ChemInform Abstract: Synthesis of a Complete Series of O‐Methyl Analogues of Naringenin and Apigenin.

Kim, Jin‐Young; Park, Kwang‐Su; Lee, Chaewoon; Chong, Youhoon

doi:10.1002/chin.200817210

Cited by 2 publications

(2 citation statements)

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“…Furthermore, the substitution of O -alkyl chains at the C-7 and C-4′ positions of the naringenin molecule was confirmed by the presence of only one singlet at 12.02–12.01 ppm, originating from the hydroxyl group at the C-5 position. The regioselectivity of the above alkylation reaction of naringenin was generally described in scientific reports [ 25 , 26 ]. In our investigation, one novel tri- O -alkyl derivative was obtained, namely 5,7,4′-tri- O -propylnaringenin ( 9a ).…”

Section: Resultsmentioning

confidence: 99%

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

et al. 2019

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In our investigation, we concentrated on naringenin (NG)—a widely studied flavanone that occurs in citrus fruits. As a result of a reaction with a range of alkyl iodides, 7 novel O-alkyl derivatives of naringenin (7a–11a, 13a, 17a) were obtained. Another chemical modification led to 9 oximes of O-alkyl naringenin derivatives (7b–13b, 16b–17b) that were never described before. The obtained compounds were evaluated for their potential antibacterial activity against Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The results were reported as the standard minimal inhibitory concentration (MIC) values and compared with naringenin and its known O-alkyl derivatives. Compounds 4a, 10a, 12a, 14a, 4b, 10b, 11b, and 14b were described with MIC of 25 µg/mL or lower. The strongest bacteriostatic activity was observed for 7-O-butylnaringenin (12a) against S. aureus (MIC = 6.25 µg/mL). Moreover, the antitumor effect of flavonoids was examined on human colon cancer cell line HT-29. Twenty-six compounds were characterized as possessing an antiproliferative activity stronger than that of naringenin. The replacement of the carbonyl group with an oxime moiety significantly increased the anticancer properties. The IC50 values below 5 µg/mL were demonstrated for four oxime derivatives (8b, 11b, 13b and 16b).

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Section: Resultsmentioning

confidence: 99%

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

et al. 2019

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“…Therefore, to find the active constituents responsible for the observed activities, phytochemical investigation was carried out, which resulted in the isolation of fourteen secondary metabolites, including two polyoxygenated cyclohexanes ( 1 and 2 ) and eleven flavonoids ( 3 - 13 ). The isolated compounds were identified using NMR spectroscopic analysis as (−)-4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0 2,4 ]octane-5,6-diol 6-acetate ( 1 ) [ 16 ], (+)-4-benzoyloxymethyl-3,8-dioxatricyclo[5.1.0.0 2,4 ]octane-5,6-diol 5-acetate ( 2 ) [ 16 ], 5-hydroxy-7-methoxyflavone ( 3 ) [ 17 ], 5-hydroxy-3,7-dimethoxyflavone ( 4 ) [ 17 ], 5,7-dimethoxyflavone ( 5 ) [ 17 ], 3,5,7-trimethoxyflavone ( 6 ) [ 17 ], 5-hydroxy-7,4′-methoxyflavone ( 7 ) [ 17 ], 5-hydroxy-3,7,4′-methoxyflavone ( 8 ) [ 17 ], 5,7,4′-trimethoxyflavone ( 9 ) [ 17 ], 3,5,7,4′-tetramethoxyflavone ( 10 ) [ 17 ], 5-hydroxy-3,7,3′,4′-tetramethoxyflavone ( 11 ) [ 17 ], 3,5,7,3′,4′-pentamethoxyflavone ( 12 ) [ 17 ], 5,7,4′-trimethoxyflavonone ( 13 ) [ 18 ], and β -sitosterol ( 14 ) [ 19 ] ( Figure 3 ).…”

Section: Resultsmentioning

confidence: 99%

Anti-Austerity Activity of Thai Medicinal Plants: Chemical Constituents and Anti-Pancreatic Cancer Activities of Kaempferia parviflora

Sun

Kim

Dibwe

et al. 2021

Plants

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Human pancreatic tumor cells have an intrinsic ability to tolerate nutrition starvation and survive in the hypovascular tumor microenvironment, the phenomenon termed as “austerity”. Searching for an agent that inhibits such tolerance to nutrient starvation and kills the pancreatic cancer cells preferentially in nutrient-starvation is a unique anti-austerity strategy in anti-cancer drug discovery. In this strategy, plant extracts and compounds are tested against PANC-1 human pancreatic cancer cell line under the conditions of nutrient-deprived medium (NDM) and nutrient-rich medium (DMEM), to discover the compounds that show selective cytotoxicity in NDM. Screening of twenty-five Thai indigenous medicinal plant extracts for their anti-austerity activity against the PANC-1 human pancreatic cancer cell line in nutrient deprived medium (NDM) resulted in the identification of four active plants, Derris scandens, Boesenbergia pandurata, Citrus hystrix, and Kaempferia parviflora, with PC50 values 0.5–8.9 µg/mL. K. parviflora extract also inhibited PANC-1 cancer cell colony formation. Phytochemical investigation of K. parviflora extract led to the isolation of fourteen compounds, including two polyoxygenated cyclohexanes (1 and 2), eleven flavonoids (3–13), and β-sitosterol (14). Stereochemical assignment of compound 1 was confirmed through X-ray analysis. All isolated compounds were tested for their preferential cytotoxicity against PANC-1 cells. Among them, 5-hydroxy-7-methoxyflavone (3) displayed the most potent activity with a PC50 value of 0.8 µM. Mechanistically, it was found to induce apoptosis in PANC-1 cell death in NDM as evident by caspase cleavage. It was also found to inhibit PANC-1 cancer cell colony formation in DMEM. Therefore, compound 3 can be considered as a potential lead compound for the anticancer drug development based on the anti-austerity strategy.

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ChemInform Abstract: Synthesis of a Complete Series of O‐Methyl Analogues of Naringenin and Apigenin.

Cited by 2 publications

References 1 publication

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

Novel O-alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity

Anti-Austerity Activity of Thai Medicinal Plants: Chemical Constituents and Anti-Pancreatic Cancer Activities of Kaempferia parviflora

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