Disease relevance of NSC718732

• Artepillin C was then added to human colon cancer WiDr cells [1].
• According to the experiments using isogenic human colorectal carcinoma cell lines, artepillin C failed to induce G(0)/G(1) arrest in the Cip1/p21-deleted HCT116 cells, but not in the wild-type HCT116 cells [1].
• From these results we conclude that artepillin C isoprene analogues could be potent lipid peroxidation inhibitors having low mitochondrial toxicity [2].
• Instead of developing into large cell cancers, as induced by Fe-NTA in control mice, adenomas showed remarkable proliferation of macrophages and local anti-oxidant activity after treatment with either propolis or artepillin C [3].
• Oral doses of 80 and 160 mg/kg body weight of propolis or 10mg/kg of artepillin C (equi-amounts to 160 mg propolis) reduced significantly the frequency of colonic aberrant crypt foci (ACF) by 39.2, 43.7 and 43.4%, respectively [4].

High impact information on NSC718732

• On the other hand, Northern blotting showed that artepillin C did not affect the expression of Kip1/p27 mRNA [1].
• We had found that artepillin C was a bioavailable antioxidant, which could be incorporated into intestinal Caco-2 and hepatic HepG2 cells without any conjugation and inhibited the oxidation of intracellular DNA [1].
• Artepillin C in Brazilian propolis induces G(0)/G(1) arrest via stimulation of Cip1/p21 expression in human colon cancer cells [1].
• Artepillin C appears to prevent colon cancer through the induction of cell-cycle arrest by stimulating the expression of Cip1/p21 and to be a useful chemopreventing factor in colon carcinogenesis [1].
• Following the Mizoroki-Heck coupling of the diprenyl-p-iodophenol 3c with methyl acrylate and then hydrolysis, we first synthesized artepillin C [3-(4-hydroxy-3,5-di(3-methyl-2-butenyl)phenyl)-2(E)-propenoic acid] (1), which is a biologically active constituent of propolis [5].

Biological context of NSC718732

• Antioxidative bioavailability of artepillin C in Brazilian propolis [6].
• Propolis and artepillin C therefore appear to inhibit lipid peroxidation and the development of pulmonary cancers [3].
• Apoptosis of human leukemia cells induced by Artepillin C, an active ingredient of Brazilian propolis [7].
• We succeeded in the synthesis of artepillin C isoprene analogues using regioselective prenylation within the range from 22% to 53% total yield [2].
• Apoptotic bodies and DNA fragmentation were induced in the cell lines after exposure to Artepillin C [7].

Anatomical context of NSC718732

• Artepillin C (AC), an active ingredient of Brazilian propolis, permeates intact across Caco-2 cells by transcellular passive diffusion [8].
• These results suggested that Artepillin C, an active ingredient of Brazilian propolis, has anti-leukemic effects with limited inhibitory effects on normal lymphocytes [7].
• These findings indicate that artepillin C activates the immune system, and possesses direct antitumor activity [9].
• Artepillin C (3,5-diprenyl-4-hydroxycinnamic acid) was also identified in both propolis and resinous exudates, and both ethanolic extracts contained the highest concentrations of this compound as compared with the rest of the chemical constituents [10].
• We designed and synthesized isoprene analogues of artepillin C, a major component of Brazilian propolis, and investigated the inhibitory activity on lipid peroxidation of rat liver mitochondria (RLM) and RLM toxicity based on isoprenomics [2].

Associations of NSC718732 with other chemical compounds

• We also conclude that elongation of the isoprene side chain of artepillin C to increase lipophilicity had little influence on the inhibitory activity toward RLM lipid peroxidation [2].
• Moreover, artepillin C and its isoprene analogues exhibited a lower inhibitory activity against adenosine 5'-triphosphate (ATP) synthesis by about two orders of magnitude than the effective inhibitory activity against RLM lipid peroxidation [2].

Gene context of NSC718732

• A tumoricidal substance was isolated from Brazilian propolis as guided by cytotoxicity assay on HuH 13 (human hepatocellular carcinoma) cell and was characterized to be 3-[4-hydroxy-3,5-bis (3-methyl-2-butenyl) phenyl]-2-propenoic acid (3,5-diprenyl-4-hydroxycinnamic acid (artepillin C)) [11].
• The absorption characteristics of artepillin C (AC), an active ingredient of Brazilian propolis, were examined by measuring permeation across Caco-2 cell monolayers [12].

Analytical, diagnostic and therapeutic context of NSC718732

• Absorption and bioavailability of artepillin C in rats after oral administration [8].
• When xenografts of human tumor cells were transplanted into nude mice, the cytotoxic effects of artepillin C were most noticeable in carcinoma and malignant melanoma [9].
• Administration of propolis by gastric intubation 2 h before or Artepillin C at either the same time, 2 h, or 5 h before the intraperitoneal injection of Fe-NTA (7 mg Fe/kg) effectively inhibited renal lipid peroxidation [13].

References