20107-95-3Relevant academic research and scientific papers
Ent-Beyerane Diterpenes as a Key Platform for the Development of ArnT-Mediated Colistin Resistance Inhibitors
Ascenzioni, Fiorentina,Botta, Bruno,Calcaterra, Andrea,Cammarone, Silvia,Cappiello, Floriana,Casciaro, Bruno,Cavinato, Luca,Corradi, Silvia,Erazo, Silvia,Ghirga, Francesca,Imperi, Francesco,Loffredo, Maria Rosa,Lucantoni, Federica,Mangoni, Maria Luisa,Mori, Mattia,Quaglio, Deborah,Stefanelli, Roberta,Vergine, Valeria
, p. 10891 - 10901 (2020)
Colistin is a last-resort antibiotic for the treatment of multidrug resistant Gram-negative bacterial infections. Recently, a natural ent-beyerene diterpene was identified as a promising inhibitor of the enzyme responsible for colistin resistance mediated by lipid A aminoarabinosylation in Gram-negative bacteria, namely, ArnT (undecaprenyl phosphate-alpha-4-amino-4-deoxy-l-arabinose arabinosyl transferase). Here, semisynthetic analogues of hit were designed, synthetized, and tested against colistin-resistant Pseudomonas aeruginosa strains including clinical isolates to exploit the versatility of the diterpene scaffold. Microbiological assays coupled with molecular modeling indicated that for a more efficient colistin adjuvant activity, likely resulting from inhibition of the ArnT activity by the selected compounds and therefore from their interaction with the catalytic site of ArnT, an ent-beyerane scaffold is required along with an oxalate-like group at C-18/C-19 or a sugar residue at C-19 to resemble L-Ara4N. The ent-beyerane skeleton is identified for the first time as a privileged scaffold for further cost-effective development of valuable colistin resistance inhibitors.
Antileishmanial activity and cytotoxicity of ent-beyerene diterpenoids
Murillo, Jilmar A.,Gil, Juan F.,Upegui, Yulieth A.,Restrepo, Adriana M.,Robledo, Sara M.,Qui?ones, Winston,Echeverri, Fernando,San Martin, Aurelio,Olivo, Horacio F.,Escobar, Gustavo
, p. 153 - 160 (2019)
We describe the in vitro activity of two natural isomeric ent-beyerene diterpenes, several derivatives and synthetic intermediates. Beyerenols 1 and 2 showed EC50 of 4.6 ± 9.4 and 5.3 ± 9.4 μg/mL against amastigotes of L. (V) brazilensis, with
Higher Isoprenoids: Part XV - Diterpenoids of Erythroxylon monogynum Roxb. (Part 2): Monogynol and Hydroxymonogynol
Kapadi, A. H.,Dev, Sukh
, p. 970 - 977 (2007/10/02)
The Structure and absolute stereochemistry of monogynol (1) and hydroxymonogynol (23), the two diterpenoids from the wood of Erythroxylon monogynum, have been unequivocally established.
