16611-84-0

Anacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain. These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (PCAF) with IC₅₀ values of 8.5 and 5 μM, respectively. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.

Anacardic acid, isolated from cashew shells or several other medicinal plants, is the general name given to a family of four different 6-alkyl salicyclic acids having varying degrees of unsaturation in the 15-carbon alkyl chain. These compounds are associated with anti-inflammatory, anti-tumor, molluscicidal, and anti-microbial activity. Literature frequently sites and gives the name anacardic acid to the completely-saturated compound (6-pentadecyl salicylic acid). Anacardic acid inhibits the histone acetyltransferase (HAT) activity of the transcription co-activators p300 and p300/CREB-binding protein-associated factor (PCAF) with IC50 values of 8.5 and 5 μM, respectively. At 25 μmol/L, anacardic acid suppresses NF-κB activation, inhibits IκB-α phosphorylation, and prohibits p65 nuclear translocation in KBM-5 cells.[Cayman Chemical]

ChEBI:Anacardic acid is a hydroxybenzoic acid that is salicylic acid substituted by a pentadecyl group at position 6. It is a major component of cashew nut shell liquid and exhibits an extensive range of bioactivities. It has a role as an EC 2.3.1.48 (histone acetyltransferase) inhibitor, an apoptosis inducer, a neuroprotective agent, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, an antibacterial agent, an anti-inflammatory agent and a plant metabolite. It is a hydroxybenzoic acid and a hydroxy monocarboxylic acid. It is functionally related to a salicylic acid.

Target IC50: 5 μM against HAT; 8.5 μM against PCAF; 2.2 μM inhibiting protein SUMO modification using RanGAP1-C2 as substrate

lncap, a classical metastatic prostate adenocarcinoma cell line, was adopted to study the effect of aa on cell growth, cycles and apoptosis. it was found that 125 m aa significantly inhibited lncap cell proliferation. in addition, the g1/s cell cycles arrest and the apoptosis of lncap cell was induced. further mechanistic study suggested that aa induced cell apoptosis via suppressing p300. [1]

diesel exhaust particle- (dep-) induced lung inflammation model was established to study the effect of aa on inflammation in mice. ten days before dep-instillation stimulation, mice were orally pretreated with 50, 150, or 250 mg/kg of aa for thirty days. all doses of aa ameliorated activities of oxidative enzymes. moreover, 50 mg/kg of aa significantly decreased the expression level of tumor necrosis factor in lung. [2]

noncompetitively inhibit histone acetyltransferase (hat) activity in prostate cancer with an ic50 value of about 5.0 m.

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1) Balasubramanyam et al. (2003), Small molecule modulators of histone acetyltransferase p300; J. Biol. Chem. 278 19134 2) Sun et al. (2006), Inhibition of histone acetyltransferase activity by anacardic acid sensitizes tumor cells to ionizing radiation; FEBS Lett. 580 4353 3) Wu et al. (2011), Anacardic acid (6-Pentadecylsalicylic acid) Inhibits Tumor Angiogenesis by Targeting Src/FAK/Rho GTPases Signaling Pathway; J. Pharmacol. Exp. Ther. 339 403 4) Omanakuttan et al. (2012), Anacardic acid Inhibits the Catalytic Activity of Matrix Metalloproteinase-2 and Matrix Metalloproteinase-9; Mol. Pharmacol. 82 614 5) Sung et al. (2008), Anacardic acid (6-nonadecyl salicylic acid), an inhibitor of histone acetyltransferase, suppresses expression of nuclear factor-kB- regulated gene products involved in cell survival, proliferation, invasion, and inflammation through inhibition of the inhibitory subunit of nuclear factor-kBα kinase, leading to potentiation of apoptosis; Blood 111 4880