• 제목/요약/키워드: gallic acid derivatives

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Protective effect of gallic acid derivatives from the freshwater green alga Spirogyra sp. against ultraviolet B-induced apoptosis through reactive oxygen species clearance in human keratinocytes and zebrafish

  • Wang, Lei;Ryu, BoMi;Kim, Won-Suk;Kim, Gwang Hoon;Jeon, You-Jin
    • ALGAE
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    • 제32권4호
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    • pp.379-388
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    • 2017
  • In the present study, we enhanced the phenolic content of 70% ethanol extracts of Spirogyra sp. (SPE, $260.47{\pm}5.21$ gallic acid equivalent $[GAE]mg\;g^{-1}$), 2.97 times to $774.24{\pm}2.61GAE\;mg\;g^{-1}$ in the ethyl acetate fraction of SPE (SPEE). SPEE was evaluated for its antiradical activity in online high-performance liquid chromatography-ABTS analysis, and the peaks with the highest antiradical activities were identified as gallic acid derivatives containing gallic acid, methyl gallate, and ethyl gallate. Isolation of ethyl gallate from Spirogyra sp. was performed for the first time in this study. In ultraviolet B (UVB)-irradiated keratinocytes (HaCaT cells), SPEE improved cell viability by 8.22%, and 23.33% and reduced accumulation of cells in the sub-$G_1$ phase by 20.53%, and 32.11% at the concentrations of 50 and $100{\mu}g\;mL^{-1}$, respectively. Furthermore, SPEE (50 and $100{\mu}g\;mL^{-1}$) reduced reactive oxygen species generation in UVB-irradiated zebrafish by 66.67% and 77.78%. This study suggests a protective activity of gallic acid and its derivatives from Spirogyra sp. against UVB-induced stress responses in both in vitro and in vivo models, suggesting a potential use of SPEE in photoprotection.

목재(木材) 부후균(腐朽菌)의 목질소(木質素) 분해효소(分解酵素) 유도(誘導)에 관하여 (Induction of Extracellular Polyphenol Oxidase from Two White-rot Fungi)

  • 김규중;신광수;홍순우
    • 한국균학회지
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    • 제14권1호
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    • pp.43-47
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    • 1986
  • 리그닌과 관련된 대표적인 페놀화합물인 ferulic acid, vanillic acid 및 gallic acid와 단백질합성저해항생제인 cycloheximide와 puromycine 중에서 Lentinus edodes JA01 경우는 gallic acid가 Pleurotus ostreatus는 ferulic acid가 각각 가장 효과적인 inducer였다. gallic acid는 2.0mM에서, ferulic acid는 1.0mM에서 induction이 가장 잘 되었다. Inducer의 처리시기는 접종후 L. edodes는 2일후에, 그리고 P. ostreatus는 3일후에 최고의 활성을 나타내었다. 또한 polyphenol oxidase activity는 균주의 생장곡선에 대체적으로 비례하여 증가하였으나, P. ostreatus 경우는 대수기에서 최고의 활성을 나타내고 그 이후 감소하였다.

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갈릭산 펩타이드 유도체를 이용한 주름개선 소재 개발 (Development of Anti-Wrinkle Materials using Galloyl-Peptide Derivatives)

  • 정해수;송미영;김형식;서효현;이정훈;이경록;홍일;모상현
    • 한국산학기술학회논문지
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    • 제16권8호
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    • pp.5452-5457
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    • 2015
  • 항산화 효능이 우수한 phytochemical에 콜라겐 합성능이 우수한 기능성 펩타이드의 결합을 통해 소재 자체의 안정성뿐만 아니라 수용액 상태에서의 분산성을 증대시켜 주름개선 효능과 더불어 우수한 화장품 소재로서의 가능성을 가진다. 이에 본 연구는 항산화, 항염 및 항암 등의 효능을 가진다고 알려져 있는 phytochemical인 갈릭산을 이용해 phytochemical-펩타이드 유도체를 개발하여 화장품 소재로서의 가능성을 시험하였다. 갈릭산에 LVH, IVH, KTTKS, YGGFM, YGGFLRKYP 총 5종의 펩타이드를 각각 합성하여 만든 갈릭산 펩타이드 유도체의 항산화 및 주름개선의 효능을 평가하고자 DPPH radical scavenging activity와 real-time PCR로 주름개선과 관련된 유전자의 발현을 확인하였다. 그 결과 5종 유도체 모두 우수한 자유 라디컬 소거능을 보였다. 또한 collagen 합성에 관여하는 유전자의 발현이 증가하였고, collagen 생성시 분비되는 펩타이드의 증가를 통해 항산화뿐만 아니라 주름개선에도 효과가 있었다. 이를 통해 갈릭산 펩타이드 유도체가 항산화 및 주름개선을 위한 화장품 소재로서의 가능성을 확인하였다.

화이트바이오텍기반 방향족화합물 개발에 관한 연구동향 (Research Trend about the Development of White Biotech-Based Aromatic Compounds)

  • 이진호
    • 한국미생물·생명공학회지
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    • 제37권4호
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    • pp.306-315
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    • 2009
  • 원유의 고갈, 반복되는 에너지 위기 및 지구온난화 문제에 기인하여 석유 대신 재생가능한 바이오매스를 사용하여 방향족 화학원료를 개발하는 연구가 광범위하게 진행되고 있다. 특히, 바이오테크놀로지를 이용한 포도당으로부터 방향족아미노산 생합성경로 중간대사체 및 그 유도체 합성기술은 벤젠유래 화합물을 포함한 많은 방향족 석유화학원료를 대체할 가능성이 있는 기술들이 개발되고 있다. 본 고는 미생물 대사공학, 생물전환, 화학공정 기술을 이용하여 hydroquinone, catechol, adipic acid, shikimic acid, gallic acid, pyrogallol, vanillin, p-hydroxycinnamic acid, p-hydroxystyrene, p-hydroxybenzoic acid, indigo, indole 3-acetic acid와 같은 방향족화합물을 어떻게 개발하고 있는지를 논하였다. 또한, 경쟁력있는 화이트바이오텍기반 방향족화합물 생산기술을 개발하기 위한 문제점 및 해결방안등을 논했다.

Anti-oxidative and Antibacterial Constituents from Sedum hybridum

  • Gendaram, Odontuya;Choi, Yoen-Hee;Kim, Young-Sup;Ryu, Shi-Yong
    • Natural Product Sciences
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    • 제17권4호
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    • pp.279-284
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    • 2011
  • Phytochemical studies on the whole extract of Sedum hybridum L., a Mongolian medicinal plant, has been undertaken to isolate active principles responsible for its anti-oxidative and antibacterial activities. Eighteen known compounds, i.e. (1) quercetin, (2) kaempferol, (3) herbacetin-8-O-${\beta}$-D-xylopyranoside, (4) myricetin, (5) gossypetin-8-O-${\beta}$-D-xylopyranoside, (6) gallic acid, (7) 2,4,6-tri-O-galloyl-D-glucopyranose, (8) 6-O-galloylarbutin, (9) myricetin-3-O-${\alpha}$-L-arabinofuranoside, (10) quercetin-3-O-${\alpha}$-L-arabinofuranoside, (11) caffeic acid, (12) ethylgallate, (13) (-) epigallocatechin-3-O-gallate, (14) palmitic acid, (15) stearic acid, (16) stearic acid ethyl ether, (17) ${\beta}$-sitosterol and (18) ${\beta}$-sitosteryl-O-${\beta}$-D-glucopyranose have been isolated and their molecular structures identified by spectroscopic analysis. Thirteen substances including seven flavonol components (1, 2, 3, 4, 5, 9 and 10), five gallic acid derivatives (6, 7, 8, 12 and 13) and caffeic acid (11) exhibited significant, dose-dependent, DPPH radical scavenging activity. Galloyl esters 12 and 13 were revealed to be main active principles for the antibacterial property of the extract of Sedum hybridum L.

지용성 비타민 C 유도체 및 갈릭산을 함유한 지질나노입자 제조 및 특성 (Preparation and Characterization of Lipid Nanoparticles Containing Fat-Soluble Vitamin C Derivatives and Gallic Acid)

  • 유지수;김자인;서재용;박영아;강유진;한지수;김진웅
    • 대한화장품학회지
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    • 제50권2호
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    • pp.103-110
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    • 2024
  • 지질나노입자(lipid nanoparticles, LNPs)란, 세포 불투과성인 치료용 핵산, 단백질 및 펩타이드와 같은 생물학적 활성 화합물을 미세한 환경 변화에 의한 분해로부터 보호해 안정적이면서 효과적인 약물전달시스템이다. 본 연구에서는 지용성 비타민 C 유도체인 테트라헥실데실아스코르베이트(tetrahexyldecyl ascorbate, THDC)의 생체 내 반감기를 효과적으로 연장시키기 위해 산화방지제인 갈릭산(gallic acid, GA)을 함유하는 지질나노입자를 개발하였다. 마이크로플루이딕스칩(microfludics chip)을 통해 상온 및 상압 조건 하에서 작고 균일한 크기로 제작하였다. 기존 마이크로플루다이저(microfluidizer)를 통해 고압 및 고온 조건 하에 제작된 리포좀과 비교하였을 때, 마이크로플루이딕스칩(microfludics chip)을 통해 제작된 LNPs인 경우, 분산 및 온도에 따른 안정성이 우수하였으며, 지용성 비타민 C 유도체의 산화 안정성을 향상시켰을 뿐 아니라 피부 흡수율도 개선된 것을 확인하였다. 향후 연구에서는 이러한 결과를 더욱 입증하기 위해 피부 개선 효과를 연구하기 위한 생체 외 및 생체 내 평가에 중점을 둘 것이다.

Phenolic Acids and Antioxidant Activities of Wild Ginseng (Panax ginseng C. A. Meyer) Leaves

  • Seog, Ho-Moon;Jung, Chang-Hwa;Kim, Yoon-Sook;Park, Hyeon-Suk
    • Food Science and Biotechnology
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    • 제14권3호
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    • pp.371-374
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    • 2005
  • The compositions and antioxidant activities of tree and hydrolyzed phenolic acids, which are aglycones of esterified phenolic acids, in wild ginseng leaves were investigated. The contents of tree and hydrolyzed phenolic acids in the wild ginseng leaves were $422.4\;{\pm}\;3.5$ and $319.6\;{\pm}\;5.7\;mg/100\;g$, respectively, as gallic acid equivalents. Free phenolic acids were composed of 55.3% benzoic acid derivatives and 44.6% phenylpropanoids. The major constituents of free phenolic acids in the ginseng leaves were syringic (139.4 mg/l00 g) and sinapic (131.2 mg/100 g) acids. On the other hand, hydrolyzed phenolic acids in the ginseng leaves were mainly composed of caffeic (59.4 mg/100 g), ferulic (49.5 mg/100 g), and p-coumaric (33.8 mg/100g) acids. Phenylpropanoid content was higher (82.7%) than benzoic acid derivatives (17.3%). $IC_{50}$ values of DPPH radical scavenging activity were $10.2\;{\mu}g/mL$ for tree phenolic acids and 8.0 mg/mL for hydrolyzed phenolic acids, as gallic acid equivalents. Hydrolyzed phenolic acids also exhibited higher hydroxyl and superoxide radical scavenging activities than free phenolic acids did. These results indicated that the antioxidant activities of the wild ginseng leaves were correlated more closely with phenylpropanoid contents than with total amount of phenolics.

Gallic Acid Inhibits STAT3 Phosphorylation and Alleviates DDS-induced Colitis via Regulating Cytokine Production

  • Jeong, Ji Hyun;Kim, Eun Yeong;Choi, Hee Jung;Chung, Tae Wook;Kim, Keuk Jun;Kim, So Yeon;Ha, Ki Tae
    • 동의생리병리학회지
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    • 제30권5호
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    • pp.338-346
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    • 2016
  • Signal transducer and activator of transcription 3 (STAT3) is associated with various human diseases, such as cancer, auto-immune disease, and intestinal inflammation. The limited and inadequate effect of standard approaches for treating inflammatory bowel disease (IBD) has prompted to develop alternative anti-colitis agents through inhibition of STAT3. Here, we show that gallic acid (GA), a 3,4,5-trihydroxybenzoic acid, markedly reduced phosphorylation of STAT3. Among the derivatives of benzoic acids, GA showed significant inhibition on STAT3 phosphorylation. In addition, GA ameliorated the dextran sodium sulfate (DSS)-induced acute colitis as determined by the measurement of symptomatic and histological indices. The suppression of DSS-induced acute colitis by GA treatment may be related to the regulation of cytokines and growth factors. Furthermore, GA inhibited phosphorylation of STAT3 in the colon tissue of DSS-treated mice. These findings may be useful in comprehending the molecular action of GA on STAT3 phosphorylation and provide novel insights into the potential application of GA in the treatment of STAT3-related inflammatory disease, such as IBD.

뱀무로부터 테르페노이드 및 페놀성 성분의 분리 (Terpenoids and Phenolics from Geum japonicum)

  • 연민혜;김주선;현유재;현진원;배기환;강삼식
    • 생약학회지
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    • 제43권2호
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    • pp.107-121
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    • 2012
  • Twenty-five compounds were isolated from the methanolic extract of Geum japonicum (Rosaceae), and their structures were identified as eleven triterpenoids [ursolic acid 3-acetate (2), cecropiacic acid 3-methyl ester (3), pomolic acid 3-acetate (5), ursonic acid (6), ursolic acid (7), pomolic acid (8), corosolic acid (9), euscaphic acid (11), arjunic acid (16), tormentic acid (18), 23-hydroxytormentic acid (21)], two saponins [rosamultin (22) and kaji-ichigoside $F_1$ (23)], two megastigmanes [blumenol A (14) and (+)-dehydrovomifoliol (15)], three flavonoids [apigenin (13), isoquercitrin (17) and tiliroside (24)], two ellagic acid derivatives [3,3'-di-O-methylellagic acid (12) and ducheside B (25)] and five others [eugenol (1), emodin (4), vanillic acid (10), gallic aldehyde (19), salidroside (20)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. This is the first report of the eleven compounds, 2~6, 10, 15, 16, 20, 23, and 25 from the genus Geum, as well as the first report of apigenin (13) and 3,3'-di-O-methylellagic acid (12) from G. japonicum. The antioxidant properties of 22 isolates (1~11, 14, 16~25) were evaluated by the intracellular reactive oxygen species (ROS) radical scavenging using 2',7'-dichlorodihydrofluorescein diacetate (DCF-DA) assay. Among them, isoquercitrin (17) showed significant scavenging activity, and gallic aldehyde (19) and ducheside B (25) showed weak scavenging activity.