861446-14-2Relevant articles and documents
Immobilized Lipase Based on Hollow Mesoporous Silicon Spheres for Efficient Enzymatic Synthesis of Resveratrol Ester Derivatives
Xu, Liu-Jia,Yang, Tao,Wang, Jing,Huang, Feng-Hong,Zheng, Ming-Ming
, p. 9067 - 9075 (2021/03/01)
Enzymatic esterification of resveratrol is crucial for its potential application in lipophilic foods and drugs. However, the poor activity of the free enzyme hinders the reaction. In this work, the highly efficient enzymatic synthesis of resveratrol ester derivatives was achieved by immobilized lipase on hydrophobic modified hollow mesoporous silicon spheres (HMSS-C8). We preliminarily explored the use of Candida sp. 99-125 lipase (CSL) for the acylation of resveratrol, with a regioselectivity toward 3-OH- over 4'-OH-acylation. HMSS-C8 provided ideal accommodation for CSL with a loading capacity of up to 652 mg/g. The catalytic efficiency of CSL@HMSS-C8 was 15 times higher than that of free CSL, and the conversion of resveratrol reached 98.7% within only 2 h, which is the fastest value recorded in the current literature. After 10 cycles, the conversion remained up to 86.3%. Benefiting from better lipid solubility, the relative oxidation stability index values of oil containing monoester derivatives were 43.1%-68.8% and 23.9%-33.2% higher than that of refined oil and oil containing resveratrol, respectively. This research provides a new pathway for efficient enzymatic synthesis of resveratrol ester derivatives and demonstrates the potential application of resveratrol monoester derivatives as a group of excellent lipid-soluble antioxidants.
Synthesis of amphiphilic resveratrol lipoconjugates and evaluation of their anticancer activity towards neuroblastoma SH-SY5Y cell line
Chillemi, Rosa,Cardullo, Nunzio,Greco, Valentina,Malfa, Giuseppe,Tomasello, Barbara,Sciuto, Sebastiano
, p. 467 - 481 (2015/05/13)
Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity.
Practical preparation of resveratrol 3-O-β-D-glucuronide
Jungong, Christian S.,Novikov, Alexei V.
, p. 3589 - 3597,9 (2020/08/31)
A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.
