التفاصيل البيبلوغرافية
| العنوان: |
Semisynthesis of Dolabellane Diterpenes: Oxygenated Analogues with Increased Activity against Zika and Chikungunya Viruses |
| المؤلفون: |
Fabián Amaya García (10530783), Claudio Cirne-Santos (308680), Caroline de Souza Barros (10530786), Ana Maria Pinto (10530789), Maria Leonisa Sanchez Nunez (10530792), Valeria Laneuville Teixeira (10530795), Jackson A. L. C. Resende (7521296), Freddy A. Ramos (3772282), Izabel C. N. P. Paixão (10530798), Leonardo Castellanos (2039737) |
| سنة النشر: |
1753 |
| المجموعة: |
Smithsonian Institution: Digital Repository |
| مصطلحات موضوعية: |
Biochemistry, Physiology, Evolutionary Biology, Ecology, Infectious Diseases, Plant Biology, Virology, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, dolabellane diterpenes, CHIKV, dolastane diterpenes, X-ray diffraction experiments, Chikungunya Viruses Brown algae, 21 semisynthetic derivatives, ZIKV, coral, acid-catalyzed epoxide ring opening, EC 50, NMR, SI |
| الوصف: |
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 (1 R ,7 R ,8 R ,11 S )-7,8-epoxy-13-keto-dolabella-3,12(18)-diene ( 2 ), isolated from Eunicea genus 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 (EC 50 ) 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. Compound 9 showed an EC 50 = 0.92 ± 0.08 μM and SI = 820 against ZIKV. |
| نوع الوثيقة: |
article in journal/newspaper |
| اللغة: |
unknown |
| Relation: |
https://figshare.com/articles/journal_contribution/Semisynthesis_of_Dolabellane_Diterpenes_Oxygenated_Analogues_with_Increased_Activity_against_Zika_and_Chikungunya_Viruses/14377272 |
| DOI: |
10.1021/acs.jnatprod.1c00199.s001 |
| الاتاحة: |
https://doi.org/10.1021/acs.jnatprod.1c00199.s001 |
| Rights: |
CC BY-NC 4.0 |
| رقم الانضمام: |
edsbas.53F713D7 |
| قاعدة البيانات: |
BASE |