• KSBB Journal
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• 제15권5호
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• pp.464-468
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• 2000

The methanol extract of Arachis hypogaea shell showed antioxidative and antimicrobial activity. The methanol extract was successively purified by solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography and octadecylsilane column chromatography. The purified active substances were isolated by high performance liquid chromatography, and were identified as 3-methoxy-4-hydroxybenzoic acid and 4-hydroxybenzoic acid by LC-MS and GC-MS. The amount of 3-methoxy-4-hydroxybenzoic acid and 4-hydroxybenzoic acid were 3.8mg and 9.8 mg per kg of shell, respectively.

• Journal of Microbiology
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• 제37권3호
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• pp.123-127
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• 1999

A Pseudomonas sp. strain DJ-12 isolated by 4-cholrobiphenyl enrichment culture technique is capable of utilizing 4-hydroxybenzoic acid as a sole source of carbon and energy. The bacterium catabolized 4-hydroxybenzoic acid through the intermediate formation of protocatechuic acid, which was further metabolized. The cell free extracts of pseudomonas sp. DJ-12, grown on 4-hydroxybenzoic acid showed higher activities of 4-hydroxyenzoate 3-hydroxylase and protocatechuate 4,5-dioxygenase, but the activity of catechnol 2,3-dioxygenase was lower. The results suggest that 4-hydroxybenzoic acid is catabolized via protocatechuic acid rather than catechol or gentisic acid in this bacterium and that the protocatechuic acid formed was metabolized through a metacleavage pathway by protocatechuate 4,5-dioxygenase.

• Journal of Microbiology
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• 제38권2호
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• pp.53-61
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• 2000

Hydroxybenzoic acids are the most important intermediates in the degradative pathways of various aromatic compounds. Microorganisms catabolize aromatic compounds by converting them to hydroxylated intermediates and then cleave the benzene nucleus with ring dioxygenases. Hydroxylation of the benzene nucleus of an aromatic compound is an essential step for the initiation and subsequent disintegration of the benzene ring. The incorporation of two hydroxyl groups is essential for the labilization of the benzene nucleus. Monohydroxybenzoic acids such as 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, and 4-hydrosybenzoic acid, opr pyrocattechuic acid that are susceptible for subsequent oxygenative cleavage of the benzene ring. These terminal aromatic intermediates are further degraded to cellular components through ortho-and/or meta-cleavage pathways and finally lead to the formation of constituents of the TCA cycle. Many groups of microorganisms have been isolated as degraders of hydroxybenzoic acids with diverse drgradative routes and specific enzymes involved in their metabolic pahtway. Various microorganisms carry out unusual non-oxidative decarboxylation of aromatic acids and convert them to respective phenols which have been documented. Futher, Pseudomonas and Bacillus spp. are the most ubiquitous microorganisms, being the principal components of microflora of most soil and water enviroments.

• Journal of Microbiology and Biotechnology
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• 제29권10호
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• pp.1636-1643
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• 2019

Two hydroxybenzoyl amines, 4-hydroxybenzoyl tyramine (4-HBT) and N-2-hydroxybenzoyl tryptamine (2-HBT), were synthesized using Escherichia coli. While 4-HBT was reported to demonstrate anti-atherosclerotic activity, 2-HBT showed anticonvulsant and antinociceptive activities. We introduced genes chorismate pyruvate-lyase (ubiC), tyrosine decarboxylase (TyDC), isochorismate synthase (entC), isochorismate pyruvate lyase (pchB), and tryptophan decarboxylase (TDC) for each substrate, 4-hydroxybenzoic acid (4-HBA), tyramine, 2-hydroxybenzoic acid (2-HBA), and tryptamine, respectively, in E. coli. Genes for CoA ligase (hbad) and amide formation (CaSHT and OsHCT) were also introduced to form hydroxybenzoic acid and amine conjugates. In addition, we engineered E. coli to provide increased substrates. These approaches led to the yield of 259.3 mg/l 4-HBT and 227.2 mg/l 2-HBT and could be applied to synthesize diverse bioactive hydroxybenzoyl amine conjugates.

• 융합정보논문지
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• 제11권5호
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• pp.104-110
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• 2021

본 연구는 니파팜의 추출방법에 따른 성분 함량의 변화를 확인하기 위해 수행되어졌다. 니파팜을 에탄올 비율, 추출시간, 추출온도에 따라 추출 후 함량을 분석하였다. 추출용매 비율에 따른 폴리페놀과 플라보노이드의 함량은 50% 에탄올로 추출할 때 각각 36.91, 27.62 mg/g으로 가장 높게 나타났다. 추출온도 및 추출시간에 따른 폴리페놀과 플라보노이드는 60℃에서 6시간 추출 시 각각 40.83, 37.63 mg/g로 가장 높은 함량을 보였다. 니파팜의 주요성분을 에탄올 비율에 따라 함량을 분석한 결과 5-O-caffeoylshikimic acid는 70% 에탄올에서 2.08 mg/g, 4-hydroxybenzoic acid는 30% 에탄올에서 0.10 mg/g, 3,4-hydroxybenzoic acid는 50% 에탄올에서 0.12 mg/g의 가장 높은 함량을 보였다. 추출방법에 따른 니파팜에 함유된 성분의 함량 변화를 통해 식품, 화장품 등 천연물 소재 개발 시 기초 연구 자료로 활용할 수 있을 것으로 기대된다.

• 한국식품과학회지
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• 제32권6호
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• pp.1403-1408
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• 2000

헛개나무 어린 줄기와 잎의 열수추출물에서 얻어진 MeOH 가용 획분에 항미생물 및 항산화 활성을 보여, 이들 활성 본체를 규명하고자 활성물질을 solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography, ODS column chromatography로 순차정제하고, HPLC등에 의해 두 종의 활성물질을 단리하여 LC-MS, GC-MS 분석에 의해 vanillic acid와 ferulic acid로 각각 동정하였다. 두 활성물질은 그람 양성 세균 및 그람 음성 세균 그리고 효모 등의 미생물에 항균 활성을 보였다. 또한, vanillic acid와 ferulic acid의 항산화 활성은 vanillic acid보다 ferulic acid가 강한 활성을 나타내, DPPH 자유라디칼 소거능을 나타내는 농도는 ferulic acid가 $14\;{\mu}g/mL(SC_{50})$을, 그리고 vanillic acid가 $8\;{\mu}g/mL(SC_{10})$이었다.

• The Plant Pathology Journal
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• 제36권6호
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• pp.608-617
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• 2020

The type III secretion system (T3SS) is a key virulence determinant in the infection process of Pseudomonas syringae pv. tomato DC3000 (Pst DC3000). Pathogen constructs a type III apparatus to translocate effector proteins into host cells, which have various roles in pathogenesis. 4-Hydroxybenozic acid and vanillic acid were identified from root extract of Sedum middendorffianum to have inhibitory effect on promoter activity of hrpA gene encoding the structural protein of the T3SS apparatus. The phenolic acids at 2.5 mM significantly suppressed the expression of hopP1, hrpA, and hrpL in the hrp/hrc gene cluster without growth retardation of Pst DC3000. Auto-agglutination of Pst DC3000 cells, which is induced by T3SS, was impaired by the treatment of 4-hydroxybenzoic acid and vanillic acid. Additionally, 2.5 mM of each two phenolic acids attenuated disease symptoms including chlorosis surrounding bacterial specks on tomato leaves. Our results suggest that 4-hydroxybenzoic acid and vanillic acid are potential anti-virulence agents suppressing T3SS of Pst DC3000 for the control of bacterial diseases.

• 한국식품과학회지
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• 제35권5호
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• pp.988-993
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• 2003

대파에 함유된 항산화 물질을 구명하고자 대파를 3가지 다른 방법으로 추출하여 대파 착즙액, 열수추출물, MeOH 추출물을 얻었다. 이들 추출물을 각각 용매분획하여 얻어진 EtOAc 가용 산성획분을 silica gel adsorption column chromatography로 정제하여 얻어진 활성획분을 GC-MS 분석하였다. 그 결과, 대파 착즙액과 열수추출물에서는 succinic acid ,fumaric acid, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxy-benzoic acid, 4-hydroxycinnamic acid 그리고 4-hydroxy-3-methoxycinnamic acid의 6종 화합물이 동정되었으며, MeOH 추출물로부터는 4-hydroxybenzoic acid, 4-hydroxy-3-methoxy-benzoic acid, 4-hydroxycinnamic acid, 4-hydroxy-3-methoxy-cinnamic acid의 4종 화합물이 동정되었다. 동정된 이들 화합물을 대상으로 DPPH radical-scavenging 활성을 검정한 결과, 4-hydroxy-3-methoxycinnamic acid가 가장 강한 항산화 활성을 나타냈다. 또한 각각의 대파추출물에 함유된 항산화 물질의 함량을 GC에 의해 정량분석한 결과, 대파 착즙액과 열수추출물 및 MeOH 추출물 모두 강한 항산화 활성을 나타내는 4-hydroxy-3-methoxycinnamic acid가 가장 많이 함유되어 있었다.

• 한국식품저장유통학회:학술대회논문집
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• 한국식품저장유통학회 2003년도 제23차 추계총회 및 국제학술심포지움
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• pp.134.1-134
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• 2003

The purpose of this study was to investigate the release of p-hydroxybenzoic acid and other compounds from cell wall materials(CWM) and their cellulose fraction from carrot with chemical and enzymatic hydrolysis. To investigate this effect on cell wall chemistry of carrot, alcohol insoluble residue(AIR) of CWM were prepared and were extracted sequentially with water, imidazole, CDTA(-1, -2), Na$_2$CO$_3$(-1, -2), KOH(0.5, 1.0 and 4M), to leave a residue. These were analysed for their carbohydrate and phenolic acids composition. Arabinose and galactose were the main noncellulosic sugars. Phenolics esterified to cell walls in carrot were found to consist primarily of p-hydroxybenzoic acid with minor contribution from vanillin, ferulic acid and p-hydroxybenzaldehyde. p-Hydroxybenzoic acid was quite strongly bound to the cell wall. The contents of p-hydroxybenzoic acid in 0.5M KOH, Na$_2$CO$_3$-2, IM KOH, and ${\alpha}$-cellulose were 2,097, 1,360, 1,140, and 717 $\mu\textrm{g}$/g AIR from CWM, respectively. Alkali labile unknown aromatic compound(C$\sub$7/H$\sub$10/O$_2$) was found in ${\alpha}$ -cellulose hydrolyzate digested with driselase and cellulase. This compound was also found in hydrolyzate of 2 M trifluoroacetic acid at 120$^{\circ}C$ for 2 hours. Driselase treatment solubilized only 46.6 $\mu\textrm{g}$/g of the p-hydroxybenzoic acid from carrot AIR. These results indicate that p-hydroxybenzoic acid was associated with neutral polysaccharides, long chain galactose and branched arabinan from graded alcohol precipitation.

• Natural Product Sciences
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• 제8권4호
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• pp.147-151
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• 2002

In the course of our work on anti-platelet constituents from plants, eight phenolic compounds, $({\pm})-syringaresinol$ (1), 4-hydroxybenzaldehyde (2), 4-hydroxybenzoic acid (3), vanillic acid (4), 4-hydroxy cinnamic acid (5), quercetin 3-O-rhamnoside (6), rutin (7), and quercetin $3-(2^G-rhamnosylrutinoside)$ (8) were isolated from the methanol extract of the leaves of Magnolia obovata. The compounds were identified based on the spectroscopic data. Compound 2, 3, 5, 6, 7 and 8 were isolated for the first time from genus Magnolia. 1 and 6 showed same order of inhibitory potencies as acetylsalicylic acid (ASA) to rat platelet aggregation induced by all the stimulators tested. The remaining six compounds showed only mild effects.