• Title/Summary/Keyword: 2, 5-dihydroxyacetophenone

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Constituents of Cynanchum auriculatum and their Inhibitory Effect on Melanogenesis in B16 Mouse Melanoma Cell Lines (이엽우피소의 성분 및 멜라닌 생성 억제활성)

  • Choi, Hyun-Gyu;Jiang, Yanfu;Roh, Eun-Mi-Ri;Kim, Young-Soo;Xu, Guang-Hua;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
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    • v.41 no.4
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    • pp.238-244
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    • 2010
  • Fourteen compounds were isolated from the roots of Cynanchum auriculatum and their chemical structures were identified as ${\beta}$-sitosterol (1), acetovanillone (2), p-hydroxyacetophenone (3), 2,4-dihydroxyacetophenone (4), 2,5-dihydroxyacetophenone (5), cynandione A (6), methyleugenol (7), daucosterol (8), Succinic acid (9), cynauriculoside A (10), wilfoside C3N (11), wilfoside C1N (12), wilfoside K1N (13) and wilfoside C1G (14). Among them, compounds 2-5 were isolated from this plant for the first time. And 2, 5-dihydroxyacetophenone (5) showed the most potent inhibitory effect on melanogenesis in B-16 mouse melanoma cell lines with $IC_{50}$ value of $20\;{\mu}M$.

Quantitative analysis of Cynanchum wilfordii Hemsley (Cynanchum wilfordii의 성분함량 분석)

  • Lee, Hye-Won;Park, So-Young;Lee, A-Young;Chae, Sung-Wook;Choi, Go-Ya;Choo, Byung-Kil;Kim, Ho-Kyoung
    • Korean Journal of Oriental Medicine
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    • v.14 no.1
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    • pp.107-111
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    • 2008
  • Objectives : Cynanchum wilfordii(Asclepiadaceae) has been traditionally used as a tonic, the prevention and treatment of various geriatric diseases in Korea. Acetophenone derivatives from C. wilfordii showed neuroprotective activity. In this study, two acetophenones were isolated and quantitative determination of acetophenones from C. wilfordii has been developed for quality stand. Methods : Three acetophenone derivatives were isolated from methanol extract of C. willfordii by the chromatographic separation. Their structures were identified as cynandione A, 2,5-dihydroxy acetophenone and cynanchone A on the basis of spectral data(MS, $^1H-NMR$, $^{13}C-NMR$) and chemical analysis. HPLC analysis was performed to determine the contents of cynandione A and 2,5-dihydroxyacetophenone in C. wilfordii. Results : According to the results, the contents of cynandione A and 2,5- dihydroxyacetophenone were 0.274%, 0.035% by HPLC, respectively. Conclusions : In these results, we have determined the contents of cynandione A and 2,5-dihydroxyacetophenone in Cynanchum wilfordii, respectively. We hope that this study will contribute to the standardization and quality control of herbal medicine.

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Determination of Peripheral Catechol O-methyltransferase (COMT) Activity in vivo using $[2-^{14}C]-3',4'-Dihydroxyacetophenone$

  • Kim, Eun-Joo;Ahn, Jong-Woong;Lee, Hye-Suk;Christ, Wolfram
    • Archives of Pharmacal Research
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    • v.14 no.4
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    • pp.290-294
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    • 1991
  • For the determination of peripheral COMT activity, we synthesized $[2-^{14}C]-3',4'-dihydroxyacetophenone([^{14}C]-DHAP)$, a model substrate closely related to catecholamines, which cannot be attacked by monoamine oxidase. After i.v.-injection of $[^{14}C]-DHAP$ in living animals, only 3',4'-dihydroxy-acetophenone (3',4'-DHAP) and 3'-methoxy-4'-hydroxyacetophenone (3'-MHAP) were detected in blood by thin layer radio chromatography. It could be speculated that 3',4'-DHAP was primarily O-methylated by COMT, followed by subsequent conjugations. The concentration of 3',4'-DHAP, a substrate for COMT, in blood at 5 min after injection of $[^{14}C]-DHAP$, were similar in all animals. The rate of 3'-MHAP formation can be therefore used as an indicator for peripheral COMT activity. The velocity of methylation in 15 min after i.v.-administration of $[^{14}C]-DHAP$ was $0.28\;{\mu}g/ml{\cdot}min$. From these results, 3',4'-DHAP was shown to be used as an appropriate substrate to determine the COMT activity in vivo.

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Phytochemical Studies on Rehmanniae Radix Preparata (숙지황(熟地黃)의 성분연구)

  • Lee, Joo-Young;Lee, Eun-Ju;Kim, Ju-Sun;Lee, Je-Hyun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.42 no.2
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    • pp.117-126
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    • 2011
  • Twenty-two compounds were isolated from the 70% ethanolic extract of Rehmanniae Radix Preparata (Scrophulariaceae) and their structures were identified as three triterpenoids [oleanolic acid (1), pomonic acid (2) and ursolic acid (5)], an iridoid, catalpol (13), four furan derivatives [5-hydroxymethyl-2-furaldehyde acetate (3), 5-hydroxymethyl-2-furfural (6), 5-hydroxymethyl-2-furancarboxylic acid (7), and 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15)], three phenethyl alcohol glycosides [darendoside B (14), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19)], four sugar derivatives [L-arabinose (11), raffinose (20), stachyose (21), and mannitol (22)], and seven others [2,5-dihydroxyacetophenone (4), succinic acid (8), daucosterol (9), ${\beta}$-sitosterol (10), adenosine (16), uridine (18) jio-cerebroside (12)]. 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 triterpenoids oleanolic acid (1), pomonic acid (2), and ursolic acid (5) from the genus Rehmannia, as well as the first report of compounds 5-hydroxymethyl-2-furaldehyde acetate (3), 2,5-dihydroxyacetophenone (4), daucosterol (9), darendoside B (14), 5-(${\alpha}$-D-galactopyranosyloxymethyl)-2-furancarboxaldehyde (15), adenosine (16), phenethyl alcohol 2-O-${\beta}$-D-xylopyranosyl(1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (17), and salidroside (19) from the Rehmanniae Radix Preparata.

Acaricidal and antimicrobial toxicities of Cyanachum paniculatum root oils and these components against Haemaphysalis longicornis and human intestinal bacteria (산해박 뿌리에서 추출한 정유 및 구성성분의 인간 장내미생물에 대한 항균활성 및 작은소피참진드기에 대한 살비활성)

  • Lee, Myung-Ji;Kim, Hui-Ju;Jeong, Ah-Hyeon;Lee, Hoi-Seon
    • Journal of Applied Biological Chemistry
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    • v.61 no.4
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    • pp.423-428
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    • 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.

Investigation on Trend Removal in Time Domain Analysis of Electrochemical Noise Data Using Polynomial Fitting and Moving Average Removal Methods

  • Havashinejadian, E.;Danaee, I.;Eskandari, H.;Nikmanesh, S.
    • Journal of Electrochemical Science and Technology
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    • v.8 no.2
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    • pp.115-123
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    • 2017
  • Electrochemical noise signals in many cases exhibit a DC drift that should be removed prior to further data analysis. Polynomial fitting and moving average removal method have been used to remove trends of electrochemical noise (EN) in time domain. The corrosion inhibition of synthesized schiff base N,N'-bis(3,5-dihydroxyacetophenone)-2,2-dimethylpropandiimine on API-5L-X70 steel in hydrochloric acid solutions were used to study the effects of drifts removal methods on noise resistance calculation. Also, electrochemical impedance spectroscopy (EIS) was used to study the corrosion inhibition property of the inhibitor. The results showed that for the calculation of $R_n$, both methods were effective in trend removal and the polynomial with m=4 and MAR with p=40 were in agreement.

Tyrosinase Inhibitory Phenolic Constituents of Smilax china Leaves (청미래덩굴 잎의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Kim, Sang Hyun;Ahn, Jong Hoon;Jeong, Ji Yeon;Kim, Seon Beom;Jo, Yang Hee;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.44 no.3
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    • pp.220-223
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    • 2013
  • In the course of screening tyrosinase inhibitory activity, total methanolic extract and EtOAc-soluble fraction of Smilax china leaves showed significant inhibitory activity. Further fractionation and isolation of the EtOAc-soluble fraction resulted in 12 phenolic compounds, which were identified as 4-hydroxybenzoic acid (1), 3,4-dihydroxybenzaldehyde (2), 3,4-dihydroxybenzoic acid (3), 3,4-dihydroxyacetophenone (4), 3-hydroxy-4-methoxy benzoic acid (5), trans-p-hydroxycinnamic acid (6), cis-p-hydroxycinnamic acid (7), trans-resveratrol (8), cis-resveratrol (9), dihydroresveratrol (10), moracin M (11) and kaempferol (12). Compounds 1-11 were first reported from this plant. Among the isolated compounds, compounds 2, 8, 9 and 12 showed strong inhibition on tyrosinase activity.

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.