Chemopreventive potential of cyclic diarylheptanoids

Ishida, Junko; Kozuka, Mutsuo; Tokuda, Harukuni; Nishino, Hoyoku; Nagumo, Shinji; Lee, Kuo Hsiung̀; Nagai, Masahiro

doi:10.1016/s0968-0896(02)00164-5

Cited by 54 publications

(16 citation statements)

References 16 publications

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“…The in vitro inhibitory effects determined in the EBV-EA assay generally have been found to correlate well with in vivo inhibitory effects on tumor promotion as reported in many studies (Konoshima et al, 1994;Ishida et al, 2000Ishida et al, , 2002Sakurai et al, 2003;Wang et al, 2006). Therefore, based on the in vitro data, only three of the most potent compounds (13, 15, and 19) were examined in a two-stage in vivo skin carcinogenesis test evaluating mouse skin papilloma induced by DMBA as an initiator and TPA as a promoter (Table 2).…”

Section: In Vivo Mouse Skin Carcinogenesis Inhibitionsupporting

confidence: 68%

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†

Hung¹,

Nakagawa‐Goto²,

Tokuda

et al. 2011

Pharmaceutical Biology

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Section: In Vivo Mouse Skin Carcinogenesis Inhibitionsupporting

confidence: 68%

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†

Hung¹,

Nakagawa‐Goto²,

Tokuda

et al. 2011

Pharmaceutical Biology

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“…The test was performed as described earlier (Tokuda et al, 1998;Ishida et al, 2002). The animals (SPF female SENCAR mice, 6-weeks-old) were divided into three experimental groups of 15 mice each.…”

Section: Two-stage Mouse Skin Carcinogenesis Test Induced By Peroxynimentioning

confidence: 99%

Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo

Iranshahi

Sahebkar

Takasaki³

et al. 2009

European Journal of Cancer Prevention

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145

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Umbelliprenin is a prenylated compound, which belongs to the class of sesquiterpene coumarins. In continuation of our earlier in-vitro finding, we determined to assess the cancer chemopreventive activity of umbelliprenin in vivo by using a two-stage carcinogenesis assay of mouse skin tumors induced by peroxynitrite as an initiator and TPA (12-O-tetradecanoylphorbol-13-acetate) as a promoter. In this assay, treatment with umbelliprenin along with peroxynitrite/TPA delayed the formation of papillomas up to week 9, and approximately 33.3 and 86.6% of the mice bore papillomas after 11 and 20 weeks of promotion, respectively. Umbelliprenin reduced the number of tumors per mouse by 45% after 20 weeks of promotion compared with the control group. Interestingly, this is equal to the corresponding value (45%) for curcumin, used as a reference standard compound in our study. In addition, the pattern of tumor promotion was slower in mice treated with umbelliprenin compared with the curcumin. Therefore, umbelliprenin might be valuable as a cancer chemopreventive agent.

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“…However, to the best of our knowledge, the structure–activity relationship (SAR) study of cyclic diarylheptanoids is very limited [80,182,183]; thus, the identification of good drug candidates has not been fruitful yet. Not only development of a facile enantioselective macrocyclization method but also more intense SAR study have become a prerequisite for realizing such a goal.…”

Section: Discussionmentioning

confidence: 99%

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Jahng

Park

2018

Molecules

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Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into meta,meta-bridged biphenyls ([7.0]metacyclophanes) and meta,para-bridged diphenyl ether heptanoids (oxa[7.1]metapara-cyclophanes). Since the isolation of curcumin from the rhizomes of turmeric (Curcuma longa) in 1815 which was named curcumin, a variety of diarylheptanoids have been isolated from a number of plant families such as Aceraceae, Actinidiaceae, Betulaceae, Burseraceae, Casuarinaceae, Juglandaceae, Leguminosae, Myricaceae, and Zingiberaceae. Earlier studies on these diarylheptanoids have been summarized on several occasions, of which the main themes only focus on isolation, structure elucidation, and the biological properties of linear types. Only a few have covered cyclic diarylheptanoids and their chemical synthesis has been covered lastly by Zhu et al. in 2000. The present paper has, therefore, covered recent progress in cyclic diarylheptanoids focusing on the isolation, structural and biological features, and chemical synthesis.

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Chemopreventive potential of cyclic diarylheptanoids

Cited by 54 publications

References 16 publications

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†

Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

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Chemopreventive potential of cyclic diarylheptanoids

Cited by 54 publications

References 16 publications

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents†

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents†

Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

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Product

Resources

About

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†

Cancer preventive agents 11. Novel analogs of dimethyl dicarboxylate biphenyl as potent cancer chemopreventive agents^†