• 제목/요약/키워드: protocatechuic acid

검색결과 135건 처리시간 0.026초

열처리 보리수 과즙과 식초의 이화학적 특성, phytochemicals 및 생리활성 (Physicochemical properties, phytochemicals, and biological activities of heat-treated Elaeagnus multiflora juice and vinegar)

  • 조계만;황정은;김수철;주옥수
    • 한국식품저장유통학회지
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    • 제25권1호
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    • pp.52-61
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    • 2018
  • 본 연구에서는 보리수 과즙에 열처리 후 식초를 제조하고 발효특성을 조사하였다. 열처리 보리수 과즙과 식초는 보리수 열매 색깔과 거의 유사하였으며, 적색도인 b 값은 각각 39.48(과즙)과 37.56(식초)이었다. 보리수 과즙을 발효하였을 때 10일 경과 시 초산균수는 4.59-4.62 log CFU/mL, pH는 3.14-3.45, 산도는 0.2-2.12%, 환원당은 0.69-35.24 mg/mL 및 알코올은 0.2%이었다. 비열처리 과즙보다 열처리 과즙이 라디칼 소거활성과 소화효소 저해활성이 높았고, 이에 상응하여 수용성 phenolics, 수용성 flavonoids, flavan-3-ols 유도체 및 phenolic acids 유도체 함량이 높았다. 한편 열처리 식초의 주요 유기산은 acetic acid(21.82 mg/mL)이었고 주요 flavan-3-ols와 phenolic acids 화합물은 catechin($72.24{\mu}g/mL$), catechin gallate($273.36{\mu}g/mL$), epigallocatechin gallate($68.35{\mu}g/mL$), protocatechuic acid ($12.84{\mu}g/mL$) 및 salicylic acid($42.29{\mu}g/mL$)가 검출되었다. $25{\mu}L/mL$ 처리 시 DPPH와 ABTS 라디칼 소거활성 및 ${\alpha}$-glucosidase와 pancreatic lipase 저해활성은 각각 79.66%, 93.99%, 90.12% 및 64.85% 이었다. 이 결과로부터 보리수 과즙의 열처리 방법을 활용한 새로운 형태의 기능성 식초 혹은 음료를 개발할 수 있을 것으로 사료된다.

Screening of ${\alpha}$-Glucosidase Inhibitory Activity of Vietnamese Medicinal Plants : Isolation of Active Principles from Oroxylum indicum

  • Nguyen, Mai Thanh Thi;Nguyen, Nhan Trung;Nguyen, Hai Xuan;Huynh, Thuy Nghiem Ngoc;Min, Byung-Sun
    • Natural Product Sciences
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    • 제18권1호
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    • pp.47-51
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    • 2012
  • Among 38 Vietnamese medicinal plant extracts investigated for their ${\alpha}$-glucosidase inhibitory activity, 35 extracts showed $IC_{50}$ values below $250{\mu}g/mL$. The MeOH extracts of the heartwood of Oroxylum indicum, the seeds of Caesalpinia sappan, and the fruits of Xanthium strumarium exhibited strong ${\alpha}$-glucosidase inhibitory activity with $IC_{50}$ values less than $50{\mu}g/mL$. Fractionation of the MeOH extract of the heartwood of O. indicum led to the isolation of oroxylin A (1), oroxyloside (2), hispidulin (3), apigenin (4), ficusal (5), balanophonin (6), 2- (1-hydroxymethylethyl)-4H,9H-naphtho[2,3-b]furan-4,9-dione (7), salicylic acid (8), p-hydroxybenzoic acid (9), protocatechuic acid (10), isovanillin (11), and ${\beta}$-hydroxypropiovanillon (12). Compounds 1 - 3, 5, 6, 8, 10, and 12 showed more potent activities, with $IC_{50}$ values ranging from 2.13 to $133.51{\mu}M$, than a positive control acabose ($IC_{50}$, $241.85{\mu}M$). The kinetic study indicated that oroxyloside (2) displayed mixed-type inhibition with inhibition constant (Ki) was $3.56{\mu}M$.

페놀성 화합물을 이용한 현지초의 UPLC 다성분 동시분석 개발 (Simultaneous Analysis of Phenolic Compounds in Geranium thunbergii Using UPLC)

  • 김세건;라미차네 라마칸타;이경희;판데야 프라카스 라즈;심상연;정현주
    • 생약학회지
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    • 제49권1호
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    • pp.15-22
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    • 2018
  • The aim of this study was to develop a UPLC method for simultaneous analysis of 8 phenolic compounds including gallic aicd (1), protocatechuic acid (2), methyl gallate (3), ellagic acid (4), kaempferol-3-arabinofranosyl-7-rhamnoside (5), kaempferitrin (6), afzelin (7) and kaempferol-7-rhamnoside (8) isolated from Geranium thunbergii which has been traditionally used as anti-diarrheal agent. The UPLC method was optimized and validated using Halo C18 column ($4.6{\times}100mm$, $2.7{\mu}m$) consisting of MeOH and 0.1% formic acid at 260 nm in 25 minutes. In quantitative analysis of 8 compounds in MeOH extract of G. thunbergii, contents of 4-6 were 12.39, 20.52 and 21.45 mg/g, respectively. These compounds were measured as major phenolic compounds in G. thunbergii and can be useful as marker compounds for its quality control. These results suggest that the UPLC method can be contributed as basic data for quality evaluation of herbal preparations.

고압처리에 의한 발아팥의 기능성 향상 효과 (Effect of Enhancement on Functionality of Germinated Adzuki Bean (Angularis angularis var. nipponensis) with High Hydrostatic Pressure (HHP) Treatment)

  • 김민영;장귀영;이윤정;김경미;강태수;이준수;정헌상
    • 한국식품영양학회지
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    • 제31권1호
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    • pp.135-142
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    • 2018
  • We investigated the influence of germination and high hydrostatic pressure (HHP) treatment conditions on the conversion of functional compounds and antioxidant activity in adzuki bean. The adzuki bean germinated at $25^{\circ}C$ for three- or six-days, and was later subjected to HHP at 0.1, 50, 100, or 150 MPa for 24 h. The highest polyphenol content (5.36 mg gallic acid equivalents (GAE)/g) and flavonoid content (0.91 mg catechin equivalents (CE)/g) were observed after germination for six days and HHP treatment at 100 MPa for 24 h, respectively. The total phenolic acid contents increased with increasing applied pressure from 88.86 to $208.26{\mu}g/g$ (100MPa, 24h). Phenolic acids are divided into two categories; those that exhibit increased content upon HHP treatment, and those that exhibit decreased content. The increasing phenolic acids were gallic acid, chlorogenic acid, (+)-catechin, ${\rho}-coumaric$ acid, ferulic acid, heperidin, salicylic acid, protocatechuic acid, cinnamic acid, naringenin. The total anthocyanin content decreased with increasing applied pressure from 22.42 mg/100 g to 6.28 mg/100 g (150 MPa, 24 h). The highest ABTS radical scavenging activity (8.02 mg eq AA/g) and DPPH radical scavenging activity (1.22 eq Trolox/g) were observed after germination for six days and HHP treatment at 100MPa for 24h, respectively. These results suggested that the combination of HHP and germination can lead to improved functionality in adzuki bean.

Liquid Chromatography Quadrupole Time-Of-Flight Tandem Mass Spectrometry for Selective Determination of Usnic Acid and Application in Pharmacokinetic Study

  • Fang, Minfeng;Wang, Hui;Wu, Yang;Wang, Qilin;Zhao, Xinfeng;Zheng, Xiaohui;Wang, Shixiang;Zhao, Guifang
    • Bulletin of the Korean Chemical Society
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    • 제34권6호
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    • pp.1684-1688
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    • 2013
  • A rapid and sensitive method for determining usnic acid of Lethariella cladonioides in rat was established using high performance liquid chromatography (HPLC) quadrupole time-of-flight (QTOF) tandem mass (MS/MS). Rat plasma was pretreated by mixture of acetonitrile and chloroform to precipitate plasma proteins. Chromatographic separation was achieved on a column ($50{\times}2.1$ mm, $5{\mu}m$) with a mobile phase consisting of water (containing $5{\times}10^{-3}$ M ammonium formate, pH was adjusted to 3.0 with formic acid) and acetonitrile (20:80, v/v) at a flow rate of 0.3 mL/min. A tandem mass spectrometric detection with an electrospray ionization (ESI) interface was conducted via collision induced dissociation (CID) under negative ionization mode. The MS/MS transitions monitored were m/z 343.0448 ${\rightarrow}$ m/z 313.2017 for usnic acid and m/z 153.1024 ${\rightarrow}$ m/z 136.2136 for protocatechuic acid (internal standard). The linear range was calculated to be 2.0-160.0 ng/mL with a detection limit of 3.0 pg/mL. The inter- and intra-day accuracy and precision were within ${\pm}7.0%$. Pharmacokinetic study showed that the apartment of usnic acid in vivo confirmed to be a two compartment open model. The method was fully valid and will probably be an alternative for pharmacokinetic study of usnic acid.

Phenolic acids in Panax ginseng inhibit melanin production through bidirectional regulation of melanin synthase transcription via different signaling pathways

  • Jianzeng Liu ;Xiaohao Xu ;Jingyuan Zhou;Guang Sun ;Zhenzhuo Li;Lu Zhai ;Jing Wang ;Rui Ma ;Daqing Zhao;Rui Jiang ;Liwei Sun
    • Journal of Ginseng Research
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    • 제47권6호
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    • pp.714-725
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    • 2023
  • Background: Our previous investigation indicated that the preparation of Panax ginseng Meyer (P. ginseng) inhibited melanogenesis. It comprised salicylic acid (SA), protocatechuic acid (PA), p-coumaric acid (p-CA), vanillic acid (VA), and caffeic acid (CA). In this investigation, the regulatory effects of P. ginseng phenolic acid monomers on melanin production were assessed. Methods: In vitro and in vivo impact of phenolic acid monomers were assessed. Results: SA, PA, p-CA and VA inhibited tyrosinase (TYR) to reduce melanin production, whereas CA had the opposite effects. SA, PA, p-CA and VA significantly downregulated the melanocortin 1 receptor (MC1R), cycle AMP (cAMP), protein kinase A (PKA), cycle AMP-response element-binding protein (CREB), microphthalmia-associated transcription factor (MITF) pathway, reducing mRNA and protein levels of TYR, tyrosinase-related protein 1 (TYRP1), and TYRP2. Moreover, CA treatment enhanced the cAMP, PKA, and CREB pathways to promote MITF mRNA level and phosphorylation. It also alleviated MITF protein level in α-MSH-stimulated B16F10 cells, comparable to untreated B16F10, increasing the expression of phosphorylation glycogen synthase kinase 3β (p-GSK3β), β-catenin, p-ERK/ERK, and p-p38/p38. Furthermore, the GSK3β inhibitor promoted p-GSK3β and p-MITF expression, as observed in CA-treated cells. Moreover, p38 and ERK inhibitors inhibited CA-stimulated p-p38/p38, p-ERK/ERK, and p-MITF increase, which had negative binding energies with MC1R, as depicted by molecular docking. Conclusion: P. ginseng roots' phenolic acid monomers can safely inhibit melanin production by bidirectionally regulating melanin synthase transcription. Furthermore, they reduced MITF expression via MC1R/cAMP/PKA signaling pathway and enhanced MITF post-translational modification via Wnt/mitogen-activated protein kinase signaling pathway.

Selective Stimulating Effect of Flavonoids on the Antioxidant Defense System in Normal and Transformed Hepatic Cell Lines

  • Kim, Beom-Tae;Lee, Jeong-Chae
    • Natural Product Sciences
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    • 제10권6호
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    • pp.296-301
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    • 2004
  • Previously, a flavonoid fraction, which consisted mainly of protocatechuic acid, fustin, fisetin, sulfuretin, and butein, here named RCMF $({\underline{R}}VS\;{\underline{c}}hloroform-{\underline{m}}ethanol\;{\underline{f}}raction)$, was prepared from a crude acetone extract of Rhus verniciflua Stokes (RVS) which is traditionally used as a food additive and as an herbal medicine. In this study, we evaluated the effects of RCMF on the antioxidant defense system using embryonic normal hepatic cell line (BNL CL.2) and its SV40-mediated transformed cell line (BNL SV A.8). This study demonstrates that RCMF selectively stimulated the antioxidant defense system of normal cells, as BNL CL.2 cells proved to be more sensitive to RCMF-mediated increases of superoxide dismutase, catalase, glutathione, and glutathione reductase than BNL SV A.8 cells. In particular, RCMF caused a significant increase in the malonaldehyde content of BNL SV A.8 cells, which is believed to be closely associated with cytotoxicity of RCMF and RCMF-mediated growth inhibition. Collectively, our findings suggest that the flavonoid fraction, RCMF, selectively stimulates the antioxidant defense system in normal rather than hepatic tumor cells.

Identification of Antioxidative Constituents from Polygonum aviculare using LC-MS Coupled with DPPH Assay

  • Shin, Hyeji;Chung, Hayeon;Park, Byoungduck;Lee, Ki Yong
    • Natural Product Sciences
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    • 제22권1호
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    • pp.64-69
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    • 2016
  • A method for simultaneously identifying antioxidative compounds was developed using time-based LC-MS coupled with DPPH assay regardless of the time consuming process. The methanolic extract of Polygonum aviculare (Polygonaceae) showed significant DPPH radical scavenging activity. Time-based DPPH assay for simultaneous identification of active compounds from the extracts of P. aviculare was used. Major peaks of ethyl acetate fraction of P. aviculare showed high DPPH radical scavenging activity. A simple phenolic compound (1) and six flavonoids (2-7) were isolated from the ethyl acetate fraction of P. aviculare by silica gel and sephadex LH-20 column chromatography. The structures of seven compounds were determined to be protocatechuic acid (1), catechin (2), myricitrin (3), epicatechin-3-O-gallate (4), avicularin (5), quercitrin (6), and juglanin (7) based on the analysis of the $^1H$-NMR, $^{13}C$-NMR and ESI-MS data. All compounds exhibited significant antioxidant activity on DPPH assay and active compounds were well correlated with predicted one.

Anti-inflammatory and Neurotrophic 2H-1-Benzopyran Derivatives of Chaenomeles sinensis

  • Ha, Young Jun;Lee, Tae Hyun;Subedi, Lalita;Kim, Hye Ryeong;Moon, Gyuri;Kim, Sun Yeou;Kim, Chung Sub
    • Natural Product Sciences
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    • 제28권1호
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    • pp.1-5
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    • 2022
  • Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based on analysis of NMR data including 1H and 13C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds (1 and 2) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC50 values of 17.14 and 19.30 μM, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.

전작잡초(田作雜草)로부터 생리활성물질(生理活性物質) 탐색(探索) (Identification of Phytotoxic Compounds and Allelopathic Effects of Various Upland Weeds)

  • 백경환;김길웅
    • 한국잡초학회지
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    • 제8권3호
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    • pp.283-290
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    • 1988
  • 개비름, 쇠별꽃, 쇠무릎, 며느리배꼽, Galinsoga ciliata 등(等)으로부터 추출용매(抽出溶媒)에 따른 상치 발아억제현상(發芽抑制現像)과 penol, 지방산(脂肪酸) 및 유기산(有機酸) 등(等)을 분리(分離) 동정(同定)한 결과(結果)는 다음과 같다. 추출용매제(抽出溶媒劑)로는 ethanol과 ether 추출액(抽出液)에서 상치의 발아억제(發芽抑制)가 가장 강(强)하게 나타났다. 총(總) phenol 함량(含量)은 Galinsoga ciliata에서 27.5 mg/10 g으로 가장 많았고, 며느리배꼽이 18.1 mg, 쇠별꽃 17.0 mg, 개비름 12.9 mg, 쇠무릎 12.8mg 순(順)이였다. Diphenol함량(含量)은 free fraction에서 Galinsoga ciliata가 9.4 mg/10g, 며느리배꼽 5.1 mg, 쇠별꽃 4.8 mg, 개비름 2.2 mg 및 쇠무릎 1.8 mg 순(順)이었으며 대체로 수용(水溶) 및 alcohol 추출(抽出)에서 강(彈)하게 억제현상(抑制現像)을 보인 종(種)들이 많은 phenol 함량(含量)을 함유(含有)하고 있었다. Phenol 물질(物質)로는 개비름에는 p-cresol, hydroquinone, ferulic, caffeic, p-cl-benzoic, p-coumaric, catechol 산(酸) 등(等)이 많이 함유(含有)되어 있었고, 쇠별꽃, 쇠무릎, 며느리배꼽 및 Galinsoga ciliata 등(等)에는 ferulic, caffeic, 7-OH-cumarin, protocatechuic 산(酸) 등(等)이 공통(共通)으로 많이 함유(含有)되어 있었다. 지방산(脂肪酸)으로는 개비름에 포화지방산(飽和脂肪酸)인 palmitic산(酸)이, 쇠별꽃, 쇠무릎, 며느리배꼽 및 갈린소가 등(等)에는 불포화지방산(不飽和脂肪酸) oleic산(酸)이 다량함유(多量含有) 되어 있었다. 유기산(有機酸)은 Galinsoga ciliata를 제외(除外)한 모든 식물종(植物種)에서 oxalic산(酸)을 많이 함유(含有)하고 있었으며, 대체로 14~22 mg/g 정도이었다.

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