34701-63-8Relevant articles and documents
Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from Thermobifida fusca YX
Rühlmann, Ansgar,Antovic, Dragutin,Müller, Thomas J. J.,Urlacher, Vlada B.
, p. 984 - 994 (2017)
Since the past decades, the plant stilbenoid resveratrol has gained significant attention of the general public as well as the research community due to its versatile medicinal properties. Apart from resveratrol, there is also an increasing interest in other plant stilbenoids because of their different potential biological activities. In order to meet the increasing demand for stilbenoids, alternative and sustainable approaches for their production are needed. We identified the cytochrome P450 monooxygenase 154E1 from Thermobifida fusca YX (CYP154E1) which enables the synthesis of (E)-4,4′-dihydroxystilbene via direct double hydroxylation of (E)-stilbene. The construction of a triple mutant led to a more than six-fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)-stilbene but also possessed remarkable activity towards ortho- and meta-substituted hydroxystilbenes leading to resveratrol, (E)-2,4′-dihydroxystilbene, (E)-2,4′,5-trihydroxystilbene and (E)-3,4′-dihydroxystilbene. The combination of protein engineering and the use of methyl-β-cyclodextrin as substrate solubilizing agent resulted in product titers of up to 4.2 g L?1 and enzyme total turnover numbers (TTN) of up to 20,000. (Figure presented.).
Synthesis and nematocidal activity of hydroxystilbenes
Ali,Kondo,Tsuda
, p. 1130 - 1136 (2007/10/02)
Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.
