메뉴 건너뛰기




Volumn 51, Issue 9, 2003, Pages 2559-2564

Pteroside A2 - A new illudane-type sesquiterpene glucoside from Pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone

Author keywords

Bracken fern; Caudatodienone; Caudatoside; Illudane glucosides; Ptaquiloside Z; Pteridium aquilinumn; Pteridium caudatum; Pteroside A2

Indexed keywords

CAUDATIODIENONE; GLUCOSIDE; KETONE; PLANT EXTRACT; PTEROSIDE A2; PYRIDINE; SESQUITERPENE; UNCLASSIFIED DRUG;

EID: 0344950553     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf026238j     Document Type: Article
Times cited : (23)

References (31)
  • 1
    • 0001345507 scopus 로고
    • Ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum
    • Niwa, H.; Ojika, M.; Wakamatsu, K.; Yamada, K.; Hirono, I.; Matsushita, K. Ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum. Tetrahedron Lett. 1983, 24, 4117-4120.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 4117-4120
    • Niwa, H.1    Ojika, M.2    Wakamatsu, K.3    Yamada, K.4    Hirono, I.5    Matsushita, K.6
  • 5
    • 0001251580 scopus 로고
    • Chemical assay of ptaquiloside, the carcinogen of Pteridium aquilinum, and the distribution of related compounds in the Pteridaceae
    • Saito, K.; Nagao, T.; Matoba, M.; Koyama, K.; Natori, S.; Murakami, T.; Saiki, Y. Chemical assay of ptaquiloside, the carcinogen of Pteridium aquilinum, and the distribution of related compounds in the Pteridaceae. Phytochemistry 1989, 28, 1605-1616.
    • (1989) Phytochemistry , vol.28 , pp. 1605-1616
    • Saito, K.1    Nagao, T.2    Matoba, M.3    Koyama, K.4    Natori, S.5    Murakami, T.6    Saiki, Y.7
  • 6
    • 0033830325 scopus 로고    scopus 로고
    • Carcinogenic effects of ptaquiloside in bracken fern and related compounds
    • Potter, D. M.; Baird, M. S. Carcinogenic effects of ptaquiloside in bracken fern and related compounds. Br. J. Cancer 2000, 83, 914-920.
    • (2000) Br. J. Cancer , vol.83 , pp. 914-920
    • Potter, D.M.1    Baird, M.S.2
  • 7
    • 77957223208 scopus 로고    scopus 로고
    • The chemistry and toxicology of bioactive compounds in bracken fern (Pteridium ssp) with special reference to chemical ecology and carcinogenesis
    • Atta-Uhr-Rahman Ed.; Elsevier Science: Amsterdam
    • Alonso-Amelot, M. E. The Chemistry and Toxicology of Bioactive Compounds in Bracken Fern (Pteridium ssp) with special reference to Chemical Ecology and Carcinogenesis. In Studies in Natural Product Chemistry; Atta-Uhr-Rahman Ed.; Elsevier Science: Amsterdam, 2002; Vol. 26, pp 685-740.
    • (2002) Studies in Natural Product Chemistry , vol.26 , pp. 685-740
    • Alonso-Amelot, M.E.1
  • 9
    • 0024272954 scopus 로고
    • Bracken (Pteridium aquilinum) - Toxic effects and toxic constituents
    • Fenwick, G. R. Bracken (Pteridium aquilinum) - toxic effects and toxic constituents. J. Sci. Food Agric. 1989, 46, 147-173.
    • (1989) J. Sci. Food Agric. , vol.46 , pp. 147-173
    • Fenwick, G.R.1
  • 10
    • 0002238247 scopus 로고    scopus 로고
    • The toxicity of bracken fern (genus Pteridium) to animals and its relevance to man
    • D'Mello, J. P. F., Ed.; CRC Press: Boca Raton, FL
    • Smith, B. L. The toxicity of bracken fern (genus Pteridium) to animals and its relevance to man. In Handbook of Plant and Fungal Toxicants; D'Mello, J. P. F., Ed.; CRC Press: Boca Raton, FL, 1997; pp 63-76.
    • (1997) Handbook of Plant and Fungal Toxicants , pp. 63-76
    • Smith, B.L.1
  • 12
    • 0028928730 scopus 로고
    • Bracken fern (Pteridium spp.) carcinogenicity and human health: - A brief review
    • Smith, B. L.; Seawright, A. A. Bracken fern (Pteridium spp.) carcinogenicity and human health: - a brief review. Nat. Toxins 1995, 3, 1-75.
    • (1995) Nat. Toxins , vol.3 , pp. 1-75
    • Smith, B.L.1    Seawright, A.A.2
  • 13
    • 0345160830 scopus 로고
    • Passage of the bracken fern carcinogen ptaquiloside into bovine milk
    • Alonso-Amelot, M. E.; Castillo, U.; De Jongh, F. Passage of the bracken fern carcinogen ptaquiloside into bovine milk. Lait 1993, 73, 323-332.
    • (1993) Lait , vol.73 , pp. 323-332
    • Alonso-Amelot, M.E.1    Castillo, U.2    De Jongh, F.3
  • 15
    • 0032347257 scopus 로고    scopus 로고
    • Excretion, through milk, of ptaquiloside in bracken-fed cows. A quantitative assessment
    • Alonso-Amelot, M. E.; Castillo, U.; Smith B. L.; Lauren, D. R. Excretion, through milk, of ptaquiloside in bracken-fed cows. A quantitative assessment. Lait 1998, 78, 413-423.
    • (1998) Lait , vol.78 , pp. 413-423
    • Alonso-Amelot, M.E.1    Castillo, U.2    Smith, B.L.3    Lauren, D.R.4
  • 16
    • 0035863373 scopus 로고    scopus 로고
    • Possible association between gastric cancer and bracken fern in Venezuela. An epidemiological study
    • Alonso-Amelot, M. E.; Avendafio, M. Possible association between gastric cancer and bracken fern in Venezuela. An epidemiological study. Int. J. Cancer 2001, 91, 252-259.
    • (2001) Int. J. Cancer , vol.91 , pp. 252-259
    • Alonso-Amelot, M.E.1    Avendafio, M.2
  • 18
    • 0002597143 scopus 로고
    • El genero pteridium en Venezuela: Taxonomía y distribución geografica
    • Ortega, F. El genero Pteridium en Venezuela: taxonomía y distribución geografica. Biollania 1991, 7, 47-56.
    • (1991) Biollania , vol.7 , pp. 47-56
    • Ortega, F.1
  • 19
    • 0036851347 scopus 로고    scopus 로고
    • Clarification of the taxonomic status and relationships of Pteridium caudatum (Dennstaedtiaceae) in Central and South America
    • Thomson, J.; Alonso-Amelot, M. E.; Clarification of the taxonomic status and relationships of Pteridium caudatum (Dennstaedtiaceae) in Central and South America. Bot. J. Linn. Soc. 2002, 3, 237-248.
    • (2002) Bot. J. Linn. Soc. , vol.3 , pp. 237-248
    • Thomson, J.1    Alonso-Amelot, M.E.2
  • 20
    • 0029562935 scopus 로고
    • Structure elucidation of 1,4-dihydroxy-2-isopropyl-5-methylphenyl-1-O-β-D-glucopyranoside, a constituent of Pteridium aquilinum var. caudatum
    • Castillo, U. F.; Wilkins, A. L.; Lauren, D. R.; McNaughton, D. E.; Smith, B. L. Structure elucidation of 1,4-dihydroxy-2-isopropyl-5-methylphenyl-1-O-β-D-glucopyranoside, a constituent of Pteridium aquilinum var. caudatum. J. Nat. Prod. 1995, 58, 1889-1891.
    • (1995) J. Nat. Prod. , vol.58 , pp. 1889-1891
    • Castillo, U.F.1    Wilkins, A.L.2    Lauren, D.R.3    McNaughton, D.E.4    Smith, B.L.5
  • 21
    • 0023630543 scopus 로고
    • Assay of ptaquiloside, the carcinogenic principle of bracken, Pteridium aquilinum, by mutagenicity testing in Salmonella typhimurium
    • Matoba, M.; Saito, E.; Salto, K.; Koyama, K.; Natori, S.; Matsushima, T.; Takimoto, N.; Assay of ptaquiloside, the carcinogenic principle of bracken, Pteridium aquilinum, by mutagenicity testing in Salmonella typhimurium. Mutagenesis 1987, 2, 419-423.
    • (1987) Mutagenesis , vol.2 , pp. 419-423
    • Matoba, M.1    Saito, E.2    Salto, K.3    Koyama, K.4    Natori, S.5    Matsushima, T.6    Takimoto, N.7
  • 22
    • 0023618277 scopus 로고
    • Ptaquiloside, a potent carcinogen for bracken fern, Pteridium aquilinum var. latiusculum; structure elucidation based on chemical and spectral evidence and reactions with amino acids, nucleosides and nucleotides
    • Ojika, M.; Wakamatsu, K.; Niwa, H.; Yamada, Y. Ptaquiloside, a potent carcinogen for bracken fern, Pteridium aquilinum var. latiusculum; structure elucidation based on chemical and spectral evidence and reactions with amino acids, nucleosides and nucleotides. Tetrahedron 1987, 43, 5261-5274.
    • (1987) Tetrahedron , vol.43 , pp. 5261-5274
    • Ojika, M.1    Wakamatsu, K.2    Niwa, H.3    Yamada, Y.4
  • 23
    • 0000437311 scopus 로고
    • Bracken fern and animal health in Australia and New Zealand
    • Thomson, J. A., Smith, R. T., Eds.; Occasional Publication No. 40; Australian Institute of Agricultural Science: Sydney, Australia
    • Smith, B. L. Bracken fern and animal health in Australia and New Zealand. In Bracken Biology and Management; Thomson, J. A., Smith, R. T., Eds.; Occasional Publication No. 40; Australian Institute of Agricultural Science: Sydney, Australia, 1990; pp 227-232.
    • (1990) Bracken Biology and Management , pp. 227-232
    • Smith, B.L.1
  • 24
    • 0001290250 scopus 로고
    • Total synthesis of natural (-) ptaquilosin, the aglycon of a potent bracken carcinogen ptaquiloside, and the (+)-enantiomer and their DNA cleaving activities
    • Kigoshi, H.; Imaamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. Total synthesis of natural (-) ptaquilosin, the aglycon of a potent bracken carcinogen ptaquiloside, and the (+)-enantiomer and their DNA cleaving activities. J. Am. Chem. Soc. 1993, 115, 3056-3065.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 3056-3065
    • Kigoshi, H.1    Imaamura, Y.2    Mizuta, K.3    Niwa, H.4    Yamada, K.5
  • 25
    • 0026794499 scopus 로고
    • Synthesis of analogues of a bracken ultimate carcinogen and their DNA cleaving activities
    • Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Synthesis of analogues of a bracken ultimate carcinogen and their DNA cleaving activities. Tetrahedron Lett. 1992, 33, 6647-6650.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6647-6650
    • Kigoshi, H.1    Tanaka, H.2    Hirokawa, J.3    Mizuta, K.4    Yamada, K.5
  • 26
    • 0028219492 scopus 로고
    • DNA damage by ptaquiloside, a potent bracken carcinogen: Detection of selective stand breaks and identification of DNA cleavage products
    • Kushida, T.; Uesugi, M.; Sugiura, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Yamada, K. DNA damage by ptaquiloside, a potent bracken carcinogen: detection of selective stand breaks and identification of DNA cleavage products. J. Am. Chem. Soc. 1994, 116, 479-486.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 479-486
    • Kushida, T.1    Uesugi, M.2    Sugiura, Y.3    Kigoshi, H.4    Tanaka, H.5    Hirokawa, J.6    Ojika, M.7    Yamada, K.8
  • 27
    • 0018375522 scopus 로고
    • Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. III. Further characterization of pterosins and pterosides, sequiterpenes and glucosides having 1-indanone skeleton, from rhizomes
    • Kuroyanagi, M.; Fukuoka, M.; Yoshihira, K.; Natori, S. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. III. Further characterization of pterosins and pterosides, sequiterpenes and glucosides having 1-indanone skeleton, from rhizomes. Chem. Pharm. Bull. 1979, 27; 592-601.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 592-601
    • Kuroyanagi, M.1    Fukuoka, M.2    Yoshihira, K.3    Natori, S.4
  • 28
    • 0001261493 scopus 로고
    • Dennstoside A, an analogue of ptaquiloside, from Dennstaedtia scabra
    • Koyama, K.;: Takatsuki, S.; Natori, S. Dennstoside A, an analogue of ptaquiloside, from Dennstaedtia scabra. Phytochemistry 1991, 30, 2080-2082.
    • (1991) Phytochemistry , vol.30 , pp. 2080-2082
    • Koyama, K.1    Takatsuki, S.2    Natori, S.3
  • 29
    • 0031771088 scopus 로고    scopus 로고
    • Ptaquiloside Z a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern Pteridium aquilinum var. caudatum
    • Castillo, U. F.; Ojika, M.; Alonso-Amelot, M.; Sakagami, Y. Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern Pteridium aquilinum var. caudatum. Bioorg. Med. Chem. 1998, 6, 2229-2233.
    • (1998) Bioorg. Med. Chem. , vol.6 , pp. 2229-2233
    • Castillo, U.F.1    Ojika, M.2    Alonso-Amelot, M.3    Sakagami, Y.4
  • 30
    • 0001397444 scopus 로고
    • The sesquiterpenoid carcinogen of bracken fern, and some analogues, from the Pteridaceae
    • Saito, K.; Nagao, T.; Takatsuki, S.; Koyama, K.; Natori, S. The sesquiterpenoid carcinogen of bracken fern, and some analogues, from the Pteridaceae. Phytochemistry, 1990, 29, 1475-1479.
    • (1990) Phytochemistry , vol.29 , pp. 1475-1479
    • Saito, K.1    Nagao, T.2    Takatsuki, S.3    Koyama, K.4    Natori, S.5
  • 31
    • 0029201060 scopus 로고
    • Comparative dynamics of ptaquiloside and pterosin B in two varieties (caudatum and arachnoideum) of neotropical bracken fern (Pteridium aquilinum L. Kuhn)
    • Alonso-Amelot, M. E.; Rodulfo, S.; Jaimes-Espinoza. R. Comparative dynamics of ptaquiloside and pterosin B in two varieties (caudatum and arachnoideum) of neotropical bracken fern (Pteridium aquilinum L. Kuhn). Biochem. Syst. Ecol. 1995, 23, 709-716.
    • (1995) Biochem. Syst. Ecol. , vol.23 , pp. 709-716
    • Alonso-Amelot, M.E.1    Rodulfo, S.2    Jaimes-Espinoza, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.