• Title/Summary/Keyword: 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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    • v.32 no.4
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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.

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

  • Kim, Kyu-Jung;Shin, Kwang-Soo;Hong, Soon-Woo
    • The Korean Journal of Mycology
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    • v.14 no.1
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    • pp.43-47
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    • 1986
  • Among the representative phenolic compounds in relation to lignin derivatives and protein synthesis inhibitors, the most effective inducer for the extracellular polyphenol oxidase (PO) of Lentinus edodes JA01 was gallic acid and ferulic acid for Pleurotus ostreatus. Optimum concentration of these inducers was 2.0 mM and 1.0 mM, respectively. Addition of gallic acid after two days culture had the best effect on production of PO enzyme of L. edodes JA01 and for P. ostreatus, and addition of ferulic acid after three days culture had the best effect. Also, in case of L. edodes JA01, polyphenol oxidase activity was parallel to growth curve, whereas the maximum enzyme activity of P. ostreatus was shown at exponential growth phase and declined thereafter.

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

  • Jung, Hae Soo;Song, Mi Young;Kim, Hyoung Sik;Seo, Hyo Hyun;Lee, Jeong Hun;Lee, Kyung Rok;Hong, Il;Moh, Sang Hyun
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.16 no.8
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    • pp.5452-5457
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    • 2015
  • Conjugating a phytochemical, a strong antioxidant, with a functional peptide not only compensates for its stability, but also improves its solubility and anti-wrinkle effects, thereby contributing to the possibility of becoming an excellent cosmetic ingredient. Thus, in this study we examined the potential cosmetic use of a phytochemical-peptide derivative using gallic acid, a phytochemical with antioxidant, anti-inflammatory, and anti-cancer effects. To evaluate the antioxidant and wrinkle-improving efficacy of 5 synthesized gallic acids conjugated with LVH, IVH, KTTKS, YGGFM, and YGGFLRKYP respectively, we observed the expression of genes related to wrinkle improvement using DPPH radical scavenging activity and real-time PCR. As a result, all 5 derivatives had excellent free radical scavenging effects. The expression level of genes involved collagen synthesis also increased, and the secreted peptides during collagen production contributed to their antioxidant and wrinkle improving effects. These results mark the potential use of gallic acid peptide derivatives as a cosmetic ingredient for anti-oxidation and wrinkle improvement.

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

  • Lee, Jin-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.4
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    • pp.306-315
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    • 2009
  • Due to the depleting petroleum reserve, recurring energy crisis, and global warming, it is necessary to study the development of white biotech-based aromatic chemical feedstock from renewable biomass for replacing petroleum-based one. In particular, the production of aromatic intermediates and derivatives in biosynthetic pathway of aromatic amino acids from glucose might be replaced by the production of petrochemical-based aromatic chemical feedstock including benzene-derived aromatic compounds. In this review, I briefly described the production technology for hydroquinone, catechol, adipic acid, shikimic acid, gallic acid, pyrogallol, vanillin, p-hydroxycinnamic acid, p-hydroxystyrene, p-hydroxybenzoic acid, indigo, and indole 3-acetic acid using metabolic engineering, bioconversion, and chemical process. The problems and possible solutions regarding development of production technology for competitive white biotech-based aromatic compounds were also discussed.

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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    • v.17 no.4
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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.

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

  • Ji Soo Ryu;Ja In Kim;Jae Yong Seo;Young-Ah Park;Yu-Jin Kang;Ji Soo Han;Jin Woong Kim
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.50 no.2
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    • pp.103-110
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    • 2024
  • Lipid nanoparticles (LNPs) are a stable and an effective system that protects cell-impermeable biologically active compounds such as nucleic acids, proteins, and peptides against degradation caused by subtle environmental changes. This study focuses on developing LNPs encapsulating gallic acid (GA), an antioxidant, to effectively prolong the half-life of tetrahexyldecyl ascorbate (THDC), a oil-soluble vitamin C derivative. These LNPs were synthesized in small, uniform sizes at room temperature and pressure conditions using a microfluidics chip. Compared to liposomes manufactured under high pressure and high temperature conditions through conventional microfluidizers, LNPs manufactured through microfluidics chips had excellent dispersion and temperature stability, and improved skin absorption as well as improved oxidative stability of fat-soluble vitamin C derivatives. Future studies will focus on ex vivo and in vivo evaluations to study skin improvement to further validate these results.

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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    • v.14 no.3
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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
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.30 no.5
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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.

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

  • Yean, Min-Hye;Kim, Ju-Sun;Hyun, Yu-Jae;Hyun, Jin-Won;Bae, Ki-Hwan;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.43 no.2
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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.