Cancer Chemopreventive Activity of Oleanane‐Type Triterpenoids from the Stem Bark of <i>Betula ermanii</i>

Yamaguchi, Chiharu; In, Yasuko; Wada, Shun‐ichi; Yamada, Takeshi; Tokuda, Harukuni; Tanaka, Reiko

doi:10.1002/cbdv.200800266

Cited by 8 publications

(4 citation statements)

References 31 publications

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“…Olean-28,13b-olide with a lactone moiety between C13 and C28 is a member of the highly-functionalized natural oleanane products that have attracted much attention because of their potential anticancer activities. [1][2][3] Unfortunately, the low natural abundance and highly challenging chemical synthesis of olean-28,13b-olides have limited the medicinal development of these compounds. To the best of our knowledge, the only known method for the synthesis of olean-28,13b-olides is to use peroxide oxidation.…”

mentioning

confidence: 99%

DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

et al. 2011

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confidence: 99%

DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

et al. 2011

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“…First, triterpenoids on leaf surface exhibit defense properties against herbivores (Reichardt et al, 1984;Laitinen et al, 2004) and its content in silver birch leaves was reported to decrease toward southern latitudes (Makhnev et al, 2012). Since some of triterpenoids have been reported from Erman's birch (Yamaguchi et al, 2009), changes in the triterpenoid content due to global warming may affect background herbivory in mature birch trees. Second, both direct and indirect effects of global warming on insect herbivores should be considered in assessing the impact of global warming, because global warming directly affects the abundance and species composition of insect herbivores by modulating their survival, development rate, and dispersal (Bale et al, 2002;Robinet and Roques, 2010;Heimonen et al, 2015).…”

Section: Prediction Of Global Warming Effectsmentioning

confidence: 99%

Response of Background Herbivory in Mature Birch Trees to Global Warming

Nakamura

Minoshima

Terada

et al. 2021

Front. For. Glob. Change

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Given the time scale based on the duration of exposure to global warming, natural climate-gradient studies and experimental manipulations have detected long-term (decades to centuries) and short-term (years to decades) ecological responses to global warming. Combination of these two complementary approaches within a single study may enable prediction of the likely responses of ecological processes to global warming. To understand how global warming affects plant–herbivore interactions within a canopy of Erman’s birch, we combined an elevational gradient study and a warming experiment involving mature birch trees in which the soil and tree branches were warmed separately. In the elevational gradient study, herbivory by chewing insects and plant growth increased as elevation decreased, and the concentrations of condensed tannins and total phenolics in the leaves decreased. In the warming experiment, soil warming alone increased herbivory, and the addition of branch warming amplified the effect on herbivory. Soil warming alone decreased the tannin concentration, and the addition of branch warming led to a further reduction. The variation in herbivory was best explained by the tannin content of leaves. Our experimental results demonstrate that the decreased tannin content of leaves due to a combination of soil and branch warming was an important driver of increased herbivory in the canopy of the mature birch trees. The similar tendencies in the short- and long-term responses imply that global warming is likely to increase background herbivory in mature birch trees by decreasing the tannin content of leaves in the canopy.

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“…Oleanane‐type triterpenoids exhibit potent antitumor promoting activities during in vivo carcinogenesis tests and possess cytotoxic activities against several cancer cell lines (VanLe et al ., ; Yamaguchi et al ., ). Oleanolic acid (3 β ‐hydroxy‐olean‐12‐en‐28‐oic acid) and its isomer ursolic acid (3 β ‐hydroxy‐urs‐12‐en‐28‐oic acid) are pentacyclic triterpenoid compounds that exist widely in food, medical herbs and other plants in the form of free acids or aglycones (Liu, ).…”

Section: Introductionmentioning

confidence: 99%

3‐O‐Acetyloleanolic Acid Induces Apoptosis in Human Colon Carcinoma Hct‐116 Cells

Yoo

Park

Cui

et al. 2012

Phytotherapy Research

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The cytotoxic effect of 3-O-acetyloleanolic acid, an oleanolic acid derivative isolated from the seeds of Vigna sinensis K., was investigated in human colon carcinoma HCT-116 cells. 3-O-acetyloleanolic acid dose-dependently inhibited the viability of HCT-116 cells. Apoptosis was characterized by detection of cell surface annexin V and sub-G1 apoptotic cell populations. The number of immunostained cells with annexin V-FITC was increased after treatment with 3-O-acetyloleanolic acid. The sub-G1 cell population was also increased. Expression of TRAIL-mediated apoptosis signaling-related death receptor DR5 was increased in 3-O-acetyloleanolic acid-treated HCT-116 cells. Activation of caspase-8 and caspase-3, critical mediators of extrinsic apoptosis signaling, was also increased by 3-O-acetyloleanolic acid. The results indicate that 3-O-acetyloleanolic acid induces apoptosis in HCT-116 cells mediated by an extrinsic apoptosis signaling cascade via up-regulation of DR5.

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Cancer Chemopreventive Activity of Oleanane‐Type Triterpenoids from the Stem Bark of Betula ermanii

Cited by 8 publications

References 31 publications

DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism

Response of Background Herbivory in Mature Birch Trees to Global Warming

3‐O‐Acetyloleanolic Acid Induces Apoptosis in Human Colon Carcinoma Hct‐116 Cells

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