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| 1 | Induced biosyntheses of a novel butyrophenone and two aromatic polyketides in the plant pathogen Stagonospora nodorum显示文摘Fungal aromatic compounds comprise an important and structurally diverse group of secondary metabolites.Several genome sequencing projects revealed many putative biosynthetic gene clusters of fungal aromatic compounds,but many of these genes seem to be silent under typical laboratory culture conditions.To gain access to this untapped reservoir of natural products,we utilized chemical epigenetic modifiers to induce the expression of dormant biosynthetic genes.As a result,the concomitant supplementation of the histone deacetylase inhibitors suberoylanilide hydroxamic acid(500mM)and nicotinamide(50mM)to the culture medium of a fungal pathogen,Stagonospora nodorum,resulted in the isolation of three aromatic compounds(1-3),including a novel natural butyrophenone,(+)-4'-methoxy-(2S)-methylbutyrophenone(1),and two known polyketides,alternariol(2)and(-)-(3R)-mellein methyl ether(3). | Xiao-Long YANG Takayoshi AWAKAWA Toshiyuki WAKIMOTO Ikuro ABE | 2013 | Natural Products and Bioprospecting2013，3，4： | 9 |
| 2 | Biosynthesis of clinically used antibiotic fusidic acid and identification of two short-chain dehydrogenase/reductases with converse stereoselectivity显示文摘Fusidic acid is the only fusidane-type antibiotic that has been clinically used. However,biosynthesis of this important molecule in fungi is poorly understood. We have recently elucidated the biosynthesis of fusidane-type antibiotic helvolic acid, which provides us with clues to identify a possible gene cluster for fusidic acid(fus cluster). This gene cluster consists of eight genes, among which six are conserved in the helvolic acid gene cluster except fusC1 and fusB1. Introduction of the two genes into the Aspergillus oryzae NSAR1 expressing the conserved six genes led to the production of fusidic acid. A stepwise introduction of fusC1 and fusB1 revealed that the two genes worked independently without a strict reaction order. Notably, we identified two short-chain dehydrogenase/reductase genes fusC1 and fusC2 in the fus cluster, which showed converse stereoselectivity in 3-ketoreduction. This is the first report on the biosynthesis and heterologous expression of fusidic acid. | Zhiqin Cao Shaoyang Li Jianming Lv Hao Gao Guodong Chen Takayoshi Awakawa Ikuro Abe Xinsheng Yao Dan Hu | 2019 | Acta Pharmaceutica Sinica B2019，9，2： | 3 |
| 3 | Epigenetic modifier-induced biosynthesis of novel fusaric acid derivatives in endophytic fungi from Datura stramonium L.显示文摘The treatment of fungi with DNA methyltransferase(DNMT)and/or histone deacetylase(HDAC)inhibitors is a promising way to activate secondary metabolite biosynthetic pathways that are dormant under normal conditions.In this study,we included an HDAC inhibitor,suberoylanilide hydroxamic acid(SBHA),in the culture medium of endophytic fungi isolated from the medicinal plant Datura stramonium L.The production of two compounds was induced in the culture supplemented with SBHA,and their structures were determined to be the fusaric acid derivatives 5-butyl-6-oxo-1,6-dihydropyridine-2-carboxylic acid and 5-(but-9-enyl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid.The result confirmed that the use of chemical epigenetic modifiers is an effective technique for promoting the expression of silent biosynthetic pathways to produce unique secondary metabolites. | Han-Jing CHEN Takayoshi AWAKAWA Jie-Yin SUN Toshiyuki WAKIMOTO Ikuro ABE | 2013 | Natural Products and Bioprospecting2013，3，1： | 2 |
| 4 | Pentaketide resorcylic acid synthesis by type Ⅲ polyketide synthase from Neurospora crassa显示文摘 | Funa N Awakawa T Horinouchi S | 2007 | J Biol Chem2007，282，14： | 1 |
| 5 | Classification of Barrett's epithelium by magnifying endoscopy显示文摘 | ENDO T AWAKAWA T TAKAHASHI H ed al | 2002 | Gastrointest Endosc2002，55，： | 1 |
| 6 | Classification of Barrett's epithelium by magnifying endoscopy 显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 7 | Classification of Barrett's epithelium by magnifying endoscopy显示文摘 | ENDO T AWAKAWA T TAKAHASHI T | 2002 | Gastrointest Endosc2002，55，： | 1 |
| 8 | Classification of Battett' s epithelium by magnifying endoscopic 显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 9 | Classification of Barrett's epithelium by magnifying endoscopy显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 10 | Classification of Barrett’s epithelium by magnifying endoscopy显示文摘 | Takao Endo Teruhito Awakawa Hiroaki Takahashi Yoshiaki Arimura Fumio Itoh Kentaro Yamashita Sigeru Sasaki Hiroyuki Yamamoto Xiufen Tang Kohzoh Imai | 2002 | Gastrointestinal Endoscopy2002，，6： | 1 |
| 11 | Extensive expansion of the chemical diversity of fusidane-type antibiotics using a stochastic combinational strategy显示文摘Fusidane-type antibiotics,represented by helvolic acid,fusidic acid and cephalosporin P1,are fungi-derived antimicrobials with little cross-resistance to commonly used antibiotics.Generation of new fusidane-type derivatives is therefore of great value,but this is hindered by available approaches.Here,we developed a stochastic combinational strategy by random assembly of all the post-tailoring genes derived from helvolic acid,fusidic acid,and cephalosporin P1 biosynthetic pathways in a strain that produces their common intermediate.Among a total of 27 gene combinations,24 combinations produce expected products and afford 58 fusidane-type analogues,of which 54 are new compounds.Moreover,random gene combination can induce unexpected activity of some post-tailoring enzymes,leading to a further increase in chemical diversity.These newly generated derivatives provide new insights into the structure-activity relationship of fusidane-type antibiotics.The stochastic combinational strategy established in this study proves to be a powerful approach for expanding structural diversity of natural products. | Xiaojun Song Jianming Lv Zhiqin Cao Huiyun Huang Guodong Chen Takayoshi Awakawa Dan Hu Hao Gao Ikuro Abe Xinsheng Yao | 2021 | Acta Pharmaceutica Sinica B2021，11，6： | 1 |
| 12 | Classification of Barrett's epithelium by magnifying endoscopy 显示文摘 | ENDO T AWAKAWA T TAKAHASHI H | 2002 | Gastrointest Endose2002，55，： | 1 |
| 13 | Classification of Barrett' s epithelium by magnifying endoscopy显示文摘 | Endo T Awakawa T Takahashi H Arimura Y | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 14 | Classification of Barrett Epithelium by Magnifying Endoscopy显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastroentest Endosc2002，55，： | 1 |
| 15 | Classification of Barrett's epithelium by magnifying endoseopy显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastrointest Endosc2002，55，： | 1 |
| 16 | Classification of Barrett'sepithelium by magnifying endoscopy显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 17 | Classification of Barrett epithelium by magnifying endoscopy 显示文摘 | Endo T Awakawa T Takahashi H | 2002 | Gastroentest Endosc2002，55，6： | 1 |
| 18 | Classification of Barretts epithelium by magnifying endoscopy 显示文摘 | ENDO T AWAKAWA T TAKAHASHI H | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 19 | Classification of Barrett's epithelium by magnifying endoscopy 显示文摘 | Endo T Awakawa T Takahashi T | 2002 | Gastrointest Endosc2002，55，6： | 1 |
| 20 | Classification of Barrett’s epithelium by magnifying endoscopy显示文摘 | Takao Endo Teruhito Awakawa Hiroaki Takahashi Yoshiaki Arimura Fumio Itoh Kentaro Yamashita Sigeru Sasaki Hiroyuki Yamamoto Xiufen Tang Kohzoh Imai | 2002 | Gastrointestinal Endoscopy2002，，6： | 1 |
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