Effective Hydrogenation of 3-(2"-furyl)- and 3-(2"-thienyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one in Selected Yeast Cultures

被引:12
|
作者
Luzny, Mateusz [1 ]
Krzywda, Martyna [1 ]
Kozlowska, Ewa [1 ]
Kostrzewa-Suslow, Edyta [1 ]
Janeczko, Tomasz [1 ]
机构
[1] Wroclaw Univ Environm & Life Sci, Dept Chem, Norwida 25, PL-50375 Wroclaw, Poland
来源
MOLECULES | 2019年 / 24卷 / 17期
关键词
biotransformation; chalcone; dihydrochalcone; yeast; sweeteners; ACTIVATED C=C-BONDS; ENANTIOSELECTIVE REDUCTION; CHALCONES; ALPHA; BIOTRANSFORMATION; DIHYDROCHALCONE; ANTIOXIDANT; SWEETENERS; ANALOGS; PRODUCE;
D O I
10.3390/molecules24173185
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Biotransformations were performed on eight selected yeast strains, all of which were able to selectively hydrogenate the chalcone derivatives 3-(2 ''-furyl)(1) and 3-(2 ''-thienyl)-1-(2'-hydroxyphenyl)-prop-2-en-1-one (3) into 3-(2 ''-furyl)-(2) and 3-(2 ''-thienyl)-1-(2'-hydroxyphenyl)-propan-1-one (4) respectively. The highest efficiency of hydrogenation of the double bond in the substrate 1 was observed in the cultures of Saccharomyces cerevisiae KCh 464 and Yarrowia lipolytica KCh 71 strains. The substrate was converted into the product with > 99% conversion just in six hours after biotransformation started. The compound containing the sulfur atom in its structure was most effectively transformed by the Yarrowia lipolytica KCh 71 culture strain (conversion > 99%, obtained after three hours of substrate incubation). Also, we observed that, different strains of tested yeasts are able to carry out the bioreduction of the used substrate with different yields, depending on the presence of induced and constitutive ene reductases in their cells. The biggest advantage of this process is the efficient production of one product, practically without the formation of side products.
引用
收藏
页数:10
相关论文
共 50 条
  • [31] Synthesis, Characterization, and Crystal Structure of (2E)-3-(4-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
    Cathryn A. Slabber
    Craig D. Grimmer
    Orde Q. Munro
    Ross S. Robinson
    Journal of Chemical Crystallography, 2018, 48 : 213 - 219
  • [32] (2E)-1-(2-Bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one
    Jasinski, Jerry P.
    Butcher, Ray J.
    Veena, K.
    Narayana, B.
    Yathirajan, H. S.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1638 - U1150
  • [33] 1-(2-Hydroxy-4-methoxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one
    Thippeswamy, G. B.
    Kumar, D. Vijay
    Jayashree, B. S.
    Sridhar, M. A.
    Prasad, J. Shashidhara
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O829 - U78
  • [34] (E)-3-(4-Fluorophenyl)-1-(2-nitro-phenyl)prop-2-en-1-one
    Pan, Zhi-fang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1414 - O1414
  • [35] (E)-3-(Furan-2-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
    Kapoor, Kamini
    Gupta, Vivek K.
    Kant, Rajni
    Pandya, Jalpa R.
    Lade, Sunil B.
    Joshi, Hitendra S.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O3185 - U1503
  • [36] (2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one
    Harrison, William T. A.
    Mayekar, A. N.
    Yathirajan, H. S.
    Narayana, B.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2552 - U385
  • [37] 1-(4-Chlorophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one
    Guo, Meng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2302 - U276
  • [38] Crystal structure of (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one
    Ezhilarasi, K. S.
    Jonathan, D. Reuben
    Vasanthi, R.
    Reyathi, R. K.
    Usha, G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O371 - U703
  • [39] (E)-1-(4-Aminophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
    Kobkeatthawin, Thawanrat
    Chantrapromma, Suchada
    Saewan, Nisakorn
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1204 - U1141
  • [40] 3-(4-Fluorophenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one
    Zhao, Pu-Su
    Wang, Xian
    Guo, Huan-Mei
    Jian, Fang-Fang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1402 - U2963