• Title/Summary/Keyword: Di-caffeoylquinic acid

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Comparison of Phenolic Acid from Shoots of Aralia elata and Kalopanax pictus Cultivated in Korea Using UPLC-DAD-ESI(+)-QToF/MS (UPLC-DAD-ESI(+)-QToF/MS를 이용한 국내산 두릅나무 및 음나무 순 내 페놀산 특성 비교)

  • Kim, Young Jin;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Asamenew, Gelila;Lee, Suji;Lee, Sang Hoon;Cha, Youn-Soo;Kim, Jung Bong
    • Korean Journal of Environmental Agriculture
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    • v.37 no.4
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    • pp.260-267
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    • 2018
  • BACKGROUND: In this study, shoots of Aralia elata and Kalopanax pictus which belong to the Araliaceae family were analyzed using UPLC-DAD-ESI(+)-QToF/MS to characterize of individual phenolic acids. METHODS AND RESULTS: Total thirteen phenolic acids were identified, and nine hydroxycinnamic acid derivatives have been identified for the first time in shoots of Aralia elata and Kalopanax pictus. For total phenolic acid content (mg/100g dry weight), shoots of Aralia elata and Kalopanax pictus showed 754.8 and 845.3 mg/100g, respectively. 5-O-Caffeoylquinic acid (49%) and 3,5-di-O-caffeoylquinic acid (44%) were found as major phenolic acids in Aralia elata, while 5-O-caffeoylquinic acid (91%) was a major component in Kalopanax pictus. CONCLUSION: On comparing the two plants, it was considered that the biosynthesis of 3,5-di-O-caffeoylquinic acid can be affected by 5-O-caffeoylquinic acid in Aralia elata.

A New Sesquiterpene Hydroperoxide from the Aerial Parts of Aster oharai

  • Choi, Sang-Zin;Lee, Sung-Ok;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.26 no.7
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    • pp.521-525
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    • 2003
  • Phytochemical works on the aerial parts of Aster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7$\alpha$-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), $\alpha$-spinasterol (3), oleanolic acid (4), $\alpha$-spinasterol 3-Ο-$\beta$-D-glucopyranoside (5), methyl 3,5-di-Ο-caffeoyl quinate (6), 3,5-di-Ο-caffeoylquinic acid (7), 3,4-di-Ο-caffeoylquinic acid (8). The chemical structures of 1-8 were established by chemical and spectroscopic methods. Compound 2 showed cytotoxicity against cultured human tumor cell lines in vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with $ED_{50}$ values ranging from 3.86-17.21 $\mu$g/mL.

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
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    • v.20 no.3
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    • pp.37-49
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    • 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.

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
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    • v.39 no.3
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    • pp.399-405
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    • 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.

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

  • Choi, Moo-Young;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.20 no.3
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    • pp.221-225
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    • 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.

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
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    • 2002.10a
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    • pp.387.3-388
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    • 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)

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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
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    • v.16 no.1
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    • pp.20-25
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    • 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.

Simultaneous Quantification Analysis of Multi-components on Erycibae Caulis by HPLC (HPLC를 이용한 정공등의 다성분 동시함량분석)

  • Jeon, Hye Jin;Liu, Ting;Whang, Wan Kyunn
    • YAKHAK HOEJI
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    • v.57 no.4
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    • pp.272-281
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    • 2013
  • In this study, we developed and validated the HPLC method using the isolated components from Erycibae caulis. Their structures were elucidated by spectroscopic methods including UV, $^1H$-NMR, $^{13}C$-NMR, FAB-Mass and ESI-Mass as Compound 1 (crypto-chlorogenic acid), Compound 2 (scopolin), Compound 3 (neochlorogenic acid) and Compound 4 (3,4-di-O-caffeoylquinic acid). Major three compounds and scopoletin were decided as representative components of Erycibae caulis. We established HPLC analytical method by using the representative components and 20 commercial samples which were collected considering to various cultivated area. The HPLC fingerprinting was successfully achieved with an AKZO NOBEL Kromasil 100-5C18 column. The mobile phase consisted of 0.5% acetic acid in water (A) and methanol (B) using gradient method of 85(A) to 50(A) for 35min. The fingerprints of chromatograms were recorded at an optimized wavelength of 330 nm. This developed analytical method was validated with specificity, selectivity, accuracy and precision. And it is suggested that scopolin, scopoletin, neochlorogenic acid, 3,4-di-O-caffeoylquinic acid were more than 0.162%, 0.133%, 0.057%, 0.044%, respectively. In addition, principal component analysis (PCA) was performed on the analytical data of 20 different Erycibae caulis samples in order to classify samples collected from different regions. We hope that this assay can be readily utilized as quality control method for Erycibae caulis.

The Comparative Study on Compositional Pattern Analysis of Decoction of Extracted Artemisia argyi by Different Extraction Time (전탕 시간에 따른 애엽의 성분패턴 비교연구)

  • Yoon, Jun-Geol;Kim, Mean-Sun;Han, Seong-Min;Hwang, Deok-Sang;Lee, Jin-Moo;Lee, Chang-Hoon;Jang, Jun-Bock
    • The Journal of Korean Obstetrics and Gynecology
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    • v.33 no.2
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    • pp.1-12
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    • 2020
  • Objectives: This study was conducted to find out the optimal extraction time for Artemisia argyi. Methods: The compositional pattern was compared with HPLC (High Performance Liquid Chromatography) and GC (Gas-Chromatography) by decocting Artemisia argyi 10, 60, 120 minutes respectively. Results: With longer extraction time, the contents of reference compounds were extracted 1.1 times more when 3,4-dicaffeoylquinic acid was extracted for 60 minutes than when extracted for 10 minutes in HPLC test, but the contents were reduced when extracted for 120 minutes compared to 60 minutes extraction time. 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, jaceosidin, and eupatilin showed the largest yield rate when extracted for 10 minutes, and it decreased as time passed. The contents of chlorogenic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, jaceosidin, scoparone, and eupatilin were detected only in 10 minutes extraction but not in 60 or 120 minutes extraction according to GC test. Conclusions: The results show that extraction time could affect the physicochemical characteristic or composition of Artemisia argy extracted. Thus, short extraction time could be useful for decoction of Artemisia argyi.

A New Coumestan Glucoside from Eclipta prostrata

  • Seo, Young Ju;Kil, Hyun Woo;Rho, Taewoong;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.289-294
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    • 2020
  • Eclipta prostrata is an annual herb, belonging to Asteraceae family, and has been traditionally used to improve immunity and treat hepatitis and bacterial disease in Korea. In this study, a new coumestan glucoside (1) along with ten known compounds (2 - 11) was isolated from E. prostrata. The chemical structures of isolates were elucidated to be wedelolactone-9-O-β-D-glucopyranoside (1), wedelolactone (2), demethylwedelolactone (3), apigenin (4), apigenin-7-sulfate (5), luteolin (6), luteolin-7-sulfate (7), luteolin-7-O-β-D-glucopyranoside (8), pratensein-7-O-β-D-glucopyranoside (9), 3,4-di-O-caffeoylquinic acid (10) and 3,5-di-O-caffeoylquinic acid (11) based on the spectroscopic evidence.