The Effects of 2′,4′-Dihydroxy-6′-methoxy-3′,5′- dimethylchalcone from Cleistocalyx operculatus Buds on Human Pancreatic Cancer Cell Lines

Tuan, Huynh Nhu; Minh, Bui Hoang; Tran, Phuong Thao; Lee, Jeong Hyung; Oanh, Ha Van; Ngo, Quynh Mai Thi; Nguyen, Yen Nhi; Lien, Pham Thi Kim; Tran, Manh Hung

doi:10.3390/molecules24142538

Cited by 24 publications

(21 citation statements)

References 30 publications

(38 reference statements)

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“…More selective drugs are required to overcome high rates of normal cell toxicity and resistance of cancer cells to conventional platinum-based chemotherapy. In recent years, considerable attention has been directed toward the effectiveness of natural products in cancer treatment [3,4].…”

Section: Introductionmentioning

confidence: 99%

Galangin, a Flavonoid from Lesser Galangal, Induced Apoptosis via p53-Dependent Pathway in Ovarian Cancer Cells

Huang

Chen

et al. 2020

Molecules

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Among women worldwide, ovarian cancer is one of the most dangerous cancers. Patients undergoing platinum-based chemotherapy might get adverse side effects and develop resistance to drugs. In recent years, natural compounds have aroused growing attention in cancer treatment. Galangin inhibited the growth of two cell lines, A2780/CP70 and OVCAR-3, more strongly than the growth of a normal ovarian cell line, IOSE 364. The IC50 values of galangin on proliferation of A2780/CP70, OVCAR-3 and IOSE 364 cells were 42.3, 34.5, and 131.3 μM, respectively. Flow cytometry analysis indicated that galangin preferentially induced apoptosis in both ovarian cancer cells with respect to normal ovarian cells. Galangin treatment increased the level of cleaved caspase-3 and -7 via the p53-dependent intrinsic apoptotic pathway by up-regulating Bax protein and via the p53-dependent extrinsic apoptotic pathway by up-regulating DR5 protein. By down-regulating the level of p53 with 20 μM pifithrin-α (PFT-α), the apoptotic rates of OVCAR-3 cells induced by galangin treatment (40 μM) were significantly decreased from 18.2% to 10.2%, indicating that p53 is a key regulatory protein in galangin-induced apoptosis in ovarian cancer cells. Although galangin up-regulated the expression of p21, it had little effect on the cell cycle of the two ovarian cancer cell lines. Furthermore, the levels of phosphorylated Akt and phosphorylated p70S6K were decreased through galangin treatment, suggesting that the Akt/p70S6K pathways might be involved in the apoptosis. Our results suggested that galangin is selective against cancer cells and can be used for the treatment of platinum-resistant ovarian cancers in humans.

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Section: Introductionmentioning

confidence: 99%

Galangin, a Flavonoid from Lesser Galangal, Induced Apoptosis via p53-Dependent Pathway in Ovarian Cancer Cells

Huang

Chen

et al. 2020

Molecules

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“…Release of mitochondrial cytochrome c . [ 101 ] Human leukemia cells (K562) IC 50 : 14.2 μM (@48 h) Cell growth inhibition and induction of apoptosis. Down-regulation of Bcl-2.…”

Section: Anticancer Activitiesmentioning

confidence: 99%

Mechanistic insights into dimethyl cardamonin-mediated pharmacological effects: A double control of the AMPK-HMGB1 signaling axis

Bailly

Vergoten

2020

Life Sciences

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Dimethyl cardamonin (DMC) has been isolated from diverse plants, notably from Cleistocalyx operculatus . We have reviewed the pharmacological properties of this natural product which displays anti-inflammatory, anti-hyperglycemic and anti-cancer properties. The pharmacological activities essentially derive from the capacity of DMC to interact with the protein targets HMGB1 and AMPK. Upon binding to HMGB1, DMC inhibits the nucleocytoplasmic transfer of the protein and its extracellular secretion, thereby blocking its alarmin function. DMC also binds to the AMP site of AMPK to activate phospho-AMPK and then to trigger downstream signals leading to the anti-inflammatory and anti-hyperglycemic effects. AMPK activation by DMC reinforces inhibition of HMGB1, to further reduce the release of the alarmin protein, likely contributing to the anticancer effects. The characterization of a tight control of DMC over the AMPK-HMGB1 axis not only helps to explain the known activities of DMC but also suggests opportunities to use this chalcone to treat other pathological conditions such as the acute respiratory distress syndrome (which affects patients with COVID-19). DMC structural analogues are also evoked.

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“…2′,4′‐Dihydroxy‐6′‐methoxy‐3′,5′‐dimethylchalcone (DMC, 1 ), a highly substituted chalcone extracted from many natural plants 17–21 has recently attracted growing attention due to its various pharmacological activities, including anti‐tumor, 22–25 antivirus, 26 anti‐oxidative, 27,28 anti‐inflammatory, 29,30 hepatoprotective, 31,32 and anti‐diabetic effects 33–35 . During our studies into the optimization of the specific pharmacological activity of 1 , we planned to tune its structure by modifying the substituents on the B and A rings, while retaining the key five functionalities present on the B ring, namely the alternatively attached three hydroxy/alkoxy groups and the two methyl groups (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Total Syntheses of 4′,6′‐Dimethoxy‐2'‐Hydroxy‐3′,5′‐Dimethylchalcone Derivatives

Lee

Park

2020

Bulletin Korean Chem Soc

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Chalcone derivatives afford several pharmacological activities. However, a general synthetic method for 2',4'‐dihydroxy‐6'‐methoxy‐3',5'‐dimethylchalcone (DMC) derivatives has not been reported thus far. To address this, the preparation of 4',6'‐dimethoxy‐2'‐hydroxy‐3',5'‐dimethylchalcone (MDMC) derivatives, modified compounds of DMC, in excellent overall yields is reported herein. These compounds have recently attracted growing attention due to their various pharmacological activities. Di‐O‐methyl‐dimethylphloroacetophenone, the key intermediate containing the B‐ring moiety, was fabricated by four efficient reaction steps from commercially available phloroglucinol in a 50.1% isolated yield overall. Our synthetic route, which constructs the chalcone skeleton in the final stage via a Claisen–Schmidt condensation of the key intermediate with the desired benzaldehyde derivative, can rapidly produce a vast library of DMC derivatives.

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The Effects of 2′,4′-Dihydroxy-6′-methoxy-3′,5′- dimethylchalcone from Cleistocalyx operculatus Buds on Human Pancreatic Cancer Cell Lines

Cited by 24 publications

References 30 publications

Galangin, a Flavonoid from Lesser Galangal, Induced Apoptosis via p53-Dependent Pathway in Ovarian Cancer Cells

Galangin, a Flavonoid from Lesser Galangal, Induced Apoptosis via p53-Dependent Pathway in Ovarian Cancer Cells

Mechanistic insights into dimethyl cardamonin-mediated pharmacological effects: A double control of the AMPK-HMGB1 signaling axis

Total Syntheses of 4′,6′‐Dimethoxy‐2'‐Hydroxy‐3′,5′‐Dimethylchalcone Derivatives

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