Transformation of trachelogenin, an aglycone of tracheloside from safflower seeds, to phytoestrogenic (-)-enterolactone by human intestinal bacteria

Food Chemistry

Volumn 134, Issue 1, 2012, Pages 74-80

  Jin, Jong Sik ^a,b   Tobo, Takafumi ^a   Chung, Mi Hwa ^a,c   Ma, Chao Mei ^a,d   Hattori, Masao ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b RIKEN   (Japan)

^c NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^d INNER MONGOLIA UNIVERSITY   (China)

Author keywords

Bacterial transformation; Enterolactone; Phytoestrogen precursor; Trachelogenin

Indexed keywords

AGLYCONES; ANAEROBIC INCUBATION; BACTERIAL TRANSFORMATION; ENTEROLACTONE; HUMAN FAECAL; INTESTINAL BACTERIA; LIGAND BINDING; MAMMALIAN LIGNANS; METABOLIC PROCESS; NATURALLY OCCURRING; OESTROGEN RECEPTORS; PHYTOESTROGENES; PLANT LIGNANS; SAFFLOWER SEEDS; TRACHELOGENIN;

BINDING ENERGY; METABOLITES; NATURAL POLYMERS;

BIOMOLECULES;

3 (3,4 DIHYDROXYBENZYL) 3 HYDROXY 4 (3 HYDROXY 4 METHOXYBENZYL) DIHYDROFURAN 2(3H)ONE; 3 (3,4 DIHYDROXYBENZYL) 3 HYDROXY 4 (3 HYDROXYBENZYL)DIHYDROFURAN 2(3H)ONE; 3 (3,4 DIHYDROXYBENZYL) 3 HYDROXY 4 (4 HYDROXY 3 METHOXYBENZYL) DIHYDROFURAN 2(3H)ONE; 3 (3,4 DIHYDROXYBENZYL) 4 (3 HYDROXYBENZYL)DIHYDROFURAN 2(3H)ONE; 3 (3,4 DIHYDROXYBENZYL) 4 (3,4 DIMETHOXYBENZYL) 3 HYDROXYDIHYDROFURAN 2(3H)ONE; 3,4 BIS(3 HYDROXYBENZYL)DIHYDROFURAN 2(3H)ONE; 3,4 BIS(3,4 DIHYDROXYBENZYL) 3 HYDROXYDIHYDROFURAN 2(3H)ONE; ENTERODIOL; ENTEROLACTONE; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; TRACHELOGENIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; EGGERTHELLA; EUBACTERIUM; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PLANT SEED; SAFFLOWER;

BACTERIA (MICROORGANISMS); CARTHAMUS TINCTORIUS; MAMMALIA;

EID: 84860364438     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.02.060     Document Type: Article

References (19)

1. M.R. Alam, S.M. Kim, J.I. Lee, S.K. Chon, S.J. Choi, and I.H. Choi Effects of safflower seed oil in osteoporosis induced-ovariectomized rats The American Journal of Chinese Medicine 34 2006 601 612
2. A.N. Begum, C. Nicolle, I. Mila, C. Lapierre, K. Nagano, and K. Fukushima Dietary lignins are precursors of mammalian lignans in rats The Journal of Nutrition 134 2004 120 127
3. S.A. Bingham, C. Atkinson, J. Liggins, L. Bluck, and A. Coward Phyto-oestrogens: Where are we now? British Journal of Nutrition 79 1998 393 406
4. E. Bowey, H. Adlercreutz, and I. Rowland Metabolism of isoflavones and lignans by the gut microflora: A study in germ-free and human flora associated rats Food and Chemical Toxicology 41 2003 631 636
5. R.A. Dixon Phytoestrogen Annual Review of Plant Biology 55 2004 225 261
6. C.R. Draper, M.J. Edel, I.M. Dick, A.G. Randall, G.B. Martin, and R.L. Prince Phytoestrogens reduce bone loss and bone resorption in oophorectomized rats The Journal of Nutrition 127 1997 1795 1799
7. S. Heinonen, T. Nurmi, K. Liukkonen, K. Poutanen, K. Wähä lä, and T. Deyama In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol Journal of Agricultural and Food Chemistry 49 2001 3178 3186
8. J.S. Jin, Y.F. Zhao, N. Nakamura, T. Akao, N. Kakiuchi, and M. Hattori Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone Biological & Pharmaceutical Bulletin 30 2007 904 911
9. J.S. Jin, Y.F. Zhao, N. Nakamura, T. Akao, N. Kakiuchi, and B.S. Min Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria Biological & Pharmaceutical Bulletin 30 2007 2113 2119
10. J.S. Jin, and M. Hattori A new mammalian lignan precursor, asarinin Food Chemistry 124 2011 895 899
11. A. Kilkkinen, P. Pietinen, T. Klaukka, J. Virtamo, P. Korhonen, and H. Adlercreutz Use of oral antimicrobials decreases serum enterolactone concentration American Journal of Epidemiology 155 2002 472 477
12. Z. Liu, N.M. Saarinen, and L.U. Thompson Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats The Journal of Nutrition 136 2006 906 912
13. M. Nose, T. Fujimoto, T. Takeda, S. Nishibe, and Y. Ogihara Structural transformation of lignan compounds in rat gastrointestinal tract Planta Medica 58 1992 520 523
14. J.L. Peñalvo, S.M. Heinonen, A.M. Aura, and H. Adlercreutz Dietary sesamin is converted to enterolactone in humans The Journal of Nutrition 135 2005 1056 1062
15. L.Q. Wang Mammalian phytoestrogens: Enterodiol and enterolactone Journal of Chromatography B 777 2002 289 309
16. L.Q. Wang, M.R. Meselhy, Y. Li, G.W. Qin, and M. Hattori Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone Chemical & Pharmaceutical Bulletin 48 2000 1606 1610
17. L.H. Xie, E.M. Ahn, T. Akao, A.A. Abdel-Hafez, N. Nakamura, and M. Hattori Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria Chemical & Pharmaceutical Bulletin 51 2003 378 384
18. L.H. Xie, T. Akao, K. Hamasaki, T. Deyama, and M. Hattori Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol Chemical & Pharmaceutical Bulletin 51 2003 508 515
19. L. Zhao, Z. Mao, and R.D. Brinton A select combination of clinically relevant phytoestrogens enhances estrogen receptor beta-binding selectivity and neuroprotective activities in vitro and in vivo Endocrinology 150 2009 770 783