26563-68-8Relevant articles and documents
Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid
Sommerwerk, Sven,Heller, Lucie,Serbian, Immo,Csuk, René
, p. 8528 - 8534 (2016/02/03)
The four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids (maslinic, augustic, bredemolic and 3-epi-maslinic acid) were easily accessed from one single starting material, oleanolic acid. The procedures allow the medium-to-large scale preparation of these valuable starting materials. Except for maslinic acid, the triterpenoic acids showed only a low cytotoxicity towards several human tumor cell lines.
Convenient and chromatography-free partial syntheses of maslinic acid and augustic acid
Sommerwerk, Sven,Csuk, René
, p. 5156 - 5158 (2014/12/11)
A convenient and chromatography-free 4-step synthesis of analytically pure maslinic acid (1, 41.2%) from oleanolic acid has been developed. Slight variations in the final steps gave an excellent yield of isomeric augustic acid (7, 71.9%).
Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
Parra, Andres,Martin-Fonseca, Samuel,Rivas, Francisco,Reyes-Zurita, Fernando J.,Medina-O'Donnell, Marta,Martinez, Antonio,Garcia-Granados, Andres,Lupia?ez, Jose A.,Albericio, Fernando
, p. 278 - 301 (2014/02/14)
A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution- and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the b16f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC 50 values between 0.31 and 15.6 μM, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs.
