Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had t...
Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had the highest inhibitory effect on hyaluronidase with 44.84%. In addition, For naringenin at concentrations of 0, 150, and $190{\mu}M$, the apparent Michaelis constants ($_{app}K_m$) were calculated to be $0.60{\pm}0.02$, $0.43{\pm}0.02$, and $0.41{\pm}0.01\;mg/mL$ of substrate, respectively; for 7-O-butyl naringenin at 0, 20, and $30{\mu}M$ concentrations, those were $0.44{\pm}0.03$ and $0.27{\pm}0.03\;mg/mL$, respectively. The $V_{max}$ values at 150 and $190{\mu}M$ naringenin were $0.59{\pm}0.02$ and $0.56{\pm}0.01\;mg/mL/min$, respectively; and those at 20 and $30{\mu}M$ 7-O-butyl naringenin were $0.50{\pm}0.02$ and $0.33{\pm}0.02\;mg/mL/min$, respectively. However, the slopes of each inhibitory reaction were not significantly different. Therefore, naringenin and 7-O-butyl naringenin were shown to be uncompetitive inhibitors. These results demonstrate the potential use of 7-O-butyl naringenin as an anti-inflammatory substance.
Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had the highest inhibitory effect on hyaluronidase with 44.84%. In addition, For naringenin at concentrations of 0, 150, and $190{\mu}M$, the apparent Michaelis constants ($_{app}K_m$) were calculated to be $0.60{\pm}0.02$, $0.43{\pm}0.02$, and $0.41{\pm}0.01\;mg/mL$ of substrate, respectively; for 7-O-butyl naringenin at 0, 20, and $30{\mu}M$ concentrations, those were $0.44{\pm}0.03$ and $0.27{\pm}0.03\;mg/mL$, respectively. The $V_{max}$ values at 150 and $190{\mu}M$ naringenin were $0.59{\pm}0.02$ and $0.56{\pm}0.01\;mg/mL/min$, respectively; and those at 20 and $30{\mu}M$ 7-O-butyl naringenin were $0.50{\pm}0.02$ and $0.33{\pm}0.02\;mg/mL/min$, respectively. However, the slopes of each inhibitory reaction were not significantly different. Therefore, naringenin and 7-O-butyl naringenin were shown to be uncompetitive inhibitors. These results demonstrate the potential use of 7-O-butyl naringenin as an anti-inflammatory substance.
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제안 방법
Hyaluronid^e is an endo-hexosaminidase which initiates the degradation of high molecular weight hyaluronic acid. In this study, the inhibitory effects of naringenin and the newly derived flavonoids, 7-(9-/er/-butoxycarbonylmethyl naringenin, 7-O~butyl naringenin, 7-0-(a-methoxycarbonyl) benzyl naringenin, and 7-O-BnO-L-Leu-carbonylmethyl) naringenin were evaluated toward hyaluronidase using an in vitro assay (Table 1). The inhibitory capacity of the 5 flavonoid in decreasing order was as follows:
With regard to tannin, luteolin, apiotenin, kaempferol, and silybin, it is known that the mode of hyaluronidase inhibition is competitive (21). In this study, the mode of inhibition by naringenin and 7-O-butyl naringenin was analyzed using Lineweaver-Burk plots of hyaluronidase activity toward hyaluronic acid in the presence of various concentt-ations of flavonoid (Fig. 2 and Table 2). For naringenin at concentrations of 0, 150, and 190 µM, the apparent Michaelis constants (K)were calculated to be 0.
Therefore, the objective of this study was to evaluate the inliibitory effects of naringenin and 4 newly derived flavonoids [7-O-Zerr-butoxycarbonybiethyl naringenin, 7- (9-butyl naringenin, 7-O-(a-methoxycartx>nyl)ben7yl naringenin and 7-(9-(BnO-L-Leu-carbonylmethyl) naringenin] on hyaluronidase using the microplate method. This will provide important information relevant to the pharmaceutical industry for the development of new ami-inflammatory drugs.
대상 데이터
Five kinds of flavonoids were used for this study; naringenin (Sigma-Aldrich), 7-O-^r-butoxycarbonyl- methyl naringenin, 7-O-butyl naringenin, 7O-(a-methoxy" carbonyl)benzyl naringenin and 7-<7-(BnO-L-Leu-carbonyl- methyl) naringenin (supplied from the Prof. Ybng-Sun Park of Chemistry Department, Konkuk University, Seoul, Korea) (Fig. 1). These flavonoids were dissolved in methanol as a stock solution for further studies.
p-Dnnethylammobenzaldehyde, sodium hyaluronate, , /V-acetyl glucosamine, and bovine hyaluronidase were purchased from Sigma-Aldrich (St Louis, MO, USA).
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