In recent years, the demand for natural, functional, and healthy foods has tended to increase. Perilla frutescens is one of the most important herb vegetable and also economic plant in korea because of its attactive ...
In recent years, the demand for natural, functional, and healthy foods has tended to increase. Perilla frutescens is one of the most important herb vegetable and also economic plant in korea because of its attactive flavor and beneficial effect on human health. Many studies have reported that this plant contains a huge amount of antioxidative phytochemicals such as flavones phenylpropanoids, and anthocyanins. Thus, an efficient evaluation method is of great important to do a quality control or breeding study of this valuable plant. There are some evaluation methods, but they have a limit on number of the standard compounds, mainly rosmarinic acid and caffeic acid. Therefore, sufficient phytochemical library and an efficient evaluation method are very necessary for setting the analytical method. In this study, we isolated twenty phytochemicals from P. frutescens and identified their structure by suing spectroscopic methods including 2D-NMR technique. Isolated compounds were represented as five phenypropanoids (1-5), two flavones (6, 7), five anthocyanins (8-12), five glycolipids (13-17) and three triterpenes (18-20). All isolated compounds were also examined for their antioxidant, tyrosinase inhibitory and lipooxygenase inhibitory activity. The results were summarized as follow. - The phenylpropanoids (1-5) were identified as caffeic acid (1), frulic acid (2), caffeic acid methylester (3), rosmarinic acid (4), and rosmarinic acid methylseter (5). The flavones (6,7) were identified as apigenin (6) and luteolin (7). - Key phytochemicals, antocyanin derivatives (8-12) were identified as cyanin (8), cyanidin-3-O-glucoside (9), caffeylcanin (10), shisonin (11), and cyanidin-3-O-coumaryl glucoside (12). - The glycolipids (13-17) were identified as 2-O-octadecatrienoyl glycerol (13), 1,2-di-O-octadecatrienoyl-3-O-galacto-pyranosyl glycerol (14), 1-O-hexadecanoyl -2-O-octadecadienoyl-3-O-galacto pyranosyl glycerol (15), 2-O-octadecatrienoyl -3-O-galacto-pyranosyl glycerol (16), and 1-O-hexadecanoyl-2-O-octadecatrienoyl-3-di -O-galacto-pyranosyl glycerol (17) - The triterpenes (18-20) were identified as b-sitosterol (18), ursolic acid (19) and oleanolic acid (20) [그림은 원문참고] - Antiradical property of the isolated compounds was examined with DPPH, which is widely used for assessing the ability of polyphenols transfer labile H-atoms into radical. Catecohlic phenylpropanoids (1, 3-5), which have a vicinal dihydroxy groups, exhibited strong free radical scavenging activities with IC50 values of 11.7, 9.7, 15.5, and 7.0 mM, respectively. All antioxidative compounds showed dose-dependent inhibitory effect on the DPPH radical. - The isolated compounds (1-5) were tested for their enzymatic inhibitory activities against tyrosinase from mushroom. All phenylpropanoids investigated apart from ferulic acid (2) exhibited a significant degree of tyrosinase inhibition (IC50 4.0~49.2 mM). O-caffeyl group in rosmaric acid derivatives (4, 5) was influenced greatly to increase the potency of the inhibitors activity, while methylated analog 2 was much less efficient (>400 mM). Mechanistic analysis showed the phenylpropanoids (1, 3-5) exhibited competitive inhibition. Mechanistic analysis also showed that hydroxy quinone moiety of phenylpropanoides were transformed into quinone by tyrosinase. - The isolated compound (1-5, 13-17) were tested for their enzymatic inhibitory activities against lipooxygenase (E.C 1.13.11.12). Among of them, phenylpropanoids (1, 3-5) and glycolipids (14-17) exhibited a significant degree of lipooxygenase inhibition. The majority of inhibitors (4, 5, 14-17) was shown to have IC50 values of 30 mM or below. Interestingly, glycolipids (13-17) were significant affected by subtle structure change. For instance, the most potent inhibitor was 17 involving which possessed a diglycoside moiety. The monoglycosylated species (14-16) was one fifth as potent, whilst the glyceride (13) species showed almost no activity at all.[표는 원문참고] To established reliable analytical method of P. frutescnes by using HPLC, rosmarinic acid and caffeic acid, and typical components of perilla, were used for optimization of extraction condition. And optimized chromatograms of each compounds were obtained and each compounds were identified with LC/MS. Standard curves (r2 ≥ 0.9892 ) were established for quality control (QC) of P. frutescens. Evaluated analytical methods were applied to QC of P. frutescens. The results were summarized as follow. 1. Concentration of polyphenol and anthocyanin at different growth stages were analyzed according the above mentioned procedures. Amounts of rosmarinic acid derivatives and anthocyanins were decreased from sampling time (beginning of the Aug.) to blooming time (mid of the Aug.), and after their critical time, both rosmarinic acid derivatives and anthocyanins were suddenly increased during the seed fruiting time (mid of the Sep.). 2. Cultivar and wild species were compared in view of polyphenols by using the developed method. Rosmarinic acid was main component at cultivar (P. frutescnes; Namcheon and Bora), while flavones (apigenin and luteolin) were main at wild species (P. setoyensis).
In recent years, the demand for natural, functional, and healthy foods has tended to increase. Perilla frutescens is one of the most important herb vegetable and also economic plant in korea because of its attactive flavor and beneficial effect on human health. Many studies have reported that this plant contains a huge amount of antioxidative phytochemicals such as flavones phenylpropanoids, and anthocyanins. Thus, an efficient evaluation method is of great important to do a quality control or breeding study of this valuable plant. There are some evaluation methods, but they have a limit on number of the standard compounds, mainly rosmarinic acid and caffeic acid. Therefore, sufficient phytochemical library and an efficient evaluation method are very necessary for setting the analytical method. In this study, we isolated twenty phytochemicals from P. frutescens and identified their structure by suing spectroscopic methods including 2D-NMR technique. Isolated compounds were represented as five phenypropanoids (1-5), two flavones (6, 7), five anthocyanins (8-12), five glycolipids (13-17) and three triterpenes (18-20). All isolated compounds were also examined for their antioxidant, tyrosinase inhibitory and lipooxygenase inhibitory activity. The results were summarized as follow. - The phenylpropanoids (1-5) were identified as caffeic acid (1), frulic acid (2), caffeic acid methylester (3), rosmarinic acid (4), and rosmarinic acid methylseter (5). The flavones (6,7) were identified as apigenin (6) and luteolin (7). - Key phytochemicals, antocyanin derivatives (8-12) were identified as cyanin (8), cyanidin-3-O-glucoside (9), caffeylcanin (10), shisonin (11), and cyanidin-3-O-coumaryl glucoside (12). - The glycolipids (13-17) were identified as 2-O-octadecatrienoyl glycerol (13), 1,2-di-O-octadecatrienoyl-3-O-galacto-pyranosyl glycerol (14), 1-O-hexadecanoyl -2-O-octadecadienoyl-3-O-galacto pyranosyl glycerol (15), 2-O-octadecatrienoyl -3-O-galacto-pyranosyl glycerol (16), and 1-O-hexadecanoyl-2-O-octadecatrienoyl-3-di -O-galacto-pyranosyl glycerol (17) - The triterpenes (18-20) were identified as b-sitosterol (18), ursolic acid (19) and oleanolic acid (20) [그림은 원문참고] - Antiradical property of the isolated compounds was examined with DPPH, which is widely used for assessing the ability of polyphenols transfer labile H-atoms into radical. Catecohlic phenylpropanoids (1, 3-5), which have a vicinal dihydroxy groups, exhibited strong free radical scavenging activities with IC50 values of 11.7, 9.7, 15.5, and 7.0 mM, respectively. All antioxidative compounds showed dose-dependent inhibitory effect on the DPPH radical. - The isolated compounds (1-5) were tested for their enzymatic inhibitory activities against tyrosinase from mushroom. All phenylpropanoids investigated apart from ferulic acid (2) exhibited a significant degree of tyrosinase inhibition (IC50 4.0~49.2 mM). O-caffeyl group in rosmaric acid derivatives (4, 5) was influenced greatly to increase the potency of the inhibitors activity, while methylated analog 2 was much less efficient (>400 mM). Mechanistic analysis showed the phenylpropanoids (1, 3-5) exhibited competitive inhibition. Mechanistic analysis also showed that hydroxy quinone moiety of phenylpropanoides were transformed into quinone by tyrosinase. - The isolated compound (1-5, 13-17) were tested for their enzymatic inhibitory activities against lipooxygenase (E.C 1.13.11.12). Among of them, phenylpropanoids (1, 3-5) and glycolipids (14-17) exhibited a significant degree of lipooxygenase inhibition. The majority of inhibitors (4, 5, 14-17) was shown to have IC50 values of 30 mM or below. Interestingly, glycolipids (13-17) were significant affected by subtle structure change. For instance, the most potent inhibitor was 17 involving which possessed a diglycoside moiety. The monoglycosylated species (14-16) was one fifth as potent, whilst the glyceride (13) species showed almost no activity at all.[표는 원문참고] To established reliable analytical method of P. frutescnes by using HPLC, rosmarinic acid and caffeic acid, and typical components of perilla, were used for optimization of extraction condition. And optimized chromatograms of each compounds were obtained and each compounds were identified with LC/MS. Standard curves (r2 ≥ 0.9892 ) were established for quality control (QC) of P. frutescens. Evaluated analytical methods were applied to QC of P. frutescens. The results were summarized as follow. 1. Concentration of polyphenol and anthocyanin at different growth stages were analyzed according the above mentioned procedures. Amounts of rosmarinic acid derivatives and anthocyanins were decreased from sampling time (beginning of the Aug.) to blooming time (mid of the Aug.), and after their critical time, both rosmarinic acid derivatives and anthocyanins were suddenly increased during the seed fruiting time (mid of the Sep.). 2. Cultivar and wild species were compared in view of polyphenols by using the developed method. Rosmarinic acid was main component at cultivar (P. frutescnes; Namcheon and Bora), while flavones (apigenin and luteolin) were main at wild species (P. setoyensis).
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