• Title/Summary/Keyword: Protocatechuic Acid

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Neuroprotective Effects of Korean Red Pine (Pinus densiflora) Bark Extract and Its Phenolics

  • Kim, Ji-Won;Im, Sungbin;Jeong, Ha-Ram;Jung, Young Sung;Lee, Inil;Kim, Kwan Joong;Park, Seung Kook;Kim, Dae-Ok
    • Journal of Microbiology and Biotechnology
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    • v.28 no.5
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    • pp.679-687
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    • 2018
  • Korean red pine (Pinus densiflora) is one of the major Pinus species in Korea. Red pine bark is removed prior to the chipping process in the wood industry and discarded as waste. However, red pine bark contains a considerable amount of naturally occurring phenolics, including flavonoids, and therefore may have a variety of biological effects. In this study, we investigated if Korean red pine bark extract (KRPBE) could protect neuronal PC-12 cells from oxidative stress and inhibit cholinesterase activity. Analysis of reversed-phase high-performance liquid chromatography results revealed four phenolics in KRPBE: vanillin, protocatechuic acid, catechin, and taxifolin. The total phenolic and flavonoid contents of KRPBE were 397.9 mg gallic acid equivalents/g dry weight (DW) and 248.7 mg catechin equivalents/g DW, respectively. The antioxidant capacities of KRPBE measured using ABTS, DPPH, and ORAC assays were 697.3, 521.8, and 2,627.7 mg vitamin C equivalents/g DW, respectively. KRPBE and its identified phenolics protected against $H_2O_2$-induced oxidative cell death in a dose-dependent manner. Acetylcholinesterase and butyrylcholinesterase, which degrade the neurotransmitter acetylcholine to terminate neurotransmission in synaptic clefts, were inhibited by treatment with KRPBE and its identified phenolics. Taken together, these results suggest that KRPBE and its constituent antioxidative phenolics are potent neuroprotective agents that can maintain cell viability under oxidative stress and inhibit cholinesterase activity.

Bioassay-Guided Isolation and Identification of Compounds from Arecae Pericarpium with Anti-inflammatory, Anti-oxidative, and Melanogenesis Inhibition Activities

  • Indriana, Amelia;Lee, Kyoung Jin;Kim, Yeong Shik
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.193-200
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    • 2016
  • This study describes the anti-inflammatory, anti-oxidant, and melanogenesis inhibition activities of methanol extract and various organic solvent fractions of Arecae Pericarpium. We examined the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells, 1,1-diphenyl-2-picrylhydrazine (DPPH) scavenging activity, mushroom tyrosinase inhibition activity and melanin contents. The study showed that, among all tested fractions, methylene chloride fraction showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells ($IC_{50}$ value $8.89{\mu}g/mL$) and DPPH radical scavenging activity ($EC_{50}$ value $21.39{\mu}g/mL$). Methylene chloride and ethyl acetate fractions similarly inhibited mushroom tyrosinase activity. Methanol extract exhibited strongest reduction of melanin content in B16F10 melanoma cells. Based on the bioactivity assay results, methylene chloride and ethyl acetate fractions were further separated. Eight phenolic compounds were isolated, which are dimeric syringol (1), catechol (2), 4-hydroxybenzaldehyde (3), vanillin (4), 4-hydroxyacetophenone (5), apocynin (6), protocatechuic acid (7) and 4-hydroxybenzoic acid (8). Among the isolated compounds tested, catechol showed the strongest inhibition of LPS-induced NO production in RAW 264.7 cells. Catechol also showed the concentration-dependent NF-${\kappa}B$ inhibition activity. Arecae Pericarpium might have potentials to be developed as anti-inflammatory agent or dermatological product for skin-whitening agent.

Studies on the Antioxidant and Whitening Effects of Cheongyang Pepper based on a Bibliometric Approach

  • Eunsoo Sohn;Hyo Jin Kim;Chang Woo Ha;Sohee Jang;Jung Hun Choi;Sung Hyeok Kim;Tae-Seong Lee;Eun-Hwa Sohn
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2023.04a
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    • pp.41-41
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    • 2023
  • Red pepper (Capsicum annuum L.) is one of the most consumed vegetable worldwide. In this study, we tried to suggest the possibility of Cheongyang pepper as a functional cosmetic material by identifying the physiological activity, especially antioxidant and whitening effects of Cheongyang pepper through bibliometric analysis and experimental studies. A bibliometric analysis was performed through co-word analysis of 8,892 papers retrieved from SCOPUS. 4 research fields were obtained by cluster mapping from VOSviewer software, among which we noted the antioxidant activity of extracts from Capsicum annum L.. Phenol as a useful ingredient of Cheongyang pepper was analyzed using HPLC (high-performance liquid chromatography). Antioxidant and whitening effects were evaluated by measuring DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity, hydrogen peroxide scavenging activity, and tyrosinase inhibitory activity. Cheongyang pepper extract showed contents of 0.106 ± 0.01 and 0.105 ± 0.02 mg/g, respectively, in the order of gallic acid and protocatechuic acid. The extract exhibited 56.95% DPPH scavenging activity and 43.97% hydrogen peroxide scavenging activity at a concentration of 1,000 ㎍/ml. In addition, 1,000 ㎍/ml of the extract inhibited tyrosinase activity by 52.44% and 42.61%, respectively in a whitening efficacy test using L-tyrosine and L-DOPA (L-3,4- dihydroxyphenylalanine) as substrates. These results suggest that Cheongyang pepper extract and its active ingredients have antioxidant and whitening effects, and the possibility of future development as a whitening functional cosmetic material.

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Antimicrobial Effects and Antioxidative Activity of Baek-bu-ja(Aconiti koreani Rhizoma) by Extraction Solvent Ratio (추출용매 비에 따른 백부자(Aconiti koreani Rhizoma) 추출물의 항균효과 및 항산화효과)

  • Yoon, So-Jung;Kim, Jeung-Hoan;Lee, Kyoung-Hwan;Kwon, Hyo-Jung;Chun, Sung-Sook;Cho, Young-Je
    • Applied Biological Chemistry
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    • v.48 no.3
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    • pp.258-262
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    • 2005
  • For the purpose of developing natural antioxidant, the antioxidative activity and antimicrobial of phenolics isolated from Baek-bu-ja (Aconiti koreani Rhizoma) were determined. Optimum extracting condition for phenolics were water extracts. HPLC analysis showed that the four major phenolic metabolites were rosemarinic, protocatechuic, caffeic and chlorogenic acids. The water extracts of Baekbuja did not have antimicrobial activity against H. pylori; however, the ethanol extracts revealed higher antimicrobial activity. Electron donation ability on DPPH of Baekbuja ethanol extract was 20% higher than other ethanol extracts. The 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid radical decolorization (ABTS) and antioxidant protection factor (PF) were determined with extracts from Aconiti koreani Rhizoma. 94% inhibition and 1.14 PF were shown on ABTS and antioxidant protection factor with 60% ethanol extracts. Also, TBARS (thiobarbituric acid reactive substances) showed $0.19\;{\mu}M$ in the control and $0.07\;{\mu}M$ in the 80% ethanol extracts. The result suggests that Baekbuja extract may be useful as potential sources of anti Helicobacter pylori, antioxidant.

Anti-inflammatory effects of ethyl acetate fraction of unripe astringent persimmon (Diospyros kaki Thunb. cv. Cheongdo-Bansi) on lipopolysaccharide-stimulated RAW 264.7 cells (지방질다당류로 자극한 RAW 264.7 세포에서 청도반시 땡감 에틸 아세테이트 분획물의 항염증 효과)

  • Park, Ye Bin;Jeong, Ha-Ram;Lee, Seung Hwan;Kim, Taewan;Kim, Dae-Ok
    • Korean Journal of Food Science and Technology
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    • v.51 no.1
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    • pp.90-96
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    • 2019
  • Unripe astringent persimmon (Diospyros kaki Thunb. cv. Cheongdo-Bansi) is a by-product produced when thinning out the superfluous fruit of persimmon. We investigated whether unripe astringent persimmon has antioxidative and anti-inflammatory effects. Unripe astringent persimmon extract was fractionated sequentially in n-hexane, chloroform, ethyl acetate, n-butanol, and water. The ethyl acetate fraction had the highest total phenolic content, total flavonoid content, and antioxidant capacity compared to those of the other fractions. Pretreatment of lipopolysaccharide-stimulated RAW 264.7 macrophages with the ethyl acetate fraction reduced nitric oxide, interleukin-6, and intracellular oxidative stress in a dose-dependent manner. Ultra-high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry analysis revealed gallic acid, protocatechuic acid, 4-hydroxybenzoic acid, quercetin-3-O-glucoside, quercetin, and p-coumaric acid as the phenolic compounds of the ethyl acetate fraction. Collectively, these findings suggest that unripe astringent persimmon is a source of functional materials that can promote antioxidative and anti-inflammatory effects.

Antioxidant capacities and β-glucan content of ethanol extract from Phellinus baumii (상황버섯(Phellinus baumii) 에탄올 추출물의 항산화능과 β-glucan 함량)

  • Bae, Hyun-Kyung;Hwang, In-Wook;Hong, Hee-Do;Chung, Shin-Kyo
    • Food Science and Preservation
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    • v.22 no.5
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    • pp.721-726
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    • 2015
  • Phellinus baumii has been used in traditional oriental medicine for the treatment of various cancer types, such as lung cancer, ovarian cancer and malignant melanoma. It has strong anti-cancer, anti-inflammatory and antioxidant activities due to its polysaccharides including glucan, schizophyllan, heteroglycan and lentinan, as well as its polyphenolics such as protocatechuic acid, caffeic acid, coumaric acid. ${\beta}$-Glucan and polyphenolics may be the most important activ ecompounds in P. baumii. Therefore, researchers have focused on these two compounds to improve their contents in extracts. In this study, P. baumii was extracted with hot-water and ethanol at different pH conditions, and their ${\beta}$-glucan contents, antioxidant activity and antioxidant contents were determined. Extraction yield was highest for the 60% ethanol extract at pH 4. The ${\beta}$-glucan contents of the hot-water extract at pH 7 was higher than those of the ethanol extracts. The antioxidant contents and antioxidant activities of the ethanol extracts were higher than those of the hot-water extracts. Extraction with 60% ethanol at pH 7 was appropriate with respect to the antioxidant capacities.

Accelerating Effect of $TNF-{\alpha}$ on the Rhus verniciflua-induced Growth Inhibition and Apoptosis in Human Osteosarcoma Cells

  • Kim, Hyun-Duck;Kook, Sung-Ho;Kim, Beom-Tae;Kim, Jong-Ghee;Jeon, Young-Mi;Lee, Jeong-Chae
    • Natural Product Sciences
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    • v.11 no.1
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    • pp.45-49
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    • 2005
  • Previously, a flavonoid fraction, which consisted mainly of protocatechuic acid, fustin, fisetin, sulfuretin, and butein, here named RCMF [${\underline{R}}hus$ verniciflua Stokes (RVS) ${\underline{c}}hloroform-{\underline{m}}ethanol\;{\underline{f}}raction$], was prepared from a crude acetone extract of RVS which is traditionally used as a food additive and as an herbal medicine. In the present study, we investigated the effects of $TNF-{\alpha}$ on RCMF-induced growth inhibition and apoptosis induction using human osteosarcoma (HOS) cells. The results from tritium uptake and MTT assays showed that $TNF-{\alpha}$ treatment itself (10 ng/ml) did not induce any cytotoxicity, but it actively accelerated RCMF-mediated cytotoxicity of HOS cells. RCMF-induced cytotoxicity and its facilitation by $TNF-{\alpha}$ was verified to be apoptotic, based on the increased DNA fragmentation and low fluorescence intensity in nuclei after propidium iodide (PI) staining of HOS cells. This speculation was further demonstrated by monitoring the Annexin V/PI double staining which could discriminate the difference between apoptotic and necrotic deaths. Collectively, our findings indicate that $TNF-{\alpha}$ accelerates RCMF-induced cytotoxicity in HOS cells.

Optimization of Subcritical Water Hydrolysis of Rutin into Isoquercetin and Quercetin

  • Kim, Dong-Shin;Lim, Sang-Bin
    • Preventive Nutrition and Food Science
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    • v.22 no.2
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    • pp.131-137
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    • 2017
  • Maximum production of isoquercetin and quercetin simultaneously from rutin by subcritical water hydrolysis (SWH) was optimized using the response surface methodology. Hydrolysis parameters such as temperature, time, and $CO_2$ pressure were selected as independent variables, and isoquercetin and quercetin yields were selected as dependent variables. The regression models of the yield of isoquercetin and quercetin were valid due to the high F-value and low P-value. Furthermore, the high regression coefficient indicated that the polynomial model equation provides a good approximation of experimental results. In maximum production of isoquercetin from rutin, the hydrolysis temperature was the major factor, and the temperature or time can be lower if the $CO_2$ pressure was increased high enough, thereby preventing the degradation of isoquercetin into quercetin. The yield of quercetin was considerably influenced by temperature instead of time and $CO_2$ pressure. The optimal condition for maximum production of isoquercetin and quercetin simultaneously was temperature of $171.4^{\circ}C$, time of 10.0 min, and $CO_2$ pressure of 11.0 MPa, where the predicted maximum yields of isoquercetin and quercetin were 13.7% and 53.3%, respectively. Hydrolysis temperature, time, and $CO_2$ pressure for maximum production of isoquercetin were lower than those of quercetin. Thermal degradation products such as protocatechuic acid and 2,5-dihydroxyacetophenone were observed due to pyrolysis at high temperature. It was concluded that rutin can be easily converted into isoquercetin and quercetin by SWH under $CO_2$ pressure, and this result can be applied for SWH of rutin-rich foodstuffs.

Phenolic Compounds from the Fruit Body of Phellinus linteus Increase Alkaline Phosphatase (ALP) Activity of Human Osteoblast-like Cells

  • Lyu, Ha-Na;Lee, Dae-Young;Kim, Dong-Hyun;Yoo, Jong-Su;Lee, Min-Kyung;Kim, In-Ho;Baek, Nam-In
    • Food Science and Biotechnology
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    • v.17 no.6
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    • pp.1214-1220
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    • 2008
  • Secondary metabolites from the fruit body of Phellinus linteus were evaluated for their proliferative effect on human osteoblast-like cells. 3-[4,5-Dimethylthiazole-2-y1]-2,5-diphenyl-tetraxolium bromide (MTT) assay and alkaline phosphatase (ALP) activity assay were used to assess the effect those isolates on the human osteoblast-like cell line (Saos-2). Activity-guided fractionation led to the isolation of ALP-activating phenolic compounds through the extraction of P. linteus, solvent partitioning, and repeated silica gel and octadecyl silica gel (ODS) column chromatographic separations. From the result of spectroscopic data including nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR), the chemical structures of the compounds were determined as 4-(4-hydroxyphenyl)-3-buten-2-one(1), 2-(3',4'-dihydroxyphenyl)-1,3-benzodioxole-5-aldehyde (2), 4-(3,4-dihydroxyphenyl)-3-buten-2-one (3), 3,4-dihydroxybenzaldehyde (4), and protocatechuic acid methyl ester (5), respectively. This study reports the first isolation of compounds 1-3 and 5 from P. linteus. In addition, all phenolic compounds stimulated proliferation of the osteoblast-like cells and increased their ALP activity in a dose-dependent manner ($10^{-8}$ to $10^{-1}\;mg/mL$). The present data demonstrate that phenolic compounds in P. linteus stimulated mineralization in bone formation caused by osteoporosis. The bone-formation effect of P. linteus seems to be mediated, at least partly, by the stimulating effect of the phenolic compounds on the growth of osteoblasts.

Physicochemical Properties and Physiological Activities of Rhus verniciflua Stem Bark Cultured with Fomitella fraxinea (장수버섯 균사체가 배양된 옻피의 이화학적 특성 및 생리활성)

  • Choi, Han-Seok;Kim, Bo-Hyun;Yeo, Soo-Hwan;Jeong, Seok-Tae;Choi, Ji-Ho;Park, Hyo-Suk;Kim, Myung-Kon
    • The Korean Journal of Mycology
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    • v.38 no.2
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    • pp.172-178
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    • 2010
  • The contents of proximate composition, free amino acids and phenolic acids in the Fomitella fraxinea cultivated-Rhus verniciflua stem bark(FRVSB), and its adipogenesis effect were investigated. The proximate composition(%) of FRVSB was as follows: moisture(7.64), ash(6.30), crude fat(3.86), crude protein(3.59) and sugar(not detected); while Rhus verniciflua stem bark(RVSB) contained 1.64, 8.09, 7.28, 6.48 and 5.39, respectively. The total free amino acids concentration was 97.41 mg% in FRVSB and 71.91 mg% in RVSB. Phosphoserine(55.06 mg%), ammonia(17.84mg%) and aspartic acid(6.05mg%) were predominant amino acids. The content of total phenolic acids was 422.89 ppm in ethanol extract and 283.86 ppm in water extract, with syringic and gallic acid as the main component. The FRVSB extracts showed a potent free radical scavenging activity for DPPH(2,2-diphenyl-1-picrylhydrazyl hydrate) with $IC_{50}$ of $28.54\;{\mu}g$(EtOH) and $54.70\;{\mu}g$(water), respectively, whereas $IC_{50}$ value of gallic acid was $1.84\;{\mu}g$. The protective effect of both ethanol and water extract the extracts against UV-induced oxidative stress in NIH3T3 was observed. The water extracts of FRVSB may promote adipogenesis in 3T3-L1 cells.