Acanthoic acid
نویسندگان
چکیده
THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,4aR,7S,8aS,10aS)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodeca-hydro-phenanthrene-1-carb-oxy-lic acid], C(20)H(30)O(2), is a pimarane-type diterpene extracted from Croton oblongifolius. There are two independent mol-ecules in the asymmetric unit. In both of these, the six-membered rings A, B and C adopt chair, boat and half-chair conformations, respectively. Rings A and B are trans-fused. The two mol-ecules in the asymmetric unit form O-H⋯O hydrogen-bonded R(2) (2)(8) dimers. The absolute configuration was assigned on the basis of the published literature on analogous structures.
منابع مشابه
Effects of acanthoic acid on TNF-alpha gene expression and haptoglobin synthesis.
Tumour necrosis factor-alpha (TNF-alpha) is a major pro-inflammatory cytokine inducing the synthesis and release of many inflammatory mediators. It is involved in immune regulation, autoimmune diseases, and inflammation. Our previous study demonstrated that acanthoic acid, (-)-pimara-9(11), 15-dien-19-oic acid, a pimaradiene diterpene isolated from Acanthopanax koreanum, inhibited TNF-alpha pro...
متن کاملEnantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid.
An enantioselective synthesis of the potent antiinflammatory agent (-)-acanthoic acid (1) is described. The successful strategy departs from (-)-Wieland-Miescher ketone (10), which is readily available in both enantiomeric forms and constitutes the starting point toward a fully functionalized AB ring system of 1. Conditions were developed for a regioselective double alkylation at the C4 center ...
متن کاملStereoselective synthesis of (-)-acanthoic acid.
[reaction: see text] The first stereoselective synthesis of (-)-acanthoic acid (1) has been designed and accomplished. Our synthetic plan departs from (-) Wieland-Miesher ketone (7) and calls upon a Diels-Alder cycloaddition reaction for the construction of the C ring of 1. The described synthesis confirms the proposed stereochemistry of 1 and represents an efficient entry into an unexplored cl...
متن کاملSynthesis of a novel family of diterpenes and their evaluation as anti-inflammatory agents.
The synthesis and biological evaluation of a new family of diterpenes, represented by structures 2 and 3, is presented. These compounds constitute isomeric analogues of acanthoic acid (1) and were examined as potent anti-inflammatory agents. Among them, methyl ester 12 exhibited a low non-specific cytotoxicity, inhibited TNF-alpha synthesis and displayed good specificity in suppressing cytokine...
متن کاملSelective activation of liver X receptors by acanthoic acid-related diterpenes.
Terpenoids constitute a large family of natural steroids that are widely distributed in plants and insects. We investigated the effects of a series of diterpenes structurally related to acanthoic acid in macrophage functions. We found that diterpenes with different substitutions at the C4 position in ring A are potent activators of liver X receptors (LXRalpha and LXRbeta) in both macrophage cel...
متن کاملAnti-inflammatory actions of acanthoic acid-related diterpenes involve activation of the PI3K p110γ/δ subunits and inhibition of NF-κB.
The effect of acanthoic acid analogs on the response to proinflammatory challenge was investigated. Some pimarane diterpenes are known activators of the LXRαβ nuclear receptors, but we show here that they also exert a rapid, potent, and selective activation of the p110γ and p110δ subunits of PI3K. Combination of these effects results in an important attenuation of the global transcriptional res...
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