• Title/Summary/Keyword: dicaffeoylquinic acid

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Extractives from Wood of Euonymus japonica (사철나무(Euonymus japonica) 목부의 추출성분)

  • Kim, Woo-Jin;Lee, Kyoung-Tae;Lee, Hak-Ju;Cho, Sung-Taig
    • Journal of Korean Society of Forest Science
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    • v.103 no.1
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    • pp.113-121
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    • 2014
  • From the bark of Euonymus japonica, ten compounds were isolated by column chromatography and identified as follows. The structures were determined as : (-)-epicatechin, (-)-epigallocatechin, vanillic acid, 2,4-dimethoxyphenol-1-glucoside, 2, 4, 6-trimethoxyphenol-glucoside, 5-caffeoylquinic acid, 4-caffeoyuinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 1, 5-dicaffeoylquinic acid.

Antioxidative Activity of Phenolic Acids Isolated from Jindalrae Flower (Rhododendron mucronulatum Turzaninow) (진달래꽃으로부터 분리된 페놀산 화합물의 항산화성에 관한 연구)

  • Kim, Mi-Ae;Jones, A. Daniel;Chung, Tae-Yung
    • Applied Biological Chemistry
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    • v.39 no.6
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    • pp.506-511
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    • 1996
  • Six phenolic acids were isolated from Jindalrae flowers (Rhododendron mucronulatum Turcz.), an edible plant in Korea. These compounds were identified as chlorogenic acid, 3,5-O-dicaffeoylquinic acid, 4,5-O-dicaffeoylquinic acid, caffeic acid, ferulic acid, and p-coumaric acid on the basis of IR, UV, $^{1}H$ and $^{13}C$ NMR, FAB-MS, ES-MS and/or El-MS data. Chlorogenic acid (0.2 g) present in both ethyl acetate and ethyl ether fractions comprised up to 38.5% of the total phenolic acid amount (0.52 g) finally recovered by means of polyamide C-200 column chromatography, preparative TLC, recrystallization, and Sephadex LH-20 column chromatography The antioxidant activities were measured in an ethanol solution of linoleic acid in the presence of ferric thiocyanate. The antioxidant efficiency increased in the order of p-coumaric acid<${\alpha}-tocopherol$

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Simultaneous Quantitative Analysis of Major Constituent of Ethanol Extract from Leaves of Helianthus annuus L. (향일규 잎의 에탄올 추출물에 대한 주요 성분 동시 정량분석)

  • Kim, Eun-Nam;Jeon, Sang-Young;Jeong, Gil-Saeng
    • Korean Journal of Pharmacognosy
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    • v.52 no.2
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    • pp.112-117
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    • 2021
  • Helianthus annuus L. has been reported with various pharmacological activities such as antibacterial, antidiabetic, and antioxidant effects. According to recent studies, H. annuus L. is known to contain components such as phenolic compounds, flavonoids, alkaloids, sesquiterpenoids, and lignans. The seeds of H. annuus L. have been reported to contain chlorogenic acid and di-O-caffeoylquinic acid as major components. However, studies on the main components and content of leaves of H. annuus L. are still incomplete. Therefore, in this study, the contents of four major components of H. annuus L. were evaluated by simultaneous quantitative analysis with high performance liquid chromatography (HPLC)-diode array detector (DAD). The isolated four compounds Caffeoylquinic acid(CQA), 3,4-dicaffeoylquinic acid(3,4-DCQA), 3,5-dicaffeoylquinic acid(3,5-DCQA) and 4,5-dicaffeoylquinic acid(4,5-DCQA) were shown in a large linearity with a correlation coefficient (R2) of 0.99. In addition, as a result of intra-inter day analysis of four major compounds by the analysis method of this study, the accuracy of 88.46% or more and less than 112.85% and excellent precision of less than 3% were shown, the content analysis showed CQA (0.383±0.018 mg/g), 3,4-DCQA (0.282±0.017 mg/g), 3,5-DCQA (1.109±0.068 mg/g), and 4,5-DCQA (0.673±0.020 mg/g).

Quantitative Analysis about Phenolic Compounds of Dendranthema Species in Korean Native Plants (국내 자생 구절초속 중 페놀화합물 함량분석)

  • Kim, Kyeong Mi;Lee, Seon Yu;Jo, Ara;Kang, Byoung Man;Ham, Seongho;Cho, Junghee;Lee, Gukyeo
    • Korean Journal of Pharmacognosy
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    • v.48 no.1
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    • pp.70-76
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    • 2017
  • Dendranthema spp are distributed in various regions in Korea. This report is the quantitative results of phenolic compounds on the 5 resources collected from all over the country. It was known that it has phenolic compounds, as an anticoagulant activities and immunoadjuvant activity of contribute to the cardiovascular effects. This was used for quantitative analysis of chlorogenic acid(CA), 3,5-Dicaffeoylquinic acid(3,5-DCA), 4,5-Dicaffeoylquinic acid(4,5-DCA) and linarin, with UPLC-PDA and LC-IT-TOF-MS. Extraction efficiency of compounds was compared by using ultrasonic extraction and reflux extraction with different extraction conditions (methods and time). In 50% MeOH extracs (30 mins) of Dendranthema zawadskii (Herb.) Tzvelev (SDZ), Dendranthema zawadskii var. yezoense (Maek.) Y.M.Lee & H.J.Choi (NDZ), Dendranthema zawadskii (Herb.) Tzvelev var. teuisectum (Kitag.) J. H. Pak (GDZ), Dendranthema careanum (H. $L{\acute{e}}v$. & Vaniot) Vorosch. (HDC) and Dendranthema zawadskii var. tenuisectum Kitag (PDZ), chlorogenic acid contents were 1.14‰, 6.95‰, 7.27‰, 1.47‰ and 2.64‰, 3,5-dicaffeoylquinic acid contents were 3.30‰, 5.60‰, 10.81‰, 2.67‰ and 1.50‰, 4,5-dicaffeoylquinic acid contents were 0.74‰, 1.93‰, 3.36‰, 0.61‰ and 0.43‰ and linarin contents were 3.90‰, 10.15‰, 0.15‰, 0.73‰ and 0.21‰, respectively.

Isolation and Antioxidative Activities of Caffeoylquinic Acid Derivatives and Flavonoid Glycosides from Leaves of Sweet Potato (Ipomoea batatas L.)

  • Kim, Hyoung-Ja;Jin, Chang-Bae;Lee, Yong-Sup
    • Biomolecules & Therapeutics
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    • v.15 no.1
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    • pp.46-51
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    • 2007
  • Bioassay-directed chromatographic fractionation of an ethyl acetate extract from leaves of sweet potato (Ipomoea batatas L.) afforded six quinic acid derivatives: 3,5-epi-dicaffeoylquinic acid (1), 3,5-dicaffeoylquinic acid (2), methyl 3,5-O-dicaffeoylquinate (3), methyl 3,4-dicaffeoylquinate (4), methyl 4,5-dicaffeoylquinic acid (5),4,5-dicaffeoylquinate (6), and two phenolic compounds: caffeic acid (7) and caffeic acid methyl ester (8) together with three flavonoids: quercetin 3-O-${\beta}$-D-glucopyranoside (9), quercetin 3-O-${\beta}$-D-glucopyranoside, isoquercitrin (10) and kaempferol 3-O-${\beta}$-D-glucopyranoside (11). The structures of these compounds were elucidated by the aid of spectroscopic methods. These compounds were assessed for antioxidant activities using three different cell-free bioassay systems. All isolates except 11 showed potent DPPH and superoxide anion radicals scavenging, and lipid peroxidation inhibitory activities. 3,5-epi-DCQA (1) and methyl quinates (3-5) along with flavonoide 9 were isolated for the first time from this plant.

Simultaneous Determination of Four Compounds from Artemisia capillaris using High Performance Liquid Chromatography-Ultraviolet Detector (HPLC-UVD) and Their Quantitative Study in Artemisia Genus

  • Ko, Kiwon;Hong, In Kee;Cho, Hyun-Jong;Kim, Young Ho;Yang, Heejung
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.109-114
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    • 2018
  • Artemisia capillaris Thunb. (Compositae) is a native herb of East Asian countries and has used for the treatment of jaundice, high liver fever, and digestive diseases for a long time, as well as being developed as the source of herbal preparations until now. The major components from A. capillaris were chlorogenic acid (1) and its derivatives substituted with caffeoyl moieties, such as 3,5-dicaffeoylquinic acid (2) and 4,5-dicaffeoylquinic acid (3), and coumarins, such as scoparone. In the study, four compounds, chlorogenic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and scoparone (4) in the 70% ethanolic extract of A. capillaris were simultaneously determined by using HPLC-UVD system. This method was validated with the terms of linearity, precious and accuracy according to ICH guidelines. The developed method was successfully applied for the quantitative analysis of Artemisia genus, A. capillaris, A. iwayomogi, A. princeps, and A. argyi, distributed in Korea.

Antioxidant and Tyrosinase Inhibitory Activities of Dicaffeoylquinic Acid Derivatives Isolated from Gnaphalium Affine D. DON (떡쑥 추출물로부터 분리된 Dicaffeoylquinic Acid 유도체들의 항산화 및 타이로시네이즈 저해 활성)

  • Im, Na Ri;Kim, Hae Soo;Ha, Ji Hoon;Noh, Geun Young;Park, Soo Nam
    • Applied Chemistry for Engineering
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    • v.26 no.4
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    • pp.470-476
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    • 2015
  • In this study, three dicaffeoylquinic acids (DCQAs) isolated from Gnaphalium affine D. DON. extracts were structurally identified and evaluated for their antioxidant activities, cellular protective effects, and tyrosinase inhibitory activities. The ethyl acetate fraction of G. affine was chromatographed, which yielded 3 DCQA derivatives of 1-3 : 3,5-dicaffoylquinic acid (3,5-DCQA, 1), 4,5-dicaffeoylquinic acid (4,5-DCQA, 2), 1,5-dicaffoylquinic acid (1,5-DCQA, 3). The structure of each compounds was determined using $^1H$ NMR and MS analyses. Compounds of 1-3 showed strong free radical (1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activities ($FSC_{50}=3.70$, 5.80, and $5.50{\mu}M$, respectively) compared to those of a commonly used lipophilic antioxidant, (+)-${\alpha}$-tocopherol ($21.90{\mu}M$). Cellular protective effects of 1-3 compounds on the $^1O_2$ sensitized photohemolysis of human erythrocytes were similar to (+)-${\alpha}$-tocopherol. 1-3 compounds also exhibited higher tyrosinase inhibitory effects ($IC_{50}=0.15$, 0.16, and 0.13 mM) compared to arbutin (0.33 mM), known as a skin-whitening agent. These results indicate that three DCQA derivatives may be applied as an antioxidant and a skin whitening agent in food or cosmetic industries.

Antithrombotic Compounds form the Leaves of Ligularia stenocephala M.

  • Yoon, Min-Ho;Cho, Chong-Woon;Lee, Jae-Won;Kim, Young-Shin;An, Gil-Hwan;Lim, Chi-Hwan
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.62-67
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    • 2008
  • The leaf extract of Ligularia stenocephala showed the highest anti-platelet aggregating activity in large numbers of edible and herbal plants. The active fraction fractionationed from L. stenocephala extract by using preparative HPLC inhibited the platelet aggregation up to above 80% and its blood coagulating time (PT and APTT) also showed similar effect to aspirin (0.2 ${\mu}g/mL$), known as an anti-thrombus compound. Two antithrombus active compounds were purified and identified as 3,5-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid, respectively, on the basis of NMR and FAB-MS spectroscopic data. Two active compounds has not only antiplatelet aggregating activity, but also has anticoagulating activity.

Effect of Ainsliaea acerifolia Extract on Anti-acetylcholinesterase and Peroxynitrite Scavenging and Analysis of Caffeoylquinic Acids (단풍취 추출물의 Acetylcholinesterase 저해 및 Peroxynitrite 소거에 대한 활성과 Caffeoylquinic Acid 성분의 분석)

  • Nugroho, Agung;Choi, Jae Sue;Song, Byong-Min;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.32 no.4
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    • pp.270-274
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    • 2019
  • Anti-acetylcholinesterase (anti-AChE) activity and peroxynitrite scavenging activity of Ainsliaea acerifolia (Compositae) were studied to find its anti-Alzheimer's activity. The $IC_{50}$ was $73.4{\mu}g/mL$ in AChE assay and $8.60{\mu}g/mL$ in peroxynitrite assay. Caffeoylquinic acids that have been reported to have anti-Alzheimer's activity were analyzed in the leaf- and stem extract by HPLC. Caffeoylquinic acids occupied 25.1% of the leaf extract which was higher than 8.1% of the stem extract. Particularly, the content of 3,5-dicaffeoylquinic acid (145.6 mg/g) was highest of the tested caffeoylquinic acids. In addition, the $IC_{50}$ values of 3,5-dicaffeoylquinic acid were shown to be $3.79{\mu}g/mL$ in peroxynitrite assay and $69.19{\mu}g/mL$ in anti-AChE assay.