Cancer chemopreventive agents, labdane diterpenoids from the stem bark of Thuja standishii (Gord.) Carr

Tanaka, Reiko; Ohtsu, Hironori; Iwamoto, Manabu; Minami, Toshifumi; Tokuda, Harukuni; Nishino, Hoyoku; Matsunaga, Shunyo; Yoshitake, Akira

doi:10.1016/s0304-3835(00)00584-x

Cited by 51 publications

(21 citation statements)

References 12 publications

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“…Many compounds that exhibited positive results in the in-vitro assay have been shown to inhibit tumor initiation or promotion in the in-vivo two-stage carcinogenesis test (Tanaka et al, 2003), including several biologically active terpenoids (Takayasu et al, 1990;Tanaka et al, 2000;Iwamoto et al, 2001;Tanaka et al, 2001Tanaka et al, , 2003. Therefore, to confirm the findings of our earlier study, we aimed to examine umbelliprenin for its in-vivo antitumor-initiating activity in a two-stage carcinogenesis assay of mouse skin tumors induced by peroxynitrite as an initiator and TPA as a promoter.…”

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confidence: 68%

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

Iranshahi

Sahebkar

Takasaki³

et al. 2009

European Journal of Cancer Prevention

152

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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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mentioning

confidence: 68%

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

Iranshahi

Sahebkar

Takasaki³

et al. 2009

European Journal of Cancer Prevention

152

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“…It is widely distributed in Cupresaceae species, especially in the genus Juniperus [39]. Previous studies have reported that it exhibits antimycobacterial [40], antitumoral [41, 42], anti-inflammatory, and antioxidant [43] activities. In this study, we showed that TCA is a dominant compound in BPLE and exerts inhibitory effects on UVB-induced MMP-1 expression, similar to BPLE.…”

Section: Discussionmentioning

confidence: 99%

Brown Pine Leaf Extract and Its Active Component Trans-Communic Acid Inhibit UVB-Induced MMP-1 Expression by Targeting PI3K

et al. 2015

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Japanese red pine (Pinus densiflora) is widely present in China, Japan, and Korea. Its green pine leaves have traditionally been used as a food as well as a coloring agent. After being shed, pine leaves change their color from green to brown within two years, and although the brown pine leaves are abundantly available, their value has not been closely assessed. In this study, we investigated the potential anti-photoaging properties of brown pine leaves for skin. Brown pine leaf extract (BPLE) inhibited UVB-induced matrix metalloproteinase-1 (MMP-1) expression to a greater extent than pine leaf extract (PLE) in human keratinocytes and a human skin equivalent model. HPLC analysis revealed that the quantity of trans-communic acid (TCA) and dehydroabietic acid (DAA) significantly increases when the pine leaf color changes from green to brown. BPLE and TCA elicited reductions in UVB-induced MMP-1 mRNA expression and activator protein-1 (AP-1) transactivation by reducing DNA binding activity of phospho-c-Jun, c-fos and Fra-1. BPLE and TCA also inhibited UVB-induced Akt phosphorylation, but not mitogen activated protein kinase (MAPK), known regulators of AP-1 transactivation. We additionally found that BPLE and TCA inhibited phosphoinositide 3-kinase (PI3K), the upstream kinase of Akt, in vitro. In summary, both BPLE and its active component TCA exhibit protective effects against UVB-induced skin aging. Taken together, these findings underline the potential for BPLE and TCA to be utilized as anti-wrinkling agents and cosmetic ingredients, as they suppress UVB-induced MMP-1 expression.

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“…Moreover, both acids have shown cytotoxic activity against BSC-1 cells [71]. Other activities described for 1 are: antimycobacterial ( Mycobacterium aurum , M. phlei , M. fortuitum and M. smegmatis ) [72], antitumoral [35,73], relaxant [74], hypolipidemic [75], testosterone 5α-reductase inhibitory [76], anti-inflammatory and antioxidant [77]. …”

Section: Biological Activitymentioning

confidence: 99%

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

et al. 2012

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Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). This paper also includes a detailed explanation of their use as chiral building blocks for the synthesis of bioactive natural products. Among other uses, communic acids have proven useful as chirons for the synthesis of quassinoids (formal), abietane antioxidants, ambrox and other perfume fixatives, podolactone herbicides, etc., featuring shorter and more efficient processes.

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Cancer chemopreventive agents, labdane diterpenoids from the stem bark of Thuja standishii (Gord.) Carr

Cited by 51 publications

References 12 publications

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

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

Brown Pine Leaf Extract and Its Active Component Trans-Communic Acid Inhibit UVB-Induced MMP-1 Expression by Targeting PI3K

Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds

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