Semi-synthesis of oxygenated dolabellane diterpenes with highly in vitro anti-HIV-1 activity |
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Affiliation: | 1. Institute of Biophotonics, School of Biomedical Science and Engineering, National Yang-Ming University, Taipei, 112, Taiwan;2. Biophotonics and Molecular Imaging Research Center (BMIRC), National Yang-Ming University, Taipei, 112, Taiwan;3. Medical Biophysics Group, Institute of Physiology and Pathophysiology, University of Heidelberg, 69120 Heidelberg, Germany |
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Abstract: | Research on dolabellane diterpenes of brown algae Dictyota spp. has shown that these diterpenoids have strong anti-HIV-1 activity, but there are not data about antiviral activity of dolabellane diterpenes isolated from octocorals, which are antipodes of those isolated from the brown algae. Dolabellanes 13-keto-1(R),11(S)-dolabella-3(E),7(E),12(18)-triene (1) and β-Araneosene (2) were isolated from the Caribbean octocoral Eunicea laciniata, and both showed low anti-HIV-1 activity and low toxicity. Since it was shown that oxygenated dolabellanes from algae have better anti-HIV-1 activity, in this work some derivatives of the main dolabellane of E. laciniata 1 were obtained by epoxidation (3), epoxide opening (4), and allylic oxidation (5). The derivatives showed significant improvement in the anti-HIV-1potency (100-fold), being compounds 3 and 5 the most active ones. Their high antiviral activities, along with their low cytotoxicity, make them promissory antiviral compounds; and it is worth noting that the absolute configuration at the ring junction in the dolabellane skeleton does not seem to be determinant in the antiviral potency of these diterpeneoids. |
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Keywords: | Antivirals Marine natural products Dolabellane diterpenes HIV-1 |
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