Substrate-enantiomer selectivity of matairesinol O-methyltransferases

Plant Biotechnology

Volumn 31, Issue 3, 2014, Pages 257-267

  Ragamustari, Safendrri Komara ^a,b   Yamamura, Masaomi ^a   Ono, Eiichiro ^c   Hattori, Takefumi ^a,e   Suzuki, Shiro ^d   Suzuki, Hideyuki ^d   Shibata, Daisuke ^d   Umezawa, Toshiaki ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Soraku   (Japan)

^d KAZUSA DNA RESEARCH INSTITUTE   (Japan)

^e UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Anthriscus sylvestris; Carthamus tinctorius; Forsythia koreana; Lignan; O methyltransferase (OMT)

Indexed keywords

ANTHRISCUS SYLVESTRIS; CARTHAMUS TINCTORIUS; FORSYTHIA VIRIDISSIMA VAR. KOREANA;

EID: 84923387910     PISSN: 13424580     EISSN: 13476114     Source Type: Journal    
DOI: 10.5511/plantbiotechnology.14.0722a     Document Type: Article

References (41)

1. Akashi T, VanEtten HD, Sawada Y, Wasmann CC, Uchiyama H, Ayabe S (2006) Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis. Phytochemistry 67: 2525-2530.
2. Akiyama K, Maruyama M, Yamauchi S, Nakashima Y, Nakato T, Tago R, Sugahara T, Kishida T, Koba Y (2007) Antimicrobiological activity of lignan: effect of benzylic oxygen and stereochemistry of 2, 3-dibenzyl-4-butanolide and 3, 4-dibenzyltetrahydrofuran lignans on activity. Biosci Biotechnol Biochem 71: 1745-1751.
3. Awale S, Lu J, Kalauni SK, Kurashima Y, Tezuka Y, Kadota S, Esumi H (2006) Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Cancer Res 66: 1751-1757.
4. Cho JY, Kim AR, Yoo ES, Baik KU, Park MH (1999) Immunomodulatory effect of arctigenin, a lignan compound, on tumour necrosis factor-alpha and nitric oxide production, and lymphocyte proliferation. J Pharm Pharmacol 51: 1267-1273.
5. da Silva R, Saraiva J, de Albuquerque S, Curti C, Donate PM, Bianco TNC, Bastos JK, Silva MLA (2008) Trypanocidal structure-activity relationship for cis-and transmethylpluviatolide. Phytochemistry 69: 1890-1894.
6. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275: 362-366.
7. Eich E, Pertz H, Kaloga M, Schulz J, Fesen MR, Mazumder A, Pommier Y (1996) (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase. J Med Chem 39: 86-95.
8. Finefield JM, Sherman DH, Kreitman M, Williams RM (2012) Enantiomeric natural products: occurrence and biogenesis. Angew Chem Int 51: 4802-4836.
9. Gasteiger E, Hoogland C, Gattiker A, Duvaud S, Wilkins MR, Appel RD, Bairoch A (2005) Protein identification and analysis tools on the ExPASy server. In: Walker JM (ed) The Proteomics Protocols Handbook. Humana Press, Totowa, New Jersey, pp 571-607.
10. Hall TA (1999) Bioedit: a user-friendly biological sequence alignment editor and analysis program for Windows 95/98/NT. Nucleic Acids Symp Ser 41: 95-98.
11. Halls SC, Lewis NG (2002) Secondary and quaternary structures of the (+)-pinoresinol-forming dirigent protein. Biochemistry 41: 9455-9461.
12. Harmatha J, Dinan L (2003) Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions. Phytochem Rev 2: 321-330.
13. Hemmati S, von Heimendahl CBI, Klaes M, Alfermann AW, Schmidt TJ, Fuss E (2010) Pinoresinol-Lariciresinol Reductases with Opposite Enantiospecificity Determine the Enantiomeric Composition of Lignans in the Different Organs of Linum usitatissimum L. Planta Med 76: 928-934.
14. Huang S-L, Yu R-T, Gong J, Feng Y, Dai Y-L, Hu F, Hu Y-H, Tao Y-D, Leng Y (2012) Arctigenin, a natural compound, activates AMP-activated protein kinase via inhibition of mitochondria complex I and ameliorates metabolic disorders in ob/ob mice. Diabetologia 55: 1469-1481.
15. Huson DH, Richter DC, Rausch C, Dezulian T, Franz M, Rupp R (2007) Dendroscope: An interactive viewer for large phylogenetic trees. BMC Bioinformatics 8: 460.
16. Joshi CP, Chiang VL (1998) Conserved sequence motifs in plant Sadenosyl-L-methionine-dependent methyltransferases. Plant Mol Biol 37: 663-674.
17. Katoh K, Asimenos G, Toh H (2009) Multiple alignment of DNA sequences with MAFFT. In: Posada D (ed) Bioinformatics for DNA Sequence Analysis (Methods in Molecular Biology). Humana Press, Totowa, New Jersey, pp 39-64.
18. Kim J-Y, Hwang J-H, Cha M-R, Yoon M-Y, Son E-S, Tomida A, Ko B, Song S-W, Shin-Ya K, Hwang Y-I, et al. (2010) Arctigenin blocks the unfolded protein response and shows therapeutic antitumor activity. J Cell Physiol 224: 33-40.
19. Koulman A, Bos R, Medarde M, Pras N, Quax WJ (2001) A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related plant species. Planta Med 67: 858-862.
20. MacRae WD, Towers GHN (1984) Biological activities of lignans. Phytochemistry 23: 1207-1220.
21. Marques JV, Kim K-W, Lee C, Costa MA, May GD, Crow JA, Davin LB, Lewis NG (2013) Next generation sequencing in predicting gene function in podophyllotoxin biosynthesis. J Biol Chem 288: 466-479.
22. Muemmler S, Rueffer M, Nagakura N, Zenk MH (1984) Sadenosyl-L-methionine: (S)-scoulerine 9-O-methyltransferase, a highly stereo-and regio-specific enzyme in tetrahydroprotoberberine biosynthesis. Plant Cell Rep 4: 36-39.
23. Nakatsubo T, Li L, Hattori T, Lu S, Sakakibara N, Chiang VL, Shimada M, Suzuki S, Umezawa T (2007) Roles of 5-hydroxy coniferyl aldehyde and caffeoyl CoA O-methyltransferases in monolignol biosynthesis in Carthamus tinctorius. Cellul Chem Technol 41: 511-520.
24. Nakatsubo T, Mizutani M, Suzuki S, Hattori T, Umezawa T (2008) Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis. J Biol Chem 283: 15550-15557.
25. Ono E, Nakai M, Fukui Y, Tomimori N, Fukuchi-Mizutani M, Saito M, Satake H, Tanaka T, Katsuta M, Umezawa T, et al. (2006) Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proc Natl Acad Sci USA 103: 10116-10121.
26. Ozawa S, Davin LB, Lewis NG (1993) Formation of (-)-arctigenin in Forsythia intermedia. Phytochemistry 32: 643-652.
27. Pickel B, Constantin M-A, Pfannstiel J, Conrad J, Beifuss U, Schaller A (2010) An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols. Angew Chem Int 49: 202-204.
28. Ragamustari SK, Nakatsubo T, Hattori T, Ono E, Kitamura Y, Suzuki S, Yamamura M, Umezawa T (2013) A novel Omethyltransferase involved in the first methylation step of yatein biosynthesis from matairesinol in Anthriscus sylvestris. Plant Biotechnol 30: 375-384.
29. Sakakibara N, Nakatsubo T, Suzuki S, Shibata D, Shimada M, Umezawa T (2007) Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stableisotope-dilution method. Org Biomol Chem 5: 802-815.
30. Sakakibara N, Suzuki S, Umezawa T, Shimada M (2003) Biosynthesis of yatein in Anthriscus sylvestris. Org Biomol Chem 1: 2474-2485.
31. Sun S, Wang X, Wang C, Nawaz A, Wei W, Li J, Wang L, Yu D-H (2011) Arctigenin suppresses unfolded protein response and sensitizes glucose deprivation-mediated cytotoxicity of cancer cells. Planta Med 77: 141-145.
32. Suzuki S, Umezawa T (2007) Biosynthesis of lignans and norlignans. J Wood Sci 53: 273-284.
33. Suzuki S, Umezawa T, Shimada M (2002) Stereochemical Diversity in Lignan Biosynthesis of Arctium lappa L. Biosci Biotechnol Biochem 66: 1262-1269.
34. Umezawa T (2003) Diversity in lignan biosynthesis. Phytochem Rev 2: 371-390.
35. Umezawa T, Isohata T, Kuroda H, Higuchi T, Shimada M (1992) Chiral HPLC and LC-MS analysis of several lignans. In: Kuwahara M, Shimada M (ed) Biotechnology in Pulp and Paper Industry. Uni Publishing, Tokyo, pp 507-512.
36. Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M (1994) Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana. Biosci Biotechnol Biochem 58: 230-234.
37. Umezawa T, Okunishi T, Shimada M (1997) Stereochemical diversity in lignan biosynthesis. Wood Res 84: 62-75.
38. Umezawa T, Ragamustari SK, Nakatsubo T, Wada S, Li L, Yamamura M, Sakakibara N, Hattori T, Suzuki S, Chiang VL (2013) A lignan O-methyltransferase catalyzing the regioselective methylation of matairesinol in Carthamus tinctorius. Plant Biotechnol 30: 97-109.
39. Umezawa T, Yamamura M, Nakatsubo T, Suzuki S, Hattori T (2011) Stereoselectivity of the biosynthesis of norlignans and related compounds. In: Gang D (ed) The Biological Activity of Phytochemicals (Recent Advances in Phytochemistry, 41), Springer, New York, pp 179-197.
40. Yamamura M, Suzuki S, Hattori T, Umezawa T (2010) Subunit composition of hinokiresinol synthase controls enantiomeric selectivity in hinokiresinol formation. Org Biomol Chem 8: 1106-1110.
41. Zubieta C, He X-Z, Dixon RA, Noel JP (2001) Structures of two natural product methyltransferases reveal the basis for substrate specificity in plant O-methyltransferases. Nat Struct Biol 8: 271-279.