Identification of lignans as major components in the phenolic fraction of olive oil

Clinical Chemistry

Volumn 46, Issue 7, 2000, Pages 976-988

  Owen, Robert W ^a   Mier, Walter ^b   Giacosa, Attilio ^d   Hull, William E ^c   Spiegelhalder, Bertold ^a   Bartsch, Helmut ^a  

^a Division of Toxicology and Cancer Risk Factors   (Germany)

^b Division of Molecular Embryology   (Germany)

^c GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

^d UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; LIGNAN; OLIVE OIL; PHENOL; PHENOL DERIVATIVE; PINORESINOL; SECOIRIDOID;

ARTICLE; CHEMICAL STRUCTURE; EXTRACTION; HYDROLYSIS; LIPID ANALYSIS; LIPID COMPOSITION; STRUCTURE ANALYSIS;

EID: 0033924913     PISSN: 00099147     EISSN: None     Source Type: Journal    
DOI: 10.1093/clinchem/46.7.976     Document Type: Article

References (40)

1. Keys A, Keys M. How to eat well and stay well, the Mediterranean way. Garden City, UK: Doubleday and Co., 1975:325pp.
2. Keys A, Aravanis C, Van Buchem H, Blackburn H, Buzina R, Djordjevic S, et al. The diet and all-causes death rate in the Seven Countries Study. Lancet 1981;2:58-61.
3. Gerber M. Olive oil and cancer. In: Hill MJ, Giacosa A, Caygill CPG, eds. Epidemiology of diet and cancer. Chichester, UK: Ellis Horwood, 1994:263-75.
4. Hill MJ, Giacosa A. The Mediterranean diet [Editorial]. Eur J Cancer Prev 1992;1:339-40.
5. La Vecchia C, Negri E, Franceschi S, Decarli A, Giacosa A, Lipworth L. Olive oil, other dietary fats, and the risk of breast cancer (Italy). Cancer Causes Control 1998;6:545-50.
6. Martin-Moreno JM, Willett WC, Gorgojo L, Banegas JR, Rodriguez-Artelejo F, Fernandez-Rodriguez JC, et al. Dietary fat, olive oil intake and breast cancer risk. Int J Cancer 1994;58:774-80.
7. Trichopoulou A, Katsouyanni K, Stuver S, Tzala L, Gnardellis C, Rimm E, et al. Consumption of olive oil and specific food groups in relation to breast cancer risk in Greece. J Natl Cancer Inst 1995;87:110-6.
8. Braga C, La Vecchia C, Francheschi S, Negri E, Parpinel M, Decarli A, et al. Olive oil, other seasoning fats, and the risk of colorectal carcinoma. Cancer 1998;82:448-53.
9. Fedeli E. Lipids of olives. Prog Chem Fats Other Lipids 1977;15:57-74.
10. Fedeli E, Testolin G. Edible fats and oils. In: Spiller GA, ed. The Mediterranean diet in health and disease. New York: Van Nostrand Reinhold, 1991:125-34.
11. Flath RA, Forrey RR, Guadagni DG. Aroma components of olive oil. J Agric Food Chem 1973;21:948-52.
12. Yoo YJ, Fedeli E, Nawar WW. The volatile components produced from olive oil by heating. Riv Ital Sostanze Grasse 1988;65:415-8.
13. Owen RW, Mier W, Giacosa A, Hull WE, Spiegelhalder B, Bartsch H. Phenolic compounds and squalene in olive oils: the concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignans and squalene. Food Chem Toxicol 2000;in press.
14. Papadopoulos G, Boskau D. Antioxidant effect of natural phenols on olive oil. J Am Oil Chem 1991;68:669-71.
15. Montedoro G, Servilli M, Miniati E. Simple and hydrolysable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. J Agric Food Chem 1992;40:1571-6.
16. Montedoro G, Servilli M, Baldioli M, Miniati E. Simple and hydrolysable phenolic compounds in virgin olive oil. 2. Initial characterisation of the hydrolysable fraction. J Agric Food Chem 1993;40:1577-80.
17. Montedoro G, Servilli M, Baldioli M, Selvaggini R, Miniati E, Macchioni A. Simple and hydrolysable phenolic compounds in virgin olive oil. 3. Spectroscopic characterisation of the secoiridoid derivatives. J Agric Food Chem 1993;41:2228-34.
18. Angerosa F, d'Alessandro N, Konstantinou P, Di Giacinto L. GC-MS evaluation of phenolic compounds in virgin olive oil. J Agric Food Chem 1995;43:1802-7.
19. Angerosa F, d'Alessandro N, Corana F, Melliero G. Characterisation of phenolic and secoiridoid aglycones present in virgin olive oil by gas chromatography-chemical ionisation mass spectrometry. J Chromatogr 1996;736:193-205.
20. Tsukamoto H, Hisada S, Nishibe S. Lignans from bark of the Olea plants, 1. Chem Pharm Bull 1984;32:2730-5.
21. Agrawal PK, Pathak AK. Influence of skeletal alteration of lignans on carbon-13 NMR chemical shifts. Magn Reson Chem 1994;32:753-73.
22. Davin BD, Bedgar DL, Katayama T, Lewis NG. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspense from its achiral precursor, coniferyl alcohol. Phytochemistry 1992;31:3869-74.
23. Kato MJ, Chu A, Davin LB, Lewis NG. Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 1998;47:583-91.
24. Tsukamoto H, Hisada S, Nishibe S. Lignans from bark of the Olea plants, 2. Chem Pharm Bull 1985;33:1232-41.
25. Setchell KDR, Lawson AM, Borriello SP, Harkness R, Gordon H, Morgan DML. Lignan formation in man-microbial involvement and possible roles in relation to cancer. Lancet 1981;2:4-7.
26. Setchell KDR, Lawson AM, Conway E, Taylor NF, Kirk DN, Cooley G, et al. The definitive identification of the lignans (rans-2,3-bis(3-hydroxybenzyl)-butyrolactone and 2,3-bis(3-hydroxybenzyl)butane-1,4-diol in human and animal urine. Biochem J 1981;197:447-58.
27. Axelson M, Sjövall J, Gustafson BE, Setchell KDR. Origin of lignans in mammals and identification of a precursor from plants. Nature 1982;298:659-60.
28. Kardono LB, Tsauri S, Pezzuto JM, Kinghorn AD. Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia. J Nat Prod 1990;53:1447-55.
29. Hirano T, Fukuoka F, Oka K, Naito T, Hosaka K, Mitsuhashi H, et al. Antiproliferative activity of mammalian lignan derivatives against the human breast carcinoma cell line, ZR-75-1. Cancer Investig 1990;8:592-602.
30. Adlercreutz H, Bannwart C, Wähälä K, Mäkelä T, Brunow G, Hase T, et al. Inhibition of human aromatase by mammalian lignans and isoflavoid phytooestrogens. J Steroid Biochem Mol Biol 1993;44:147-53.
31. Wang C, Mäkelä T, Hase T, Adlercreutz H, Kurzer MS. Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes. J Steroid Biochem Mol Biol 1994;50:205-12.
32. Thompson LU, Robb P, Serraino M, Cheung F. Mammalian lignan production from various foods. Nutr Cancer 1991;16:43-52.
33. Serraino M, Thompson LU. The effect of flaxseed consumption on the initiation and promotional stages of mammary carcinogenesis. Nutr Cancer 1992;17:153-9.
34. Serraino M, Thompson LU. The effect of flaxseed supplementation on early risk markers for mammary carcinogenesis. Cancer Lett 1991;60:135-42.
35. Adlercreutz H, Fotsis T, Heikkinen R, Dwyer JT, Woods M, Goldin BR, et al. Excretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian women and in women with breast cancer. Lancet 1982;2:1295-9.
36. Adlercreutz H, Fotsis T, Bannwart C, Wähälä K, Mäkelä T, Brunow G, et al. Determination of urinary lignans and phytoestrogen metabolites, potential antioestrogens and anticarcinogens, in urine of women on various habitual diets. J Steroid Biochem 1986;25:791-7.
37. Ingram D, Sanders K, Kolybaba M, Lopez D. Case-control study of phyto-oestrogens and breast cancer. Lancet 1997;350:990-4.
38. Nishibe S, Tsukamoto H, Hisada S, Nikaido T, Ohmoto T, Sankawa U. Inhibition of cyclic AMP phosphodiesterase by lignans and coumarins of Olea and Fraxinus barks. Shoyakugaku Zasshi 1986;40:89-94.
39. Shimizu S, Akimoto K, Shinmen Y, Kawashima H, Sugano M, Yamada H. Sesamin is a potent and specific inhibitor of Δ5 desaturase in polyunsaturated fatty acid biosynthesis. Lipids 1991;26:512-6.
40. Kang MH, Mait M, Tsujihara N, Osawa T. Sesamolin inhibits lipid peroxidation in rat liver and kidney. J Nutr 1998;128:1018-22.