Identification of cembratriene-4,6-diol as antitumor-promoting agent from cigarette smoke condensate

Saito, Yutaka; Takizawa, Hajime; Konishi, Sumie; Yoshida, Daisuke; Mizusaki, Shigenobu

doi:10.1093/carcin/6.8.1189

Cited by 55 publications

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“…They were screened for inhibition of the induction of Epstein-Barr virus early antigen in Raji cells by TPA. 1) Sarcophytol A, derived from marine organisms, was screened since it is structurally related to α-CBT and β-CBT.…”

Section: Discussionmentioning

confidence: 99%

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Disaccharide Esters Screened for Inhibition of Tumor Necrosis Factor‐α Release Are New Anti‐cancer Agents

Okabe

Suganuma

Tada

et al. 1999

Japanese Journal of Cancer Research

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Tumor necrosis factor‐α (TNF‐α) is a proinflammatory cytokine playing a part in various pathological states. Non‐toxic inhibitors of TNF‐α release are thought to be promising agents for cancer prevention. We found that the acetone fraction of the tobacco leaf surface lipid containing glucose esters and sucrose esters inhibited both TNF‐α release from BALB/3T3 and KATO III cells induced by okadaic acid and tumor promotion by okadaic acid on mouse skin initiated with 7,12‐dimethylbenz(a)anthracene (DMBA). Next, we investigated the inhibition of TNF‐α release with synthetic disaccharide esters, such as 6,6′‐di‐0‐alkanoyl‐α,α‐trehaloses (6,6′‐diester‐trehaloses), 4,4′‐di‐0‐alkanoyl‐α,α‐trehaloses (4,4′‐diester‐trehaloses) and 6,6′‐diamino‐6,6′‐dideoxy‐N, N′‐dial‐kanoyl‐α,α‐trehaloses (6,6′‐diamide‐trehaloses) bearing fatty acids of various chain lengths, and n‐ dodecyl‐β‐D‐maltoside as a disaccharide monoester. 6,6′‐Diester‐trehaloses and 4,4′‐diester‐treha‐loses of C 8 to C 14 fatty acids, 6,6′‐diamide‐trehaloses of C 8 to C 14 fatty acids, and n‐dodecyl‐β‐D‐maltoside all inhibited TNF‐α release in a dose‐dependent manner. The IC 50 values are 7.4‐14.8 μM for 6,6′‐diester‐trehaloses (C 8 to C 12 ), 14.6‐21.6 μM 4,4′‐diester‐trehaloses (C 8 to C 12 ), 2.9‐15.0 μM for 6,6′‐diamide‐trehaloses (C 8 to C 14 ) and 23 μM for dodecyl‐β‐D‐maltoside. Both 6,6′‐di‐O‐octanoyl‐α,α‐trehalose (C 8 , designated as SS555) and n‐dodecyl‐β‐D‐maltoside (C 12 ) inhibited tumor promotion by okadaic acid on mouse skin initiated with DMBA. Percentages of tumor‐bearing mice in week 15 of tumor promotion were reduced from 60.0 to 13.3 with SS555, and to 46.7 with n‐dodecyl‐β‐D‐maltoside. Moreover, SS555 inhibited TNF‐α gene expression mediated through inhibition of AP‐1 activation, but not NF‐αB activation. This paper reports that diester‐trehaloses of C 8 to C 12 fatty acids and mimics of disaccharide monoesters such as n‐dodecyl‐β‐D‐maltoside appear to be potential cancer‐preventive agents of a new type.

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Section: Discussionmentioning

confidence: 99%

“…1) Based on the structural similarity of α-CBT to sarcophytol A, isolated from the soft coral Sarcophyton glaucum, 2) we found that sarcophytol A inhibited tumor promotion on mouse skin by three TPA-type tumor promoters (TPA itself, teleocidin, and aplysiatoxin), and okadaic acid.…”

mentioning

confidence: 95%

Disaccharide Esters Screened for Inhibition of Tumor Necrosis Factor‐α Release Are New Anti‐cancer Agents

Okabe

Suganuma

Tada

et al. 1999

Japanese Journal of Cancer Research

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“…1), which are the major components in the cuticular wax of Nicotiana tabacum [1], inhibited the promoting ef fect of 12-O-tetradecanoylphorbol-13-acetate (TPA), a potent tumor promotor, on skin tumor formation in mice initiated with 7,12-dimethylbenz[a]anthracene [2]Up to date, TPA has been studied in many systems and has been shown to induce many biological events both in vitro and in vivo. These effects include induc tion of ornithine decarboxylase (ODC) [3,4], induc tion of Epstein-Barr-virus-associated early antigen [5], stimulation of the incorporation of inorganic phos phate into phospholipids [6], activation of membranebound enzymes such as phospholipase A2 [7], and activation of Ca2 +-activated phospholipid-dependent protein kinase (protein kinase C) [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Inhibition of 12-O-Tetradecanoylphorbol-13-Acetate-Stimulated <sup>32</sup>P<sub>i</sub> Incorporation into Phospholipids and Protein Phosphorylation by 2,7, 11-Cembratriene-4,6-Diol, an Antitumor-Promoting Agent

Saito

Nishino²,

Yoshida³

et al. 1988

Oncology

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A possible mechanism of antitumor-promoting activity of Α-2,7,1 l-cembratriene-4,6-diol (Α-CBT) was studied. Α-CBT inhibited the ³²P_i; incorporation into phospholipids of HeLa cells stimulated by 12–O-tetradecanoylphorbol-13-acetate (TPA). In contrast to the property to interact with calmodulin of many other antitumor-promoting agents, which were proved to inhibit TPA-stimulated ³²P_i incorporation into phospholipids, Α-CBT did not show any interaction with calmodulin; i.e., the fluorescence of N-phenyl-l-naphthyl-amine enhanced by binding with Ca²⁺-calmodulin was not influenced by treatment with a-CBT. TPA-stimulated phosphorylation of 47-kilodalton protein, which is phosphorylated by protein kinase C in human platelets, was found to be inhibited by a-CBT. However, the specific binding of ³H-TPA to mouse epidermal particulate fraction was not inhibited by treatment with Α-CBT. These results suggest that Α-CBT inhibits the activity of protein kinase C by another mode of action rather than the effect on its receptor site, and that this action and calmodulin-independent inhibitory effect on phospholipid metabolism of Α-CBT may play a certain role in its antitumor-promoting activity in vivo.

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“…2 ) cx-and P-CBT also inhibited the induction of ornithine decarboxylase activity by TPA in mouse epiderrnis 2 ); this short-term in vivo assay system is used for detecting tumor promoters 4 )' and anti-tumor promoters. S ) Furthermore, these CBT inhibited the promoting effect of TPA on skin tumor formation initiated with 7,12-dimethylbenz[a]anthracene in mice.…”

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confidence: 96%

“…S ) Furthermore, these CBT inhibited the promoting effect of TPA on skin tumor formation initiated with 7,12-dimethylbenz[a]anthracene in mice. 2 ) These results prompted us to examine the relationship between the anti-tumor promoting activity and the structure of CBT and its derivatives. In this study, we tested the inhibitory effects of CBT derivatives on the induction of EBV-EA by TPA.…”

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confidence: 99%

Inhibitory Effects of Cembratriene- 4,6-diol Derivatives on the Induction of Epstein-Barr Virus Early Antigen by 12-O-Tetradecanoylphorbol- 13-acetate

Saito

Tsujino

Kaneko

et al. 1987

Agricultural and Biological Chemistry

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Identification of cembratriene-4,6-diol as antitumor-promoting agent from cigarette smoke condensate

Cited by 55 publications

References 0 publications

Disaccharide Esters Screened for Inhibition of Tumor Necrosis Factor‐α Release Are New Anti‐cancer Agents

Disaccharide Esters Screened for Inhibition of Tumor Necrosis Factor‐α Release Are New Anti‐cancer Agents

Inhibition of 12-O-Tetradecanoylphorbol-13-Acetate-Stimulated <sup>32</sup>P<sub>i</sub> Incorporation into Phospholipids and Protein Phosphorylation by 2,7, 11-Cembratriene-4,6-Diol, an Antitumor-Promoting Agent

Inhibitory Effects of Cembratriene- 4,6-diol Derivatives on the Induction of Epstein-Barr Virus Early Antigen by 12-O-Tetradecanoylphorbol- 13-acetate

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