masaomi-portal/published_papers/54085068 Fernando Satoshi Tutihashi Mitsuki Hirota Masaomi Yamamura Keisuke Kobayashi Takefumi Hattori Yuki Tobimatsu Björn Robert Hamberger Toshiaki Umezawa Pinoresinol/Lariciresinol Reductases and Secoisolariciresinol Dehydrogenases Involved in the Specific Production of (+)-Enantiomer of Matairesinol in Daphne genkwa Abstract Lignans are phenylpropanoid dimers in which the monomers are linked by the central carbon atoms of their propyl side chains. In addition to the biosynthesis of biologically active lignans, the unique stereochemical mechanisms of biosynthetic reactions have been a long-standing interest. The enantiomeric composition of pinoresinol and lariciresinol—the two lignans farthest upstream in the lignan biosynthetic pathway—varies greatly among the plant species; these compounds are not enantiomerically pure and are mixtures of both enantiomers. The enantiomeric composition of the next intermediate, secoisolariciresinol, also varies by plant species, with some being enantiomerically pure. Conversely, the next compound, matairesinol, is always enantiomerically pure. In most cases, it is levorotatory, while the opposite dextrorotatory enantiomer, (+)-matairesinol, has been obtained from Thymelaeaceae plants, including Daphne genkwa. The conversion of pinoresinol to secoisolariciresinol via lariciresinol is catalyzed by pinoresinol/lariciresinol reductases (PLRs). Secoisolariciresinol is then oxidized by secoisolariciresinol dehydrogenases (SIRDs) to afford matairesinol. Many PLRs from various plant species preferentially reduce (+)-pinoresinol to (-)-secoisolariciresinol, while others preferentially reduce (-)-pinoresinol to (+)-secoisolariciresinol. However, the specific formation and accumulation of (+)-matairesinol in Thymelaeaceae plants remain unknown. This study demonstrated that DgPLRs selectively reduce (-)-lariciresinol but not (+)-lariciresinol, resulting in the formation of (+)-secoisolariciresinol. Furthermore, DgSIRDs were found to selectively oxidize (+)-secoisolariciresinol over (-)-secoisolariciresinol, yielding (+)-matairesinol. Thus, the selectivity of DgPLRs for lariciresinol enantiomers rather than pinoresinol enantiomers and the selectivity of DgSIRDs for secoisolariciresinol enantiomers are responsible for the accumulation of nearly enantiomerically pure (+)-secoisolariciresinol and enantiomerically pure (+)-matairesinol in D. genkwa. Oxford University Press (OUP) Plant and Cell Physiology 1471-9053 null null 20260428 10.1093/pcp/pcag054 masaomi-portal/published_papers/46261276 Keisuke Kobayashi Masaomi Yamamura Bunzo Mikami Akira Shiraishi Masato Kumatani Honoo Satake Eiichiro Ono Toshiaki Umezawa Anthriscus sylvestris Deoxypodophyllotoxin Synthase Involved in the Podophyllotoxin Biosynthesis. Tetrahydrofuran ring formation from dibenzylbutyrolactone lignans is a key step in the biosynthesis of aryltetralin lignans including deoxypodophyllotoxin and podophyllotoxin. Previously, Fe(II)- and 2-oxoglutarate-dependent dioxygenase (2-ODD) from Podophyllum hexandrum (Himalayan mayapple, Berberidaceae) was found to catalyze the cyclization of a dibenzylbutyrolactone lignan, yatein, to give deoxypodophyllotoxin and designated as deoxypodophyllotoxin synthase (DPS). Recently, we reported that the biosynthesis of deoxypodophyllotoxin and podophyllotoxin evolved in a lineage-specific manner in phylogenetically unrelated plant species such as P. hexandrum and Anthriscus sylvestris (cow parsley, Apiaceae). Therefore, a comprehensive understanding of the characteristics of DPSs that catalyze the cyclization of yatein to deoxypodophyllotoxin in various plant species is important. However, for plant species other than P. hexandrum, the isolation of the DPS enzyme gene and the type of the enzyme, e.g. whether it is 2-ODD or another type of enzyme such as cytochrome P-450, have not been reported. In this study, we report the identification and characterization of A. sylvestris DPS (AsDPS). Phylogenetic analysis showed that AsDPS belonged to the 2-ODD superfamily and shared moderate amino acid sequence identity (40.8%) with P. hexandrum deoxypodophyllotoxin synthase (PhDPS). Recombinant protein assay indicated that AsDPS and PhDPS differ in terms of the selectivity of substrate enantiomers. Protein modeling using AlphaFold2 and site-directed mutagenesis indicated that the Tyr305 residue of AsDPS probably contributes to substrate recognition. This study advances our understanding of the podophyllotoxin biosynthetic pathway in A. sylvestris and provides new insight into 2-ODD involved in plant secondary (specialized) metabolism. Plant & cell physiology 64 12 1436 1448 20231221 10.1093/pcp/pcad103 37948767 masaomi-portal/published_papers/41553719 Masaomi Yamamura Masato Kumatani Akira Shiraishi Yu Matsuura Keisuke Kobayashi Ayano Suzuki Atsushi Kawamura Honoo Satake Safendrri Komara Ragamustari Shiro Suzuki Hideyuki Suzuki Daisuke Shibata Shingo Kawai Eiichiro Ono Toshiaki Umezawa Two O-Methyltransferases from Phylogenetically Unrelated Cow Parsley (Anthriscus sylvestris) and Hinoki-Asunaro (Thujopsis dolabrata var. hondae) as a Signature of Lineage-Specific Evolution in Lignan Biosynthesis. O-Methyltransferases (OMTs) play important roles in antitumor lignan biosynthesis. To date, six OMTs catalyzing the methylation of dibenzylbutyrolactone lignans as biosynthetic precursors of antitumor lignans have been identified. However, there is still no systematic understanding of the diversity and regularity of the biosynthetic mechanisms among various plant lineages. Herein, we report the characterization of two OMTs from Anthriscus sylvestris and Thujopsis dolabrata var. hondae [designated as AsSecoNorYatein (SNY) OMT and TdSNYOMT] together with the six known OMTs to evaluate their diversity and regularity. Although A. sylvestris 5-O-methylthujaplicatin (SecoNorYatein) and 4-O-demethylyatein (NorYatein) OMT (AsSNYOMT) and TdSNYOMT accept 5-O-methylthujaplicatin and 4-O-demethylyatein as substrates, phylogenetic analysis indicated that these two OMTs shared low amino acid sequence identity, 33.8%, indicating a signature of parallel evolution. The OMTs and the six previously identified OMTs were found to be diverse in terms of their substrate specificity, regioselectivity and amino acid sequence identity, indicating independent evolution in each plant species. Meanwhile, two-entropy analysis detected four amino acid residues as being specifically acquired by dibenzylbutyrolactone lignan OMTs. Site-directed mutation of AsSNYOMT indicated that two of them contributed specifically to 5-O-methylthujaplicatin methylation. The results provide a new example of parallel evolution and the diversity and regularity of OMTs in plant secondary (specialized) metabolism. Plant & cell physiology 64 1 124 147 20230216 10.1093/pcp/pcac164 36412832 masaomi-portal/published_papers/40054608 Andri Fadillah Martin Yuki Tobimatsu Pui Ying Lam Naoyuki Matsumoto Takuto Tanaka Shiro Suzuki Ryosuke Kusumi Takuji Miyamoto Yuri Takeda-Kimura Masaomi Yamamura Taichi Koshiba Keishi Osakabe Yuriko Osakabe Masahiro Sakamoto Toshiaki Umezawa Lignocellulose molecular assembly and deconstruction properties of lignin-altered rice mutants Abstract Bioengineering approaches to modify lignin content and structure in plant cell walls have shown promise for facilitating biochemical conversions of lignocellulosic biomass into valuable chemicals. Despite numerous research efforts, however, the effect of altered lignin chemistry on the supramolecular assembly of lignocellulose and consequently its deconstruction in lignin-modified transgenic and mutant plants is not fully understood. In this study, we aimed to close this gap by analyzing lignin-modified rice (Oryza sativa L.) mutants deficient in 5-HYDROXYCONIFERALDEHYDE O-METHYLTRANSFERASE (CAldOMT) and CINNAMYL ALCOHOL DEHYDROGENASE (CAD). A set of rice mutants harboring knockout mutations in either or both OsCAldOMT1 and OsCAD2 was generated in part by genome editing and subjected to comparative cell wall chemical and supramolecular structure analyses. In line with the proposed functions of CAldOMT and CAD in grass lignin biosynthesis, OsCAldOMT1-deficient mutant lines produced altered lignins depleted of syringyl and tricin units and incorporating noncanonical 5-hydroxyguaiacyl units, whereas OsCAD2-deficient mutant lines produced lignins incorporating noncanonical hydroxycinnamaldehyde-derived units. All tested OsCAldOMT1- and OsCAD2-deficient mutants, especially OsCAldOMT1-deficient lines, displayed enhanced cell wall saccharification efficiency. Solid-state nuclear magnetic resonance (NMR) and X-ray diffraction analyses of rice cell walls revealed that both OsCAldOMT1- and OsCAD2 deficiencies contributed to the disruptions of the cellulose crystalline network. Further, OsCAldOMT1 deficiency contributed to the increase of the cellulose molecular mobility more prominently than OsCAD2 deficiency, resulting in apparently more loosened lignocellulose molecular assembly. Such alterations in cell wall chemical and supramolecular structures may in part account for the variations of saccharification performance of the OsCAldOMT1- and OsCAD2-deficient rice mutants. Oxford University Press (OUP) Plant Physiology 1532-2548 in press 1 70 86 20220919 10.1093/plphys/kiac432 masaomi-portal/published_papers/36324628 Masaomi Yamamura Miyamoto Takuji Takada Rie Widyajayantie Dwi Windiastri Esti Vincentia Nugroho Satya Umezawa Toshiaki A microscale protocol for alkaline nitrobenzene oxidation of lignins using a readily available reactor Lignin 2 19 24 20210612 masaomi-portal/published_papers/36324629 Nge Thi Thi Yamada Tatsuhiko Tobimatsu Yuki Masaomi Yamamura Ishii Ryo Tanaike Osamu Ebina Takeo Fractionation and Characterization of Glycol Lignins by Stepwise-pH Precipitation of Japanese Cedar/Poly(ethylene glycol) Solvolysis Liquor ACS Sustainable Chemistry & Engineering 2168-0485 9 2 756 764 20210107 10.1021/acssuschemeng.0c06892 masaomi-portal/published_papers/38053310 Yoko Okahisa Keisuke Kojiro Hatsuki Ashiya Takeru Tomita Yuzo Furuta Masaomi Yamamura Toshiaki Umezawa Age-dependent and radial sectional differences in the dynamic viscoelastic properties of bamboo culms and their possible relationship with the lignin structures <title>Abstract</title> Age is an important factor that dictates bamboo's mechanical properties. In Japan, bamboo plants aged 3–5 years are selected for use as materials because of their robustness and decorative or craft-friendly characteristics. In this study, the age-dependent and radial sectional differences in bamboo's dynamic viscoelastic properties in relation to lignin structural variation, were evaluated. We used <italic>Phyllostachys pubescens</italic> samples at the current year and at 1.5, 3.5, 6.5, 9.5, 12.5, and 15.5 years of age. There was a clear age dependence in the peak temperature of tan <italic>δ</italic> and in the yield of thioacidolysis products derived from <italic>β</italic>-O-4 lignin structures. The highest peak temperature tan <italic>δ</italic> value was detected in 3.5-year-old bamboo, which contained the highest amount of the thioacidolysis products. Moreover, tan <italic>δ</italic>'s peak temperature was always higher on the outer side, and the ratio of S/G thioacidolysis products was always higher on the inner side of bamboo plants of all ages. These results suggest that changes in bamboo's thermal softening properties from aging are caused by the maturation and degradation of lignin in bamboo. Springer Science and Business Media LLC Journal of Wood Science 1611-4663 66 1 66 66 20201200 10.1186/s10086-020-01914-y masaomi-portal/published_papers/36324630 Yonekura-Sakakibara Keiko Masaomi Yamamura Matsuda Fumio Ono Eiichiro Nakabayashi Ryo Sugawara Satoko Mori Tetsuya Tobimatsu Yuki Umezawa Toshiaki Saito Kazuki Seed-coat protective neolignans are produced by the dirigent protein AtDP1 and the laccase AtLAC5 in Arabidopsis <title>Abstract</title>Lignans/neolignans are generally synthesized from coniferyl alcohol (CA) in the cinnamate/monolignol pathway by oxidation to generate the corresponding radicals with subsequent stereoselective dimerization aided by dirigent proteins (DIRs). Genes encoding oxidases and DIRs for neolignan biosynthesis have not been identified previously. In Arabidopsis thaliana, the DIR AtDP1/AtDIR12 plays an essential role in the 8-O-4′ coupling in neolignan biosynthesis by unequivocal structural determination of the compound missing in the atdp1 mutant as a sinapoylcholine (SC)-conjugated neolignan, erythro-3-{4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-hydroxymethylethoxy]-3,5-dimethoxyphenyl}acryloylcholine. Phylogenetic analyses showed that AtDP1/AtDIR12 belongs to the DIR-a subfamily composed of DIRs for 8-8′ coupling of monolignol radicals. AtDP1/AtDIR12 is specifically expressed in outer integument 1 cells in developing seeds. As a putative oxidase for neolignan biosynthesis, we focused on AtLAC5, a laccase gene coexpressed with AtDP1/AtDIR12. In lac5 mutants, the abundance of feruloylcholine (FC)-conjugated neolignans decreased to a level comparable to those in the atdp1 mutant. In addition, SC/FC-conjugated neolignans were missing in the seeds of mutants defective in SCT/SCPL19, an enzyme that synthesizes SC. These results strongly suggest that AtDP1/AtDIR12 and AtLAC5 are involved in neolignan biosynthesis via SC/FC. A tetrazolium penetration assay showed that seed coat permeability increased in atdp1 mutants, suggesting a protective role of neolignans in A. thaliana seeds. Oxford University Press (OUP) The Plant Cell 1532-298X 33 129 152 20201127 10.1093/plcell/koaa014 masaomi-portal/published_papers/36324631 Yoko Okahisa Keisuke Kojiro Hatsuki Ashiya Takeru Tomita Yuzo Furuta Masaomi Yamamura Toshiaki Umezawa Age-dependent and radial sectional differences in the dynamic viscoelastic properties of bamboo culms and their possible relationship with the lignin structures Journal of Wood Science 1611-4663 66 66 null null 20200925 10.1186/s10086-020- masaomi-portal/published_papers/47573866 Umezawa Toshiaki Tobimatsu Yuki Yamamura Masaomi Miyamoto Takuji Takeda Yuri Koshiba Taichi Takada Rie Lam Pui Ying Suzuki Shiro Sakamoto Masahiro Lignin Metabolic Engineering in Grasses for Primary Lignin Valorization Lignocellulose biomass is indispensable for establishing sustainable societies. Trees and large-sized grasses are the major sources of lignocellulose biomass. Moreover, large-sized grasses greatly surpass trees in terms of lignocellulose biomass productivity. With an overall aim to improve lignocellulose usability, it is vital to improve lignin content and simplify lignin structures in biomass plants via lignin metabolic engineering. In this mini review, recent studies of lignin metabolic engineering of grass biomass plants mainly from the authors' research group are summarized, which includes characterization of lignocellulose properties of large-sized grass biomass plants and the augmentation of lignin content and simplification of lignin structures in grasses. The Lignin Society Lignin 2759-0755 1 30 41 20200914 10.62840/lignin.1.0_30 1390018583807314560 masaomi-portal/published_papers/36324632 Ramachandran Vasagi Tobimatsu Yuki Masaomi Yamamura Sano Ryosuke Umezawa Toshiaki Demura Taku Ohtani Misato Plant-specific Dof transcription factors VASCULAR-RELATED DOF1 and VASCULAR-RELATED DOF2 regulate vascular cell differentiation and lignin biosynthesis in Arabidopsis Plant Molecular Biology 1573-5028 104 263 281 20200801 10.1007/s11103-020-01040-9 masaomi-portal/published_papers/36324633 Nge Thi Thi Tobimatsu Yuki Masaomi Yamamura Takahashi Shiho Takata Eri Umezawa Toshiaki Yamada Tatsuhiko Effect of heat treatment on the chemical structure and thermal properties of softwood-derived glycol lignin. Molecules 1420-3049 25 1167 1167 20200505 10.3390/molecules25051167 masaomi-portal/published_papers/36324634 Miyamoto Takuji Takada Rie Tobimatsu Yuki Suzuki Shiro Masaomi Yamamura Keishi Osakabe Yuriko Osakabe Sakamoto Masahiro Umezawa Toshiaki Double knockout of OsWRKY36 and OsWRKY102 boosts lignification with altering culm morphology of rice. Breeding to enrich lignin, a major component of lignocelluloses, in plants contributes to enhanced applications of lignocellulosic biomass into solid biofuels and valuable aromatic chemicals. To collect information on enhancing lignin deposition in grass species, important lignocellulose feedstocks, we generated rice (Oryza sativa) transgenic lines deficient in OsWRKY36 and OsWRKY102, which encode putative transcriptional repressors for secondary cell wall formation. We used CRISPR/Cas9-mediated targeted mutagenesis and closely characterized their altered cell walls using chemical and nuclear magnetic resonance (NMR) methods. Both OsWRKY36 and OsWRKY102 mutations significantly increased lignin content by up to 28 % and 32 %, respectively. Additionally, OsWRKY36/OsWRKY102-double-mutant lines displayed lignin enrichment of cell walls (by up to 41 %) with substantially altered culm morphology over the single-mutant lines as well as the wild-type controls. Our chemical and NMR analyses showed that relative abundances of guaiacyl and p-coumarate units were slightly higher and lower, respectively, in the WRKY mutant lignins compared with those in the wild-type lignins. Our results provide evidence that both OsWRKY36 and OsWRKY102 are associated with repression of rice lignification. Plant Science 0168-9452 296 110466 110466 20200312 10.1016/j.plantsci.2020.110466 32539998 masaomi-portal/published_papers/36324635 Martin Fadillah Andri Tobimatsu Yuki Kusumi Ryosuke Matsumoto Naoyuki Miyamoto Takuji Lam Ying Pui Masaomi Yamamura Koshiba Taichi Sakamoto Masahiro Umezawa Toshiaki Altered lignocellulose chemical structure and molecular assembly in CINNAMYL ALCOHOL DEHYDROGENASE-deficient rice. Scientific Reports 2045-2322 9 17153 17153 20191120 10.1038/s41598-019-53156-8 masaomi-portal/published_papers/36324636 Pui Ying Lam Yuki Tobimatsu Naoyuki Matsumoto Shiro Suzuki Wu Lan Yuri Takeda Masaomi Yamamura Masahiro Sakamoto John Ralph Clive Lo Toshiaki Umezawa OsCAldOMT1 is a bifunctional O-methyltransferase involved in the biosynthesis of tricin-lignins in rice cell walls Scientific Reports 2045-2322 9 1 13 20190812 10.1038/s41598-019-47957-0 masaomi-portal/published_papers/36324637 Shiro Suzuki Hideyuki Suzuki Koji Tanaka Masaomi Yamamura Daisuke Shibata Toshiaki Umezawa De novo transcriptome analysis of needles of Thujopsis dolabrata var. hondae Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1347-6114 36 2 113 118 20190625 10.5511/plantbiotechnology.19.0220a masaomi-portal/published_papers/36324638 Pui Ying Lam Andy C.W. Lui Masaomi Yamamura Lanxiang Wang Yuri Takeda Shiro Suzuki Hongjia Liu Fu-Yuan Zhu Mo-Xian Chen Jianhua Zhang Umezawa Toshiaki Yuki Tobimatsu Clive Lo Recruitment of specific flavonoid B-ring hydroxylases for two independent biosynthesis pathways of flavone-derived metabolites in grasses In rice (Oryza sativa), OsF2H and OsFNSII direct flavanones to independent pathways that form soluble flavone C-glycosides and tricin-type metabolites (both soluble and lignin-bound), respectively. Production of soluble tricin metabolites requires CYP75B4 as a chrysoeriol 5'-hydroxylase. Meanwhile, the close homologue CYP75B3 is a canonical flavonoid 3'-hydroxylase (F3'H). However, their precise roles in the biosynthesis of soluble flavone C-glycosides and tricin-lignins in cell walls remain unknown. We examined CYP75B3 and CYP75B4 expression in vegetative tissues, analyzed extractable flavonoid profiles, cell wall structure and digestibility of their mutants, and investigated catalytic activities of CYP75B4 orthologues in grasses. CYP75B3 and CYP75B4 showed co-expression patterns with OsF2H and OsFNSII, respectively. CYP75B3 is the sole F3'H in flavone C-glycosides biosynthesis, whereas CYP75B4 alone provides sufficient 3',5'-hydroxylation for tricin-lignin deposition. CYP75B4 mutation results in production of apigenin-incorporated lignin and enhancement of cell wall digestibility. Moreover, tricin pathway-specific 3',5'-hydroxylation activities are conserved in sorghum CYP75B97 and switchgrass CYP75B11. CYP75B3 and CYP75B4 represent two different pathway-specific enzymes recruited together with OsF2H and OsFNSII, respectively. Interestingly, the OsF2H-CYP75B3 and OsFNSII-CYP75B4 pairs appear to be conserved in grasses. Finally, manipulation of tricin biosynthesis through CYP75B4 orthologues can be a promising strategy to improve digestibility of grass biomass for biofuel and biomaterial production. The New Phytologist 1469-8137 223 1 204 219 20190318 10.1111/nph.15795 masaomi-portal/published_papers/36324639 Miyamoto Takuji Takada Rie Tobimatsu Yuki Takeda Yuri Suzuki Shiro Masaomi Yamamura Keishi Osakabe Yuriko Osakabe Sakamoto Masahiro Umezawa Toshiaki OsMYB108 loss-of-function enriches p-coumaroylated and tricin lignin units in rice cell walls. Breeding approaches to enrich lignins in biomass could be beneficial to improving the biorefinery process because lignins increase biomass heating value and represent a potent source of valuable aromatic chemicals. However, despite the fact that grasses are promising lignocellulose feedstocks, limited information is yet available for molecular-breeding approaches to upregulate lignin biosynthesis in grass species. In this study, we generated lignin-enriched transgenic rice (Oryza sativa), a model grass species, via targeted mutagenesis of the transcriptional repressor OsMYB108 using CRISPR/Cas9-mediated genome editing. The OsMYB108-knockout rice mutants displayed increased expressions of lignin biosynthetic genes and enhanced lignin deposition in culm cell walls. Chemical and two-dimensional nuclear magnetic resonance (NMR) analyses revealed that the mutant cell walls were preferentially enriched in γ-p-coumaroylated and tricin lignin units, both of which are typical and unique components in grass lignins. NMR analysis also showed that the relative abundances of major lignin linkage types were altered in the OsMYB108 mutants. The plant Journal 98 6 975 987 20190218 10.1111/tpj.14290 30773774 masaomi-portal/published_papers/36324640 Yuri Takeda Yuki Tobimatsu Masaomi Yamamura Toshiyuki Takano Masahiro Sakamoto Toshiaki Umezawa Comparative evaluations of lignocellulose reactivity and usability in transgenic rice plants with altered lignin composition Springer Science and Business Media LLC Journal of Wood Science 1611-4663 65 6 1 11 20190213 10.1186/s10086-019-1784-6 masaomi-portal/published_papers/42522824 Toshiaki Umezawa 梅澤俊明 Masaomi Yamamura 山村正臣 Eiichiro Ono 小埜栄一郎 Akira Shiraishi 白石慧 Safendrri Komara Ragamustari サフェンドリ・コマーラ・ラガムスタリ Recent Advances in Lignan OMT Studies リグナンOMT に関する最新研究動向 Japan Wood Society Mokuzai Gakkaishi 木材学会誌 1880-7577 65 1 1 12 20190125 10.2488/jwrs.65.1 masaomi-portal/published_papers/36324641 Takuji Miyamoto, Asako Mihashi, Masaomi Yamamura, Yuki Tobimatsu, Shiro Suzuki, Rie Takada, Yoshinori Kobayashi, Toshiaki Umezawa Comparative analysis of lignin chemical structures of sugarcane bagasse pretreated by alkaline, hydrothermal, and dilute sulfuric acid methods Industrial Crops and Products 0926-6690 121 124 131 20181001 10.1016/j.indcrop.2018.04.077 masaomi-portal/published_papers/36324642 Takuji Miyamoto Masaomi Yamamura Yuki Tobimatsu Shiro Suzuki Miho Kojima Keiji Takabe Yoshifumi Terajima Asako Mihashi Yoshinori Kobayashi Toshiaki Umezawa A comparative study of the biomass properties of Erianthus and sugarcane: lignocellulose structure, alkaline delignification rate, and enzymatic saccharification efficiency A comprehensive understanding of the structure and properties of gramineous lignocelluloses is needed to facilitate their uses in biorefinery. In this study, lignocelluloses from fractionated internode tissues of two taxonomically close species, Erianthus arundinaceus and sugarcane (Saccharum spp.), were characterized. Our analyses determined that syringyl (S) lignins were predominant over guaiacyl (G) or p-hydroxyphenyl (H) lignins in sugarcane tissues; on the other hand, S lignin levels were similar to those of G lignin in Erianthus tissues. In addition, tricin units were detected in sugarcane tissues, but not in Erianthus tissues. Distributions of lignin inter-monomeric linkage types were also different in Erianthus and sugarcane tissues. Alkaline treatment removed lignins from sugarcane tissues more efficiently than Erianthus tissues, resulting in a higher enzymatic digestibility of sugarcane tissues compared with Erianthus tissues. Our data indicate that Erianthus biomass displayed resistance to alkaline delignification and enzymatic digestion. Bioscience, Biotechnology, and Biochemistry 1347-6947 82 7 1143 1152 20180703 10.1080/09168451.2018.1447358 29558856 masaomi-portal/published_papers/36324643 Takeda Yuri Tobimatsu Yuki Karlen D. Steven Koshiba Taichi Suzuki Shiro Masaomi Yamamura Murakami Shinya Mukai Mai Takefumi Hattori Keishi Osakabe Ralph John Sakamoto Masahiro Umezawa Toshiaki Downregulation of p-COUMAROYL ESTER 3HYDROXYLASE in rice leads to altered cell wall structures and improves biomass saccharification Wiley The Plant Journal 1365-313X 95 5 796 811 20180611 10.1111/tpj.13988 masaomi-portal/published_papers/36324644 Nge Thi Thi Tobimatsu Yuki Takahashi Shiho Takata Eri Yamamura Masaomi Miyagawa Yasuyuki Ikeda Tsutomu Umezawa Toshiaki Yamada Tatsuhiko Isolation and characterization of polyethylene glycol (PEG)-modified glycol lignin via PEG solvolysis of softwood biomass in a large-scale batch reactor American Chemical Society (ACS) ACS Sustainable Chemistry & Engineering 2168-0485 6 6 7841 7848 20180514 10.1021/acssuschemeng.8b00965 masaomi-portal/published_papers/36324645 Tarmadi Didi Tobimatsu Yuki Yamamura Masaomi Miyamoto Takuji Miyagawa Yasuyuki Umezawa Toshiaki Yoshimura Tsuyoshi NMR studies on lignocellulose deconstructions in the digestive system of the lower termite Coptotermes formosanus Shiraki. Scientific Reports 2045-2322 8 1 9 20180122 10.1038/s41598-018-19562-0 masaomi-portal/published_papers/36324646 Tarmadi Didi Yoshimura Tsuyoshi Tobimatsu Yuki Yamamura Masaomi Umezawa Toshiaki Effects of lignins as diet components on the physiological activities of a lower termite, Coptotermes formosanus Shiraki Journal of Insect Physiology 0022-1910 103 57 63 20171014 masaomi-portal/published_papers/36324647 Didi Tarmadi Tsuyoshi Yoshimura Yuki Tobimatsu Masaomi Yamamura Takuji Miyamoto Yasuyuki Miyagawa Toshiaki Umezawa The effects of various lignocelluloses and lignins on physiological responses of a lower termite, Coptotermes formosanus Journal of Wood Science 1611-4663 63 464 472 20170716 10.1007/s10086-017-1638-z masaomi-portal/published_papers/36324648 Yuri Takeda Taichi Koshiba Yuki Tobimatsu Shiro Suzuki Shinya Murakami Masaomi Yamamura Md Mahabubur Rahman Toshiyuki Takano Takefumi Hattori Masahiro Sakamoto Toshiaki Umezawa Regulation of CONIFERALDEHYDE 5-HYDROXYLASE expression to modulate cell wall lignin structure in rice. Planta 1432-2048 246 337 349 20170418 10.1007/s00425-017-2692-x masaomi-portal/published_papers/36324649 Pui Ying Lam Yuki Tobimatsu Yuri Takeda Masaomi Yamamura Toshiaki Umezawa Clive Lo Disrupting Flavone Synthase II alters lignin and improves biomass digestibility. Lignin, a ubiquitous phenylpropanoid polymer in vascular plant cell walls, is derived primarily from oxidative couplings of monolignols (-hydroxycinnamyl alcohols). It was discovered recently that a wide range of grasses, including cereals, utilize a member of the flavonoids, tricin (3',5'-dimethoxyflavone), as a natural comonomer with monolignols for cell wall lignification. Previously, we established that cytochrome P450 93G1 is a flavone synthase II (OsFNSII) indispensable for the biosynthesis of soluble tricin-derived metabolites in rice (). Here, our tricin-deficient mutant was analyzed further with an emphasis on its cell wall structure and properties. The mutant is similar in growth to wild-type control plants with normal vascular morphology. Chemical and nuclear magnetic resonance structural analyses demonstrated that the mutant lignin is completely devoid of tricin, indicating that FNSII activity is essential for the deposition of tricin-bound lignin in rice cell walls. The mutant also showed substantially reduced lignin content with decreased syringyl/guaiacyl lignin unit composition. Interestingly, the loss of tricin in the mutant lignin appears to be partially compensated by incorporating naringenin, which is a preferred substrate of OsFNSII. The mutant was further revealed to have enhanced enzymatic saccharification efficiency, suggesting that the cell wall recalcitrance of grass biomass may be reduced through the manipulation of the flavonoid monomer supply for lignification. Plant Physiology 1532-2548 174 2 972 985 20170406 10.1104/pp.16.01973 masaomi-portal/published_papers/36324650 Koshiba Taichi Yamamoto Naoki Tobimatsu Yuki Yamamura Masaomi Suzuki Shiro Hattori Takefumi Mukai Mai Noda Soichiro Shibata Daisuke Sakamoto Masahiro Umezawa Toshiaki MYB-mediated upregulation of lignin biosynthesis in Oryza sativa towards biomass refinery. Plant Biotechnology 1342-4580 34 1 7 15 20170300 masaomi-portal/published_papers/38623199 Taichi Koshiba Naoki Yamamoto Yuki Tobimatsu Masaomi Yamamura Shiro Suzuki Takefumi Hattori Mai Mukai Soichiro Noda Daisuke Shibata Masahiro Sakamoto Toshiaki Umezawa MYB-mediated upregulation of lignin biosynthesis in Oryza Sativa towards biomass refinery Lignin encrusts lignocellulose polysaccharides, and has long been considered an obstacle for the efficient use of polysaccharides during processes such as pulping and bioethanol fermentation. However, lignin is also a potential feedstock for aromatic products and is an important by-product of polysaccharide utilization. Therefore, producing biomass plant species exhibiting enhanced lignin production is an important breeding objective. Herein, we describe the development of transgenic rice plants with increased lignin content. Five Arabidopsis thaliana (Arabidopsis) and one Oryza sativa (rice) MYB transcription factor genes that were implicated to be involved in lignin biosynthesis were transformed into rice (O. sativa L. ssp. japonica cv. Nipponbare). Among them, three Arabidopsis MYBs (AtMYB55, AtMYB61, and AtMYB63) in transgenic rice T1 lines resulted in culms with lignin content about 1.5-fold higher than that of control plants. Furthermore, lignin structures in AtMYB61-overexpressing rice plants were investigated by wet-chemistry and two-dimensional nuclear magnetic resonance spectroscopy approaches. Our data suggested that heterologous expression of AtMYB61 in rice increased lignin content mainly by enriching syringyl units as well as p-coumarate and tricin moieties in the lignin polymers. We contemplate that this strategy is also applicable to lignin upregulation in large-sized grass biomass plants, such as Sorghum, switchgrass, Miscanthus and Erianthus. Japanese Society for Plant Cell and Molecular Biology 日本植物細胞分子生物学会 Plant Biotechnology 1347-6114 34 1 1 9 20170000 10.5511/plantbiotechnology.16.1201a masaomi-portal/published_papers/38623201 宮本託志林晃大山村正臣飛松裕基鈴木史朗児嶋美穂高部圭司梅澤俊明 4-4-1 大型イネ科バイオマス植物エリアンサスのリグノセルロース性状解析(4-4 植物の代謝成分と農作物の品質，2016年度佐賀大会) 一般社団法人日本土壌肥料学会日本土壌肥料学会講演要旨集 62 77 77 20160000 10.20710/dohikouen.62.0_77_1 masaomi-portal/published_papers/36324651 Tomoyuki Nakatsubo Safendrri Komara Ragamustari Takefumi Hattori Eiichiro Ono Masaomi Yamamura Laigeng Li Vincent L. Chiang Toshiaki Umezawa A new O-methyltransferase for monolignol synthesis in Carthamus tinctorius. A novel type of O-methyltransferase (OMT) cDNA was isolated from maturing seeds of Carthamus tinctorius (safflower). The deduced sequence of the OMT protein showed moderate sequence identity (52%) with C. tinctorius 5-hydroxyconiferaldehyde O-methyltransferase 1 (CAldOMT1). Phylogenetic analysis showed that the novel OMT did not belong to the typical CAldOMT [=caffeic acid OMT (CAOMT)] cluster. The recombinant protein of the OMT catalyzed 3- (or 5-) O-methylation of hydroxycinnamaldehydes and hydroxycinnamyl alcohols, while it showed only weak or moderate activity toward hydroxycinnamates and hydroxycinnamoyl coenzyme A esters. Therefore, this OMT was designated as C. tinctorius 5-hydroxyconiferaldehyde/5-hydroxyconiferyl alcohol OMT (CtAAOMT). The time profile of CtAAOMT gene expression in C. tinctorius matched the patterns of lignin accumulation. Taken together, our data strongly suggest that along with CtCAldOMT1, CtAAOMT is involved in biosynthesis of syringyl lignin. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 31 545 553 20141225 10.5511/plantbiotechnology.14.0903a masaomi-portal/published_papers/36324652 Safendrri Komara Ragamustari Masaomi Yamamura Eiichiro Ono Takefumi Hattori Shiro Suzuki Hideyuki Suzuki Daisuke Shibata Toshiaki Umezawa Substrate-enantiomer selectivity of matairesinol O-methyltransferases Plant Biotechnology 1347-6114 31 3 257 267 20140925 10.5511/plantbiotechnology.14.0722a 2-s2.0-84923387910 masaomi-portal/published_papers/36324653 Safendrri Komara Ragamustari Tomoyuki Nakatsubo Takefumi Hattori Eiichiro Ono Yu Kitamura Shiro Suzuki Masaomi Yamamura Toshiaki Umezawa A novel O-methyltransferase involved in the first methylation step of yatein biosynthesis from matairesinol in Anthriscus sylvestris. Yatein is an important biosynthetic precursor of the lignan podophyllotoxin. In Anthriscus sylvestris, yatein biosynthesis is preceded by two regioselective methylations involving the intermediates: thujaplicatin and 5-O-methylthujaplicatin. The two methylation steps are most likely catalyzed by plant O-methyltransferases (OMTs). In this paper, we report the isolation and characterization of a cDNA encoding an OMT involved in the first methylation step. The OMT cDNA was isolated from an A. sylvestris cDNA library prepared from roots and young shoots. The OMT was expressed as a recombinant protein using the pET expression system. Of the substrates that were tested, the recombinant OMT exclusively catalyzed regioselective methylation of thujaplicatin to produce 5-O-methylthujaplicatin, and thus was designated as A. sylvestris thujaplicatin OMT (AsTJOMT). Kinetic analysis with its substrate (thujaplicatin) showed that AsTJOMT had a Km value of 3.8 µM and kcat value of 0.29 min-1. Quantitative real-time polymerase chain reaction showed that AsTJOMT had the highest expression level in roots compared with other organs. This was in accordance with plant protein assays in which specific activity for thujaplicatin was significantly higher in roots compared with other organs. To the best of our knowledge, this is the first report on the isolation and characterization of a thujaplicatin-specific plant OMT. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 30 4 375 384 20130925 10.5511/plantbiotechnology.13.0527b masaomi-portal/published_papers/36324656 Taichi Koshiba Norie Hirose Mai Mukai Masaomi Yamamura Takefumi Hattori Shiro Suzuki Masahiro Sakamoto Toshiaki Umezawa Characterization of 5-hydroxyconiferaldehyde O-methyltransferase in Oryza sativa Little is known regarding syringyl lignin biosynthesis in rice (Oryza sativa L. cv. Nipponbare). In the present study, the role of rice caffeic acid O-methyltransferase (OsCOMT1, Q6ZD89), was examined. The recombinant OsCOMT1 catalyzed the 5-Omethylation of 5-hydroxyferulate (5-HFA) and 5-hydroxyconiferaldehyde (5-HCAld). 5-HCAld inhibited 5-HFA methylation by this O-methyltransferase (OMT), while 5-HFA mitigated self-inhibition in 5-HCAld methylation. A rice plant in which OsCOMT1 expression was downregulated exhibited weakened cell wall staining with Wiesner reagent in vascular bundle cells and sclerenchyma tissue, compared with wild-type plants. The lignin content of transgenic rice plants was decreased and the syringyl lignin content reduced largely compared with that of the wild type. Taken together, these data indicated that OsCOMT1 functioned as a 5-HCAld OMT (OsCAldOMT1) in the biosynthetic pathway to syringyl lignin. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 30 2 157 167 20130625 10.5511/plantbiotechnology.13.0219a masaomi-portal/published_papers/36324655 Noda Soichiro Takahashi Yoshinori Tsurumaki Yuta Yamamura Masaomi Nishikubo Nobuyuki Yamaguchi Masatoshi Sakurai Nozomu Suzuki Hideyuki Demura Taku Shibata Daisuke Umezawa Toshiaki ATL54, a RING-H2 domain protein selected by a gene co-expression network analysis, is associated with secondary cell wall formation in Arabidopsis. Biosynthesis of plant secondary cell walls is controlled by several master transcription factors. Ubiquitin ligases, which mediate ubiquitination of proteins, including transcription factors in the protein degradation pathway, are also believed to regulate secondary wall biosynthesis; however, the exact ubiquitin ligases involved in secondary wall formation have not yet been identified. We conducted a gene co-expression network analysis and found that ATL54, annotated as a RING-finger protein, was highly co-expressed with several transcription factor and enzyme genes involved in secondary wall formation. A recombinant ATL54 protein showed ubiquitin ligase activity. The expression of several biosynthetic genes of cellulose, lignin, and xylan in apical portions of inflorescence stems was up-regulated by ATL54 knock-out. The expression of Xylem Cysteine Peptidase1 (XCP1), which participates in the programmed cell death process of xylem tracheary elements, was down-regulated in middle stem portions of both ATL54-knock-out and ATL54-overexpressed mutants. Alteration of ATL54 expression levels did not, however, affect lignin and polysaccharide content and composition in whole mature stems. Our results suggest that ATL54 is an E3 ubiquitin ligase involved in secondary wall biosynthesis and programmed cell death during xylogenesis. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 30 2 169 177 20130625 10.5511/plantbiotechnology.13.0304a masaomi-portal/published_papers/36324654 Umezawa Toshiaki Ragamustari Komara Safendrri Nakatsubo Tomoyuki Wada Shohei Li Laigeng Yamamura Masaomi Sakakibara Norikazu Takefumi Hattori Suzuki Shiro Chiang L. Vincent A lignan O-methyltransferase catalyzing the regioselective methylation of matairesinol in Carthamus tinctorius. Lignans are a group of plant phenolic compounds with various biological activities, including antitumor and antioxidant properties. O-Methylation is a critical step in biosynthesis of these compounds. However, little is known about the O-methyltransferase (OMT) enzymes that catalyze lignan O-methylation. We discovered a highly regioselective OMT activity in safflower (Carthamus tinctorius) seeds that catalyzed the methylation of matairesinol, a dibenzylbutyrolactone lignan, into 4′-O-methylmatairesinol (arctigenin) but not 4-O-methylmatairesinol (isoarctigenin). By examining such OMT activity in correlation with OMT transcript abundances during seed development, we cloned a few putative OMT cDNAs and produced their recombinant proteins in Escherichia coli. Among them, one protein exhibited O-methylation activity for matairesinol with the regioselectivity identical to that of the plant protein, and was named C. tinctorius matairesinol OMT (CtMROMT). CtMROMT did not show any detectable OMT activities towards phenylpropanoid monomers under the reaction conditions tested, while it methylated flavonoid apigenin efficiently into 4′-O-methylapigenin (acacetin). However, quantitative real-time polymerase chain reaction analysis demonstrated that expression of the CtMROMT gene was synchronized with the CtMROMT activity profile and arctigenin accumulation in the plant. These results demonstrated that CtMROMT is a novel plant OMT for lignan methylation. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 30 2 97 109 20130625 10.5511/plantbiotechnology.12.1230a masaomi-portal/published_papers/36324657 Masaomi Yamamura Soichiro Noda Takefumi Hattori Amiu Shino Jun Kikuchi Keiji Takebe Shuichiro Tagane Mitsuru Gau Naohiro Uwatoko Masahiro Mii Shiro Suzuki Daisuke Shibata Toshiaki Umezawa Characterization of lignocellulose of Erianthus arundinaceus in relation to enzymatic saccharification efficiency. This article has been retracted at the request of the authors and under the agreement between the Editor-in-chief, Taku Demura and the authors. Japanese Society for Plant Cell and Molecular Biology 日本植物細胞分子生物学会 Plant Biotechnology 1342-4580 30 25 35 20130325 10.5511/plantbiotechnology.12.1127a masaomi-portal/published_papers/36324658 Masaomi Yamamura Takefumi Hattori Shiro Suzuki Daisuke Shibata Toshiaki Umezawa Microscale thioacidolysis method for the rapid analysis of β-O-4 substructures in lignin Thioacidolysis is a method to detect the β-O-4 substructures of lignin, and has been employed as a diagnostic test for the presence of lignin. However, the conventional thioacidolysis protocol is low-throughput and is a bottleneck in the characterization of lignins in a large number of samples such as transgenic lines. Recently, a rapid analysis protocol for thioacidolysis was reported. In this study, we modified mainly the work-up process. Our microscale protocol showed higher yields of thioacidolysis products than the conventional protocol. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 29 4 419 423 20120925 10.5511/plantbiotechnology.12.0627a masaomi-portal/published_papers/36324659 Masaomi Yamamura Kinya Akashi Akiho Yokota Takefumi Hattori Shiro Suzuki Daisuke Shibata Toshiaki Umezawa Characterization of Jatropha curcas lignins Lignins of Jatropha curcas organs were qualitatively and quantitatively characterized by thioglycolic acid, thioacidolysis, and nitrobenzene oxidation methods. The lignin content of the seed coat was 49.4%, and was the highest among various organs of the plant, while the stem had 15.9% lignin, within the range of usual lignin contents of angiosperm trees. Lignin aromatic components of all organs were composed of guaiacyl and syringyl units. Nitrobenzene oxidation indicated that the ratios of syringyl to guaiacyl lignins in the fruit coat and stem were higher than those in other organs. This study provides basic data for the total utilization of J. curcas wood. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 29 2 179 183 20120625 10.5511/plantbiotechnology.12.0515b masaomi-portal/published_papers/38395446 Masaomi Yamamura Yuichiro Otake Soichiro Noda Takefumi Hattori Keiji Takabe Shiro Suzuki Nozomu Sakurai Hideyuki Suzuki Masakazu Ike Ken Tokuyasu Jun Kikuchi Daisuke Shibata Toshiaki Umezawa CHARACTERIZATION OF LIGNIN AND RELATED COMPOUNDS OF ERIANTHUS RAVENNAE PHARMACEUTICAL BIOLOGY 1388-0209 50 5 671 672 20120500 masaomi-portal/published_papers/36324660 Masaomi Yamamura Shohei Wada Norikazu Sakakibara Tomoyuki Nakatsubo Shiro Suzuki Takefumi Hattori Migiwa Takeda Nozomu Sakurai Hideyuki Suzuki Daisuke Shibata Toshiaki Umezawa Occurrence of guaiacyl/p-hydroxyphenyl lignin in Arabidopsis thaliana T87 cells Arabidopsis thaliana is the most widely used model plant in the area of plant biosciences, and the cell line T87 is one of the most commonly used lines in Arabidopsis cell cultures. The characteristics of lignins in cultured cells often differ from those of lignins in intact plants. To date, nothing is known about the lignins of T87 cells. In this study, we characterized lignins of T87 cells using six analytical methods; phloroglucinol staining, thioacidolysis, nitrobenzene oxidation, alkaline hydrolysis, and Klason and acetyl bromide methods. These analyses clearly showed that lignins of T87 cells are composed of guaiacyl and p-hydroxyphenyl units, and are quite different from lignin found in the Arabidopsis inflorescence stem, which is composed of guaiacyl and syringyl units. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 28 1 1 8 20110325 10.5511/plantbiotechnology.10.0823c masaomi-portal/published_papers/36324661 Masaomi Yamamura Takefumi Hattori Shiro Suzuki Daisuke Shibata Toshiaki Umezawa Microscale alkaline nitrobenzene oxidation method for high-throughput determination of lignin aromatic components. The nitrobenzene oxidation method is widely used for structural analysis of lignin. However, the conventional nitrobenzene oxidation method has several drawbacks including the requirement of a sizeable amount of sample material and the rather slow completion of the reaction process. In this paper, we describe a microscale nitrobenzene oxidation method using deuterium-labeled vanillin and syringaldehyde as internal standards. Using this method, we show that the microscale nitrobenzene oxidation method realized high-throughput determination of lignin components using a small amount of sample, i.e. 10 mg per reaction, and high reproducibility. Due to the small sample sizes, the oxidation reaction and extraction steps of a number of samples can be completed in parallel, thus enabling us to process more than 40 samples per day. Japanese Society for Plant Cell and Molecular Biology Plant Biotechnology 1342-4580 27 4 305 310 20100925 10.5511/plantbiotechnology.27.305 masaomi-portal/published_papers/36324662 Masaomi Yamamura Shiro Suzuki Takefumi Hattori Toshiaki Umezawa Subunit composition of hinokiresinol synthase controls enantiomeric selectivity in hinokiresinol formation Asparagus officinalis hinokiresinol synthase (HRS) is composed of two subunits, HRSalpha and HRSbeta. Individually, each subunit forms (E)-hinokiresinol (EHR) from 4-coumaryl 4-coumarate, whereas a mixture of both subunits forms (Z)-hinokiresinol (ZHR) from the same substrate. In this study, we analyzed the enantiomeric compositions of ZHR and EHR formed after incubation of 4-coumaryl 4-coumarate with recombinant subunit proteins, recHRSalpha and/or recHRSbeta, and with naturally occurring A. officinalis ZHR. The enantiomeric composition of ZHR formed by the mixture of recHRSalpha and recHRSbeta was (+)-100% enantiomer excess (e.e.), identical to that of A. officinalis ZHR. In contrast, the enantiomeric compositions of EHR formed by recHRSalpha and recHRSbeta, individually, were (-)-20.6 and (-)-9.0% e.e., respectively. These results clearly demonstrate that the subunit composition of A. officinalis HRS controls not only cis/trans isomerism but also enantioselectivity in hinokiresinol formation. Organic & Biomolecular Chemistry 1477-0539 8 5 1106 1110 20100106 10.1039/B918656E masaomi-portal/published_papers/39663014 鈴木史朗山村正臣梅澤俊明ヒノキレジノール合成酵素化学と生物 592-594 null null 20080000 10.1271/kagakutoseibutsu.46.592 masaomi-portal/published_papers/36324663 Shiro Suzuki Masaomi Yamamura Takefumi Hattori Tomoyuki Nakatsubo Toshiaki Umezawa The subunit composition of hinokiresinol synthase controls geometrical selectivity in norlignan formation. Proceedings of the National Academy of Sciences of the United States of America 0027-8424 104 21008 21013 20071226 10.1073/pnas.0710357105 masaomi-portal/published_papers/36324664 Shiro Suzuki Masaomi Yamamura Mikio Shimada Toshiaki Umezawa A heartwood norlignan, (E)-hinokiresinol, is formed from 4-coumaryl 4-coumarate by a Cryptomeria japonica enzyme preparation An enzyme preparation from the cultured cells of Cryptomeria japonica catalyses the formation of a heartwood norlignan, (E)-hinokiresinol, from two distinct phenylpropanoid monomers: 4-coumaroyl CoA and 4-coumaryl alcohol, and from a dimer: 4-coumaryl 4-coumarate. Chemical Communications 1359-7345 24 2838 2839 20041028 10.1039/b409686j masaomi-portal/misc/38392688 陳旭石森元幸岩田洋佳山村正臣飛松裕基梅澤俊明藤原徹山崎清志高梨秀樹藤本優堤伸浩米田淳一小柴太一徳永毅鐘ケ江弘美 4-4-4 Comparison of different methods and datasets for genome-wide association study -a case study in sorghum(4-4 植物の代謝成分と農作物の品質 2020年度岡山大会) 一般社団法人日本土壌肥料学会日本土壌肥料学会講演要旨集 2424-0575 66 72 72 20200000 10.20710/dohikouen.66.0_72_1 1390004951537212672 masaomi-portal/misc/44045929 山村正臣高田依里飛松裕基大橋康典山田竜彦梅澤俊明梅澤俊明近赤外/ケモメトリックスによるPEG薬液特性の迅速解析日本木材学会大会研究発表要旨集(完全版)(CD-ROM) 1349-0532 69th null null 20190000 masaomi-portal/misc/37279942 Tarmadi Didi Yoshimura Tsuyoshi Tobimatsu Yuki Yamamura Masaomi Miyamoto Takuji Miyagawa Yasuyuki Umezawa Toshiaki The effects of various lignocelluloses and lignins on physiological responses of a lower termite, Coptotermes formosanus Japan Wood Research Society 日本木材学会 Journal of wood science : official journal of the Japan Wood Research Society 1435-0211 63 5 464 472 20170000 masaomi-portal/misc/38053308 Toshiaki Umezawa Safendrri Komara Ragamustari Eiichiro Ono Masaomi Yamamura O-Methyltransferases Involved in Lignan Biosynthesis FORMATION, STRUCTURE, AND ACTIVITY OF PHYTOCHEMICALS, VOL 45 0079-9920 45 99 114 20150000 10.1007/978-3-319-20397-3_4 masaomi-portal/misc/38623184 Toshiaki Umezawa Masaomi Yamamura Tomoyuki Nakatsubo Shiro Suzuki Takefumi Hattori Stereoselectivity of the Biosynthesis of Norlignans and Related Compounds BIOLOGICAL ACTIVITY OF PHYTOCHEMICALS 0079-9920 41 179 197 20110000 10.1007/978-1-4419-7299-6_12 masaomi-portal/misc/38053307 Tomoyuki Nakatsubo Masaomi Yamamura Shiro Suzuki Hattori Takefumi Toshiaki Umezawa Stereochemical mechanisms for lignan and norlignan biosynthesis ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 0065-7727 237 null null 20090300 masaomi-portal/misc/40003858 鈴木史朗山村正臣服部武文中坪朋文梅澤俊明ヒノキレジノール生成反応の幾何選択性はヒノキレジノール合成酵素のサブユニット組成に依存する第49回日本植物生理学会年会，札幌，p. 143，2008． null null 20080000 10.14841/jspp.2008.0.0143.0 masaomi-portal/books_etc/36324677 山村正臣梅澤俊明リグニンの迅速評価システム CMC Publishing Co.,Ltd. 株式会社シーエムシー出版 20200300 masaomi-portal/books_etc/36324679 Masaomi Yamamura 山村正臣 3.5.2 ニトロベンゼン酸化分解法のミクロ化(分担執筆) 弘前大学出版会 20160200 masaomi-portal/books_etc/36324678 Masaomi Yamamura 山村正臣 3.5.6 チオアシドリシス法のミクロ化(分担執筆) 弘前大学出版会 20160200