Inhibitory effects of dehydrozingerone and related compounds on 12-O-tetradecanoylphorbol-13-acetate induced Epstein–Barr virus early antigen activation

Motohashi, Noriko; Yamagami, Chisako; Tokuda, Harukuni; Konoshima, Takao; Okuda, Yoko; Okuda, Masumi; Mukainaka, Teruo; Nishino, Hoyoku; Saito, Yutaka

doi:10.1016/s0304-3835(98)00239-0

Cited by 34 publications

(24 citation statements)

References 13 publications

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“…Structure-activity relationship (SAR) correlations of curcumin analogs as antitumor promoting agents have also been investigated [4,5]. Dehydrozingerone ( 1 ) and isoeugenol ( 3 ), which have similar catechol skeletons, but different alkenyl side chains, had stronger antitumor promotion effects than curcumin [6]. In the search for antitumor promoters from natural sources, the antitumor promoting properties of phenylpropanoids have also been reported [7–9].…”

Section: Introductionmentioning

confidence: 99%

Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents

Tatsuzaki

Nakagawa‐Goto

Tokuda

et al. 2010

Journal of Asian Natural Products Research

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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 5×10 2 , 1×10 2 , 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.

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Section: Introductionmentioning

confidence: 99%

Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents

Tatsuzaki

Nakagawa‐Goto

Tokuda

et al. 2010

Journal of Asian Natural Products Research

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“…1, one of pungent constituents of ginger rhizome, also exhibits a wide range of biological activities [33][34][35]. Although conjugate enone system is presented in this phenolic compound, its structure differs from chalcones; instead of the aryl group to the carbonyl is connected the methyl one.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of O-alkyl derivatives of dehydrozingerone analogues

Muškinja¹,

Ratkovic²,

Ranković³

et al. 2016

Kragujevac J Sci

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ABSTRACT. Vanillin and isobuthyl methyl ketone (4-methylpentan-2-one) reacts under Claisen-Schmidt conditions yielding corresponding dehydrozingerone analogue, (E)-1-(4-hydroxy-3-methoxyphenyl)-5-methylhex-1-en-3-one. A small series of its O-alkyl derivatives was prepared by alkylation of free phenolic group with corresponding alkyl halides. Products had been tested for their biological activity and demonstrated relatively strong in vitro antimicrobial activity towards different strains of bacteria and fungi. All new compounds were well characterized by IR, 1 H and 13 C NMR spectroscopy and physical data.

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“…A direct comparison of a nonallylic ketocyclopentane-containing plant hormone, methyl jasmonate, with the same compound made into an allylic ketone by incorporating a double bond in the D 2 position, showed 29 times the growth inhibitory potency in the latter [Ishi et al, 2004]. In a comparison of benzylacetone, a non-allylic ketone, with benzalacetone (which has the required double bond), the latter exhibited much more anti-tumor activity [Motohashi et al, 1998]. A triple bond was even more effective than the double bond.…”

Section: Introductionmentioning

confidence: 99%

Drug design: hiding in full view

Radin

2008

Drug Development Research

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Compounds that can produce potent biological effects in cells encompass a variety of structural motifs. Many of these compounds share a structural feature that has rarely been noted. It is an allylic cluster of atoms, a 3-carbon chain with a double bond between two of the atoms and an oxygen atom at the other end. The oxygen can be in a hydroxyl group, or in an ether or ketal or ester linkage, or simply a carbonyl form. In the latter case, the linkage is an allylic ketone (ene-one) structure. Nitrogen is often seen in equivalent forms. Inclusion of at least one allylic moiety appears to be able to turn a modestly active or inert compound into an effective drug or toxin. Some compounds lack the allylic moiety but develop one by enzymatic action, usually via cytochrome P-450 enzymes. These metabolites probably represent the active drug forms. The above concepts seem to be radically simplistic and improbable, but the evidence supporting them and the explanations for the biological activities are hidden ''in plain view.'' Comparisons with the pleiotropic activities of the allylic sphingolipid, ceramide, indicate that many allylic drugs operate by controlling the state of protein phosphorylation, by activating proteases, by generating reactive oxygen species, by slowing mitochondrial electron transport, or by lowering cellular glutathione concentrations. Drug Dev Res 69: [15][16][17][18][19][20][21][22][23][24][25] 2008 r2008 Wiley-Liss, Inc.

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Inhibitory effects of dehydrozingerone and related compounds on 12-O-tetradecanoylphorbol-13-acetate induced Epstein–Barr virus early antigen activation

Cited by 34 publications

References 13 publications

Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents

Cancer preventive agents 10. Prenylated dehydrozingerone analogs as potent chemopreventive agents

Synthesis of O-alkyl derivatives of dehydrozingerone analogues

Drug design: hiding in full view

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