• Title/Summary/Keyword: 3,4-dihydroxycinnamic acid

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

  • Lee, Hyang-Hee;Ma, Seung-Jin;Moon, Jae-Hak;Park, Keun-Hyung
    • Applied Biological Chemistry
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    • v.41 no.2
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    • pp.191-196
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    • 1998
  • The MeOH extract from root of Pulsatilla koreana was showed antimicrobial activities against bacteria and yeast. The antimicrobial active substances of MeOH extract were successfully purified with solvent fractionation, silica gel adsorption column chromatography and Sephadex LH-20 column chromatography. The purified two active substances were isolated by HPLC and identified as 4-hydroxy-3-methoxycinnamic acid and 3,4-dihydroxycinnamic acid by MS, $^{1}H-NMR$ and $^{13}C-NMR$.

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

  • Ma, Seung-Jin;Kuk, Ju-Hee;Ko, Byoung-Seob;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.28 no.3
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    • pp.600-603
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    • 1996
  • The methanol extract of Aralia elata bark showed antimicrobial activities against bacteria, yeast and fungi. The active components were successively purified with solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography, silica gel partition column chromatography and HPLC. The active substances were separated with HPLC where 1% acetic acid-MeOH (60 : 40, v/v) was used as mobile phase. The isolated active substance ($t_r$ 17.1 min) was identified as trans-3,4-dihydroxycinnamic acid by $MS,\;^1H-NMR\;and\;^13C-NMR$.

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

  • Yoon, In;Cho, Jeong-Yong;Kuk, Ju-Hee;Wee, Ji-Hyang;Jang, Mi-Young;Ahn, Tae-Hoe;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.34 no.5
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    • pp.898-904
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    • 2002
  • The ehtyl acetate-soluble acidic fractions from juice and cake of Rubrs coreanum fruit showed DPPH radical-scavenging activity. Each fraction was purified through silica gel adsorption column chromatography. The compounds in the ethyl acetate-soluble acidic fraction of juice were identified as 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid, and 3,4-dihydroxycinnamic acid by GC-MS. The compounds in the ethyl acetate-soluble acidic fraction of cake were also identified as succinic acid, 3,4-dihydroxybenzoic acid, citric acid, 3,4,5,-trihydroxybenzoic acid, and 3,4-dihydroxycinnamic acid by GC-MS. Antioxidative activity of the identified compounds were evaluated by DPPH radical-scavenging assay and hydroxyl radical-scavenging activity assay.

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

  • Min, Kyung-Rak;Kim, Jin-Jun;Park, Sun-Gyoo;Lee, Jeong-Rai;Kang, Seh-Hoon;Kim, Young-Soo
    • YAKHAK HOEJI
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    • v.42 no.2
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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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    • v.26 no.1
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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.

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

  • In, Seo-Ji;Lee, Dae-Young;Seo, Kyeong-Hwa;Nam, Tae-Gyu;Kim, Dae-Ok;Kim, Geum-Soog;Noh, Hyung-Jun;Kim, Gye-Won;Seo, Woo-Duck;Kang, Hee-Cheol;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.55 no.4
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    • pp.217-220
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    • 2012
  • The fruits of Acanthopanax sessiliflorus Seeman (Araliaceae) were extracted with 70% aqueous ethanol at room temperature. The concentrated extract was partitioned with ethyl acetate (EtOAc), n-butyl alcohol, and $H_2O$, successively. From the EtOAc fraction, two compounds were isolated through the repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies. According to the results of physicochemical and spectroscopic data including NMR, mass spectrometry, and infrared spectroscopy, the chemical structures of the compounds were determined as 3,5-dihydroxycinnamic acid (1) and protocatechuic acid (2). Compound 1 was isolated from the fruits of A. sessiliflirus Seeman for the first time. And the compounds were evaluated for the radical scavenging the antioxidant capacity using 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)diammonium salt, 1,1-diphenyl-2-picrylhydrazy, and oxygen radical absorbance capacity assay.

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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    • v.23 no.4
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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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    • v.19 no.1
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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.