• Journal of Microbiology and Biotechnology
• /
• v.34 no.2
• /
• pp.467-475
• /
• 2024

ρ-Hydroxyacetophenone is an important and versatile compound that has been widely used in medicine, cosmetics, new materials, and other fields. At present, there are two ways to obtain ρ-hydroxyacetophenone. One is to extract it from plants, such as Artemisia capillaris Thunb and Cynanchum otophyllum Schneid, and the other is to synthesize it by using chemical methods. Of these two methods, the second is the main one, although it has problems, such as flammable and explosive reagents, difficult separation of by-products, and harsh reaction conditions. To solve these issues, we adopted genetic engineering in this study to construct engineered Escherichia coli containing Hped gene or EbA309 gene. Whole-cell biotransformation was conducted under the same conditions to select the engineered E. coli with the higher activity. Orthogonal tests were conducted to determine the optimal biotransformation condition of the engineered E. coli. The results showed that the optimal condition was as follows: substrate concentration of 40 mmol/l, IPTG concentration of 0.1 mmol/l, an induction temperature of 25℃, and a transformation temperature of 35℃. Under this condition, the effects of transformation time on the ρ-hydroxyacetophenone concentration and cell growth were further studied. We found that as the transformation time extended, the ρ-hydroxyacetophenone concentration showed a gradually increasing trend. However, when the ρ-hydroxyacetophenone concentration increased to 1583.19 ± 44.34 mg/l in 24 h, cell growth was inhibited and then entered a plateau. In this research, we realized the synthesis of ρ-hydroxyacetophenone by biotransformation, and our findings lay a preliminary foundation for further improving and developing this method.

• Journal of Applied Biological Chemistry
• /
• v.61 no.4
• /
• pp.423-428
• /
• 2018

Anaerobic growth-inhibiting and acaricidal activities of 2'-hydroxy-5'-methoxyacetophenone derived from Cyanachum paniculatum oil and its derivatives against five intestinal bacteria (Bifidobacterium bifidum, B. longum, Clostridium pefringens, Escherichia coli and Lactobacillus casei) and Haemaphysalis longicornis were examined. In the packet test against the larvae of H. longicornis, none of the C. paniculatum oil exhibited acaricidal activity, while the C. paniculatum oil showed only antimicrobial activity against five intestinal bacteria in the disc diffusion method. Based on the inhibition zones and MIC values, 2',4'-dimethoxyacetophenone, 2',5'-dimethoxyacetophenone, 2'-hydroxy-4'-methoxyacetophenone, 2'-hydroxy-5'-methoxyacetophenone, 2'-methoxyacetophenone, and 4'-methoxyacetophenone, containing a methyl group on the acetophenone skeleton, possessed growthinhibiting activities against C. perfringens and E. coli. However, acetophenone, 2'-hydroxyacetophenone, 4'-hydroxyacetophenone, 2',4'-hydroxyacetophenone and 2',5'-hydroxyacetophenone, which contained a hydroxyl group on the acetophenone skeleton, had no growth-inhibiting activity against intestinal bacteria. These results indicated that 2'-hydroxy-5'-methoxyacetophenone and its derivatives could potentially be developed as natural antimicrobial agents to specific control of C. perfringens and E. coli.

• Korean Journal of Pharmacognosy
• /
• v.19 no.3
• /
• pp.188-192
• /
• 1988

An aromatic hydrocarbon, $mp\;79{\sim}80^{\circ},\;C_{11}H_{12}O_5$, was first isolated from Phyllostachys sp. and identified as 1, 4-benzenedicarboxylic and 2'-hydroxyethylmethyl ester. Five compounds isolated after alkali hydrolysis were identified as vanillin, 4-hydroxyacetophenone, terephthalic acid, 4-hydroxybenzaldehyde and friedelin.

• Journal of the Korean Applied Science and Technology
• /
• v.26 no.2
• /
• pp.186-190
• /
• 2009

In the previous study, we reported the antioxidative activity and inhibition of melanogenesis of Ligularia stenocephala extracts. In this study, inhibitory effect on elastase and production type I procollagen were investigated. The compounds which was investigated were 4-hydroxyacetophenone, vanillin, chlorogenic acid, caffeic acid isolated from Ligularia stenocephala. They were slightly mild on elastase inhibition activity but 4-hydroxyacetophenone, vanillin exhibited good inhibition activity on collagen production. These results suggest that Ligularia stenocephala may have potential as an anti-aging ingredient in cosmetics.

• Journal of the Korea Institute of Information and Communication Engineering
• /
• v.15 no.4
• /
• pp.1000-1006
• /
• 2011

We examined the effects of various phenolic compounds, Ti plasmids(octopine, nopaline) and A. tumefaciens on the vir gene expression. Nine phenolic compounds were tested using 3 types of Ti plasmid and 3 strains of A. tumefaciens on the vir gene expression. It was also investigated how the levels of vir gene expression could be related to specific phenolic compounds. Six phenolic compounds as 4-hydroxyacetophenone, phenol, catechol, resorcinol, acetosyringone and vanillin had exhibited a strong effect on the vir gene expression of A. tumefaciens MW107 containing nopaline Ti plasmid. The vir genes of A. tumefaciens MW105 and MW108 containing octopine Ti plasmids were remarkably stimulated only by acetosyringone. Thus, it appeared that the vir gene inducing abilities were differed by the kinds of phenolic compounds, A. tumefaciens and Ti plasmids.

• Textile Coloration and Finishing
• /
• v.27 no.4
• /
• pp.301-308
• /
• 2015

This study optimizes dyeing conditions for polyamide-imide fabric using cationic dyes. Dyeing and fastness characteristics of polyamide-imide fabric were investigated with three cationic dyes and 2-hydroxyacetophenone as a swelling agent under various dyeing conditions such as dye and swelling agent concentrations, dyeing temperature and time, pH of dye bath. The dyeing properties were evaluated in terms of dye exhaustion, K/S value and color fastness. The optimized dyeing temperature and time were $130^{\circ}C$ for 90 min for the dyes. Under weak acidic conditions in the range pH 5 to 7, the exhaustion of cationic dyes could be enhanced leading to higher adsorption. Wash and rubbing fastness properties were generally good, while light fastness was slightly low, which can be attributed to the poor photo-stability of the cationic dyes.

• Archives of Pharmacal Research
• /
• v.24 no.3
• /
• pp.194-197
• /
• 2001

The phytochemical study of the aerial parts of Artemisia japonica ssp. littoricola (Asteraceae) led to the isolation of two acetylenic compounds, (3R)-dehydrofalcarinol (2) and (3R)-dehydrofalcarindiol (6), two sesquiterpenes, $1{\beta}$, $6{\alpha}$-dihydroxy-4(15)-eudesmene (5) and oplodiol (8), and four phenolic compounds, eugenol (1), vanillin (3), 3'-methoxy-4'- hydroxy-trrans-cinnamaldehyde (4) and p-hydroxyacetophenone (7). Their structures were determined by chemical and spectroscopic methods.

• Journal of Korean Society of Forest Science
• /
• v.95 no.4
• /
• pp.429-434
• /
• 2006

The dried needles (1.5 kg) of Picea abies Karsten were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of n-hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-n-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$-, $^{13}C$-NMR, FAB and EI-MS. (+)-catechin (compound I), (-)-epicatechin (compound II), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound III), 4-hydroxyacetophenone (compound IV) were isolated from the ethyl acetate soluble fraction and (+)-catechin (compound I), protocatechuic acid (compound V) were isolated from the $H_2O$ soluble fraction of P. abies needle. The antioxidative activities of each fraction and the isolated compounds were tested by DPPH radical scavenging method, and EtOAc soluble fraction, (+)-catechin and (-)-epicatechin showed similar values to ${\alpha}$-tocopherol and BHT as controls.

• Korean Chemical Engineering Research
• /
• v.61 no.1
• /
• pp.109-115
• /
• 2023

The extraction and adsorption characteristics for three phenolic ketones with high physicochemical similarity among phenolic compounds, which are alcohol fermentation inhibitors in lignocellulosic biomass hydrolysates, were investigated. The most suitable basic extractant for selectively separating acetosyringone from three phenol ketones by reactive extraction was found to be trioctylphosphine oxide. In addition, it was found that adsorption using XAD16, a polymer neutral resin adsorbent, or physical extraction using hexane, was a suitable separation method for separation of 4'-hydroxyacetophenone (HAP) and acetovanillone (AVO). A five-step fractionation process including extraction and adsorption mentioned above has been first proposed to separate and concentrate the three phenol ketones present at equal mass percentages. When physical extraction with n-hexane and re-extraction with an aqueous NaOH solution were used as the steps 4 and 5 in the fractionation process respectively, it was possible to obtain almost 70% or more of the purity of three phenolic ketones.

• Korean Journal of Soil Science and Fertilizer
• /
• v.33 no.4
• /
• pp.253-260
• /
• 2000

The virulence(vir) genes in Ti plasmid at Agrobacterium tumefaciens are expressed by a phenolic compound synthesized at plant wound site. The vir genes inducing abilities of 8 phenolic compounds were tested using three wild type strains of A. tumefaciens. It was also investigated how the levels of vir gene expression among the strains tested could be related to the kinds of specific phenolic compounds. Five phenolic compounds like as 4-hydroxyacetophenone, phenol, catechol, resorcinol, and vanillin had exhibited a strong effect on the vir gene expression of A. tumefaciens MW102 whereas they did not be either non-functional or weakly inducible to the vir gene expression of other strains i.e. A. tumefaciens MW105 and MW108. Furthermore, the vir gene of A. tumefaciens MW102 was lowly expressed by acetosyringone that exposed an strong effect on the vir gene induction of other two strains. Thus, it appeared that the vir gene inducing abilities were differed by the kinds of phenolic compounds and Ti plasmids. In conclusion, we suppose that a change in vir gene inducing ability could be resulted from a difference of sensor protein expressed by vir A gene.