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1.  Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents 
Dehydrozingerone analogs and related compounds were screened as potential antitumor promoters by using the in vitro short-term 12-O-tetradecanphorbol-13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation assay. Among 40 synthesized compounds, the prenylated analogs 16 and 34–36 showed the most significant and promising activity (100% inhibition of activation at 1×10 3 mol ratio/TPA, and 82–80%, 37–35%, 13–11% inhibition at 5×102, 1×102, 1×10 mol ratio/TPA, respectively) in this screening. Their activity profiles were comparable to that of the reference standard curcumin. While a prenyl moiety conferred potent chemopreventive activity, an extended prenyl unit such as a farnesyl moiety did not improve activity. Because in vitro inhibitory effects in this assay generally correlate well with in vivo inhibitory effects on tumor promotion, our results strongly suggested that prenylated 16 and 34–36 are likely to be promising antitumor promoters.
PMCID: PMC2856110  PMID: 20390770
dehydrozingerone; antitumor-promoting effect; Epstein-Barr virus; two-stage carcinogenesis
2.  Antitumor Agents 255. Novel Glycyrrhetinic Acid-Dehydrozingerone Conjugates as Cytotoxic Agents 
Bioorganic & medicinal chemistry  2007;15(18):6193-6199.
Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or ursolic acid (UA). In an in vitro anticancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 μM, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anticancer drug discovery and development.
PMCID: PMC2034305  PMID: 17591444
Glycyrrhetinic acid; Dehydrozingerone; Conjugation; Cytotoxicity
3.  Dehydrozingerone, Chalcone, and Isoeugenol Analogs as In Vitro Anticancer Agents# 
Journal of natural products  2006;69(10):1445-1449.
Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogs 27−35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multi-drug resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 μg/mL. Furthermore, dehydrozingerone analog 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 μg/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 μg/mL, respectively) cells, suggesting that they are not substrates for the p-glycoprotein drug efflux pump.
PMCID: PMC2532514  PMID: 17067159

Results 1-3 (3)