Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 65, Issue 11, Pages 2299-2306Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.6b05697
Keywords
food additive; vanillin; apocynin; antimetastatic; focal adhesion kinase
Funding
- Chulabhorn Research Institiute
- Chulabhorn Graduate Institute
- Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education
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The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin inhibiting invasion, with IC50 values of 23.3 +/- 7.4 to 41.3 +/- 4.2 mu M for the dimers, which are 26-34-fold lower than IC50 values of vanillin and apocynin (p < 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAR and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin. has antimetastatic potential greater than that of the flavoring agent vanillin.
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