Discovery of a sesamin-metabolizing microorganism and a new enzyme

Proceedings of the National Academy of Sciences of the United States of America

Volumn 113, Issue 32, 2016, Pages 9087-9092

  Kumano, Takuto ^a   Fujiki, Etsuko ^a   Hashimoto, Yoshiteru ^a   Kobayashi, Michihiko ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Lignan; Sesamin|metabolism; Tetrahydrofolate

Indexed keywords

ASARININ; BACTERIAL ENZYME; EPISESAMIN; PIPERINE; SESAMIN; SESAMINOL; SESAMOLIN; TETRAHYDROFOLIC ACID; UNCLASSIFIED DRUG; 1,3 DIOXOLANE DERIVATIVE; LIGNAN;

AMINO ACID SEQUENCE; BACTERIAL GROWTH; BACTERIAL STRAIN; CARBON SOURCE; CONFERENCE PAPER; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME SUBSTRATE; MICROBIAL METABOLISM; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; SEQUENCE ANALYSIS; SEQUENCE HOMOLOGY; SINOMONAS; SOIL MICROFLORA; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; MICROBIOLOGY; MICROCOCCACEAE; MUTATION;

DIOXOLES; KINETICS; LIGNANS; MICROCOCCACEAE; MUTATION; SOIL MICROBIOLOGY; SUBSTRATE SPECIFICITY;

EID: 84982908669     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1605050113     Document Type: Article

References (38)

1. Kobayashi M, Shimizu S (1998) Metalloenzyme nitrile hydratase: Structure, regulation, and application to biotechnology. Nat Biotechnol 16(8):733-736.
2. Komeda H, Hori Y, Kobayashi M, Shimizu S (1996) Transcriptional regulation of the Rhodococcus rhodochrous J1 nitA gene encoding a nitrilase. Proc Natl Acad Sci USA 93(20):10572-10577.
3. Nomura J, et al. (2013) Crystal structure of aldoxime dehydratase and its catalytic mechanism involved in carbon-nitrogen triple-bond synthesis. Proc Natl Acad Sci USA 110(8):2810-2815.
4. Hassaninasab A, Hashimoto Y, Tomita-Yokotani K, Kobayashi M (2011) Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism. Proc Natl Acad Sci USA 108(16):6615-6620.
5. Hearon W-M, MacGregor W-S (1955) The naturally occurring lignans. Chem Rev 55(5): 957-1067.
6. Umezawa T (2003) Diversity in lignan biosynthesis. Phytochem Rev 2(3):371-390.
7. Fukuda Y, Nagata M, Osawa T, Namiki M (1986) Chemical aspects of the antioxidative activity of roasted sesame seed oil, and the effect of using the oil for frying. Agric Biol Chem 50(4):857-862.
8. Hirose N, et al. (1991) Inhibition of cholesterol absorption and synthesis in rats by sesamin. J Lipid Res 32(4):629-638.
9. Tsuruoka N, Kidokoro A, Matsumoto I, Abe K, Kiso Y (2005) Modulating effect of sesamin, a functional lignan in sesame seeds, on the transcription levels of lipid- and alcohol-metabolizing enzymes in rat liver: A DNA microarray study. Biosci Biotechnol Biochem 69(1):179-188.
10. Miyawaki T, et al. (2009) Antihypertensive effects of sesamin in humans. J Nutr Sci Vitaminol (Tokyo) 55(1):87-91.
11. Utsunomiya T, Chavali S-R, Zhong W-W, Forse R-A (2000) Effects of sesamin-supplemented dietary fat emulsions on the ex vivo production of lipopolysaccharideinduced prostanoids and tumor necrosis factor alpha in rats. Am J Clin Nutr 72(3): 804-808.
12. Yasuda K, Ikushiro S, Kamakura M, Ohta M, Sakaki T (2010) Metabolism of sesamin by cytochrome P450 in human liver microsomes. Drug Metab Dispos 38(12):2117-2123.
13. Sakaki T, et al. (2012) Metabolism of sesamin by CYPs and UGTs in human liver. J Food Drug Anal 20(1):376-379.
14. Moazzami A-A, Andersson R-E, Kamal-Eldin A (2007) Quantitative NMR analysis of a sesamin catechol metabolite in human urine. J Nutr 137(4):940-944.
15. Miyake Y, et al. (2005) Antioxidative catechol lignans converted from sesamin and sesaminol triglucoside by culturing with Aspergillus. J Agric Food Chem 53(1):22-27.
16. Liu Z, Saarinen N-M, Thompson L-U (2006) Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats. J Nutr 136(4):906-912.
17. Kiso Y (2004) Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: A DNA microarray study. Biofactors 21(1-4):191-196.
18. Prasad K (2000) Antioxidant activity of secoisolariciresinol diglucoside-derived metabolites, secoisolariciresinol, enterodiol, and enterolactone. Int J Angiol 9(4): 220-225.
19. Peterson J, et al. (2010) Dietary lignans: Physiology and potential for cardiovascular disease risk reduction. Nutr Rev 68(10):571-603.
20. Cunnane S-C, et al. (1995) Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr 61(1):62-68.
21. Hallund J, Tetens I, Bügel S, Tholstrup T, Bruun J-M (2008) The effect of a lignan complex isolated from flaxseed on inflammation markers in healthy postmenopausal women. Nutr Metab Cardiovasc Dis 18(7):497-502.
22. Nakai M, et al. (2003) Novel antioxidative metabolites in rat liver with ingested sesamin. J Agric Food Chem 51(6):1666-1670.
23. Leys D, Basran J, Scrutton N-S (2003) Channelling and formation of 'active' formaldehyde in dimethylglycine oxidase. EMBO J 22(16):4038-4048.
24. Ida K, Moriguchi T, Suzuki H (2005) Crystal structure of heterotetrameric sarcosine oxidase from Corynebacterium sp. U-96. Biochem Biophys Res Commun 333(2): 359-366.
25. Schuller D-J, Reisch C-R, Moran M-A, Whitman W-B, Lanzilotta W-N (2012) Structures of dimethylsulfoniopropionate-dependent demethylase from the marine organism Pelagabacter ubique. Protein Sci 21(2):289-298.
26. Nishikawa S, et al. (1998) Cloning and sequencing of the Sphingomonas (Pseudomonas) paucimobilis gene essential for the O demethylation of vanillate and syringate. Appl Environ Microbiol 64(3):836-842.
27. Masai E, et al. (2004) A novel tetrahydrofolate-dependent O-demethylase gene is essential for growth of Sphingomonas paucimobilis SYK-6 with syringate. J Bacteriol 186(9):2757-2765.
28. Abe T, Masai E, Miyauchi K, Katayama Y, Fukuda M (2005) A tetrahydrofolate-dependent O-demethylase, LigM, is crucial for catabolism of vanillate and syringate in Sphingomonas paucimobilis SYK-6. J Bacteriol 187(6):2030-2037.
29. Lee H-H, Kim D-J, Ahn H-J, Ha J-Y, Suh S-W (2004) Crystal structure of T-protein of the glycine cleavage system: Cofactor binding, insights into H-protein recognition, and molecular basis for understanding nonketotic hyperglycinemia. J Biol Chem 279(48): 50514-50523.
30. Hiratsuka T, et al. (2008) An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321(5896):1670-1673.
31. Ahmad M, et al. (2011) Identification of DypB from Rhodococcus jostii RHA1 as a lignin peroxidase. Biochemistry 50(23):5096-5107.
32. Van der Geize R, et al. (2007) A gene cluster encoding cholesterol catabolism in a soil actinomycete provides insight into Mycobacterium tuberculosis survival in macrophages. Proc Natl Acad Sci USA 104(6):1947-1952.
33. Marín L, Miguélez E-M, Villar C-J, Lombó F (2015) Bioavailability of dietary polyphenols and gut microbiota metabolism: antimicrobial properties. BioMed Res Int 2015:905215.
34. Nishiyama T, Hashimoto Y, Kusakabe H, Kumano T, Kobayashi M (2014) Natural lowmolecular mass organic compounds with oxidase activity as organocatalysts. Proc Natl Acad Sci USA 111(48):17152-17157.
35. Tucker G-T, et al. (1994) The demethylenation of methylenedioxymethamphetamine ("ecstasy") by debrisoquine hydroxylase (CYP2D6). Biochem Pharmacol 47(7): 1151-1156.
36. Buswell J-A, Cain R-B (1973) Microbial degradation of piperonylic acid by Pseudomonas fluorescens. FEBS Lett 29(3):297-300.
37. Hasse D, et al. (2013) Structure of the homodimeric glycine decarboxylase P-protein from Synechocystis sp. PCC 6803 suggests a mechanism for redox regulation. J Biol Chem 288(49):35333-35345.
38. Okamura-Ikeda K, et al. (2010) Crystal structure of aminomethyltransferase in complex with dihydrolipoyl-H-protein of the glycine cleavage system: Implications for recognition of lipoyl protein substrate, disease-related mutations, and reaction mechanism. J Biol Chem 285(24):18684-18692.