• Title/Summary/Keyword: ellagic acid

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Variation of the Contents of Triterpenoids and Tannins Depending on Growth and Infection in the Leaves of Rubus crataegifolius and Rubus parvifolius

  • Kim, Min-Young;Rhim, Tae-Jin;Lim, Sang-Cheol;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.21 no.1
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    • pp.14-19
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    • 2015
  • Several $19{\alpha}$-hydroxyursane-type triterpenoids and hydrolysable tannins have beneficial effects on human health. Rubus crataegifolius (Rosaceae) has the cleft simple leaf whereas R. parvifolius has pinnate compound leaves. This research was aimed to find the variation in the contents of the triterpenoids and tannins between the infected versus uninfected leaves of R. coreanus and R. parvifolius and between young versus mature leaves. Triterpenoids and tannins were quantitatively analyzed by HPLC. Six triterpenoids including tormentic acid, euscaphic acid, 23-hydroxytormentic acid, coreanoside $F_1$, kaji-ichigoside $F_1$ and niga-ichigoside $F_1$ were used for standard compounds. Gallotannins and ellagitannins were quantitatively evaluated using the indicatives of methyl gallate and ellagic acid. The infected leaves of R. crataegifolius contained higher levels of triterpenoids and tannin than the uninfected leaves; however, lower quantity of total tannin was observed in the mature leaves than in the young leaves. Although the pinnate compound leaves of R. parvifolius exhibited similar tendency of those compositional variation with R. crataegifolius each other, its contents of triterpenoids do not considerably vary. Variation of the contents of triterpenoids and tannins were particularly distinct in R. crataegifolius by growth and infection.

Terpenoids and Phenolics from Geum japonicum (뱀무로부터 테르페노이드 및 페놀성 성분의 분리)

  • Yean, Min-Hye;Kim, Ju-Sun;Hyun, Yu-Jae;Hyun, Jin-Won;Bae, Ki-Hwan;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.43 no.2
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    • pp.107-121
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    • 2012
  • Twenty-five compounds were isolated from the methanolic extract of Geum japonicum (Rosaceae), and their structures were identified as eleven triterpenoids [ursolic acid 3-acetate (2), cecropiacic acid 3-methyl ester (3), pomolic acid 3-acetate (5), ursonic acid (6), ursolic acid (7), pomolic acid (8), corosolic acid (9), euscaphic acid (11), arjunic acid (16), tormentic acid (18), 23-hydroxytormentic acid (21)], two saponins [rosamultin (22) and kaji-ichigoside $F_1$ (23)], two megastigmanes [blumenol A (14) and (+)-dehydrovomifoliol (15)], three flavonoids [apigenin (13), isoquercitrin (17) and tiliroside (24)], two ellagic acid derivatives [3,3'-di-O-methylellagic acid (12) and ducheside B (25)] and five others [eugenol (1), emodin (4), vanillic acid (10), gallic aldehyde (19), salidroside (20)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. This is the first report of the eleven compounds, 2~6, 10, 15, 16, 20, 23, and 25 from the genus Geum, as well as the first report of apigenin (13) and 3,3'-di-O-methylellagic acid (12) from G. japonicum. The antioxidant properties of 22 isolates (1~11, 14, 16~25) were evaluated by the intracellular reactive oxygen species (ROS) radical scavenging using 2',7'-dichlorodihydrofluorescein diacetate (DCF-DA) assay. Among them, isoquercitrin (17) showed significant scavenging activity, and gallic aldehyde (19) and ducheside B (25) showed weak scavenging activity.

Influence of Abnormally Low Temperatures on Growth, Yield, and Biologically Active Compounds of Strawberry (이상 저온조건이 딸기의 생육, 수량 및 생리활성 성분에 미치는 영향)

  • Lee, Gyu-Bin;Choe, Yun-Ui;Park, Eun-Ji;Wang, Ziyu;Li, Mei;Li, Ke;Park, Young-Hoon;Choi, Young-Whan;Kang, Nam-Jun;Kang, Jum-Soon
    • Journal of Environmental Science International
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    • v.26 no.3
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    • pp.381-392
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    • 2017
  • The present study aimed to investigate the effects of low temperature on the growth, yield, quality, and biologically active compounds of strawberry and obtain basic information for developing a technology for stable growth of strawberry in greenhouses. Growth of strawberry, including leaf number, area, and length, plant height, and dry weight was better at the optimum growth temperature of $20^{\circ}C$ than at a lower temperature of $15^{\circ}C$. At the low temperature of $15^{\circ}C$, the cultivar 'Maehyang' was more tolerant and displayed better growth rate than 'Seolhyang'. At $15^{\circ}C$, the fruit production per week and fruit weight was lower than that at $20^{\circ}C$. In contrast, fruit length and diameter were not significantly different between the two growth temperatures. Growth temperature also did not affect the fruit color index, Hunter L, a, b value, or fruit firmness. However, the sugar content of strawberries grown at $15^{\circ}C$ was higher by 0.8 and 1.5 Brix for 'Seolhyang' and 'Maehyang', respectively, than of those grown at $20^{\circ}C$. There was no difference in the content of fisetin, a biologically active compound, for 'Seolhyang' at both growth temperatures, however, the fisetin content of 'Maehyang' was higher at $20^{\circ}C$ than at $15^{\circ}C$. Cinchonine and ellagic acid content of 'Seolhyang' was higher at $20^{\circ}C$ than at $15^{\circ}C$, whereas that of 'Maehyang' was higher at $15^{\circ}C$ than at $20^{\circ}C$. Quercetin content showed no significant differences with respect to growth temperature, however, it tended to increase at $20^{\circ}C$. The cinnamic acid content of 'Seolhyang' was higher at $15^{\circ}C$ than at $20^{\circ}C$, whereas that of 'Maehyang' increased at $20^{\circ}C$. Collectively, the biologically active compounds of strawberry were affected by growth temperature. Moreover, the content of these compounds tended to increase at $20^{\circ}C$, the optimum growth temperature, rather than at the sub-optimal growth temperature of $15^{\circ}C$.

An Ellagic Acid Rhamnoside from the Roots of Potentilla discolor with Protein Glycation and Rat Lens Aldose Reductase Inhibitory Activity

  • Jang, Dae-Sik;Yoo, Nam-Hee;Kim, Jong-Min;Lee, Yun-Mi;Yoo, Jeong-Lim;Kim, Young-Sook;Kim, Jin-Sook
    • Natural Product Sciences
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    • v.13 no.2
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    • pp.160-163
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    • 2007
  • Four glycosides, rosamultin (1), tetracentronside B (2), 4-O-methylellagic acid 3-O-${\alpha}$-$_L$-rhamnopyranoside (3), and vanillic acid 4-O-${\beta}$-$_L$-glucopyranoside (4), isolated from the roots extract of Potentilla discolor, were subjected to in vitro bioassays to evaluate the inhibitory activity on advanced glycation end products (AGEs) formation and rat lens aldose reductase (RLAR). Compound 3 exhibited a significant inhibitory activity against both AGEs formation and RLAR with IC$_{50}$ values of 79.5 and 8.03 ${\mu}$M, respectively. All the compounds (1-4) were isolated for the first time from this plant.

Peroxynitrite scavengers from Phellinus linteus

  • Jeong, Da-Mi;Jung, Hyun-Ah;Kang, Hye-Sook;Choi, Jae-Sue
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.1-11
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    • 2008
  • Peroxynitrite ($(ONOO^-)$ is a cytotoxic species formed from nitric oxide and superoxide anion, which are highly implicated in the pathogenesis of oxidative stress-mediated diseases. The aim of this study was to investigate the scavenging effects of Phellinus linteus on authentic $ONOO^-$, and further phytochemical studies are planned that will attempt to identify the active principles. From the active EtOAc fraction, a mixture of fungisterol and 5-dihydroergosterol (1), a mixture of betulin and 1,2-benzenedicarboxylic acid bis (2-methyl heptyl) ester (2), protocatechualdehyde (3), protocatechuic acid (4), cirsiumaldehyde (5), hispidin (6), caffeic acid (7), phelligridin D (8), uracil (9), gallic acid (10), 2,5-dihydroxybenzoic acid (11), ferulic acid (12), 2,3-dihydroxybenzaldehyde (13), arbutin (14), isoferulic acid (15), guanosine (16), and ellagic acid (17) were isolated, and their structures were characterized based on spectroscopic data. All compounds except 3, 6, 7 and 16 were isolated for the first time from P. linteus. Compounds 3, 4, 6-8, 10-15, and 17 showed potent scavenging activity on $ONOO^-$, with $IC_{50}$ values of $2.06\;{\pm}\;0.10$, $3.45\;{\pm}\;0.57$, $0.71\;{\pm}\;0.05$, $2.78\;{\pm}\;0.36$, $5.42\;{\pm}\;0.26$, $1.13\;{\pm}\;0.02$, $1.82\;{\pm}\;0.17$, $0.91\;{\pm}\;0.19$, $1.59\;{\pm}\;0.09$, $1.88\;{\pm}\;0.07$, $1.22\;{\pm}\;0.37$, and $2.01\;{\pm}\;0.02\;{\mu}M$, respectively, as compared to the positive control, DL-penicillamine, with an $IC_{50}$ value of $5.04\;{\pm}\;0.06\;{\mu}M$.

Antimicrobial activity and protective effect of Geranium thunbergii against oxidative DNA damage via antioxidant effect (현초의 항산화 활성에 의한 산화적 DNA 손상 보호효과 및 항균활성)

  • Kwon, Tae-Hyung;Lee, Su-Jin;Park, Jae-Ho;Kim, Taewan;Park, Jung-Ja;Park, Nyun-Ho
    • Food Science and Preservation
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    • v.24 no.3
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    • pp.325-333
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    • 2017
  • This study aimed to investigate the various biological activities of Geranium thunbergii such as antimicrobial activity and protective effect against oxidative damage. To evaluate its antioxidant and antimicrobial activities, we first performed methanol extraction; this methanol extract was further partitioned using various solvents. And then, its antioxidant activity was measured using various assays including total phenolic content and protection against oxidative DNA damage, and antimicrobial activities were examined using minimum inhibiting concentration (MIC) test, and paper disc method. In addition, high-performance liquid chromatography was performed to analyze the major chemical components of ethyl acetate fraction. The G. thunbergii fraction with ethyl acetate exhibited higher antioxidant and antimicrobial activities than the other fractions. The results showed that G. thunbergii ethyl acetate fraction at $50{\mu}g/mL$ had strong DPPH and ABTS radical scavenging activities of 80.88% and 80.12%, respectively. In addition, the ethyl acetate fraction protected DNA from the oxidative damage induced by ferrous ion and hydroxyl radicals and showed high antimicrobial activity with diameter of inhibition zones ranging from 13.33 to 15.67 mm. High-performance liquid chromatography analysis revealed the major phenolic compounds of G. thunbergii to be ellagic acid and gallic acid. These results suggest that G. thunbergii might protect DNA against oxidative stress induced by reactive oxygen species and can be utilized as a natural source of antioxidant and antimicrobial agent in the food industry.

Flavonoids inhibit the AU-rich element binding of HuC

  • Kwak, Ho-Joong;Jeong, Kyung-Chae;Chae, Min-Ju;Kim, Soo-Youl;Park, Woong-Yang
    • BMB Reports
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    • v.42 no.1
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    • pp.41-46
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    • 2009
  • Post-transcriptional regulation of mRNA stability by Hu proteins is an important mechanism for tumorigenesis. We focused on the molecular interactions between the HuC protein and AU-rich elements (AREs) to find chemical inhibitors of RNA-protein interactions using RNA electrophoretic mobility shift assay with non-radioactive probes. Screening of 52 natural compounds identified 14 candidate compounds that displayed potent inhibitory activity. Six (quercetin, myricetin, (-)-epigallocatechin gallate, ellagic acid, (-)-epicatechin gallate, and rhamnetin) were categorized as phytochemicals, and their $IC_{50}$ values were low ($0.2-1.8\;{\mu}M$).

Dendropanax morbifera and Rubus coreanus Miq. Extracts Inhibits the Formation of Uric Acid Crystal by Reducing Xanthine Oxidase Activity

  • Hurh, Joon;Simu, Shakina Yesmin;Han, Yaxi;Ahn, Jong-Chan;Yang, Deok-Chun
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2018.04a
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    • pp.95-95
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    • 2018
  • Uric acid is the end product of purine metabolism in human body, originating from hypoxanthine after enzyme catalysis by Xanthine oxidase (XOD). Hyperuricemia results as a result of either over-generation of uric acid or a reduction in its excretion. In silico modelling methods such as Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) prediction, Autodock 4.2.6 program were used to study the potential inhibitory compounds of XOD. Also we investigated the inhibition of XOD activity by using the extracts of Dendropanax morbifera and Rubus coreanus Miq spectrophotometrically. According to ADMET data, several compounds from D. morbifera and R. coreanus plants, were found to be more potent in inhibiting the XOD activity than allopurinol. XOD inhibitory activity is evaluated by quantifying the formation of uric acid by measuring the absorbance at 290 m ($A_{290}$).D. morbifera extract inhibited XOD activity at $250{\mu}g/ml$, however the extracts from R. coreanus has inhibited XOD activity at $25{\mu}g/ml$. The major compound of R. coreanus, ellagic acid significantly increased the inhibition rate from $9{\mu}g/ml$ and showed a 71% suppression rate at $15{\mu}g/ml$. Finally, these results suggested a potential inhibitory activities of the extracts from D. morbifera and R. coreanus Miq, but further research is needed to validate to ensure their safe usage as drug.

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Polyphenolic Metabolites of the Flowers of Tamarix tetragyna

  • El-Mousallami, Amani M.D.;Hussein, Sahar A.M.;Nawwar, Mahmoud A.M.
    • Natural Product Sciences
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    • v.6 no.4
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    • pp.193-198
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    • 2000
  • Phytochemical study of the constitutive polyphenolics of the flower aqueous alcohol extract of Tamarix tetragyna was carried out. The new sulphated flavonol, quercetin 3',4'-dimethyl ether $3-O-KSO_3$ as well as the new natural galloyl glucose, $2-O-galloyl-({\alpha}/{\beta})-^4C_1-glucopyranose$ were isolated and characterized. The known sulphated flavonols, kaempferol 7,4-dimethyl ether $3,5-di-O-KSO_3$, quercetin 7-methyl ether $3,3',4'-tri-O-KSO_3$, quercetin 7,4'-dimethyl ether $3-O-KSO_3$ and quercetin $3-O-KSO_3$ and the known sulphated phenolics, isoferulic acid $3-O-KSO_3$ and ellagic acid 4,4'-dimethyl ether $3-O-KSO_3$ were also separated and identified. The structures were established by conventional methods of analysis and confirmed by $^1H-,\;^{13}C-NMR$ and negative ESI-mass spectrometry. 2D-homonuclear chemical shift correlation NMR experiment was applied for the new natural galloylglucose.

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Far Infrared Ray Irradiation Stimulates Antioxidant Activity in Vitis flexuosa THUNB. Berries

  • Eom, Seok-Hyun;Jin, Cheng-Wu;Park, Hyoung-Jae;Kim, Eun-Hye;Chung, Ill-Min;Kim, Myong-Jo;Yu, Chang-Yeon;Cho, Dong-Ha
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.5
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    • pp.319-323
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    • 2007
  • Wild grapes have been used as traditional medicinal use and alcoholic beverage production in Korea. The objective of this study is to improve antioxidant properties in Sae-muru by far infrared ray (FIR) treatment, with expecting potential benefits of FIR treatment for wild grape products during manufacturing processes. FIR treatment in berries induced increased content of catechin, epicatechin gallate, epigallocatechin gallate, gallic acid, rutin, ellagic acid, and resveratrol, while content of epicatechin and epigallocatechin was decreased. Although FIR treatment resulted either increased or decreased chemical component groups, presenting in HPLC chromatograms, antioxidant activity in Sae-muru extract was significantly increased by the FIR treatment. Our results suggest that FIR treatment should be an efficient process in the production of high content of bioactive molecules in Sae-muru.