Tissue distribution and elimination of estrogenic and anti-inflammatory catechol metabolites from sesaminol triglucoside in rats

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 13, 2010, Pages 7693-7700

  Jan, Kuo Ching ^a   Ku, Kuo Lung ^b   Chu, Yan Hwa ^a   Hwang, Lucy Sun ^c   Ho, Chi Tang ^c,d  

^a FOOD INDUSTRY RESEARCH AND DEVELOPMENT INSTITUTE   (Taiwan)

^b NATIONAL CHIAYI UNIVERSITY   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^d RUTGERS UNIVERSITY   (United States)

Author keywords

Catechol metabolites; Estrogenic activity; Inflammation; Sesaminol triglucoside; Tissue distribution

Indexed keywords

ANTIINFLAMMATORY AGENT; CATECHOL; CATECHOL DERIVATIVE; ESTROGEN; GLUCOSIDE; PLANT EXTRACT; SESAMINOL TRIGLUCOSIDE;

ANIMAL; ARTICLE; CELL LINE; CHEMISTRY; HUMAN; METABOLISM; MOUSE; RAT; SESAME; SPRAGUE DAWLEY RAT; TISSUE DISTRIBUTION; SESAMUM;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CATECHOLS; CELL LINE; ESTROGENS; GLUCOSIDES; HUMANS; MICE; PLANT EXTRACTS; RATS; RATS, SPRAGUE-DAWLEY; SESAMUM; TISSUE DISTRIBUTION;

MAMMALIA; MURINAE; RATTUS; SESAMUM INDICUM;

EID: 77954549438     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1009632     Document Type: Article

References (34)

1. Rowland, I.; Faughnan, M.; Hoey, L.; Wähälä, K.; Williamson, G.; Cassidy, A. Bioavailability of phytoestrogens. Br. J. Nutr. 2003, 89, S45-S58.
2. Axelson, M.; Setchell, K. D. R. The excretion of lignans in rats evidence for an intestinal bacterial source for this new group of compounds. FEBS Lett. 1981, 123, 337-342.
3. Heinonen, S.; Nurmi, T.; Liukkonen, K.; Poutanen, K.; Wähälä, K.; Deyama, T.; Nishibe, S.; Adlercreutz, H. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. J. Agric. Food Chem. 2001, 49, 3178-3186.
4. Peñalvo, J. L.; Haajanen, K. M.; Botting, N.; Adlercreutz, H. Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry. J. Agric. Food Chem. 2005, 53, 9342-9347.
5. Peñalvo, J. L.; Heinonen, S. M.; Aura, A. M.; Adlercreutz, H. Dietary sesamin is converted to enterolactone in humans. J. Nutr. 2005, 135, 1056-1062.
6. Valsta, L. M.; Kilkkinen, A.; Mazur, W.; Nurmi, T.; Lampi, A. M.; Ovaskainen, M. L.; Korhonen, T.; Adlercreutz, H.; Pietinen, P. Phyto-oestrogen database of foods and average intake in Finland. Br. J. Nutr. 2003, 89, S31-S38.
7. Milder, I. E.; Feskens, E. J.; Arts, I. C.; Bueno de Mesquita, H. B.; Hollman, P. C.; Kromhout, D. Intake of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in Dutch men and women. J. Nutr. 2005, 135, 1202-1207.
8. Katsuzaki, H.; Osawa, T.; Kawakishi, S. Chemistry and antioxidative activity of lignan glucosides in sesame seed. In Food Phytochemicals for Cancer Prevention II; Ho, C. T., Osawa, T., Huang, T. Rosen, R. T., Eds.; ACS Symposium Series Vol 547; American, Chemical Society: Washington, D.C, 1994; pp 275-280.
9. Miyake, Y.; Fukumoto, S.; Okada, M.; Sakaide, K.; Nakamura, Y.; Osawa, T. Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. J. Agric. Food Chem. 2005, 53, 12-27.
10. Kuriyama, S.; Murui, T. Scavenging of hydroxy radicals by lignan glucosides in germinated sesame seeds. Nippon Noueei Kagaku Kaishi 1995, 69, 703-705.
11. Jan, K. C.; Hwang, L. S.; Ho, C. T. Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota. J. Agric. Food Chem. 2009, 57, 6101-6106.
12. Katsuzaki, H.; Kawakishi, S.; Osawa, T. Sesaminol glucosides in sesame seeds. Phytochemistry 1994, 35, 773-776.
13. Axelson, M.; Sjovall, J.; Gustafsson, B. E.; Setchell, K. D. Origin of lignans in mammals and identification of a precursor from plants. Nature. 1982, 298, 659-660.
14. Borriello, S. P.; Setchell, K. D.; Axelson, M.; Lawson, A. M. Production and metabolism of lignans by the human fecal flora. J. Appl. Bacteriol. 1985, 58, 37-43.
15. Setchell, K. D.; Lawson, A. M.; Mitchell, F. L.; Adlercreutz, H.; Kirk, D. N.; Axelson, M. Lignans in man and in animal species. Nature 1980, 287, 740-742.
16. Talavera, S.; Felgines, C.; Texier, O.; Besson, C.; Gil-Izquierdo, A.; Lamaison, J. L.; Remesy, C. Anthocyanin metabolism in rats and their distribution to digestive area, kidney, and brain. J. Agric. Food Chem. 2005, 18, 3902-3908.
17. Hsiu, S. L.; Tsao, C. W.; Tsai, Y. C.; Ho, H. J.; Chao, P. D. Determinations of morin, quercetin and their conjugate metabolites in serum. Biol, Pharm. Bull. 2001, 24, 967-969.
18. de Boer, V. C.; Dihal, A. A.; van der Woude, H.; Arts, I. C.; Wolffram, S.; Alink, G. M.; Rietjens, I. M.; Keijer, J.; Hollman, P. C. Tissue distribution of quercetin in rats and pigs. J. Nutr. 2005, 135, 1718-1725.
19. Noami, M.; Igarashi, K.; Kasuya, F.; Ohta, M.; Kanamori-Kataoka, M.; Seto, Y. Study on the analysis of capsaicin glucuronide in rat urine by liquid chromatography-mass spectrometry after enzymatic hydrolysis. J. Health Sci. 2006, 52, 660-665.
20. Prior, R. L.; Hoang, H.; Gu, L.; Wu, X.; Bacchiocca, M.; Howard, L.; Hampsch-Woodill, M.; Huang, D.; Ou, B.; Jacob, R. Assays for hydrophilic and lipophilic antioxidant capacity (oxygen radical absorbance capacity (ORACFL)) of plasma and other biological and food samples. J. Agric. Food Chem. 2003, 51, 3273-3279.
21. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 1999, 26, 1231-1237.
22. Durocher, Y.; Perret, S.; Thibaudeau, E.; Gaumond, M. H.; Kamen, A.; Stocco, R.; Abramovitz, M. A reporter gene assay for highthroughput screening of G-protein-coupled receptors stably or transiently expressed in HEK293 EBNA cells grown in suspension culture. Anal. Biochem. 2000, 284, 316-326.
23. Cheng, W. Y.; Kuo, Y. H.; Huang, C. J. Isolation and identification of novel estrogenic compounds in yam tuber (Dioscorea alata Cv. Tainung No. 2). J. Agric. Food Chem. 2007, 55, 7350-7358.
24. Hong, Y. H.; Chao, W. W.; Chen, M. L.; Lin, B. F. Ethyl acetate extracts of alfalfa (Medicago sativa L.) sprouts inhibit lipopolysaccharide-induced inflammation in vitro and in vivo. J. Biomed. Sci. 2009, 16, 64.
25. Jan, K. C.; Hwang, L. S.; Ho, C. T. Tissue distribution and elimination of sesaminol triglucoside and its metabolites in rat. Mol. Nutr. Food Res. 2009, 53, 815-825.
26. Wang, L. Q.; Meselhy, M. R.; Li, Y.; Qin, G. W.; Hattori, M. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem. Pharm. Bull, 2000, 48, 1606-1610.
27. Larson, R. A. The antioxidants of higher plants. Phytochemistry 1988, 27, 969-978.
28. Rice-Evans, C. S.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20, 933-956.
29. Jeng, K. C.; Hou, R. C.; Wang, J. C.; Ping, L. I. Sesamin inhibits lipopolysaccharide-induced cytokine production by suppression of p38 mitogen-activated protein kinase and nuclear factor-κB. Immunol. Lett. 2005, 97, 101-106.
30. Lee, S. Y.; Son, D. J.; Lee, Y. K.; Lee, J. W.; Lee, H. J.; Yun, Y. W.; Ha, T. Y.; Hong, J. T. Inhibitory effect of sesaminol glucosides on lipopolysaccharide-induced NF-kappaB activation and target gene expression in cultured rat astrocytes. Neurosci. Res. 2006, 56, 204-212.
31. Sheng, H.; Hirose, Y.; Hata, K.; Zheng, Q.; Kuno, T.; Asano, N.; Yamada, Y.; Hara, A.; Osawa, T.; Mori, H. Modifying effect of dietary sesaminol glucosides on the formation of azoxymethane-induced premalignant lesions of rat colon. Cancer Lett. 2007, 246, 63-68.
32. Morito, K.; Hirose, T.; Kinjo, J.; Hirakawa, T.; Okawa, M.; Nohara, T.; Ogawa, S.; Inoue, S.; Muramatsu, M.; Masamune, Y. Interaction of phytoestrogens with estrogen receptors alpha and beta. Biol. Pharm. Bull. 2001, 24, 351-356.
33. Penttinen-Damdimopoulou, P. E.; Power, K. A.; Hurmerinta, T. T.; Nurmi, T.; van der Saag, P. T.; Mäkelä, S. I. Dietary sources of lignans and isoflavones modulate responses to estradiol in estrogen reporter mice. Mol. Nutr. Food Res. 2009, 53, 996-1006.
34. Anagnostis, A.; Papadopoulos, A. I. Effects of a diet rich in sesame (Sesamum indicum) pericarp on the expression of oestrogen receptor alpha and oestrogen receptor beta in rat prostate and uterus. Br. J. Nutr. 2009, 102, 703-708.