Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

Shankar, Thangaraj; Tsao, Wen-Shing; Luo, Yiwei; Lee, Yean‐Jang; Chang, Chia‐Fu; Lin, Chun‐Cheng; Uang, Biing‐Jiun; Yu, Chia-Chun; Guh, Jih‐Hwa; Teng, Che-Ming

doi:10.1016/j.tet.2011.06.054

Cited by 17 publications

(15 citation statements)

References 43 publications

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“…[51] More recently, the synthesis of similar compounds was proposed in order to explore their overall effects on breast cancer and establish their structure-activity relationships. [53] Further studies have evaluated the mode of action of 11 against tumor cells and the apoptotic signaling cascade elicited in human glioblastoma multiforme (GBM). Compound 11 produced a dose-dependent decrease in viability of GBM cells by triggering apoptosis.…”

Section: Phenanthropyrans and Phenanthrenes As Possible Medicinal Agentsmentioning

confidence: 99%

“…The authors concluded that Akt inactivation, followed by Bad activation, mitochondrial dysfunction, caspase‐3 activation, and AIF release contributed to denbinobin‐induced cell apoptosis . More recently, the synthesis of similar compounds was proposed in order to explore their overall effects on breast cancer and establish their structure–activity relationships …”

Section: Introductionmentioning

confidence: 99%

“…Due to the interest in the medicinal chemistry on denbinobin outlines, a retro ‐synthetic methodology aimed at obtaining the desired structure was recently proposed . Other groups proposed synthetic schemes for moniliformediquinone ( 10 ) and calanquinone A ( 8 ) as potent inhibitors of breast cancer …”

Section: Introductionmentioning

confidence: 99%

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Bioactive Secondary Metabolites from Orchids (Orchidaceae)

Sut

Maggi

Dall’Acqua

2017

Chemistry & Biodiversity

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The Orchidaceae family is the largest group of flowering plants in the Angiosperm monocotyledons spread on our planet. Its members, called orchids, are herbs or epiphytes with showy flowers distributed mainly in tropical regions. Several classes of phytoconstituents have been so far isolated from therapeutically-used orchids showing a great chemical diversity. Among them, phenolic derivatives have been studied for their biological activities, especially in the field of cancer, inflammation, and neurodegeneration. On the other hand, limited information has been so far obtained on the numerous alkaloids and terpenoids isolated from several orchid species. Recent articles revealed pronounced effects of some alkaloids on the CNS. Published literature on orchids that are used in traditional medicine has been reviewed in this work indicating a great potential of such organisms as source of chemical entities for the development of new drugs.

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Section: Phenanthropyrans and Phenanthrenes As Possible Medicinal Agentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bioactive Secondary Metabolites from Orchids (Orchidaceae)

Sut

Maggi

Dall’Acqua

2017

Chemistry & Biodiversity

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“…Calanquinone A (Fig. 1A) was totally synthesized and the structure identification and purity were also provided elsewhere (Thangaraj et al, 2012). …”

Section: Methodsmentioning

confidence: 99%

“…Calanquinone A, isolated from Calanthe arisanesis, has been reported to display potent cytotoxic activity against a wide variety of cancer types (Thangaraj et al, 2012; Lee et al, 2008). However, the anticancer mechanism has not been identified.…”

Section: Introductionmentioning

confidence: 99%

Calanquinone A induces anti-glioblastoma activity through glutathione-involved DNA damage and AMPK activation

Liu

Hsu

Lee

et al. 2014

European Journal of Pharmacology

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Glioblastoma, a highly malignant glioma, is resistant to both radiation and chemotherapy and is an intractable problem in clinical treatment. New therapeutic approaches are in urgent need. Calanquinone A, an herbal constituent, displayed anti-proliferative activity against glioblastoma cells, including A172, T98 and U87. Flow cytometric analysis showed an S phase arrest and a subsequent apoptosis to calanquinone A action. Further identification demonstrated a rapid increase of γH2A.X formation at S phase. The data together with comet tail formation and Chk1 activation indicated DNA damage response. N-acetyl cysteine (an antioxidant and a glutathione precursor) and exogenously applied glutathione, but not trolox (an antioxidant), completely abolished calanquinone A-induced effects. Immunofluorescence assay revealed that calanquinone A decreased the intracellular glutathione levels in both A172 and T98 cells. However, calanquinone A, by itself, did not conjugate glutathione. The data suggested that the decrease of cellular glutathione predominantly contributed to the anticancer mechanism. Furthermore, calanquinone A induced the activation of AMP-activated protein kinase (AMPK) and the inhibition of p70S6K activity. Rhodamine efflux assay showed that calanquinone A did not block efflux activity, indicating that calanquinone A was not a P-glycoprotein substrate. In summary, the data suggest that calanquinone A displays anti-glioblastoma activity through a decrease of cellular glutathione levels that subsequently induces DNA damage stress and AMPK activation, leading to cell cycle arrest at S-phase and apoptotic cell death. Furthermore, calanquinone A does not serve as a P-glycoprotein substrate, suggesting a potential for further development in anti-glioblastoma therapy.

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