Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

Liang, Chengyuan; Pei, Shaomeng; Ju, Weihui; Jia, Minyi; Tian, Danni; Tang, Yonghong; Mao, Gennian

doi:10.1016/j.ejmech.2017.03.053

Cited by 24 publications

(17 citation statements)

References 34 publications

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“…It is noteworthy that the antioxidant activity was evaluated for the first time for Compound 11 . Isocoumarins and benzofuranones from natural sources are excellent antioxidants, antitumor, and antimicrobe agents [21,22,23,24]. However, no fungal species from genus Epicoccum have been reported to produce antioxidant metabolites.…”

Section: Resultsmentioning

confidence: 99%

The Purification, Characterization, and Biological Activity of New Polyketides from Mangrove-Derived Endophytic Fungus Epicoccum nigrum SCNU-F0002

et al. 2019

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Six new polyketides, including one coumarin (1), two isocoumarins (2 and 3), dihydroradicinin (4), and two benzofuranone derivatives (7 and 8), together with seven known analogues (5–6 and 9–13) were isolated from the culture of the mangrove endophytic fungus Epicoccum nigrum SCNU-F0002. The structures were elucidated on the interpretation of spectroscopic data. The absolute configuration of Compounds 2 and 3 were determined by comparison of their ECD spectra with the data of their analogue dihydroisocoumarins described in the literature. The absolute configuration of 4 was determined by single-crystal X-ray diffraction. All the compounds were screened for their antioxidant, antibacterial, anti-phytopathogenic fungi and cytotoxic activities. Using a DPPH radical-scavenging assay, Compounds 10–13 showed potent antioxidant activity with IC50 values of 13.6, 12.1, 18.1, and 11.7 μg/mL, respectively. In addition, Compounds 6 and 7 showed antibacterial effects against Bacillus subtilis (ATCC 6538), Escherichia coli (ATCC 8739), and Staphylococcus aureus (ATCC 6538), with MIC values in the range of 25–50 μg/mL.

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Section: Resultsmentioning

confidence: 99%

The Purification, Characterization, and Biological Activity of New Polyketides from Mangrove-Derived Endophytic Fungus Epicoccum nigrum SCNU-F0002

et al. 2019

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“…Bergenin is the C-glucoside of 4- O -methyl gallic acid and can be found in several medicinal plants, including Bergenia crassifolia and Corylopsis spicata ( Liang et al, 2017 ). Bergenin has been reported to have multiple biological activities, including antiarthritic ( Jain et al, 2014 ; Singh et al, 2017 ), immunomodulatory ( Wang et al, 2017 ; Kumar et al, 2019 ), antidiabetic ( Veerapur et al, 2012 ), osteogenic ( Hou et al, 2019 ), neuroprotective ( Barai et al, 2019 ; Ji et al, 2019 ), and wound-healing effects ( Mukherjee et al, 2013 ).…”

Section: Introductionmentioning

confidence: 99%

Bergenin as a Novel Urate-Lowering Therapeutic Strategy for Hyperuricemia

Chen

Zhu

et al. 2020

Front. Cell Dev. Biol.

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Bergenin is a C-glucoside of 4-O-methyl gallic acid isolated from several medicinal plants and has multiple biological activities. The aim of this study was to assess the potential usefulness of bergenin in hyperuricemia. We found that bergenin reduced serum urate levels in hyperuricemia mice by promoting renal and gut uric acid excretion. Bergenin treatment increased Abcg2 expression both in the kidneys and intestine, while the expression of Slc2a9 was suppressed in the kidney and increased in the intestine. Moreover, bergenin induced ABCG2 expression in HK-2 and Caco-2 cells, as well as SLC2A9 in Caco-2 cells, via the activation of PPARγ. Nevertheless, bergenin suppressed SLC2A9 expression in HK-2 cells by inhibiting the nuclear translocation of p53. Furthermore, bergenin decreased the serum levels of IL-6, IL-1β, and TNF-α in hyperuricemia mice, and promoted a polarization shift from the M1 to M2 phenotype in RAW264.7 cells. In conclusion, these findings provide evidence supporting the further development of bergenin as a novel therapeutic strategy for hyperuricemia.

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“…For example, Chen and co-workers synthesized a series of hybrids of scopoletin and substituted cinnamic acid as antitumor agents and the derivatives showed significant enhancement of antitumor activity as compared with the parent compound scopoletin [38]. Mao et al adopted molecular hybridization strategy to produce bergenin-cinnamic acid hybrids and the evaluation of their antitumor activity also proved that the hybrid compounds were superior to bergenin [39]. These stimulated us to design and synthesize the hybrids of sophora alkaloids and cinnamic acid as antitumor agents by molecular hybridization strategy with improved affinity and efficacy.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Molecular Hybrids of Sophora Alkaloids and Cinnamic Acids as Potential Antitumor Agents

Shang

et al. 2020

Molecules

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Twenty-five sophora alkaloids-cinnamic acid hybrids (including matrine-cinnamic acid hybrids, sophoridine-cinnamic acid hybrids, and sophocarpine-cinnamic acid hybrids) were designed, synthesized, and evaluated in vitro against three human tumor cell lines (HeLa, HepG2 and A549) with cisplatin as a positive control. Some matrine-cinnamic acid and sophoridine-cinnamic acid compounds exhibited potent effect against all three cancer cell lines, such as compounds 5b, 5e, 5g, and 6d. The structure-activity relationship study of the synthesized compounds was also performed. Preliminary mechanistic studies indicated that compounds 5e and 6d could induce apoptosis in HepG2 cell line. Further, compounds 5e and 6d altered mitochondrial membrane potential and produced ROS leading to cell apoptosis of HepG2 cells. Overall, our findings suggested that these compounds may provide promising lead compounds for further development as antitumor agents by structural modification.

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Synthesis and in vitro and in vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

Cited by 24 publications

References 34 publications

The Purification, Characterization, and Biological Activity of New Polyketides from Mangrove-Derived Endophytic Fungus Epicoccum nigrum SCNU-F0002

The Purification, Characterization, and Biological Activity of New Polyketides from Mangrove-Derived Endophytic Fungus Epicoccum nigrum SCNU-F0002

Bergenin as a Novel Urate-Lowering Therapeutic Strategy for Hyperuricemia

Design and Synthesis of Molecular Hybrids of Sophora Alkaloids and Cinnamic Acids as Potential Antitumor Agents

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