• 제목/요약/키워드: 3,4-dihydroxycinnamic acid

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백두옹에서 항미생물 활성을 갖는 4-Hydroxy-3-methoxycinnamic Acid와 3,4-Dihydroxycinnamic Acid의 분리 및 동정 (Isolation and Characterization of 4-Hydroxy-3-methoxycinnamic Acid and 3,4-Dihydroxycinnamic Acid with Antimicrobial Activity from Root of Pulsatilla koreana)

  • 이향희;마승진;문제학;박근형
    • Applied Biological Chemistry
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    • 제41권2호
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    • pp.191-196
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    • 1998
  • 할미꽃 $(Pulsatilla\;koreana\;N_{AKAI})$ 뿌리인 백두옹의 MeOH 추출물이 세균과 효모 등의 미생물에 대해 항미생물 활성을 나타내자 백두옹에 함유된 항미생물 활성물질의 탐색을 시도하였다. MeOH 추출물을 생물검정법을 지표로 solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography 등으로 정제하고, HPLC에 의해 활성물질을 분리하였다. 분리된 두 활성물질은 MS, $^{1}H-NMR$, $^{13}C-NMR$에 의해 4-hydroxy-3-methoxycinnamic acid와 3,4-dihydroxycinnamic acid로 동정되었다.

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두릅수피에서 항미생물 활성을 갖는 3,4-Dihydroxycinnamic Acid의 분리 (Isolation of 3,4-Dihydroxycinnamic Acid with Antimicrobial Activity from Bark of Aralia elata)

  • 마승진;국주희;고병섭;박근형
    • 한국식품과학회지
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    • 제28권3호
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    • pp.600-603
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    • 1996
  • 두릅나무(Aralia elata $S_{EEMANN}$) 껍질의 MeOH추출물이 세균과 호모, 곰팡이 등에 대한 항미생물 활성을 보여 solvent fractionation, Silica gel adsorption chromatography, Sephadex LH-20 column chromatography, silica gel partition chromatography, HPLC 등의 기법으로 활성물질을 순차 정제하여 얻어진 활성물질을 1% acetic acid-MeOH (60 : 40, v/v)용매계의 HPLC에 의해 분리하였다. 분리된 성분($t_r$ 17.1 min)의 활성본체를 구명하기 위하여 $MS,\;^1H-NMR\;and\;^13C-NMR$. 등을 이용하여 기기분석한 결과, trans-3,4-dihydroxycinnamic acid로 동정되었다. 3,4-dihydroxycinnamic acid가 두릅에서 항미생물 활성물질로서 분리, 동정된 것은 처음으로 생각된다.

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복분자에 함유된 항산화물질의 동정 및 활성 (Identification and Activity of Antioxidative Compounds from Rubus coreanum Fruit)

  • 윤인;조정용;국주희;위지향;장미영;안태회;박근형
    • 한국식품과학회지
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    • 제34권5호
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    • pp.898-904
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    • 2002
  • 복분자를 착즙하여 착즙액과 잔사로 나누고, 각 추출물을 용매분획하여 얻어진 각 획분을 대상으로 DPPH radical-scavenging 활성을 측정하였더니, 각 추출물의 EtOAc 가용산성획분에서 비교적 강한 활성이 나타났다. 이들 획분에 함유된 활성물질을 규명하고자 silica gel column chromatography로 정제한 다음 활성획분을 GC-MS 분석을 실시한 결과, 복분자 착즙액의 EtOAc 가용 산성획분에 함유된 물질로 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, and 3,4-dihydroxycinnamic acid 등이 동정되었고, 잔사 MeOH 추출물의 EtOAc 가용 산성획분에 함유된 물질로 succinic acid, 3,4-dihydroxybenzoic acid, citric acid, 3,4,5-trihydroxybenzoic acid, 3,4-dihydroxycinnamic acid가 동정되었다. DPPH radical-scavenging 활성과 hydroxyl radical에 의한 malonaldehyde 생성억제 효과활성 등의 방법으로 동정된 물질의 항산화 활성이 평가되었다.

흰쥐 다형핵백혈구의 fMLP로 유도한 유주현상에 대한 신나믹산 유사체의 억제효과 (Inhibitory Effects of Cinnamic Acid Analogs on fMLP-Induced Chemotaxis of Rat Polymorphonuclear Leukocytes)

  • 민경락;김진준;박선규;이정래;강세훈;김영수
    • 약학회지
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    • 제42권2호
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    • pp.165-169
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    • 1998
  • Inhibitory effects of 16 cinnamic acid analogs on formyl-Met-Leu-Phe(fMLP)-induced chemotaxis of rat polymorphonuclear leukocytes were determined by using a microchemotaxis appa ratus. 3,4-Dlhydrocinnamic acid called as caffeic acid exhibited the highest inhibitory effect on the chemotaxis among cinnamic acid analogs tested in this study. Hydroxycinnamic acids exhibited stronger inhibitory effects on the chemotaxis than cinnnamic acid. Hydroxycinnamic acids with one hydroxy group at ortho, meta or para position exhibited similar inhibitory effects on the chemotaxis with corresponding methoxy cinnamic acids, but 3,4-dihydroxycinnamic acid did stronger inhibitory effects than 3,4-dimethoxycinnamic acid. 3,4-Dimethoxycinnamic acid exhibited weaker inhibitory effects on the chemotaxis than 1,2-dimethoxy-4-propenylbenzene and 3,4-dimethoxy cinnamonitrile with -CH=CHCN or -CH=$CHCH_3$, group instead of -CH=CHCOOH group. 4-Hydroxy cinnamic acid and 3,4-dihydroxycinnamic acid exhibited stronger exhibitory effects on the chemotaxis than 3-(4-hydroxyphenyl) propionic acid and 3,4-dihydroxyhydrocinnamic acid with -$CH_2CH_2$COOH group instead of -CH=CHCOOH group.

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Anti-Thrombosis Activity of Sinapic Acid Isolated from the Lees of Bokbunja Wine

  • Kim, Mi-Sun;Shin, Woo-Chang;Kang, Dong-Kyoon;Sohn, Ho-Yong
    • Journal of Microbiology and Biotechnology
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    • 제26권1호
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    • pp.61-65
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    • 2016
  • From the lees of bokbunja wine (LBW) made from Rubus coreanus Miquel, we have identified six compounds (1: trans-4-hydroxycinnamic acid; 2: trans-4-hydroxy-3-methoxycinnamic acid; 3: 3,4-dihydroxycinnamic acid; 4: 4-hydroxy-3-methoxybenzoic acid; 5: 3,5-dimethoxy-4-hydroxybenzoic acid; and 6: 3,5-dimethoxy-4-hydroxycinnamic acid (sinapic acid)) through silica gel chromatography and UHPLC-MS. The compounds 1-6 showed strong anticoagulation and platelet aggregation inhibitory activities without hemolytic effect against human red blood cells. To date, this is the first report of the in vitro anti-thrombosis activity of sinapic acid. Our results suggest that different cinnamic and benzoic acid derivatives are closely linked to the anti-thrombosis activity of LBW, and sinapic acid could be developed as a promising anti-thrombosis agent.

오가피(Acanthopanax sessiliflorus Seeman) 열매로부터 분리한 페놀 화합물의 항산화활성 (Anti-oxidant activity of Phenolic Compound Isolated from the Fruits of Acanthopanax sessiliflorus Seeman)

  • 인서지;이대영;서경화;남태규;김대옥;김금숙;노형준;김계원;서우덕;강희철;백남인
    • Journal of Applied Biological Chemistry
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    • 제55권4호
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    • pp.217-220
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    • 2012
  • 오가피(Acanthopanax sessiliflorus Seeman) 열매를 실온에서 70% ethanol (EtOH)로 추출하고 이 추출물을 ethyl acetate (EtOAc) 분획, n-butyl alcohol 분획, $H_2O$ 분획으로 나누었다. EtOAc 분획에 대하여 silica gel, octadecyl silica gel 및 Sephadex LH-20 column chromatography를 반복 실시하여 2종의 화합물을 분리, 정제하였다. NMR, infrared spectroscopy, 및 electron ionization/mass spectrometry 등의 spectrum을 해석하여, 화합물 1과 화합물 2를 각각 3,5-dihydroxycinnamic acid과 protocatechuic acid 로 구조를 결정하였다. 화합물 1은 오가자에서는 처음으로 분리된 화합물이다. 또한 이 화합물에 대한 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)diammonium salt, 1,1-diphenyl-2-picrylhydrazyl 및 oxygen radical absorbance capacity radical 소거능을 이용한 항산화 활성을 측정하였는데, 모두 vitamin C보다 2배 이상 활성이 높은 것으로 나타났다.

Protective Effects of Cinnamic Acid Derivatives on Gastric Lesion

  • Lee, Sun Yi;Hwang, In Young;Jeong, Choon Sik
    • Natural Product Sciences
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    • 제23권4호
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    • pp.299-305
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    • 2017
  • P-methoxycinnamic acid and 3,4,5-trimethoxycinnamic acid are the compounds found in Polygalae Radix, the root of Polygala tenuifolia Willdenow, and have been reported to have hepatoprotective and anti-neurodegenerative effects. On the other hand, there are no reports of their effects on gastric lesions. This study examined the inhibitory effects of cinnamic acids, including p-methoxycinnamic acid, 3,4,5-trimethoxycinnamic acid, and 8 compounds (cinnamic acid, 2-(trifluoromethyl) cinnamic acid, 3-(trifluoromethyl) cinnamic acid, trans-4-(trifluoromethyl) cinnamic acid, 4-(dimethylamino) cinnamic acid, 3,4-(methylenedioxy) cinnamic acid and 3,4-dihydroxycinnamic acid), which were selected based on their presence in medicinal herbs and molecular weight, against gastric lesions. Animal models were used to confirm the protective effects on acute gastritis caused by the administration of HCl/EtOH. Gastric acid inhibition was examined by an acid-neutralizing test and the proton pump ($H^+/K^+$-ATPase) inhibiting activity. In addition, antioxidant tests were performed and the gastric emptying rate was determined. The results showed that cinnamic acid, p-methoxycinnamic acid, and 3,4,5-trimethoxycinnamic acid had an inhibitory effect on gastric lesions.

Cytotoxic and Anti-oxidant Constituents from the Aerial Parts of Aruncus dioicus var. kamtschaticus

  • Zhao, Bing Tian;Jeong, Su Yang;Vu, Viet Dung;Min, Byung Sun;Kim, Young Ho;Woo, Mi Hee
    • Natural Product Sciences
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    • 제19권1호
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    • pp.66-70
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    • 2013
  • Ten compounds (1 - 10), palmitic acid (1), 10-nonacosanol (2), pentacosan-1-ol (3), phytol (4), ${\beta}$-sitosterol (5), ${\beta}$-sitosterol-3-O-${\beta}$-D-glucopyranoside (6), 2,4-dihydroxycinnamic acid (7), hyperoside (8), uridine (9) and adenosine (10), were isolated from the n-hexane and EtOAc-soluble fractions of the aerial parts of A. dioicus var. kamtschaticus (Rosaceae). The structures of these compounds were elucidated on the basis of spectroscopic evidence. All compounds (1 - 10) were isolated for the first time from this plant. Cytotoxicity of 1 - 10 against Jurkat T (T-lymphocytic leukemia cells), HeLa (Human cervical epitheloid carcinoma cells), MCF-7 (Human breast cancer cells), and HL-60 (Human promyelocytic leukemia cells) cell lines was measured. Compound 6 showed good cytotoxicity against HL-60 cell line with $IC_{50}$ value of 8.13 ${\mu}g/mL$. In addition, compounds 7 and 8 exhibited antioxidant activity with $IC_{50}$ values of 16.30 and 12.42 ${\mu}g/mL$, respectively.