Edible Plants Containing Naturally Occurring Carcinogens in Japan
1993; Oxford University Press; Volume: 84; Issue: 10 Linguagem: Inglês
10.1111/j.1349-7006.1993.tb02791.x
ISSN1876-4673
Autores Tópico(s)Plant Pathogens and Resistance
ResumoJapanese Journal of Cancer ResearchVolume 84, Issue 10 p. 997-1006 Open Access Edible Plants Containing Naturally Occurring Carcinogens in Japan Iwao Hirono, Iwao Hirono Department of Pathology, Fujita Health University School of Medicine, 1-98 Dengakugakubo, Kutsukake-cho, Toyoake, Aichi 470-11Search for more papers by this author Iwao Hirono, Iwao Hirono Department of Pathology, Fujita Health University School of Medicine, 1-98 Dengakugakubo, Kutsukake-cho, Toyoake, Aichi 470-11Search for more papers by this author First published: October 1993 https://doi.org/10.1111/j.1349-7006.1993.tb02791.xCitations: 16AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat REFERENCES 1) Kurland , L. T. and Mulder , D. W. Epidemiologic investigations of amyotrophic lateral sclerosis . Neurology , 4 , 355 – 378 ( 1954 ). 10.1212/WNL.4.5.355 CASPubMedWeb of Science®Google Scholar 2) Whiting , M. G. Toxicity of cycads . Econ. Bot. , 17 , 271 – 302 ( 1963 ). 10.1007/BF02860136 CASGoogle Scholar 3) Anderson , J. L. and Hall , W. T. Neurotoxic effects from cycad leaves . Fed. Proc. , 23 , 1349 ( 1964 ). CASWeb of Science®Google Scholar 4) Laqueur , G. L. , Mickelsen , O. , Whiting , M. G. and Kurland , L. T. Carcinogenic properties of nuts from Cycas circinalis L. indigenous to Guam . J. Natl. Cancer Inst. , 31 , 919 – 951 ( 1963 ). CASPubMedWeb of Science®Google Scholar 5) Laqueur , G. L. Carcinogenic effects of cycad meal and cycasin, methylazoxymethanol glycoside, in rats and effects of cycasin in germfree rats . Fed. Proc. , 23 , 1386 – 1387 ( 1964 ). CASPubMedWeb of Science®Google Scholar 6) Nishida , K. , Kobayashi , A. and Nagahama , T. Cycasin, a new toxic glycoside of Cycas revoluta Thunb. I. Isolation and structure of cycasin . Bull. Agric. Chem. Soc. Jpn. , 19 , 77 – 84 ( 1955 ). 10.1271/bbb1924.19.77 CASWeb of Science®Google Scholar 7) Riggs , N. V. Glucosyloxyazoxymethane, a constituent of the seeds of Cycas circinalis L . Chem. Ind. (London) , 926 ( 1956 ). CASWeb of Science®Google Scholar 8) Nishida , K. , Kobayashi , A. , Nagahama , T. , Kojima , K. and Yamane , M. Cycasin, a new toxic glycoside of Cycas revoluta Thunb. IV. Pharmacology of cycasin . J. Jpn. Biochem. Soc. , 28 , 218 – 223 ( 1956 ). CASGoogle Scholar 9) Spatz , M. , McDaniel , E. G. and Laqueur , G. L. Cycasin excretion in conventional and germfree rats . Proc. Soc. Exp. Biol. Med. , 121 , 417 – 422 ( 1966 ). 10.3181/00379727-121-30793 CASPubMedWeb of Science®Google Scholar 10) Spatz , M. , Smith , D. W. E. , McDaniel , E. G. and Laqueur , G. L. Role of intestinal microorganisms in determining cycasin toxicity . Proc. Soc. Exp. Biol. Med. , 124 , 691 – 697 ( 1967 ). 10.3181/00379727-124-31826 CASPubMedWeb of Science®Google Scholar 11) Kobayashi , A. and Matsumoto , H. Studies on methylazoxymethanol, the aglycone of cycasin. Isolation, biological, and chemical properties . Arch. Biochem. Biophys. , 110 , 373 – 380 ( 1965 ). 10.1016/0003-9861(65)90137-2 CASPubMedWeb of Science®Google Scholar 12) Laqueur , G. L. and Matsumoto , H. Neoplasms in female Fischer rats following intraperitoneal injection of methylazoxymethanol . J. Natl. Cancer Inst. , 37 , 217 – 232 ( 1966 ). CASPubMedWeb of Science®Google Scholar 13) Spatz , M. , Laqueur , G. L. and Holmes , J. M. Carcinogenic effects of methylazoxymethanol (MAM) in hamsters . Proc. Am. Assoc. Cancer Res. , 10 , 86 ( 1969 ). Web of Science®Google Scholar 14) Narisawa , T. and Nakano , H. Carcinoma of the large intestine of rats induced by rectal infusion of methylazoxymethanol . Gann , 64 , 93 – 95 ( 1973 ). CASPubMedWeb of Science®Google Scholar 15) Fushimi , K. Tumor induction in rats given consecutive injections of methylazoxymethanol acetate . Acta Sch. Med. Univ. Gifu , 22 , 729 – 750 ( 1974 ). CASGoogle Scholar 16) Zedeck , M. S. and Sternberg , S. S. A model system for studies of colon carcinogenesis: tumour induction by a single injection of methylazoxymethanol acetate . J. Natl. Cancer Inst. , 53 , 1419 – 1421 ( 1974 ). 10.1093/jnci/53.5.1419 CASPubMedWeb of Science®Google Scholar 17) Smith , D. W. E. Mutagenicity of cycasin aglycone (methylazoxymethanol), a naturally occurring carcinogen . Science , 152 , 1273 – 1274 ( 1966 ). 10.1126/science.152.3726.1273 CASPubMedWeb of Science®Google Scholar 18) Laqueur , G. L. , McDaniel , E. G. and Matsumoto , H. Tumor induction in germfree rats with methylazoxymethanol (MAM) and synthetic MAM acetate . J. Natl. Cancer Inst. , 39 , 355 – 371 ( 1967 ). CASPubMedWeb of Science®Google Scholar 19) Spatz , M. Hydrolysis of cycasin by β-D-glucosidase in skin of newborn rats . Proc. Soc. Exp. Biol. Med. , 128 , 1005 – 1008 ( 1968 ). 10.3181/00379727-128-33179 CASWeb of Science®Google Scholar 20) Spatz , M. , Laqueur , G. L. and Hirono , I. Hydrolysis of cycasin by β-D-glucosidase in subcutis of newborns . Fed. Proc. , 27 , 722 ( 1968 ). Web of Science®Google Scholar 21) Laqueur , G. L. and Spatz , M. Toxicology of cycasin . Cancer Res. , 28 , 2262 – 2267 ( 1968 ). CASPubMedWeb of Science®Google Scholar 22) Hirono , I. , Laqueur , G. L. and Spatz , M. Tumor induction in Fischer and Osborne-Mendel rats by a single administration of cycasin . J. Natl. Cancer Inst. , 40 , 1003 – 1010 ( 1968 ). CASPubMedWeb of Science®Google Scholar 23) Hirono , I. , Shibuya , C. and Fushimi , K. Tumor induction in C57BL/6 mice by a single administration of cycasin . Cancer Res. , 29 , 1658 – 1662 ( 1969 ). CASPubMedWeb of Science®Google Scholar 24) Hirono , I. and Shibuya , C. High incidence of pulmonary tumors in dd mice by a single injection of cycasin . Gann , 61 , 403 – 407 ( 1970 ). CASPubMedWeb of Science®Google Scholar 25) Hirono , I. , Hayashi , K. , Mori , H. and Miwa , T. Carcinogenic effects of cycasin in Syrian golden hamsters and the transplantability of induced tumors . Cancer Res. , 31 , 283 – 287 ( 1971 ). CASPubMedWeb of Science®Google Scholar 26) Shibuya , C. and Hirono , I. Relations between postnatal days of mice and carcinogenic effect of cycasin . Gann , 64 , 109 – 110 ( 1973 ). CASPubMedWeb of Science®Google Scholar 27) Hirono , I. , Laqueur , G. L. and Spatz , M. Transplantability of cycasin-induced tumors in rats, with emphasis on nephroblastomas . J. Natl. Cancer Inst. , 40 , 1011 – 1025 ( 1968 ). CASPubMedWeb of Science®Google Scholar 28) Fukunishi , R. , Terashi , S. , Watanabe , K. and Kawaji , K. High yield of hepatic tumors in rats by cycasin . Gann , 63 , 575 – 578 ( 1972 ). CASPubMedWeb of Science®Google Scholar 29) Spatz , M. Carcinogenic effect of cycad meal in guinea pigs . Fed. Proc. , 23 , 1384 – 1385 ( 1964 ). CASPubMedWeb of Science®Google Scholar 30) Watanabe , K. , Iwashita , H. , Muta , K. , Hamada , Y. and Hamada , K. Hepatic tumors of rabbits induced by cycad extract . Gann , 66 , 335 – 339 ( 1975 ). CASPubMedWeb of Science®Google Scholar 31) Stanton , M. F. Hepatic neoplasms of aquarium fish exposed to Cycas circinalis . Fed. Proc. , 25 , 661 ( 1966 ). Web of Science®Google Scholar 32) Hirono , I. Carcinogenicity and neurotoxicity of cycasin with special reference to species differences . Fed. Proc. , 31 , 1493 – 1497 ( 1972 ). CASPubMedWeb of Science®Google Scholar 33) Gabridge , M. G. , Denunzio , A. and Legator , M. S. Cycasin: detection of associated mutagenic activity in vivo . Science , 163 , 689 – 691 ( 1969 ). 10.1126/science.163.3868.689 CASPubMedWeb of Science®Google Scholar 34) Matsushima , T. , Matsumoto , H. , Shirai , A. , Sawamura , M. and Sugimura , T. Mutagenicity of the naturally occurring carcinogen cycasin and synthetic methylazoxymethanol conjugates in Salmonella typhimurium . Cancer Res. , 39 , 3780 – 3782 ( 1979 ). CASPubMedWeb of Science®Google Scholar 35) Teas , H. J. and Dyson , J. G. Mutation in Drosophila by methylazoxymethanol, the aglycone of cycasin . Proc. Soc. Exp. Biol. Med. , 125 , 988 – 990 ( 1967 ). 10.3181/00379727-125-32256 CASPubMedWeb of Science®Google Scholar 36) Evans , W. C. , Evans , E. T. R. and Hughes , L. E. Studies on bracken poisoning in cattle. Part 1 . Br. Vet. J. , 110 , 295 – 306 ( 1954 ). 10.1016/S0007-1935(17)50222-5 Google Scholar 37) Evans , I. A. and Mason , J. Carcinogenic activity of bracken . Nature , 208 , 913 – 914 ( 1965 ). 10.1038/208913a0 CASPubMedWeb of Science®Google Scholar 38) Pamukcu , A. M. and Price , J. M. Induction of intestinal and urinary bladder cancer in rats by feeding bracken fern (Pteris aquilina) . J. Natl. Cancer Inst. , 43 , 275 – 281 ( 1969 ). PubMedWeb of Science®Google Scholar 39) Hirono , I. , Aiso , S. , Hosaka , S. , Yamaji , T. and Haga , M. Induction of mammary cancer in CD rats fed bracken diet . Carcinogenesis , 4 , 885 – 887 ( 1983 ). 10.1093/carcin/4.7.885 CASPubMedWeb of Science®Google Scholar 40) Ogino , H. , Fujimoto , M. and Hirono , I. Reexamination of histological findings of ileal sarcomas induced in rats given diet containing bracken fern . J. Cancer Res. Clin. Oncol. , 112 , 6 – 10 ( 1986 ). 10.1007/BF00394931 CASPubMedWeb of Science®Google Scholar 41) Hirono , I. , Shibuya , C. , Shhnizu , M. and Fushimi , K. Carcinogenic activity of processed bracken used as human food . J. Natl. Cancer Inst. , 48 , 1245 – 1250 ( 1972 ). CASPubMedWeb of Science®Google Scholar 42) Hirono , I. , Shibuya , C. , Fushimi , K. and Haga , M. Studies on carcinogenic properties of bracken, Pteridium aquilinum . J. Natl. Cancer Inst. , 45 , 179 – 188 ( 1970 ). CASPubMedWeb of Science®Google Scholar 43) Hirono , I. , Aiso , S. , Yamaji , T. , Niwa , H. , Ojika , M. , Wakamatsu , K. and Yamada , K. Hyperplastic nodules of the liver induced in rats fed bracken diet . Cancer Lett. , 22 , 151 – 155 ( 1984 ). 10.1016/0304-3835(84)90112-5 CASPubMedWeb of Science®Google Scholar 44) Hirono , I. , Sasaoka , I. , Shibuya , C. , Shimizu , M. , Fushimi , K. , Mori , H. , Kato , K. and Haga , M. Natural carcinogenic products of plant origin . Gann Monogr. Cancer Res. , 17 , 205 – 217 ( 1975 ). CASGoogle Scholar 45) Evans , I. A. The radiomimetic nature of bracken toxin . Cancer Res. , 28 , 2252 – 2261 ( 1968 ). CASPubMedWeb of Science®Google Scholar 46) Pamukcu , A. M. , Ertürk , E. , Price , J. M. and Bryan , G. T. Lymphatic leukemia and pulmonary tumors in female Swiss mice fed bracken fern (Pteris aquilina) . Cancer Res. , 32 , 1442 – 1445 ( 1972 ). CASPubMedWeb of Science®Google Scholar 47) Hirono , I. Natural carcinogenic products of plant origin . Crit. Rev. Toxicol. , 8 , 235 – 277 ( 1981 ). 10.3109/10408448109109659 PubMedWeb of Science®Google Scholar 48) Ushijima , J. , Matsukawa , K. , Yuasa , A. and Okada , M. Toxicities of bracken fern in guinea pigs . Jpn. J. Vet. Sci. , 45 , 593 – 602 ( 1983 ). 10.1292/jvms1939.45.593 CASPubMedWeb of Science®Google Scholar 49) Pamukcu , A. M. , Goksoy , S. K. and Price , J. M. Urinary bladder neoplasms induced by feeding bracken fern (Pteris aquilina) to cows . Cancer Res. , 27 , 917 – 924 ( 1967 ). Web of Science®Google Scholar 50) Price , J. M. and Pamukcu , A. M. The induction of neoplasms of the urinary bladder of the cow and the small intestine of the rat by feeding bracken fern (Pteris aquilina) . Cancer Res. , 28 , 2247 – 2251 ( 1968 ). CASPubMedWeb of Science®Google Scholar 51) Pamukcu , A. M. , Olson , C. and Price , J. M. Assay of fractions of bovine urine for carcinogenic activity after feeding bracken fern (Pteris aquilina) . Cancer Res. , 26 , 1745 – 1753 ( 1966 ). CASPubMedWeb of Science®Google Scholar 52) Pamukcu , A. M. , Price , J. M. and Bryan , G. T. Assay of fractions of bracken fern (Pteris aquilina) for carcinogenic activity . Cancer Res. , 30 , 902 – 905 ( 1970 ). CASPubMedWeb of Science®Google Scholar 53) Evans , I. A. and Osman , M. A. Carcinogenicity of bracken and shikimic acid . Nature , 250 , 348 – 349 ( 1974 ). 10.1038/250348a0 CASPubMedWeb of Science®Google Scholar 54) Hikino , H. , Takahashi , T. , Arihara , S. and Takemoto , T. Structure of pteroside B, glycoside of Pteridium aquilinum var. latiusculum . Chem. Pharm. Bull. , 18 , 1488 – 1489 ( 1970 ). 10.1248/cpb.18.1488 CASWeb of Science®Google Scholar 55) Fukuoka , M. , Kuroyanagi , M. , Toyama , M. , Yoshihira , K. and Natori , S. Pterosins J, K, and L and six acylated pterosins from bracken, Pteridium aquilinum var. latiusculum . Chem. Pharm. Bull. , 20 , 2282 – 2285 ( 1972 ). CASWeb of Science®Google Scholar 56) Saito , M. , Umeda , M. , Enomoto , M. , Hatanaka , Y. , Natori , S. , Yoshihira , K. , Fukuoka , M. and Kuroyanagi , M. Cytotoxicity and carcinogenicity of pterosins and pterosides, 1-indanone derivatives from bracken (Pteridium aquilinum) . Experientia , 31 , 829 – 831 ( 1975 ). 10.1007/BF01938490 CASPubMedWeb of Science®Google Scholar 57) Takatori , K. , Nakano , S. , Nagata , S. , Okumura , K. , Hirono , I. and Shimizu , M. Pterolactam, a new compound isolated from bracken . Chem. Pharm. Bull. , 20 , 1087 ( 1972 ). 10.1248/cpb.20.1087 CASWeb of Science®Google Scholar 58) Wang , C. Y. , Chiu , C. W. , Pamukcu , A. M. and Bryan , G. T. Identification of carcinogenic tannin isolated from bracken fern (Pteridium aquilinum) . J. Natl. Cancer Inst. , 56 , 33 – 36 ( 1976 ). 10.1093/jnci/56.1.33 CASPubMedWeb of Science®Google Scholar 59) Hirono , I. , Fushimi , K. and Matsubara , N. Carcinogenicity test of shikimic acid in rats . Toxicol. Lett. , 1 , 9 – 10 ( 1977 ). 10.1016/0378-4274(77)90013-3 CASWeb of Science®Google Scholar 60) Hirono , I. , Ushimaru , Y. , Kato , K. , Mori , H. and Sasaoka , I. Carcinogenicity of boiling water extract of bracken, Pteridium aquilinum . Gann , 69 , 383 – 388 ( 1978 ). PubMedWeb of Science®Google Scholar 61) Pamukcu , A. M. , Wang , C. Y. , Hatcher , J. and Bryan , G. T. Carcinogenicity of tannin and tannin-free extracts of bracken fern (Pteridium aquilinum) in rats . J. Natl. Cancer Inst. , 65 , 131 – 136 ( 1980 ). CASPubMedWeb of Science®Google Scholar 62) Pamukcu , A. M. , Yalciner , S. , Hatcher , J. F. and Bryan , G. T. Quercetin, a rat intestinal and bladder carcinogen present in bracken fern (Pteridium aquilinum) . Cancer Res. , 40 , 3468 – 3472 ( 1980 ). CASPubMedWeb of Science®Google Scholar 63) Saito , D. , Shirai , A. , Matsushima , T. , Sugimura , T. and Hirono , I. Test of carcinogenicity of quercetin, a widely distributed mutagen in food . Teratog. Carcinog. Mutagen. , 1 , 213 – 221 ( 1980 ). 10.1002/tcm.1770010209 CASPubMedGoogle Scholar 64) Hirono , I. , Ueno , I. , Hosaka , S. , Takanashi , H. , Matsushima , T. , Sugimura , T. and Natori , S. Carcinogenicity examination of quercetin and rutin in ACI rats . Cancer Lett. , 13 , 15 – 21 ( 1981 ). 10.1016/0304-3835(81)90081-1 CASPubMedWeb of Science®Google Scholar 65) Morino , K. , Matsukura , N. , Kawachi , T. , Ohgaki , H. , Sugimura , T. and Hirono , I. Carcinogenicity test of quercetin and rutin in golden hamsters by oral administration . Carcinogenesis , 3 , 93 – 97 ( 1982 ). 10.1093/carcin/3.1.93 CASPubMedWeb of Science®Google Scholar 66) Takanashi , H. , Aiso , S. , Hirono , I. , Matsushima , T. and Sugimura , T. Carcinogenicity test of quercetin and kaempferol in rats by oral administration . J. Food Saf. , 5 , 55 – 60 ( 1983 ). 10.1111/j.1745-4565.1983.tb00455.x CASWeb of Science®Google Scholar 67) Nakabayashi , T. Isolation of astragalin and isoquercitrin from bracken, Pteridium aquilinum . Bull Agric. Chem. Soc. Jpn. , 19 , 104 – 109 ( 1955 ). 10.1271/bbb1924.19.104 CASWeb of Science®Google Scholar 68) Wang , C. Y. , Pamukcu , A. M. and Bryan , G. T. Isolation of fumaric acid, succinic acid, astragalin, isoquercitrin and tiliroside from Pteridium aquilinum . Phytochemistry , 12 , 2298 – 2299 ( 1973 ). 10.1016/0031-9422(73)85140-4 CASWeb of Science®Google Scholar 69) Ito , N. , Hagiwara , A. , Tamano , S. , Kagawa , M. , Shibata , M. A. , Kurata , Y. and Fukushima , S. Lack of carcinogenicity of quercetin in F344/DuCrj rats . Jpn. J. Cancer Res. , 80 , 317 – 325 ( 1989 ). 10.1111/j.1349-7006.1989.tb02313.x CASPubMedWeb of Science®Google Scholar 70) Niwa , H. , Ojika , M. , Wakamatsu , K. , Yamada , K. , Hirono , I. and Matsushita , K. Ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum . Tetrahedron Lett. , 24 , 4117 – 4120 ( 1983 ). 10.1016/S0040-4039(00)88276-3 CASWeb of Science®Google Scholar 71) Niwa , H. , Ojika , M. , Wakamatsu , K. , Yamada , K. , Ohba , S. , Saito , Y. , Hirono , I. and Matsushita , K. Stereochemistry of ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum . Tetrahedron Lett. , 24 , 5371 – 5372 ( 1983 ). 10.1016/S0040-4039(00)87871-5 CASWeb of Science®Google Scholar 72) Hirono , I. , Yamada , K. , Niwa , H. , Shizuri , Y. , Ojika , M. , Hosaka , S. , Yamaji , T. , Wakamatsu , K. , Kigoshi , H. , Niiyama , K. and Uosaki , Y. Separation of carcinogenic fraction of bracken fern . Cancer Lett. , 21 , 239 – 246 ( 1984 ). 10.1016/0304-3835(84)90001-6 CASPubMedWeb of Science®Google Scholar 73) Ojika , M. , Kigoshi , H. , Kuyama , H. , Niwa , H. and Yamada , K. Studies on Pteridium aquilinum var. latiusculum, IV. Isolation of three p-hydroxystyrene glycosides and an efficient method for the isolation of ptaquiloside, an unstable bracken carcinogen . J. Nat. Prod. , 48 , 634 – 637 ( 1985 ). 10.1021/np50040a019 CASPubMedWeb of Science®Google Scholar 74) Hirono , I. , Aiso , S. , Yamaji , T. , Mori , H. , Yamada , K. , Niwa , H. , Ojika , M. , Wakamatsu , K. , Kigoshi , H. , Niiyama , K. and Uosaki , Y. Carcinogenicity in rats of ptaquiloside isolated from bracken . Gann , 75 , 833 – 836 ( 1984 ). CASPubMedWeb of Science®Google Scholar 75) Hirono , I. , Ogino , H. , Fujimoto , M. , Yamada , K. , Yoshida , Y. , Ikagawa , M. and Okumura , M. Induction of tumors in ACI rats given a diet containing ptaquiloside, a bracken carcinogen . J. Natl. Cancer Inst. , 79 , 1143 – 1149 ( 1987 ). CASPubMedWeb of Science®Google Scholar 76) Hirono , I. , Kono , Y. , Takahashi , K. , Yamada , K. , Niwa , H. , Ojika , M. , Kigoshi , H. , Niiyama , K. and Uosaki , Y. Reproduction of acute bracken poisoning in a calf with ptaquiloside, a bracken constituent . Vet. Rec. , 115 , 375 – 378 ( 1984 ). 10.1136/vr.115.15.375 CASPubMedWeb of Science®Google Scholar 77) Hirono , I. , Ito , M. , Yagyu , S. , Haga , M. , Wakamatsu , K. , Kishikawa , T. , Nishikawa , O. , Yamada , K. , Ojika , M. and Kigoshi , H. Reproduction of progressive retinal degeneration (bright blindness) in sheep by administration of ptaquiloside contained in bracken . J. Vet. Med. Sci. , in press . Google Scholar 78) Van der Hoeven , J. C. M. , Lagerweij , W. J. , Posthumus , M. A. , van Veldhuizen , A. and Holterman , H. A. J. Aquilide A, a new mutagenic compound isolated from bracken fern (Pteridium aquilinum (L.) Kuhn) . Carcinogenesis , 4 , 1587 – 1590 ( 1983 ). 10.1093/carcin/4.12.1587 CASPubMedWeb of Science®Google Scholar 79) Mori , H. , Sugie , S. , Hirono , I. , Yamada , K. , Niwa , H. , Ojika , M. , Wakamatsu , K. and Kigoshi , H. Genotoxicity of ptaquiloside, a bracken carcinogen, in the hepatocyte primary culture/DNA-repair test . Mutat. Res. , 143 , 75 – 78 ( 1985 ). 10.1016/0165-7992(85)90108-3 CASPubMedWeb of Science®Google Scholar 80) Matoba , M. , Saito , E. , Saito , K. , Koyama , K. , Natori , S. , Matsushima , T. and Takimoto , M. ( née Muramatsu ) . Assay of ptaquiloside, the carcinogenic principle of bracken, Pteridium aquilinum, by mutagenicity testing in Salmonella typhimurium . Mutagenesis , 2 , 419 – 423 ( 1987 ). 10.1093/mutage/2.6.419 CASPubMedWeb of Science®Google Scholar 81) Nagao , T. , Saito , K. , Hirayama , E. , Uchikoshi , K. , Koyama , K. , Natori , S. , Morisaki , N. , Iwasaki , S. and Matsushima , T. Mutagenicity of ptaquiloside, the carcinogen in bracken, and its related illudane-type sesquiterpenes. I. Mutagenicity in Salmonella typhimurium . Mutat. Res. , 215 , 173 – 178 ( 1989 ). 10.1016/0027-5107(89)90181-4 CASPubMedWeb of Science®Google Scholar 82) Kamon , S. and Hirayama , T. Epidemiology of cancer of the esophagus in Miye, Nara and Wakayama prefecture with special reference to the role of bracken fern . Proc. Jpn. Cancer Assoc., 34th Annu. Meet. , 211 ( 1975 ). Google Scholar 83) Hirono , I. , Hosaka , S. and Kuhara , K. Enhancement by bracken of induction of tumors of the upper alimentary tract by N-propyl-N-nitrosourethan . Br. J. Cancer , 46 , 423 – 427 ( 1982 ). 10.1038/bjc.1982.219 CASPubMedWeb of Science®Google Scholar 84) Evans , I. A. , Widdop , B. , Jones , R. S. , Barber , G. D. , Leach , H. , Jones , D. L. and Mainwaring-Burton , R. The possible human hazard of the naturally occurring bracken carcinogen . Biochem. J. , 124 , 28 – 29 ( 1971 ). 10.1042/bj1240029Pa CASGoogle Scholar 85) Evans , I. A. , Jones , R. S. and Mainwaring-Burton , R. Passage of bracken fern toxicity into milk . Nature , 237 , 107 – 108 ( 1972 ). 10.1038/237107a0 CASPubMedWeb of Science®Google Scholar 86) Pamukcu , A. M. , Ertürk , E. , Yalciner , S. , Milli , U. and Bryan , G. T. Carcinogenic and mutagenic activities of milk from cows fed bracken fern (Pteridium aquilinum) . Cancer Res. , 38 , 1556 – 1560 ( 1978 ). CASPubMedWeb of Science®Google Scholar 87) Saito , K. , Nagao , T. , Matoba , M. , Koyama , K. , Natori , S. , Murakami , T. and Saiki , Y. Chemical assay of ptaquiloside, the carcinogen of Pteridium aquilinum, and the distribution of related compounds in the Pteridaceae . Phytochemistry , 28 , 1605 – 1611 ( 1989 ). 10.1016/S0031-9422(00)97808-7 CASWeb of Science®Google Scholar 88) Mclean , E. K. The toxic action of pyrrolizidine (senecio) alkaloid . Pharmacol. Rev. , 22 , 429 – 483 ( 1970 ). CASPubMedGoogle Scholar 89) Schoental , R. , Head , M. A. and Peacock , P. R. Senecio alkaloids: primary liver tumours in rats as a result of treatment with (i) a mixture of alkaloids from S. Jacobaea Lin.; (ii) retrorsine; (iii) isatidine . Br. J. Cancer , 8 , 458 – 465 ( 1954 ). 10.1038/bjc.1954.49 CASPubMedWeb of Science®Google Scholar 90) Svoboda , D. J. and Reddy , J. K. Malignant tumors in rats given lasiocarpine . Cancer Res. , 32 , 908 – 913 ( 1972 ). CASPubMedWeb of Science®Google Scholar 91) Hirono , I. , Shimizu , M. , Fushimi , K. , Mori , H. and Kato , K. Carcinogenic activity of Petasites japonicus Maxim., a kind of coltsfoot . Gann , 64 , 527 – 528 ( 1973 ). PubMedWeb of Science®Google Scholar 92) Yamada , K. , Tatematsu , H. , Suzuki , M. , Hirata , Y. , Haga , M. and Hirono , I. Isolation and the structures of two new alkaloids, petasitenine and neopetasitenine, from Petasites japonicus Maxim . Chem. Lett. , 461 – 464 ( 1976 ). 10.1246/cl.1976.461 Web of Science®Google Scholar 93) Hirono , I. , Mori , H. , Yamada , K. , Hirata , Y. , Haga , M. , Tatematsu , H. and Kanie , S. Carcinogenic activity of petasitenine, a new pyrrolizidine alkaloid isolated from Petasites japonicus Maxim . J. Natl. Cancer Inst. , 58 , 1155 – 1157 ( 1977 ). 10.1093/jnci/58.4.1155 CASPubMedWeb of Science®Google Scholar 94) Hirono , I. , Mori , H. and Culvenor , C. C. J. Carcinogenic activity of coltsfoot, Tussilago farfara L . Gann , 67 , 125 – 129 ( 1976 ). CASPubMedWeb of Science®Google Scholar 95) Culvernor , C. C. J. , Edgar , J. A. , Smith , L. W. and Hirono , I. The occurrence of senkirkine in Tussilago farfara . Aust. J. Chem. , 29 , 229 – 230 ( 1976 ). 10.1071/CH9760229 Google Scholar 96) Schoental , R. Hepatotoxic activity of retrorsine, senkirkine and hydroxysenkirkine in newborn rats, and the role of epoxides in carcinogenesis by pyrrolizidine alkaloids and aflatoxins . Nature , 227 , 401 – 402 ( 1970 ). 10.1038/227401a0 CASPubMedWeb of Science®Google Scholar 97) Hirono , I. , Haga , M. , Fujii , M. , Matsuura , S. , Matsubara , N. , Nakayama , M. , Furuya , T. , Hikichi , M. , Takanashi , H. , Uchida , E. , Hosaka , S. and Ueno , I. Induction of hepatic tumors in rats by senkirkine and symphytine . J. Natl. Cancer Inst. , 63 , 469 – 472 ( 1979 ). CASPubMedWeb of Science®Google Scholar 98) Hirono , I. , Mori , H. and Haga , M. Carcinogenic activity of Symphytum officinale . J. Natl. Cancer Inst. , 61 , 865 – 869 ( 1978 ). CASPubMedWeb of Science®Google Scholar 99) Furuya , T. and Araki , K. Studies on constituents of crude drugs. I. Alkaloids of Symphytum officinale Linn . Chem. Pharm. Bull. , 16 , 2512 – 2516 ( 1968 ). 10.1248/cpb.16.2512 CASPubMedWeb of Science®Google Scholar 100) Furuya , T. and Hikichi , M. Alkaloids and triterpenoids of Symphytum officinale . Phytochemistry , 10 , 2217 – 2220 ( 1971 ). 10.1016/S0031-9422(00)97225-X CASWeb of Science®Google Scholar 101) Hirono , I. , Ueno , I. , Aiso , S. , Yamaji , T. and Haga , M. Carcinogenic activity of Farfugium japonicum and Senecio cannabifolius . Cancer Lett. , 20 , 191 – 198 ( 1983 ). 10.1016/0304-3835(83)90048-4 CASPubMedWeb of Science®Google Scholar 102) Niwa , H. , Ishiwata , H. and Yamada , K. Isolation of petasitenine, a carcinogenic pyrrolizidine alkaloid from Farfugium japonicum Kitam . J. Nat. Prod. , 48 , 1003 – 1004 ( 1985 ). 10.1021/np50042a031 CASWeb of Science®Google Scholar 103) Furuya , T. , Murakami , K. and Hikichi , M. Senkirkine, a pyrrolizidine alkaloid from Farfugium japonicum . Phytochemistry , 10 , 3306 – 3307 ( 1971 ). 10.1016/S0031-9422(00)97403-X CASWeb of Science®Google Scholar 104) Niwa , H. , Ishiwata , H. and Yamada , K. Separation and determination of macrocyclic pyrrolizidine alkaloids of the otonecine type present in the edible plant Petasites japonicus by reversed phase high-performance liquid chromatography . J. Chromatogr. , 257 , 146 – 150 ( 1983 ). 10.1016/S0021-9673(01)88166-8 CASPubMedWeb of Science®Google Scholar 105) Yamanaka , H. , Nagao , M. , Sugimura , T. , Furuya , T. , Shirai , A. and Matsushima , T. Mutagenicity of pyrrolizidine alkaloids in the Salmonella/mammalian-micro-some test . Mutat. Res. , 68 , 211 – 216 ( 1979 ). 10.1016/0165-1218(79)90152-6 CASPubMedWeb of Science®Google Scholar 106) Williams , G. M. , Mori , H. , Hirono , I. and Nagao , M. Genotoxicity of pyrrolizidine alkaloids in the hepatocyte primary culture/DNA-repair test . Mutat. Res. , 79 , 1 – 5 ( 1980 ). 10.1016/0165-1218(80)90141-X CASPubMedWeb of Science®Google Scholar 107) Takanashi , H. , Umeda , M. and Hirono , I. Chromosomal aberrations and mutation in cultured mammalian cells induced by pyrrolizidine alkaloids . Mutat. Res. , 78 , 67 – 77 ( 1980 ). 10.1016/0165-1218(80)90027-0 CASPubMedWeb of Science®Google Scholar 108) Hirono , I. , Mori , H. , Haga , M. , Fujii , M. , Yamada , K. , Hirata , Y. , Takanashi , H. , Uchida , E. , Hosaka , S. , Ueno , I. , Matsushima , T. , Umezawa , K. and Shirai , A. Edible plants containing carcinogenic pyrrolizidine alkaloids in Japan . In " Naturally Occurring Carcinogens-Mutagens and Modulators of Carcinogenesis ," ed. E. C. Miller , J. A. Miller , I. Hirono , T. Sugimura and S. Takayama , pp . 79 – 87 ( 1979 ). Japan Sci. Soc. Press, Tokyo/Univ. Park Press , Baltimore . Google Scholar Citing Literature Volume84, Issue10October 1993Pages 997-1006 ReferencesRelatedInformation
Referência(s)