153081-59-5Relevant articles and documents
Semisynthesis of Dolabellane Diterpenes: Oxygenated Analogues with Increased Activity against Zika and Chikungunya Viruses
Amaya García, Fabián,Cirne-Santos, Claudio,de Souza Barros, Caroline,Pinto, Ana Maria,Sanchez Nunez, Maria Leonisa,Laneuville Teixeira, Valeria,Resende, Jackson A. L. C.,Ramos, Freddy A.,Paix?o, Izabel C. N. P.,Castellanos, Leonardo
, p. 1373 - 1384 (2021)
Brown algae and soft corals represent the main marine sources of dolabellane diterpenes. The antiviral activity of dolabellanes has been studied for those isolated from algae, whereas dolabellanes isolated from soft corals have been barely studied. In this work, a collection of dolabellane diterpenes consisting of five natural and 21 semisynthetic derivatives was constructed, and their antiviral activities against Zika (ZIKV) and Chikungunya (CHIKV) viruses were tested. Dolabellatrienone (1) and (1R,7R,8R,11S)-7,8-epoxy-13-keto-dolabella-3,12(18)-diene (2), isolated fromEuniceagenus soft corals, were employed to obtain 21 dolabellane and dolastane diterpenes by reactions such as allylic oxidations, reductions, acid-catalyzed epoxide ring opening, and acetylations. All of the compounds were identified by a combination of one- and two-dimensional NMR, mass spectrometry, and X-ray diffraction experiments. The cytotoxicites against Vero cells and the antiviral activities against ZIKV and CHIKV was tested to calculate the half-maximal effective concentration (EC50) and selectivity indexes (SIs). In general, the addition of oxygen-containing functional groups improved the bioactivity of dolabellane and dolastane diterpenes against ZIKV and CHIKV replication. Compound9showed an EC50= 0.92 ± 0.08 μM and SI = 820 against ZIKV.
Structures and Reactivities of New Dolabellane Diterpenoids from the Caribbean Gorgonian Eunicea laciniata
Shin, Jongheon,Fenical, William
, p. 3392 - 3398 (2007/10/02)
Five new diterpenoids of the dolabellane class (3-7) have been isolated from the Caribbean gorgonian Eunicea laciniata Duchassaing and Michelotti.The structures of these metabolites were defined by combined spectra and chemical methods.The conformation and reactivity of the 11-membered ring of the dolabellanes was investigated by 1H NMR nuclear Overhauser enhancement difference spectroscopy (NOEDS) and by selected chemical transformations involving transannular cyclizations.