Inhibitory effect of 5-hydroxy-4-(2-phenyl-(E)-ethenyl)-2(5H)-furanone, a novel synthesized retinoid, on azoxymethane-induced intestinal carcinogenesis in rats

Mori, Hideki; Yoshimi, Naoki; Sugie, Shigeyuki; Tanaka, Takuji; Morishita, Yukio; Jin-long, Gao; Tamai, Yoshin; Torihara, Masahiro; Yamahara, Johji

doi:10.1016/0304-3835(92)90220-p

Cited by 18 publications

(7 citation statements)

References 6 publications

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“…A novel retinoidal compound, 5-hydroxy-4-(2-phenyl-(E)-ethenyl)-2(5H)-furanone (KYN-54), was found to be chemopreventive of AOM-induced intestinal carcinogenesis [22]. This compound exerts effectiveness by exposure during postinitiation phase [23] as well as initiation phase [22]. Our recent study also indicated that this chemical is also effective in preventing oral carcinogenesis [24].…”

Section: Carotenoids and Related Chemicalsmentioning

confidence: 93%

“…Such chemopreventive effects of the oxygenated carotenoids may not depend on their provitamin A activity, but relate to their effectiveness as antioxidants and free radical scavengers. A novel retinoidal compound, 5-hydroxy-4-(2-phenyl-(E)-ethenyl)-2(5H)-furanone (KYN-54), was found to be chemopreventive of AOM-induced intestinal carcinogenesis [22]. This compound exerts effectiveness by exposure during postinitiation phase [23] as well as initiation phase [22].…”

Section: Carotenoids and Related Chemicalsmentioning

confidence: 98%

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Chemoprevention by naturally occurring and synthetic agents in oral, liver, and large bowel carcinogenesis

et al. 1997

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A number of naturally occurring compounds and several related synthetic agents were confirmed to exert chemopreventive properties against carcinogenesis in the digestive organs. Phenolic compounds, widely distributed as plant constituents, possess chemopreventive activities in tongue, liver, and large bowel of rodents. Of them, a simple phenolic protocatechuic acid seems to be a promising compound. Organosulfur compounds contained in the cruciferous vegetables and known to activate detoxifying enzymes are regarded as a candidate group for cancer preventive agents. We proved a strong protective effect of S-methylmethanethiosulfonate, a constituent in these vegetables, on azoxymethane (AOM)-induced large bowel carcinogenesis. Some oxygenated carotenoids (xanthophylls) are reported to have antitumor effects. Naturally occurring xanthophylls astaxanthin and canthaxanthin have considerable preventive activities on 4-nitroquinoline-1-oxide (4-NQO)-induced tongue carcinogenesis and AOMinduced large bowel carcinogenesis. A novel synthesized retinoidal butenolide, KYN-54, which suppresses large bowel as well as tongue carcinogenesis, could be a useful agent for prevention of digestive organ cancers. Some trace elements are known to have anticarcinogenic effects. Magnesium hydroxide, a protective agent in colorectal carcinogenesis, inhibits c-myc expression and ornithine decarboxylase activity in the mucosal epithelium of the intestine. Our results show that many agents with preventive effects in tongue, liver, and large bowel control carcinogen-induced hyperproliferation of cells in these organs. Carcinogens used to induce large bowel cancers also induce apoptosis in the target sites. Telomerase activity is increased in the tissues of preneoplastic as well as neoplastic lesions in experimental models such as dimethylbenz [a]anthracene-induced oral carcinogenesis in hamsters. These could be useful biomarkers in studies for cancer chemoprevention.

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Section: Carotenoids and Related Chemicalsmentioning

confidence: 93%

Section: Carotenoids and Related Chemicalsmentioning

confidence: 98%

Chemoprevention by naturally occurring and synthetic agents in oral, liver, and large bowel carcinogenesis

et al. 1997

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“…3 . Chemical shifts (δ, ppm) and coupling constants (J, Hz) obtained by first-order analysis of the spectra were measured relative to tetramethylsilane and fluorotrichloromethane.…”

Section: Discussionmentioning

confidence: 95%

“…Our investigation into fluorine-containing butenolides was stimulated by the fact that the butenolide ring is a com-ponent of several classes of bioactive natural compounds and that fluoro substituents such as F, CF 3 or OCF 3 are generally powerful modifiers of the chemical and biological properties of organic compounds, [11,12] as evidenced by hundreds of pharmaceuticals and biocides. Some fluorinated analogues of tetronic and -ascorbic acids have recently been prepared [13] for biochemical studies and 2-fluoro-4-hydroxy-3-styrylbut-2-en-4-olide was even found to exhibit a phospholipase inhibitory effect.…”

Section: Introductionmentioning

confidence: 99%

“…Some natural butenolides exhibit antitumour activity, [1] cytotoxic properties towards human tumour cells, [2] intestinal carcinogenicity inhibition, [3] significant activity against lymphotic leukemia systems [4] and also HIV-1 protease-inhibitor activity. [5] Some analogues of natural butenolides have also been proven to have antitumour [6] and antitumour-promoter activity.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3‐Fluorofuran‐2(5H)‐ones Based on Z/E Photoisomerisation and Cyclisation of 2‐Fluoro‐4‐hydroxybut‐2‐enoates

et al. 2007

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Mixtures of some (E)‐ and (Z)‐2‐fluoroalk‐2‐enoates prepared from the corresponding 2‐hydroxycarbonyl compounds and ethyl 2‐(diethoxyphosphoryl)‐2‐fluoroacetate have been transformed in high conversions into the target 3‐fluorofuran‐2(5H)‐ones by an efficient Z/E photoisomerisation of noncyclisable Z isomers followed by acid‐catalysed cyclisation. In contrast, the acid‐catalysed deprotection of ethyl (E)‐ and (Z)‐4‐[tert‐butyl(dimethyl)silyloxy]‐2‐fluoro‐4‐phenylbut‐2‐enoates resulted in the displacement of vinylicfluorine, affording ethyl (E)‐2‐oxo‐4‐phenylbut‐3‐enoate. 3‐Fluoro‐4‐phenylfuran‐2(5H)‐one was transformed into 2‐[tert‐butyl(dimethyl)silyloxy]‐3‐fluoro‐5‐methylfuran as a novel fluorinated building block.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Protective Role of Dietary Factors in Carcinogenesis of Digestive Organs

Mori

Tanaka

Sugie

et al. 1997

Food Factors for Cancer Prevention

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Inhibitory effect of 5-hydroxy-4-(2-phenyl-(E)-ethenyl)-2(5H)-furanone, a novel synthesized retinoid, on azoxymethane-induced intestinal carcinogenesis in rats

Cited by 18 publications

References 6 publications

Chemoprevention by naturally occurring and synthetic agents in oral, liver, and large bowel carcinogenesis

Chemoprevention by naturally occurring and synthetic agents in oral, liver, and large bowel carcinogenesis

Synthesis of 3‐Fluorofuran‐2(5H)‐ones Based on Z/E Photoisomerisation and Cyclisation of 2‐Fluoro‐4‐hydroxybut‐2‐enoates

Protective Role of Dietary Factors in Carcinogenesis of Digestive Organs

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