Synthesis and anti-herpes activity of some a-ring functionalized dehydroabietane derivatives
Dehydroabietic acid 5 was converted to the exo-cyclic olefin 7 which was used as a versatile intermediate in the synthesis of A-ring hydroxylated compounds such as 13 and 16 which showed HSV-2 inhibitory activity in the standard plaque assay.
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Cited by (24)
Two distinctly fluorescent BioAIEgens originated from the combination of natural rosin and chromophoric triphenylamine
2023, Journal of Molecular StructureCitation Excerpt :Hence, the transformation of low-added to high-added value of rosin products is a hot topic for forest product researchers. Dehydroabietic acid (DA) is a natural product with hydrogenated phenanthrene structure purified from disproportionated rosin [23–26]. The alicyclic ring of DA is rigid, which may can restrict molecular motion.
Bioconversion of ecotoxic dehydroabietic acid using Rhodococcus actinobacteria
2018, Journal of Hazardous MaterialsCitation Excerpt :Currently, it is important not only to find effective ways to neutralize toxic DHA, but also to obtain new compounds on its basis. The known DHA derivatives have a wide range of biological activities, i.e. antiulcer [43,44], antimicrobial [45], fungicidal [46,47], anxiolytic [48], antiviral [47,49], and antitumour [44,47,50], and also can be used as intermediates to synthesize bioactive compounds [51]. Numerous examples of biodegradation with the formation of stable metabolites (use of inhibitors) or targeted DHA bioconversions are described in the literature.
The natural phytochemical dehydroabietic acid is an anti-aging reagent that mediates the direct activation of SIRT1
2015, Molecular and Cellular EndocrinologyCitation Excerpt :All statistical tests were two-sided, and the threshold for statistical significance was 0.05 (*p < 0.05). Despite the numerous biological activities that have been reported for DAA (Kang et al., 2009; Ohwada et al., 2003; Savluchinske-Feio et al., 2007; Tagat et al., 1994; Takahashi et al., 2011; Tanaka et al., 2008; Tolmacheva et al., 2006; Wada et al., 1985), the anti-aging effect of DAA has surprisingly not been studied. We used the Caenorhabditis elegans (C. elegans) wild-type N2 strain as a model organism of aging, to observe the lifespan extension effects of DAA.
Design, synthesis and in vitro evaluation of novel dehydroabietic acid derivatives containing a dipeptide moiety as potential anticancer agents
2015, European Journal of Medicinal ChemistryCitation Excerpt :DHA is a natural occurring diterpenic resin acid, which can be easily isolated from commercial disproportionated rosin [4]. Recent reports indicate that DHA and its derivatives exhibited wide range of biological activities, such as antiulcer, antimicrobial, antifungal, anti-inflammatorily, anti-pepsin, anxiolytic, antiviral, antitumor, and cytotoxic activities [5–11]. Modern studies have indicated that DHA and some derivatives have been reported to have anticancer activity in many human cancer cells such as cervical carcinoma cells, hepatocellular carcinoma cells and breast cancer cells, as well as its analogs [12,13].
Synthetic derivatives of aromatic abietane diterpenoids and their biological activities
2014, European Journal of Medicinal ChemistryCitation Excerpt :DHA (2) has exhibited strong inhibitory effects on Epstein–Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and was selected to examine effects on in vivo two-stage mouse skin carcinogenesis. It exhibited high activity in this antitumour-promoting test [23]. Two oxidation products of methyl abietate, compounds 24a and 24b (Fig. 6), have displayed weak cytotoxicity against KB cells (IC50 = 4.5 and 5.8 μg/mL, respectively) [24].
Synthesis and biological evaluation of dehydroabietic acid derivatives
2010, European Journal of Medicinal ChemistryCitation Excerpt :For example, they have shown antiulcer [3], antimicrobial [4], anxiolytic [5], antiviral [6], antitumor [7], and cytotoxic activities [8]. Recent studies have demonstrated that DHA and some derivatives are chemical modulators, particularly openers, of large-conductance calcium-activated K+ channels (BK channels) [9]. This feature makes DHA a new scaffold in the treatment of acute stroke, epilepsy, asthma, hypertension, gastric hypermotility and psychoses.