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Volumn 46, Issue 12, 1998, Pages 4874-4884

Partial Synthesis and Structural Elucidation of the Oxidative Metabolites of Lycopene Identified in Tomato Paste, Tomato Juice, and Human Serum

Author keywords

1,16 Didehydro 2,6 cyclolycopen 5 ol; 2,5 diepoxide; 2,6 cyclolycopene 1,5 diol; 2,6 cyclolycopene 1,5 epoxide; Carotenoid metabolites; HPLC mass spectrometry; Lycopene 1,6; Lycopene 5,6 epoxide; Lycopene oxidation products; New serum carotenoids; NMR

Indexed keywords

LYCOPERSICON ESCULENTUM;

EID: 0542393701     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980322a     Document Type: Article
Times cited : (48)

References (25)
  • 1
    • 0005839532 scopus 로고
    • Carotene epoxides of Lycopersicon escculentum
    • Ben-Aziz, A.; Britton, G.; Goodwin, T. W. Carotene epoxides of Lycopersicon escculentum. Phytochemistry 1973, 12, 2759-2764.
    • (1973) Phytochemistry , vol.12 , pp. 2759-2764
    • Ben-Aziz, A.1    Britton, G.2    Goodwin, T.W.3
  • 2
    • 0542367775 scopus 로고
    • On some cleavage products of boron trifluoride complexes of α-carotene, lycopene, and γ-carotene
    • Bush, W.; Zechmeister, L. On some cleavage products of boron trifluoride complexes of α-carotene, lycopene, and γ-carotene. J. Am. Chem. Soc. 1958, 80, 2991-2999.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 2991-2999
    • Bush, W.1    Zechmeister, L.2
  • 3
    • 0000764440 scopus 로고
    • NMR of Carotenoids
    • Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser: Basel
    • Englert, G. NMR of Carotenoids. In Carotenoids; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; Birkhäuser: Basel, 1995; Vol. 1B, pp 147-260.
    • (1995) Carotenoids , vol.1 B , pp. 147-260
    • Englert, G.1
  • 5
    • 84892075405 scopus 로고
    • Carotenoid structures, old and new problems
    • Eugster, C. H. Carotenoid structures, old and new problems. Pure Appl. Chem. 1985, 57, 639-647.
    • (1985) Pure Appl. Chem. , vol.57 , pp. 639-647
    • Eugster, C.H.1
  • 7
    • 84987505467 scopus 로고
    • Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro- and tetradehydrolycopenes
    • Hengartner, U.; Bernhard, K.; Meyer, K.; Englert, G.; Glinz, E. Synthesis, isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of lycopene and of some acetylenic didehydro- and tetradehydrolycopenes. Helv. Chim. Acta 1992, 75, 1848-1865.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 1848-1865
    • Hengartner, U.1    Bernhard, K.2    Meyer, K.3    Englert, G.4    Glinz, E.5
  • 8
    • 0026655945 scopus 로고
    • Separation and identification of carotenoids and their oxidation products in extracts of human plasma
    • Khachik, F.; Beecher, G. R.; Goli, M. B.; Lusby, W. R.; Smith, J. C. Separation and identification of carotenoids and their oxidation products in extracts of human plasma. Anal. Chem. 1992a, 64 (18), 2111-2122.
    • (1992) Anal. Chem. , vol.64 , Issue.18 , pp. 2111-2122
    • Khachik, F.1    Beecher, G.R.2    Goli, M.B.3    Lusby, W.R.4    Smith, J.C.5
  • 9
    • 0000744072 scopus 로고
    • The effect of food preparation on qualitative and quantitative distribution of major carotenoid constituents of tomatoes and several green vegetables
    • Khachik, F.; Goli, M. B.; Beecher, G. R.; Holden, J.; Lusby, W. R.; Tenorio, M. D.; Barrera, M. R. The effect of food preparation on qualitative and quantitative distribution of major carotenoid constituents of tomatoes and several green vegetables. J. Agric. Food Chem. 1992b, 40 (3), 390-398.
    • (1992) J. Agric. Food Chem. , vol.40 , Issue.3 , pp. 390-398
    • Khachik, F.1    Goli, M.B.2    Beecher, G.R.3    Holden, J.4    Lusby, W.R.5    Tenorio, M.D.6    Barrera, M.R.7
  • 10
    • 0029023834 scopus 로고
    • Lutein, lycopene, and their oxidative metabolites in chemoprevention of cancer
    • Khachik, F.; Beecher, G. R.; Smith, Jr., J. C. Lutein, lycopene, and their oxidative metabolites in chemoprevention of cancer. J. Cell. Biochem. 1995, 22, 236-246.
    • (1995) J. Cell. Biochem. , vol.22 , pp. 236-246
    • Khachik, F.1    Beecher, G.R.2    Smith Jr., J.C.3
  • 11
    • 0031570089 scopus 로고    scopus 로고
    • Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum
    • Khachik, F.; Spangler, C. J.; Smith Jr., J. C.; Canfield, L. M.; Pfander, H.; Steck, A. Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. Anal. Chem. 1997a, 69, 1873-1881.
    • (1997) Anal. Chem. , vol.69 , pp. 1873-1881
    • Khachik, F.1    Spangler, C.J.2    Smith Jr., J.C.3    Canfield, L.M.4    Pfander, H.5    Steck, A.6
  • 12
    • 0011341184 scopus 로고    scopus 로고
    • Bioavailability, Metabolism, and Possible Mechanism of Chemoprevention by Lutein and Lycopene in Humans
    • Ohigashi, H., Osawa, T., Terao, J., Watanabe, S., Yoshikawa, T., Eds.; Springer-Verlag: Tokyo
    • Khachik, F.; Steck, A.; Pfander, H. Bioavailability, Metabolism, and Possible Mechanism of Chemoprevention by Lutein and Lycopene in Humans. In Food Factors for Cancer Prevention; Ohigashi, H., Osawa, T., Terao, J., Watanabe, S., Yoshikawa, T., Eds.; Springer-Verlag: Tokyo, 1997b; pp 542-547.
    • (1997) Food Factors for Cancer Prevention , pp. 542-547
    • Khachik, F.1    Steck, A.2    Pfander, H.3
  • 13
    • 0542441304 scopus 로고    scopus 로고
    • Proposed mechanisms for the formation of synthetic and naturally occurring metabolites of lycopene in tomato products and human serum
    • Khachik, F.; Pfander, H.; Traber, B. Proposed mechanisms for the formation of synthetic and naturally occurring metabolites of lycopene in tomato products and human serum. J. Agric. Food Chem. 1998, 46, 4885-4890.
    • (1998) J. Agric. Food Chem. , vol.46 , pp. 4885-4890
    • Khachik, F.1    Pfander, H.2    Traber, B.3
  • 16
    • 84987588016 scopus 로고
    • Optically active lycopene epoxides and lycopene glycoles: Synthesis and chiroptical properties
    • Meier, H.; Uebelhart, P.; Eugster, C. H. Optically active lycopene epoxides and lycopene glycoles: synthesis and chiroptical properties. Helv. Chim. Acta 1986, 69, 106-123.
    • (1986) Helv. Chim. Acta , vol.69 , pp. 106-123
    • Meier, H.1    Uebelhart, P.2    Eugster, C.H.3
  • 17
    • 0030272801 scopus 로고    scopus 로고
    • Inhibitory effects of natural carotenoids, α-carotene, β-carotene, lycopene and lutein on colonic aberrant crypt foci formation in rats
    • Narisawa, T.; Fukaura, Y.; Hasebe, M.; Ito, M.; Aizawa, R.; Murakoshi, M.; Uemura, S.; Khachik, F.; Nishino, H. Inhibitory effects of natural carotenoids, α-carotene, β-carotene, lycopene and lutein on colonic aberrant crypt foci formation in rats. Cancer Lett. 1996, 107, 137-142.
    • (1996) Cancer Lett. , vol.107 , pp. 137-142
    • Narisawa, T.1    Fukaura, Y.2    Hasebe, M.3    Ito, M.4    Aizawa, R.5    Murakoshi, M.6    Uemura, S.7    Khachik, F.8    Nishino, H.9
  • 18
    • 0031796421 scopus 로고    scopus 로고
    • Chronic ingestion of lycopene-rich tomato juice or lycopene supplements significantly increases plasma concentrations of lycopene and related tomato carotenoids in humans
    • in press
    • Paetau, I.; Khachik, F.; Brown, E. D.; Beecher, G. R.; Kramer, T. R.; Chittams, J.; Clevidence, B. A. Chronic ingestion of lycopene-rich tomato juice or lycopene supplements significantly increases plasma concentrations of lycopene and related tomato carotenoids in humans. Am. J. Clin. Nutr. 1998, 68, in press.
    • (1998) Am. J. Clin. Nutr. , vol.68
    • Paetau, I.1    Khachik, F.2    Brown, E.D.3    Beecher, G.R.4    Kramer, T.R.5    Chittams, J.6    Clevidence, B.A.7
  • 21
    • 0030474043 scopus 로고    scopus 로고
    • Lycopene: A biologically important carotenoid for humans?
    • Stahl, W.; Sies, H. Lycopene: a biologically important carotenoid for humans? Arch. Biochem. Biophys. 1996, 336, 1-9.
    • (1996) Arch. Biochem. Biophys. , vol.336 , pp. 1-9
    • Stahl, W.1    Sies, H.2
  • 22
    • 0002714675 scopus 로고
    • Rapid chromatographic technique for preparative separations with moderate resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid chromatographic technique for preparative separations with moderate resolution. J. Org. Chem. 1978, 43, 2923-2925.
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 24
    • 0000118469 scopus 로고
    • Synthesis of 4-(2-methyl-5-isopropenyl-1-cyclopenten-1-yl)butan-2-one. A by-product in the synthesis of pseudoionone
    • Wolinsky, J.; Slabaugh, M. R.; Gibson, T. Synthesis of 4-(2-methyl-5-isopropenyl-1-cyclopenten-1-yl)butan-2-one. A by-product in the synthesis of pseudoionone. J. Org. Chem. 1964, 29, 3740.
    • (1964) J. Org. Chem. , vol.29 , pp. 3740
    • Wolinsky, J.1    Slabaugh, M.R.2    Gibson, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.