17861-18-6Relevant articles and documents
Room-Temperature meta-Functionalization: Pd(II)-Catalyzed Synthesis of 1,3,5-Trialkenyl Arene and meta-Hydroxylated Olefin
Bera, Milan,Sahoo, Santosh K.,Maiti, Debabrata
, p. 3575 - 3579 (2016)
Development of meta-C-H functionalization reactions at room temperature continues to be a tough challenge. Use of a phosphonate linkage allowed a Pd (II)-catalyzed meta-C-H functionalization at room temperature while incorporating a cyanophenol-based dire
Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells
Tan, Yu-Jia,Ali,Tee, Sheng-Yang,Teo, Jun-Ting,Xi, Yu,Go, Mei-Lin,Lam
, (2019/08/20)
Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability.
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 (2017/03/27)
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.).
