• Title/Summary/Keyword: 5-O-caffeoylquinic acid

Search Result 47, Processing Time 0.026 seconds

Pancreatic Lipase Inhibitors in the Roots of Taraxacum ohwianum, a Herb Used in Korean Traditional Medicine (민들레 뿌리로부터 Pancreatic lipase 저해 물질의 분리)

  • Kim, Tae-Wan;Kim, Tae-Hoon
    • Food Science and Preservation
    • /
    • v.18 no.1
    • /
    • pp.53-58
    • /
    • 2011
  • Activity-guided isolation from an ethylacetate-soluble fraction of a 70% (v/v) ethanolic extract from the roots of Taraxacum ohwianum, using a pancreatic lipase inhibition assay, resulted in isolation and identification of five phenolic metabolites of previously known structure; these were 3,5-di-O-caffeoylquinic acid, chicoric acid, caffeic acid, protocatechuic aldehyde, and luteolin. All structures were confirmed by NMR and MS scpectroscopic data. Of these compounds 3,5-di-O-caffeoylquinic acid exhibited the most potent inhibitory activity, with $IC_{50}$ of $65.1{\pm}0.7\;{\mu}M$ against pancreatic lipase.

Development and Validation of HPLC-PDA Method and Pattern Recognition Analyses Using Eight Marker Compounds for the Quality Control Between the Seeds of Cuscuta chinensis Lam. and Cuscuta japonica Choisy

  • Nguyen, Duc Hung;Zhao, Bing Tian;Le, Duc Dat;Ma, Eun Sook;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
    • /
    • v.25 no.4
    • /
    • pp.334-340
    • /
    • 2019
  • Cuscuta chinensis Lam. and Cuscuta japonica Choisy are parasitic plants. C. chinensis seeds were traditionally used for treatment of kidney and liver deficiencies. C. japonica seeds were used as tonic medicine to improve liver function and strengthen kidneys, treatment of high blood pressure, chronic diarrhea, and sore eyes. Cuscutae Semen are seeds of only C. chinensis in Korean Herbal Pharmacopoeia (K.H.P.). The developed HPLC-PDA method easily, accurately, and sensitively quantified using eight marker compounds [hyperoside (1), astragalin, (2), quercetin (3), kaempferol (4), chlorogenic acid (5), 3,4-di-O-caffeoylquinic acid (6), 1,5-di-O-caffeoylquinic acid (7), and 4,5-di-O-caffeoylquinic acid (8)]. In addition, the method may be used to distinguish seeds between C. chinensis Lam. and C. japonica Choisy. Furthermore, the result from the current study was applied to clarify samples between steam processed and unprocessed samples of C. chinensis by pattern analysis.

Extraction Conditions of Radical Scavenging Caffeoylquinic Acids from Gomchui (Ligularia fischeri) Tea (곰취차로부터 라디칼 소거능을 갖는 Caffeoylquinic Acid류 화합물의 추출조건)

  • Kim, Sang-Min;Kang, Suk-Woo;Um, Byung-Hun
    • Journal of the Korean Society of Food Science and Nutrition
    • /
    • v.39 no.3
    • /
    • pp.399-405
    • /
    • 2010
  • After Gomchui tea was prepared from leaves of Ligularia fischeri (Ledeb.) Turcz by blanching method, the antioxidant activity of major compounds in Gomchui tea was assessed. On-line HPLC-ABTS analysis revealed that caffeoylquinic acids (chlorogenic acids), such as 5-O-caffeoylquinic acid (5-CQA), 3,4-di-O-caffeoylquinic acid (3,4-DCQA), 3,5-di-O-caffeoylquinic acid (3,5-DCQA) and 4,5-di-O-caffeoylquinic acid (4,5-DCQA), were the major antioxidant compounds in Gomchui tea. The extraction efficiency of these compounds were examined in the various conditions such as extraction temperature, time and solvent. The results demonstrated that the extraction amount with water increased in proportion to extraction time (1~10 min) and temperature ($8{\sim}80^{\circ}C$). These active compounds were also extracted with water even at $8^{\circ}C$ (60% of $80^{\circ}C$), indicating that water is very good extraction solvent for extraction of these antioxidant constituents. However, the extraction efficiency of these compounds decreased when ethanol percentage in water increased. The extraction efficiency between Gomchui powder (no blanching) and tea was significantly different, and 60% of total antioxidant compounds in tea was removed from fresh leaves into water in blanching process, especially 3,5-DCQA (over 90%). Meanwhile, the sonication method didn't affect the extraction of these compounds in all solvents. These results suggest that Gomchui tea can be a good candidate for the tea beneficial to human health.

Antioxidant Activities of Phenolic Derivatives from Dipsacus asper Wall. (II)

  • Hung, Tran Manh;Thuong, Phuong Thien;Youn, Ui-Joung;Zhang, Xin Feng;Min, Byung-Sun;Woo, Mi-Hee;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
    • /
    • v.14 no.2
    • /
    • pp.107-112
    • /
    • 2008
  • The six phenolic compounds isolated from the root of Dipsacus asper, 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4-5-di-O-caffeoylquinic acid (5), methyl 4,5-di-O-caffeoyl quinate (6) were continuously evaluated for their antioxidant activity using superoxide radical scavenging and AAPH-mediated (LDL) oxidation assay. The results demonstrated that compounds 1 - 6 had remarkable antioxidant activities with the $IC_50$ values ranging from 12.0 to $2.8{\mu}M$ in superoxide radical scavenging. They also inhibited AAPH-mediated low-density lipoprotein LDL oxidation by the generation of thiobarbituric acid reactive substances (TBARS) with $IC_50$ ranging from 6.7 to $8.7{\mu}M$.

Analysis of polyphenolic metabolites from Artemisia gmelinii Weber ex Stechm. and regional comparison in Korea

  • Park, Mi Hyeon;Kim, Doo-Young;Jang, Hyun-Jae;Jo, Yang Hee;Jeong, Jin Tae;Lee, Dae Young;Baek, Nam-In;Ryu, Hyung Won;Oh, Sei-Ryang
    • Journal of Applied Biological Chemistry
    • /
    • v.62 no.4
    • /
    • pp.433-439
    • /
    • 2019
  • Artemisia species are widely used as food ingredients and raw material in traditional medicine. However, to date, the secondary metabolites of Artemisia gmelinii Weber ex Stechm. have not been sufficiently investigated. The secondary metabolites of A. gmelinii, which was collected from representative regions in Chungbuk, Gangwon, and Gyeongbuk, were analyzed using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-QTof MS) combined with an unsupervised principal component analysis (PCA) multivariate analysis. In the loading scatter plot of PCA, significant changes in metabolites were observed between the regions, ten metabolites (3: 5-O-caffeoylquinic acid, 4: 4-O-caffeoylquinic acid, 8: trans-melilotoside, 12: quercetin 3-O-hexoside, 15: 3,4-O-dicaffeoylquinic acid, 17: 3,5-O-dicaffeoylquinic acid, 18: 4,5-O-dicaffeoylquinic acid, 19: syringaldehyde, 20: caffeoylquinic acid derivative, and 23: icariside II) were evaluated as key markers among twenty-five identified metabolites. Interestingly, the contents of the identified marker significantly differed between the three groups. This is the first study to report the presence of marker metabolites and their correlating geographical cultivation in A. gmelinii.

Isolation of Phenolics, Nucleosides, Saccharides and an Alkaloid from the root of Aralia cordata

  • Hyun, Sook-Kyung;Jung, Hyun-Ah;Min, Byung-Sun;Jung, Jee-H.;Choi, Jae-Sue
    • Natural Product Sciences
    • /
    • v.16 no.1
    • /
    • pp.20-25
    • /
    • 2010
  • Fourteen compounds were isolated from the n-BuOH fraction of the roots of Aralia cordata (syn. = A. continentalis). Through spectroscopic method, the chemical structures were elucidated as: caffeic acid (1), protocatechuic acid (2), thymidine (3), uridine (4), methyl-$\alpha$-D-fructofuranoside (5), a mixture (3 : 1) of $\beta$-D-fructopyranoside and $\beta$-D-fructofuranoside (6), 1-methyl 1,2,3,4-tetrahydro-$\beta$-carboline-3-carboxylic acid (7), methyl-$\beta$-D-fructofuranoside (8), sucrose (9), 5-caffeoylquinic acid (chlorogenic acid) (10), 3-caffeoylquinic acid (neochlorogenic acid) (11), 4-caffeoylquinic acid (cryptochlorogenic acid) (12), 3,5-di-O-caffeoylquinic acid (13), and 1-kestose [$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\alpha$-D-glucopyranoside] (14). Among them, compounds 5, 7, 8, and 10 - 14 were isolated from this plant for the first time.

Analysis of Free Amino Acids and Polyphenol Compounds from Lycopene Variety of Cherry Tomatoes (방울토마토 라이코펜 품종의 유리아미노산 및 폴리페놀 화합물의 분석)

  • Kim, Hyen-Ryung;Ahn, Jun-Bae
    • Culinary science and hospitality research
    • /
    • v.20 no.3
    • /
    • pp.37-49
    • /
    • 2014
  • In order to elucidate the usefulness of Lycopene, a cherry tomato variety, as a food material, the compositions of free amino acids, amino acid metabolites and polyphenol compounds were analyzed using HPLC and LC-MS/MS method. Lycopene contained eighteen free amino acids except for L-Cys and L-Try. L-Glu was the most abundant free amino acid, followed by L-Gln and L-Asp. The percentages of L-Glu, L-Gln and L-Asp of total free amino acid were 55.5%, 15.9% and 9.9% respectively. Lycopene contained essential amino acids with the exception of tryptophan. The following amino acid metabolites were found : ${\gamma}$-aminobutyric acid(GABA), carnitine(L-Car), o-phosphoethanolamine(o-Pea), hydroxylysine(Hyl) phosphoserine (p-Ser), N-methyl-histidine(Me-His), ethanolamine($EtNH_2$). Especially, GABA known as a neurotransmitter was present at a high level(305.99 mg/100 g dry weight). We identified the following polyphenol compounds in the cherry tomatoes : caffeic acid-hexose isomer I (CH I), caffeic acid-hexose isomer II (CH II), 3-caffeoylquinic acid(3-CQA), 5-caffeoylquinic acid(5-CQA), caffeoylquinic acid isomer(CQAI), quercetin-hexose-deoxyhexose-pentose(QTS), quercetin-3-rutinoside(Q-3-R), di-caffeoylquinic acid(di-CQA), tri-caffeoylquinic acid(tri-CQA), naringenin chalcone(NGC). Large quantities of Q-3-R and NGC known as bioactive compounds were found. These results revealed that Lycopene variety contained various nutritional and bioactive compounds and would be a potent functional food material.

Antinocicepetive Effects of 3,4-Dicaffeoyl Quinic Acid of Ligularia fischeri var. spiciformis

  • Choi, Moo-Young;Park, Hee-Juhn
    • Korean Journal of Plant Resources
    • /
    • v.20 no.3
    • /
    • pp.221-225
    • /
    • 2007
  • The plant Ligularia fischeri var. spiciformis (Compositae) is a candidate for available functional foods. It has been used to treat diabetes mellitus and rheumatoid arthritis. We have reported the isolation of a new eremophilanolide named 6-oxoeremophilenolide and cytotoxic intermedeol together with the isolation of hydrophilic constituents, chlorogenic acid, 3,4-di-O-caffeoylquinic acie (3), and 5-O-[1-butyl]-3,4-di-O-caffeoylquinic acid. Compound 3 was again isolated by combination of silica gel- and ODS column chromatography for the anti-nociceptive action. Compound 3 and 4 were assayed in hot plate- and writhing tests in the rat. Although the three derivatives of caffeic acid exhibited significant anti-nociceptive effects at 10 mg/kg dose (i.p.),(activity potency: 4>3). These results suggest that compound 3 is responsible for at least rheumatoid arthritis, and caffeic acid moiety is the active moiety of dicaffeoylquinic acid.

Chemical Constituents from the Fruits of Prunus mume

  • Jin, Qinghao;Lee, Chul;Lee, Jin-Woo;Lee, In-Sun;Lee, Mi-Kyeong;Jeon, Won-Kyung;Hwang, Bang-Yeon
    • Natural Product Sciences
    • /
    • v.18 no.3
    • /
    • pp.200-203
    • /
    • 2012
  • The chromatographic separation of a methanol extract of Prunus mume (Rosaceae) led to the isolation of 5-hydroxymethyl-2-furaldehyde (1), 4-O-caffeoylquinic acid methyl ester (2), prunasin (3), 5-O-caffeoylquinic acid methyl ester (4), benzyl-O-${\beta}$-D-glucopyranoside (5), and liquiritigenin-7-O-${\beta}$-D-glucopyranoside (6). Their structures were determined by 1D, 2D-NMR and MS data analysis as well as by comparison of their data with the published values.

Antinocicepetive effects of 3,4-Dicaffeoyl Quinic Acid of Ligularia fischerivar. spiciformis, caffeic acid and its methyl ester

  • Choi, Jong-Won;Lee, Kyung-Tae;Kim, Won-Bae;Jung, Hyun-Ju;Park, Hee-Juhn
    • Proceedings of the PSK Conference
    • /
    • 2002.10a
    • /
    • pp.387.3-388
    • /
    • 2002
  • The plant Ligularia fischerivar. spiciformis(Compositae) is a candidate for available functional foods. It has been used to treat diabetes mellitus and rheumatoid arthritis. We have reported the isolation of a new eremophilanolide named 6-oxoeremophilenolide and cytotoxic intermedeol together with the isolation of hydrophilic constituents. chlorgenic acid. 3.4-di-O-caffeoylquinic acid(1). and 5-O-[1-butyl]-3.4-di-O-caffeoylquinic acid. (omitted)

  • PDF