Semi-synthesis of oxygenated dolabellane diterpenes with highly in vitro anti-HIV-1 activity

Marine natural products

“…779 A modular approach to a number of cladiellin MNPs using a gold-catalysed tandem reaction of 1,7-diynes has been reported. 780 Hippuristanol (Isis hippuris) 781 analogues have been evaluated as inhibitors of eukaryotic translation initiation, 782 cembranoid and ergosterol MNPs from Vietnamese cnidarians were found to exhibit selective in vitro activity against T. brucei, 783 a number of diterpenes (Sinularia maxima) were found to be modest to poor inhibitors of NF-kB transcriptional activation, 784 structurally simpler analogues of fuscol/eunicol exhibit comparable or better anti-inammatory activity in the mouse ear edema assay, 785 semi-synthetic oxygenated dolabellane diterpenes exhibit in vitro anti-HIV activity, 786 further semisynthetic examples of hydoxysterols were found to induce pregnane X receptor transactivation, 787 exibilide 788 exhibits in vivo anti-neuroinammatory activity in rats, 789 11-epi-sinulariolide acetate inhibits carcinoma cell migration and invasion by suppressing a number of phosphorylationdependent pathways, 790 13-acetoxysarcocrassolide induces apoptosis in carcinoma cells by activation of p38/JNK and suppression of PI3K/AKT pathways, 791 and cembranoids from Sarcophyton glaucum exhibit cytotoxicity towards a murine melanoma cell line. 792,793 9 Bryozoans There were only three reports (containing 19 compounds) of new metabolites isolated from bryozoans in 2014, which is a large increase on 2013 when only one new metabolite was reported from this understudied phylum.…”

Dolabella‐3,7,18‐triene, the main constituent of the essential oil of the white lotus flower (Nymphaea lotus, Nymphaeaceae)

“…Pardo‐Vargas et al . (2014) furthered their investigation on dolabellene diterpenoids and their anti‐HIV activities, isolating 13‐keto‐1(R),11(S)‐dolabella‐3(E),7(E),12(18)‐triene from Caribbean octocorals of the species Eunicea laciniata . This compound showed low anti‐HIV‐1 activity and low toxicity, but their derivatives obtained by epoxidation and allylic oxidation showed significant improvement in the anti‐HIV‐1 potency.…”

Structure-Activity Relationship (SAR) Studies to Maximize the Activity of Compounds Isolated from Octocorals

“…Supported by the fact that oxygenated dolabellanes, isolated from brown algae, showed good antiviral activity [27,28], the authors of this article obtained derivatives 16-18 by epoxidation, by epoxide opening and by allylic oxidation, respectively. These oxygenated compounds showed significant improvement in the antiHIV-1 potency (100-fold) [29]. Their high antiviral activity, along with their low cytotoxicity, makes them promising antiviral compounds, and is a good example of the usefulness of this strategy to improve the biological activity of marine natural products.…”