• Title/Summary/Keyword: Phenolic glucoside

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A Phenolic Glucoside Isolated from Prunus serrulata var. spontanea and its Peroxynitrite Scavenging Activity

  • Jung Hyun Ah;Chung Hae Young;Kang Sam Sik;Hyun Sook Kyung;Kang Hye Sook;Choi Jae Sue
    • Archives of Pharmacal Research
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    • v.28 no.10
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    • pp.1127-1130
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    • 2005
  • A new phenolic glucoside (1), pursargentoside, was isolated from the leaves of Prunus serrulata var. spontanea, along with three other known compounds, orobol 7-O-glucoside (2), $1{\beta}$, $2{\alpha}$, $3{\alpha}$, 24-tetrahydroxy-urs-12-en-28-oic acid (3), and chlorogenic acid (4). The structure of pursargentoside (1) was identified by spectroscopic data analysis including 1D and 2D NMR spectroscopy, as 2-O-${\beta}$-(6'-benzoyl)-glucopyranosyl o-(Z)-coumaric acid. Compounds 1, 2, and 4 exhibited ONOO- scavenging activity, whereas compound 3 was determined to be virtually inactive.

Antioxidant Properties and Quantification of Phenolic Compounds from Safflower (Carthamus tinctorius L.) Seeds

  • Kim, Eun-Ok;Oh, Ji-Hae;Lee, Sung-Kwon;Lee, Jun-Young;Choi, Sang-Won
    • Food Science and Biotechnology
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    • v.16 no.1
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    • pp.71-77
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    • 2007
  • The antioxidant properties of twelve phenolic compounds, including matairesinol 4'-O-$\beta$-D-glucoside, 8'-hydroxyarctigenin 4'-O-$\beta$-D-glucoside, matairesinol, 8'-hydroxyarctigenin, N-feruloylserotonin 5-O-$\beta$-D-glucoside, N-(p-coumaroyl)-serotonin-5-O-$\beta$-D-glucoside, N-feruloylserotonin, N-(p-coumaroyl)serotonin, luteolin 7-O-$\beta$-D-glucoside, luteolin, acacetin 7-O-$\beta$-glucuronide, and acacetin, isolated from defatted safflower (Carthamus tinctorius L.) seeds were evaluated with regard to the DPPH, superoxide and hydroxyl radicals. Additionally, levels of phenolic compounds were determined by HPLC in two cultivars of safflower seeds. Among them, four serotonin derivatives showed potent DPPH ($IC_{50}=10.83-21.75\;{\mu}M$) and hydroxyl ($IC_{50}=75.93-374.63\;{\mu}M$) radical scavenging activities, and their activities were significantly stronger than that of ${\alpha}-tocopherol$. Four flavonoids ($IC_{50}=170.65-275.83\;{\mu}M$) and four lignans ($IC_{50}=114.22-406.10\;{\mu}M$) exhibited significant superoxide and hydroxyl radical scavenging activities, respectively, whereas these compounds contained less activity toward the DPPH and hydroxyl radicals than serotonin derivatives. The levels of serotonin derivatives, lignans and flavonoids in safflower seeds of two cultivars ranged from 49.30 to 260.40, 3.72 to 158.90, and 11.72 to 214.97 mg% (dry base), respectively. Of the two cultivars, 'Cheongsu' had somewthat higher concentrations of phenolic compounds than 'Uisan'. These results suggest that phenolic compounds in safflower seeds may playa role as protective phytochemical antioxidants against reactive oxygen-mediated pathological diseases.

Study on Phenolic Compounds in Lettuce Samples Cultivated from Korea Using UPLC-DAD-QToF/MS (국내 재배 상추로부터 UPLC-DAD-QToF/MS를 이용한 페놀화합물 성분 비교 연구)

  • Kim, Heon-Woong;Lee, Seon-Hye;Asamenew, Gelila;Lee, Min-Ki;Lee, Suji;Park, Jin Ju;Choi, Youngmin;Lee, Sang Hoon
    • The Korean Journal of Food And Nutrition
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    • v.32 no.6
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    • pp.717-729
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    • 2019
  • The chemical informs about 70 individual phenolic compounds were constructed from various lettuce samples based on literature sources and analytical data. A total of 30 phenolic compounds including quercetin 3-O-glucuronide, quercetin 3-O-(6''-O- malonyl) glucoside, cyanidin 3-O-(6''-O-malonyl)glucoside, chlorogenic acid and chicoric acid as major components were identified in 6 lettuce samples from Korea using UPLC-DAD-QToF/MS on the basis of constructed library. Among these, quercetin 3,7-di-O-glucoside(m/z 627 [M+H]+), quercetin 3-O-(2''-O-malonyl)glucoside(morkotin C, m/z 551 [M+H]+), quercetin 3-O-(6''- O-malonyl)glucoside methyl ester(m/z 565 [M+H]+), 5-O-cis-p-coumaroylquinic acid(m/z 339 [M+H]+) and 5-O-caffeoylquinic acid methyl ester(m/z 369 [M+H]+) were newly confirmed from the lettuce samples. In total content of phenolic compounds, 4 red lettuce samples(2,947.7~7,535.6 mg/100 g, dry weight) showed higher than green lettuce(2,687.3 mg) and head lettuce(320.1 mg).

Quantitative Changes in Phenolic Compounds of Safflower (Carthamus tinctorius L.) Seeds during Growth and Processing

  • Kim, Eun-Ok;Lee, Jun-Young;Choi, Sang-Won
    • Preventive Nutrition and Food Science
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    • v.11 no.4
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    • pp.311-317
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    • 2006
  • Phenolic compounds in safflower seeds were recently found to stimulate bone formation and increase plasma HDL cholesterol levels in estrogen deficient rats, and to inhibit melanin synthesis. Nine phenolic compounds: $N-feruloylserotonin-5-O-{\beta}-D-glucoside,\;8'-hydroxyarctigenin-4'-O-{\beta}-D-glucoside,\;luteolin-7-O-{\beta}-D-glucoside$, N-(p-coumaroyl)serotonin, N-feruloylserotonin, 8'-hydroxy arctigenin (HAG), luteolin (LT), $acacetin-7-O-{\beta}-D-glucuronide$ (ATG) and acacetin (AT), were quantified by HPLC in safflower (Carthamus tinctorius L.) seeds during growth and processing. During growth, levels of the nine phenolic compounds in the seeds increased progressively with increasing growth stages, reached a maximum on July 30 (42nd day after flowering), and then remained relatively constant. During the roasting process, levels of phenolic compounds, except HAG, LT and AT, generally decreased with increased roasting temperature and time, whereas those of HAG, LT and AT increased progressively with increased roasting temperature and time. During the steaming process, levels of other phenolic compounds except HAG and AT generally tended to increase with increased steaming time, whereas those of HAG and AT were scarcely changed. During the microwave treatment, quantitative changes of phenolic compounds were similar to the roasting process, although there were some differences in levels of phenolic compounds between two heat treatments. These results suggest that the steamed safflower seeds after harvesting on late July may be useful as potential dietary supplement source of phenolic compounds for prevention of several pathological disorders, such as atherosclerosis and osteoporosis and aging.

Relationship of Phenolic Compounds and Free-radical Scavenging Activity in Black and Red Rice Extract

  • Hu, Gao-Sheng;Xu, Kai-Xiu;Jeong, Soon Jae;Kim, Doh-Hoon
    • Korean Journal of Breeding Science
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    • v.42 no.2
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    • pp.129-138
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    • 2010
  • Total phenolic content, total anthocyanin content and antioxidant activity were analyzed from rice samples collected in Korea, Japan and China. The results showed that the total phenolic content and free-radical scavenging activity differed significantly in these rice lines. The correlation between content and activity was subsequently investigated. The results showed that in black rice, anthocyanin was the major phenolic component and that both phenolic content and anthocyanin content were closely correlated with free-radical scavenging activity. Reverse Phase High Performance Liquid Chromatography (RP-HPLC) data showed that cyanidin-3-O-glucoside and peonidin-3-O-glucoside composed about 90% of the total anthocyanin content in black rice and in red rice. In the red rice extract, the total phenolic content produced a high correlation coefficient with antioxidant activity but correlated very poorly with the total anthocyanin content. The $OD_{458}$ and the $OD_{500}$ values which represent the proanthocyanidin content of the rice extract, produced high correlation coefficients with antioxidant activity and total phenolic content. These results suggest that the $OD_{458}$ and the $OD_{500}$ values can be used to evaluate the quality of red rice. In addition, based on the data obtained, a competitive accumulation model of anthocyanin and proanthocyanidin in black and red rice was proposed.

Biological Activity of Phenolic Compounds in Seeds and Leaves of Safflower (Carthamus tinctorius L.)

  • Lee, Won-Jung;Cho, Sung-Hee;Lee, Jun-Young;Park, Sang-Won
    • Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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    • 2003.04a
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    • pp.22-39
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    • 2003
  • Biological activity of phenolic compounds in seeds and leaves of safflower (Carthamu tinctorius L.) were evaluated using several in vitro and in vivo assays. Six phenolic constituents were isolated from the seeds and identified as N-feruloylserotonia, N- (p-coumaroyl)serotonin, matairesinol, 8′-hydroxyarctigenin, acacetin 7-O-$\beta$-D-glucoside (tilianine) and acacetin. Six phenolic compounds exhibited considerable antioxidative activity, and especially two serotonins showed potent DPPH radical scavenging activity and antiperoxidative activity against rat liver microsomal lipid peroxidation induced by the hydroxyl radical generated via a Fenton-type reaction. Additionally, six phenolic compounds possessed comparable cytotoxicity against three cancer cells, Hela cell, MCF-7 and HepG2 cell, and particularly acacetin and its glycosides had the most potent cytotoxicity. Moreover, we found that feeding safflower seeds attenuated bone loss, and lowered levels of plasma and liver lipids in ovariectomized rats. Serotonins, lignans and flavones stimulated proliferation of the osteoblast-like cells in a dose-dependent manner (10$^{-15}$ ~10$^{-6}$ M), as potently as E$_2$ (17$\beta$-estradiol). Particularly, serotonins were mainly responsible for bone-protecting and lipid lowering effects in ovariectomized rats. Meanwhile, eight flavonoids, including a novel quercetin-7-O-(6"-O-acetyl)-$\beta$-D-glucopyranoside and seven kown flavonoids, luteolin quercetin, luteolin 7-O-$\beta$-D-glucopyranoside, luteolin-7-O-(6"-O-acetyl)-$\beta$-D-gluco-pyranoside, quercetin 7-O- -glucopyranoside, acacetin 7-O-$\beta$-D-glucuronide and apigenin-6-C-$\beta$-D-glucopyranosyl-8-C-$\beta$-D-glucopyranoside were first isolated and identified from safflower leaf. Among these flavonoids, luteolin-acetyl-glucoside and $\beta$quercetin- acetyl-glucoside showed potent antioxidative activities against 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. Luteolin, quercetin and their corresponding glycosides also exhibited strong antioxidative activity, while acacetin glucuronide and apigenin-6, 8-di-C-glucoside were relatively less active. Finally, changes in phenolic compositions were also determined by HPLC in the safflower seed and leaf during growth stages and roasting process to produce standardized supplement powerds. These results suggest that phenolic compounds in the roasted safflower seed and leaf may be useful as potential sources of therapeutic agents against several pathological disorders such as carcinogenesis, atherosclerosis and osteoporosis.

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Phenolic Constituents from the Flowers of Synurus excelsus (큰수리취 꽃의 페놀성 성분)

  • Lee, Il-Kyun;Yang, Min-Cheol;Lee, Kyu-Ha;Choi, Sang-Un;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.38 no.2 s.149
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    • pp.181-186
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    • 2007
  • Seven phenolic compounds, scopoletin (1), caffeic acid methyl ester (2), apigenin 7-O-${\alpha}$-L-rhamnosyl-(1${\rightarrow}$6)-O-${\alpha}$-D-glucoside (3), isorhamnetin 7-O-${\alpha}$-D-glucoside (4), isorhamnetin 3-O-${\alpha}$-D-glucoside (5), luteolin (6), and quercetin 3-methyl ether (7) were isolated from the methanol extract of the flowers of S. excelsus. Their structures were established by chemical and spectroscopic methods. The isolated compounds were tested for their cytotoxicity against four human cancer cell lines in vitro using a SRB method. The compounds 4 and 7 showed moderate cytotoxicity with ED$_{50}$ values ranging from 1.59 to 13.14${\mu}$g/ml.

Phenolic compounds in domestic and imported grape cultivars in Korea (국내산 포도와 수입산 포도의 페놀계화합물 함량)

  • Jung, Sung Min;Kim, Su Jin;Hur, Youn Young
    • Korean Journal of Food Science and Technology
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    • v.52 no.3
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    • pp.205-211
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    • 2020
  • In this study, fruit phenolics were investigated with using LC/MS and HPLC analysis in order to compare the differences between domestic ('Campbell Early', 'Kyoho', 'Heukbosuk', and 'Hongju SDS') and imported ('Crimson SDS' and 'Thomson SDS') grapes. In the case of fruit characteristics, imported grape 'Crimson SDS' and 'Thompson SDS', had lighter skin weight (300-350 mg/berry) and hard flesh (5.2-5.6 kg·f) than domestic grape cultivar. The phenolic compound contents of 'Crimson SDS' skin was higher, but resveratrol (25-29 mg/kg), quercetin (350-380 mg/kg), and myricetin (31-32 mg/kg) contents were similar in to those of 'Hongju SDS'. The anthocyanin content was different from differed between grape cultivars. 'Hongju SDS' grape was showed higher in Delphinidin-3-glucose (D3G) levels, and 'Crimson SDS' was showed higher in Peonidin-3-glucoside (P3G) levels. The contents of phenolic compounds were investigated differently for each grape berry part. Catechin, epicatechin, procyanidin B1, and B2 were found in grape seeds.

Phenolic Compounds from the Bark of Salix gilgiana (내버들 수피의 페놀 성분)

  • 황완균;장영수;김일혁
    • YAKHAK HOEJI
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    • v.39 no.2
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    • pp.193-199
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    • 1995
  • For the investigation medicinal resources for Salix species, the studies were carried out to evaluate the pharmaco-constituents in the bark of Salix gilgiana (Salicaceae) which have been used as anti-inflammation, analgesic and diuretic agents in folk remedies in Korea. From aqueous fraction of the MeOH extract, (+)-catechin(l), 1-O-p-coumaroyl glucoside(II), 1-O-feruloyl glucoside(III) and p-hydroxyacetophenone glucoside(IV) were isolated by column chromatographic separation using Amberlite XAD-2, ODS-gel and Sephadex LH-20 and the structure of these compounds were elucidated by physico-chemical evidence($^{1}$H-NMR, $^{13}$C-NMR, IR, El-Mass and G.C.) and by comparison with authentic samples.

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