 methoxy psoralene dans les produits solaires
    • Herpol-Borremans, M.; Masse, M. O.; Grimee, R. Furocoumarines dans les finies essentielles identification et dosage du 5 methoxy psoralene dans les produits solaires. J. Pharm. Belg. 1985, 40, 147-158.
    • (1985) J. Pharm. Belg. , vol.40 , pp. 147-158
    • Herpol-Borremans, M.1    Masse, M.O.2    Grimee, R.3
  • 12
    • 0026453418 scopus 로고
    • Peroxynitrite formation from macrophage-derived nitrite oxide
    • Ischiropoulos, H.; Zhu, L.; Beckman, J. S. Peroxynitrite formation from macrophage-derived nitrite oxide. Arch. Biochem. Biophys. 1992, 298, 446-451.
    • (1992) Arch. Biochem. Biophys. , vol.298 , pp. 446-451
    • Ischiropoulos, H.1    Zhu, L.2    Beckman, J.S.3
  • 13
    • 0030011886 scopus 로고    scopus 로고
    • Inhibitory effects of d-limonen on the development of colonie aberrant crypt foci induced by azoxymethane in F344 rats
    • Kawamori, T.; Tanaka, T.; Hirose, M.; Ohnishi, M.; Mori, H. Inhibitory effects of d-limonen on the development of colonie aberrant crypt foci induced by azoxymethane in F344 rats. Carcinogenesis 1996, 17, 369-372.
    • (1996) Carcinogenesis , vol.17 , pp. 369-372
    • Kawamori, T.1    Tanaka, T.2    Hirose, M.3    Ohnishi, M.4    Mori, H.5
  • 14
    • 0024540440 scopus 로고
    • Role of free radicals in tumor promotion and progression
    • Slaga, T. J., Klein-Szanto, A. J. P., Boutwell, R. K., Stevenson, D. E., Spitzer, H. L., D'Motto, B., Eds.; Alan R. Liss, Inc.: New York
    • Kensler, T. W.; Egner, P. A.; Taffe, B. G.; Trush, M. A. Role of free radicals in tumor promotion and progression. In Skin Carcinogenesis; Slaga, T. J., Klein-Szanto, A. J. P., Boutwell, R. K., Stevenson, D. E., Spitzer, H. L., D'Motto, B., Eds.; Alan R. Liss, Inc.: New York, 1989; pp 233-248.
    • (1989) Skin Carcinogenesis , pp. 233-248
    • Kensler, T.W.1    Egner, P.A.2    Taffe, B.G.3    Trush, M.A.4
  • 15
    • 0003103589 scopus 로고
    • Inhibition of chemically induced carcinogenesis by citrus limonoids
    • Ho, C.-T., Osawa, T., Huang, M.-T., Rosen, R. T., Eds.; American Chemical Society: Washington, DC
    • Lam, L. K. T.; Zhang, J.; Hasegawa, S.; Schut, H. A. J. Inhibition of chemically induced carcinogenesis by citrus limonoids. In Food Phytochemicals for Cancer Prevention?; Ho, C.-T., Osawa, T., Huang, M.-T., Rosen, R. T., Eds.; American Chemical Society: Washington, DC, 1994; pp 209-219.
    • (1994) Food Phytochemicals for Cancer Prevention? , pp. 209-219
    • Lam, L.K.T.1    Zhang, J.2    Hasegawa, S.3    Schut, H.A.J.4
  • 16
    • 0025091727 scopus 로고
    • Sever phototoxic burn following celery ingestion
    • Ljunggren, B. Sever phototoxic burn following celery ingestion. Arch. Dermal. 1990, 126, 1334-1336.
    • (1990) Arch. Dermal. , vol.126 , pp. 1334-1336
    • Ljunggren, B.1
  • 17
    • 0021288848 scopus 로고
    • - production by human neutrophils. The preparation and assay of NADPH oxidase/containing particles from human neutrophilis
    • - production by human neutrophils. The preparation and assay of NADPH oxidase/containing particles from human neutrophilis. Method Enzymol. 1984, 105, 358-365.
    • (1984) Method Enzymol. , vol.105 , pp. 358-365
    • Markert, M.1    Andrew, P.C.2    Babior, B.M.3
  • 18
    • 0028547392 scopus 로고
    • Potential Health-Promoting Properties of Citrus Flavonoids
    • Middleton, E.; Kandaswami, C. Potential Health-Promoting Properties of Citrus Flavonoids. Food Technol. 1994, 48, 115-119.
    • (1994) Food Technol. , vol.48 , pp. 115-119
    • Middleton, E.1    Kandaswami, C.2
  • 19
    • 0000457516 scopus 로고
    • Inhibition of oral carcinogenesis by green coffee beans and limonoid glucosides
    • Huang, M.-T., Osawa, T., Ho, C.-T., Rosen, R. T., Eds.; American Chemical Society: Washington, DC
    • Miller, E. G.; Gonzales-Sanders, A. P.; Couvillon, A. M.; Wight, J. M.; Hasegawa, S.; Lam, L. K. T.; Sunahara, G. I. Inhibition of oral carcinogenesis by green coffee beans and limonoid glucosides. In Food Phytochemicals for Cancer Prevention?; Huang, M.-T., Osawa, T., Ho, C.-T., Rosen, R. T., Eds.; American Chemical Society: Washington, DC, 1994; pp 220-229.
    • (1994) Food Phytochemicals for Cancer Prevention? , pp. 220-229
    • Miller, E.G.1    Gonzales-Sanders, A.P.2    Couvillon, A.M.3    Wight, J.M.4    Hasegawa, S.5    Lam, L.K.T.6    Sunahara, G.I.7
  • 20
    • 0002575295 scopus 로고    scopus 로고
    • Isolation of eriocitrin (eriodictyol 7-rutinoside) from lemon fruit (Citrus limon Burm. f.) and its antioxidative activity
    • Miyake, Y.; Yamamoto, K.; Osawa, T. Isolation of eriocitrin (eriodictyol 7-rutinoside) from lemon fruit (Citrus limon Burm. f.) and its antioxidative activity. Food Sci. Technol. Int. Tokyo 1997a, 3, 84-89.
    • (1997) Food Sci. Technol. Int. Tokyo , vol.3 , pp. 84-89
    • Miyake, Y.1    Yamamoto, K.2    Osawa, T.3
  • 21
    • 0000007536 scopus 로고    scopus 로고
    • Isolation of C-glucosylflavone from lemon peel and antioxidative activity of flavonoid compounds in lemon fruit
    • Miyake, Y.; Yamamoto, K.; Morimitsu, Y.; Osawa, T. Isolation of C-glucosylflavone from lemon peel and antioxidative activity of flavonoid compounds in lemon fruit. J. Agric. Food Chem. 1997b, 45, 4619-4623.
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 4619-4623
    • Miyake, Y.1    Yamamoto, K.2    Morimitsu, Y.3    Osawa, T.4
  • 22
    • 0031870664 scopus 로고    scopus 로고
    • Protective effects of lemon flavonoids on oxidative stress in diabetic rats
    • Miyake, Y.; Yamamoto, K.; Tsujihara, N.; Osawa, T. Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Lipids 1998, 33, 689-695.
    • (1998) Lipids , vol.33 , pp. 689-695
    • Miyake, Y.1    Yamamoto, K.2    Tsujihara, N.3    Osawa, T.4
  • 23
    • 0001607911 scopus 로고
    • Glyceroglycolipids from Citrus hystrix, a traditional herb in Thailand, potently inhibit the tumor promoting activity of 12-O-tetradecanoylphorbol 13-acetate in mouse skin
    • Murakami, A.; Nakamura, A.; Koshimizu, K.; Ohigashi, H. Glyceroglycolipids from Citrus hystrix, a traditional herb in Thailand, potently inhibit the tumor promoting activity of 12-O-tetradecanoylphorbol 13-acetate in mouse skin. J. Agric. Food Chem. 1995, 43, 2779-2783.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 2779-2783
    • Murakami, A.1    Nakamura, A.2    Koshimizu, K.3    Ohigashi, H.4
  • 24
    • 0030019570 scopus 로고    scopus 로고
    • Antitumor promotion with food phytochemicals: A strategy for cancer chemoprevention
    • Murakami, A.; Ohigashi, H.; Koshimizu, K. Antitumor promotion with food phytochemicals: a strategy for cancer chemoprevention. Biosci. Biotech. Biochem. 1998, 60, 1-8.
    • (1998) Biosci. Biotech. Biochem. , vol.60 , pp. 1-8
    • Murakami, A.1    Ohigashi, H.2    Koshimizu, K.3
  • 25
    • 0030982126 scopus 로고    scopus 로고
    • Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of Superoxide generation in leukocytes
    • Murakami, A.; Kuki, W.; Takahashi, Y.; Yonei, H.; Nakamura, Y.; Ohto, Y.; Ohigashi, H.; Koshimizu, K. Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of Superoxide generation in leukocytes. Jpn. J. Cancer Res. 1997, 88, 4443-4452.
    • (1997) Jpn. J. Cancer Res. , vol.88 , pp. 4443-4452
    • Murakami, A.1    Kuki, W.2    Takahashi, Y.3    Yonei, H.4    Nakamura, Y.5    Ohto, Y.6    Ohigashi, H.7    Koshimizu, K.8
  • 26
    • 0032902314 scopus 로고    scopus 로고
    • Identification of coumarins from the fruit of citrus hystrix DC as inhibitors of nitric oxide generation in mouse macrophage RAW 264.7 cells
    • Murakami, A.; Gao, G.; Kim, O. K.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Jiwajinda, S.; Koshimizu, K.; Ohigashi, H. Identification of coumarins from the fruit of citrus hystrix DC as inhibitors of nitric oxide generation in mouse macrophage RAW 264.7 cells. J. Agric. Food Chem. 1999, 47, 333-339.
    • (1999) J. Agric. Food Chem. , vol.47 , pp. 333-339
    • Murakami, A.1    Gao, G.2    Kim, O.K.3    Omura, M.4    Yano, M.5    Ito, C.6    Furukawa, H.7    Jiwajinda, S.8    Koshimizu, K.9    Ohigashi, H.10
  • 27
    • 0023155008 scopus 로고
    • 7-Geranyloxycoumarine from juice oil of hassaku (Citrus hassaku) and antimicrobial effects of related coumarins
    • Nakatani, N.; Tamada, Y.; Fuwa, H. 7-Geranyloxycoumarine from juice oil of hassaku (Citrus hassaku) and antimicrobial effects of related coumarins. Agric. Biol. Chem. 1987, 51, 419-423.
    • (1987) Agric. Biol. Chem. , vol.51 , pp. 419-423
    • Nakatani, N.1    Tamada, Y.2    Fuwa, H.3
  • 28
    • 0028092958 scopus 로고
    • Nitric oxide synthases: Roles, tolls, and controls
    • Nathan, C.; Xie, Q. Nitric oxide synthases: roles, tolls, and controls. Cell 1994, 78, 915-918.
    • (1994) Cell , vol.78 , pp. 915-918
    • Nathan, C.1    Xie, Q.2
  • 29
    • 0001211995 scopus 로고
    • Antitumor promoters from edible plants
    • Ho, C.-T., Osawa, T., Huang, M.-T., Rosen, R. T., Eds.; American Chemical Society, Washington, DC
    • Ohigashi, H.; Murakami, A.; Koshimizu, K. Antitumor promoters from edible plants. In Food Phytochemicals for Cancer Prevention?; Ho, C.-T., Osawa, T., Huang, M.-T., Rosen, R. T., Eds.; American Chemical Society, Washington, DC, 1994; pp 251-261.
    • (1994) Food Phytochemicals for Cancer Prevention? , pp. 251-261
    • Ohigashi, H.1    Murakami, A.2    Koshimizu, K.3
  • 31
    • 0003820481 scopus 로고
    • Chemical composition of lemon oil. I. Isolation of series of substituted coumarins
    • Stanley, W. L.; Vannier, S. H. Chemical composition of lemon oil. I. Isolation of series of substituted coumarins. J. Am. Chem. Soc. 1957, 79, 3488-3491.
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 3488-3491
    • Stanley, W.L.1    Vannier, S.H.2
  • 33
    • 85006848729 scopus 로고    scopus 로고
    • Inhibitory of colon carcinogenesis by nonnutritive constituents in food
    • Tanaka, T.; Mori, H. Inhibitory of colon carcinogenesis by nonnutritive constituents in food. J. Toxicol. Pathol. 1996, 9, 139-149.
    • (1996) J. Toxicol. Pathol. , vol.9 , pp. 139-149
    • Tanaka, T.1    Mori, H.2
  • 36
    • 0023032498 scopus 로고
    • Inhibitory effects of ursolic and oleanolic acid on skin tumor promotion by 12-O-tetradecanoylphorbol 13-acetate
    • Tokuda, H.; Ohigashi, H.; Koshimizu, K.; Ito, Y. Inhibitory effects of ursolic and oleanolic acid on skin tumor promotion by 12-O-tetradecanoylphorbol 13-acetate. Cancer Lett. 1986, 33, 279-283.
    • (1986) Cancer Lett. , vol.33 , pp. 279-283
    • Tokuda, H.1    Ohigashi, H.2    Koshimizu, K.3    Ito, Y.4
  • 37
    • 0018991197 scopus 로고
    • Chemistry and utilization of phenylpropanoids including flavonoids, coumarins and lignans
    • Tom, J. M.; Ulubelen, A. Chemistry and utilization of phenylpropanoids including flavonoids, coumarins and lignans. J. Agric. Food Chem. 1980, 28, 188-196.
    • (1980) J. Agric. Food Chem. , vol.28 , pp. 188-196
    • Tom, J.M.1    Ulubelen, A.2
  • 40
    • 0027141759 scopus 로고
    • Prevention-therapy-basic science and the resolution of the cancer problem: Presidential address
    • Wattenberg, L. W. Prevention-therapy-basic science and the resolution of the cancer problem: presidential address. Cancer Res. 1993, 53, 5890-5896.
    • (1993) Cancer Res. , vol.53 , pp. 5890-5896
    • Wattenberg, L.W.1
  • 41
    • 0031003224 scopus 로고    scopus 로고
    • Destruction of bystander cells by tumor cells transfected with inducible nitric oxide (NO) synthase gene
    • Xie, K.; Huang, S.; Dong, Z.; Juang, S. H.; Wang, Y.; Fidler I. J. Destruction of bystander cells by tumor cells transfected with inducible nitric oxide (NO) synthase gene. J. Natl. Cancer Inst. 1997, 89, 421-427.
    • (1997) J. Natl. Cancer Inst. , vol.89 , pp. 421-427
    • Xie, K.1    Huang, S.2    Dong, Z.3    Juang, S.H.4    Wang, Y.5    Fidler, I.J.6
  • 42


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