• 한국자원식물학회지
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• 제20권3호
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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.

• 대한한방부인과학회지
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• 제33권2호
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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.

• Journal of Applied Biological Chemistry
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• 제62권4호
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• pp.433-439
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• 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.

• Natural Product Sciences
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• 제10권4호
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• pp.182-189
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• 2004

To find the action mechanism of the MeOH extract (LFS) of Ligularia fischeri var. spiciformis herbs (Compositae) and its active component, 3,4-dicaffeoylquinic acid (DCQA) on antihepatotoxicity, the effect was investigated on hepatic lipid perxodation and drug-metabolizing enzyme activities in acetaminophen-treated rat. Pretreatment with 250 mg/kg LFS (p.o.) and 10 mg/kg DCQA (p.o.) significantly decreased hepatic lipid peroxidation caused by acetaminophen injection. Further, LFS and DCQA inhibited hepatic microsomal enzyme activation such as hepatic P-450 cytochrome $b_5$, aniline hydroxylase and aminopyrine N-demethylase, suggesting that the two substances might effectively prevent the metabolic activation or scavenge electrophilic intermediates capable of causing hepatotoxicity. Both LFS and DCQA increased hepatic glutathione content and glutathione reductase activity, indicating that both resultantly prevented hepatotoxicity via antioxidative mechanism. Therefore, it was found that LFS had antihepatotoxicity based on the antioxidative action of DCQA.

• Natural Product Sciences
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• 제16권3호
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• pp.164-168
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• 2010

High-performance liquid chromatographic method with diode-array detector and electrospray ionization with multi-stage tandem mass spectroscopy (HPLC/DAD/ESI-$MS^n$) was used to identify the major constituents in a methanolic extract of Eclipta prostrata. The chromatographic separation was performed on a C18 column. Acetonitrile-water was used as a mobile phase. HPLC/DAD/ESI-$MS^n$ allowed the characterization of constituents of E. prostrata, mainly triterpenoids (eclalbasaponin I, II, III, IV, VI), flavonoids (luteolin 7-O-glucoside, demethylwedelolactone, wedelolactone, luteolin, demetylwedelolactone sulfate, luteolin sulfate, apigenin sulfate) and phenolic acids (5-O-caffeoylquinic acid, 3, 4-O-dicaffeoylquinic acid, 3, 5-O-dicaffeoylquinic acid, 4, 5-Odicaffeoylquinic acid).

• 한국식품영양과학회지
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• 제46권6호
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• pp.759-764
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• 2017

당뇨합병증에 효과적인 천연물 유래의 신소재를 개발하기 위하여 본 연구를 수행하여 단풍취 70% 에탄올 추출물의 EtOAc 가용부로부터 최종당화산물 생성 억제능($IC_{50}=5.5{\pm}1.1{\mu}g/mL$)을 확인하였다. 활성을 나타내는 성분의 동정을 위하여 $C_{18}$겔 등을 활용한 칼럼크로마토그래피를 수행하여 4종의 dicaffeoylquinic acid 유도체 화합물을 분리하였고, 각 화합물의 화학구조는 NMR 스펙트럼 데이터 해석 및 표품과의 HPLC 직접 비교를 통하여 methyl 3,5-di-O-caffeoyl-epi-quinate(1), 3,5-di-O-caffeoyl-epi-quinic acid(2), 4,5-di-O-caffeoyl-quinic acid(3) 및 methyl 4,5-di-O-caffeoyl-quinate(4)로 동정하였다. 이들 화합물에 대해 최종당화산물 생성 억제능을 평가한 결과 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 $0.4{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $0.6{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었다. 또한, 이들 물질에 대해 $ABTS^+$ 소거 활성을 평가하여 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 라디칼 소거 활성인 $14.6{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 구조 이성질체인 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $18.8{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 확인하였다. 단풍취에서 분리한 화합물의 활성은 caffeic acid의 결합방식 및 methyl화 여부에 따른 화합물의 구조에 따라 다름이 시사되었다. 향후 우수한 활성을 나타낸 이들 화합물의 in vivo 실험을 통한 활성기작의 검증이 필요하다고 생각된다. 또한, 추가적인 연구를 통하여 식의약 소재로 활용이 가능한 새로운 천연신소재 발굴을 위한 기초자료제공 및 당뇨합병증에 효과적인 천연 물질의 상업화를 위한 귀중한 자료로 활용할 수 있으리라 판단된다.

• 한국식품영양과학회지
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• 제45권11호
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• pp.1610-1616
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• 2016

섬쑥부쟁이로부터 고요산혈증 개선에 도움을 주는 기능성 식품 개발을 위하여 최적의 에탄올 추출물 탐색과 high performance liquid chromatography-ultraviolet(HPLC-UV) 분석방법에 의한 validation을 실시하였다. 지표성분으로 3,5-dicaffeoylquinic acid(3,5-DCQA)를 선정하여 표준화를 실시하였으며 검출법 확립을 위한 3,5-DCQA 정량분석은 Luna RP-18 칼럼($4.6{\times}250mm$, $5{\mu}m$)을 이용하여 1% 초산용액과 메탄올을 전개용매로 사용하였다. 용출은 1.0 mL/min의 유속으로 기울기 용출(gradient elution) 방법을 이용하였으며, 320 nm 파장에서 검출한 피크 면적을 이용하여 검량곡선을 작성하여 분석하였다. 본 연구에서 확립한 분석법으로 특이성, 직선성, 정밀성, 정확성, 회수율을 검색하였다. 3,5-DCQA의 검량선으로부터 상관계수($R^2$) 0.9999의 우수한 직선성과 intra-day와 inter-day 분석에서 90% 이상의 회수율과 5% 미만의 RSD를 나타내 정밀성과 정확성을 입증하였다. 검출한계는 $2.68{\mu}g/mL$였고 정량한계는 $8.11{\mu}g/mL$로 나타났다. 섬쑥부쟁이 에탄올 추출물(AGE)은 70과 $80^{\circ}C$에서 30, 50, 70, 80% 에탄올로 3, 4, 5, 6시간 동안 각각 추출하였으며, 지표물질의 검량곡선을 활용하여 각각의 AGE로부터 3,5-DCQA의 함량을 분석하였다. 본 시험법으로 분석한 3,5-DCQA의 함량은 $70^{\circ}C$에서 추출한 70% AGE가 $52.59{\pm}3.45mg/Aster$ glehni 100g의 함량을 나타내 가장 우수하게 나타났다. 그러나 섬쑥부쟁이 추출물에 함유된 5-caffeoylquinic acid(5-CQA)의 함량 비교분석은 에탄올 함량이나 추출 시간에 따른 함량 변화가 미미하게 나타났다. 또한, 다양한 AGE에 대하여 XOD 저해 효능을 검색하였을 때, 3,5-DCQA의 함량이 가장 높은 $70^{\circ}C$에서 추출한 70% AGE에서 우수한 효능을 나타내 기능성 원료 표준화를 위한 적합한 분석법임이 검증되었다. 따라서 본 연구를 통하여 확립된 3,5-DCQA의 분석법은 섬쑥부쟁이 에탄올 추출물로부터 개별인정형 건강기능식품 기능성 원료 개발을 위한 유용한 자료로 활용될 것으로 생각한다.

• 한국식품과학회지
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• 제51권1호
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• pp.81-89
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• 2019

이연구는 고지방식이로 인한 비만 및 대사장애에 대한 3,5-diCQA의 효과를 확인하는 동시에 클로로겐산과의 상대적인 생리 활성을 확인하였다. 클로로겐산은 이전에 보고된 연구결과에서처럼 고지방식이를 섭취하는 쥐의 체중 증가를 효과적으로 억제하였으며, 3,5-diCQA와 비교하였을 때에도 그 효과가 상대적으로 우수하였다. 내장지방의 무게를 측정한 결과 3,5-diCQA와 클로로겐산 모두 내장지방의 축적을 효과적으로 억제하였으며, 이러한 이유는 두 샘플 모두 지방조직에서의 AMPK의 활성화가 증가된 것과 관련이 있는 것으로 보인다. 또한 이 두 샘플은 비만으로 인해 발생하는 산화적 스트레스로부터 간조직을 보호하는 효과가 있었다. 그러나 간조직에서의 지방축적을 확인한 결과에서 클로로겐산은 여전히 간의 지방축적을 억제하는 것으로 확인되었지만 3,5-diCQA는 오히려 간의 지방축적을 증가시킨 것이 확인되었다. 이러한 결과는 3,5-diCQA가 간조직에서 Akt의 활성을 증가시킨 것과 관련이 있는 것으로 보이며 이 증가된 Akt로 인해 3,5-diCQA 그룹의 내당능 개선이 클로로겐산 그룹보다도 우수하였지만 간에서의 지방 축적을 증가시킨 것으로 판단된다.

• 한국자원식물학회:학술대회논문집
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• 한국자원식물학회 2018년도 추계학술대회
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• pp.99-99
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• 2018

The major aim of this work is the research of secondary metabolites isolated from the aerial parts of Petasites japonicus. The plant material is extracted with a polar solvent, which is 95% by volume methanol at room temperature. The concentrated extract was partitioned as EtOAc, n-BuOH, and $H_2O$ fractions. From the EtOAC and n-BuOH fraction, two bakkenolides and two caffoylquinic acid were isolated using the Diaion HP-20, silica gel, ODS-A, and Sephadex LH-20 column chromatographies. According to the results of the results of physico-chemical and spectroscopic data including NMR, MS and UV. The chemical structures of the compounds were respectively determined as bakkenolide B (1), bakkenolide D (2), 1,5-dicaffeoylquinic acid (3), and 5-O-caffeoylquinic acid (4). These results suggest that the compounds isolated from the aerial parts of this plant were almost identical with known components of Petasites japonicus. However, it is necessary to investigate more about the difference of amounts of constituents according to harvest area and time.

• 생약학회지
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• 제48권3호
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• pp.243-247
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• 2017

To find the anti-Alzheimer's activity of Cacalia hastata var. orientalis (Compositae), caffeoylquinic acids were analyzed in this plant by HPLC and the inhibitory activities of the extract on cholinesterases including acetylcholinesterase (AChE) and butyrylcholinesterse (BChE) and peroxynitrite ($ONOO^-$) were assayed. Sum of caffeoylquinic acids in the 80% MeOH extract was quantitatively higher in leaves (35.8% of the extract) than in stems (3.7%). The compound, 3,5-dicaffeoylquinic acid, was contained in the highest amount in the leaf (44.32 mg/g dry weight). The $IC_{50}s$ of the 80% MeOH extract were shown to be $67.45{\mu}g/ml$ for AChE, and $8.59{\mu}g/ml$ (for $ONOO^-$), respectively, suggesting that the leaves would have the anti-Alzheimer's activity due to the high content of caffeoylquinic acids.