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( Ou Yang Qi ),( Pu Wang ),( Jin Huang ),( Jin Bo Cai ),( Jun Yao He ) 한국미생물 · 생명공학회 2013 Journal of microbiology and biotechnology Vol.23 No.3
(R)-[3,5-Bis(trifluoromethyl)phenyl] ethanol is a key chiral intermediate for the synthesis of aprepitant. In this paper, an efficient synthetic process for (R)-[3,5- bis(trifluoromethyl)phenyl] ethanol was developed via the asymmetric reduction of 3,5-bis(trifluoromethyl) acetophenone, catalyzed by Leifsonia xyli CCTCC M 2010241 cells using isopropanol as the co-substrate for cofactor recycling. Firstly, the substrate and product solubility and cell membrane permeability of biocatalysts were evaluated with different co-substrate additions into the reaction system, in which isopropanol manifested as the best hydrogen donor of coupled NADH regeneration during the bioreduction of 3,5-bis(trifluoromethyl) acetophenone. Subsequently, the optimization of parameters for the bioreduction were undertaken to improve the effectiveness of the process. The determined efficient reaction system contained 200mM of 3,5-bis(trifluoromethyl) acetophenone, 20% (v/v) of isopropanol, and 300 g/l of wet cells. The bioreduction was executed at 30oC and 200 rpm for 30 h, and 91.8% of product yield with 99.9% of enantiometric excess (e.e.) was obtained. The established bioreduction reaction system could tolerate higher substrate concentrations of 3,5- bis(trifluoromethyl) acetophenone, and afforded a satisfactory yield and excellent product e.e. for the desired (R)-chiral alcohol, thus providing an alternative to the chemical synthesis of (R)-[3,5-bis(trifluoromethyl)phenyl] ethanol.
Xia, Likai,Narasimhulu, Manchala,Li, Xin,Shim, Jae-Jin,Lee, Yong-Rok Korean Chemical Society 2010 Bulletin of the Korean Chemical Society Vol.31 No.3
This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.
Likai Xia,Manchala Narasimhulu,Xin Li,심재진,이용록 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.3
This paper describes a new synthetic approach for biologically interesting geranylated acetophenones. The first total syntheses of 1-(5-geranyloxy-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone and 1-[5-geranyloxy-7-hydroxy-2- methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl]ethanone, isolated from Melicope semecarpifolia, were carried out starting from commercially available 2,4,6-trihydroxyacetophenone.
Asymmetric Bioconversion of Acetophenone in Nano-Sized Emulsion Using Rhizopus oryzae
( Qing Zhi Li ),( Yang Shi ),( Le He ),( Hui Zhao ) 한국미생물 · 생명공학회 2016 Journal of microbiology and biotechnology Vol.26 No.1
The fungal morphologies and pellet sizes were controlled in acetophenone reduction by Rhizopus oryzae. The acetophenone conversion and (S)-phenylethanol enantiomeric excesses (e.e.) reached the peak after 72 h of incubation when using pellets with 0.54 mm diameter, which showed an excellent performance compared with suspended mycelia, clumps, and pellets with 0.65 or 0.75 mm diameter. Furthermore, nano-sized acetophenone was used as asubstrate to improve the performances of biotransformation work. The results showed that the conversion of nanometric acetophenone and (S)-phenylethanol e.e. reached the maximum (both >99%) after 32 h of incubation when using 0.54 mm diameter pellets, at least 24 h in advance of the control group. On the other hand, Tween 80 and 1, 2-propylene glycol showed low or no toxicity to cells. In conclusion, pellets and acetophenone nanoemulsions synergistically result in superior performances of acetophenone reduction.
Kim, Min-Gi,Yang, Ji-Yeon,Lee, Hoi-Seon American Chemical Society 2013 Journal of agricultural and food chemistry Vol.61 No.31
<P>This study evaluated the acaricidal activities of acetophenone and its derivatives for their potentials as natural acaricides using an impregnated fumigant bioassay against Dermatophagoides spp. and Tyrophagus putrescentiae. On the basis of the LD<SUB>50</SUB> values against <I>D. farinae</I>, 3′-methoxyacetophenone (0.41 μg/cm<SUP>2</SUP>) was 89.9 times more toxic than DEET (36.87 μg/cm<SUP>2</SUP>), followed by 4′-methoxyacetophenone (0.52 μg/cm<SUP>2</SUP>), 2′-methoxyacetophenone (0.75 μg/cm<SUP>2</SUP>), 2′-hydroxy-5′-methoxyacetophenone (1.03 μg/cm<SUP>2</SUP>), 2′-hydroxy-4′-methoxyacetophenone (1.29 μg/cm<SUP>2</SUP>), acetophenone (1.48 μg/cm<SUP>2</SUP>), 2′-hydroxyacetophenone (1.74 μg/cm<SUP>2</SUP>), 2′,5′-dimethoxyacetophenone (1.87 μg/cm<SUP>2</SUP>), 2′,4′-dimethoxyacetophenone (2.10 μg/cm<SUP>2</SUP>), and benzyl benzoate (9.92 μg/cm<SUP>2</SUP>). In regard to structure–activity relationships between acaricidal activity and functional radicals (hydroxyl and methoxy groups) on the acetophenone skeleton, a monomethoxy group (2′-, 3′-, and 4′-methoxyacetone) on the acetophenone skeleton was more toxic than were the other groups (2′,4′- and 2′,5′-dimethoxyacetophenone, 2′- and 4′-hydroxyacetophenone, 2′-hydroxy-4′-methoxyacetophenone, 2′-hydroxy-5′-methoxyacetophenone, and 4′-hydroxy-3′-methoxyacetophenone). These results indicated that acaricidal activity against three mite species changed with the introduction of functional radicals (hydroxyl and methoxy groups) onto the acetophenone skeleton.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jafcau/2013/jafcau.2013.61.issue-31/jf402330p/production/images/medium/jf-2013-02330p_0003.gif'></P>
Han, Ah-Reum,Paik, Young-Sook The Korean Society for Applied Biological Chemistr 2010 Applied Biological Chemistry (Appl Biol Chem) Vol.53 No.6
Two new acetophenone glncosides, 2,6-dihydroxy-4-methoxyacetophenone 3-C-${\beta}$-D-glucoside (1) and 2,6-dihydroxy-4-methoxyacetophenone 3-C-${\beta}$-D-(6'-O-ganoyl)glucoside (2), together with three known compounds, eugenin (3), 8-C-glucosylnoreugenin (4), and gallic acid (5) were isolated from the EtOAc soluble fraction of the MeOH extract of clove buds (Syzygium aromaticum). Of these, compound 2 showed significant prolyl endopeptidase inhibitory activity with $IC_{50}$ value of $17.2{\pm}1.1\;{\mu}M$, suggesting it may have potential use against memory impairment and cognitive decline.
Phenolic Constituents from the Aerial Parts of Artemisia stolonifera
Lee, Kang-Ro,Hong, Seung-Woo,Kwak, Jong-Hwan,Pyo, Suhkneung,Jee, Ok-Pyo The Pharmaceutical Society of Korea 1996 Archives of Pharmacal Research Vol.19 No.3
Two acetophenone glycosides, 2, 4-dihydroxy-6-methoxy acetophenone $4-O-\beta-D-glucopyranoside(I)$, 2, 4, 6-trihydroxy acetophenone $2-O-\beta-D-glucopyranoside(II)$, together with coniferin(III) were isolated from the aerial parts of Artemisia stolonifera (Max.) Kom. The structures of the compounds were elucidated on the basis of spectroscopic evidence. Compound IIwas also confirmed as a new phenolic glycoside from natural sources. In addition, compound I induced cytostatic activity of macrophasges, while compounds II and III did not.
Vahid Mahdavi,Ali Monajemi 한국화학공학회 2013 Korean Journal of Chemical Engineering Vol.30 No.12
A series of cobalt and manganese catalysts supported on SBA-15 with different loading of Mn+2 and Co+2were synthesized. These samples were characterized by SEM and XRD techniques. The catalytic activity of these samples was evaluated in the oxidation of ethylbenzene (EB) to produce acetophenone (AP) and benzoic acid (BA) in the liquid phase using tert-butylhydroperoxide (TBHP) as an oxidant. The effects of Co-Mn loading, TBHP : EB molar ratio and temperature on acetophenone and benzoic acid yields were studied by Box-Behnken experimental design to optimize the production of acetophenone and benzoic acid in liquid system.
A New Acetophenone of Aerial Parts from Rumex aquatica
Hwanmin Yoon,박지은,오미현,김경희,Junghoon Han,황완균 한국생약학회 2005 Natural Product Sciences Vol.11 No.2
A new acetophenone named rumexin (3-hydroxy-5-methyl-4-O-β-D-glucopyranosyl acetophenone)was isolated from methanolic extract of Rumex aquatica together with eight known compounds, quercetin-3-O-β-β-D-glucopyranoside, quercetin-3-O-α-L-rhamnoside, emodin-8-O-β-D-glucopyranoside, cafeic acid, 1-O-cafeoyl-β-D-glucopyranoside, 1-methyl cafeic acid, kaempferol-3-O-β-D-glucuropyranoside.All of the above compounds were isolated from Rumex aquatica for the first time, and structures of compoundswere established by spectroscopic means.
A new acetophenone glycoside from the flower buds of Syzygium aromaticum (cloves)
Ryu, B.,Kim, H.M.,Woo, J.H.,Choi, J.H.,Jang, D.S. Elsevier 2016 Fitoterapia Vol.115 No.-
<P>A new acetophenone, 2,4,6-trihydroxy-3-methylacetophenone-2-O-beta-D-glucoside (1), together with 21 known compounds; one acetophenone (2), four chromone glycosides (3-6), six phenylpropanoids (7-12), six sesquiterpenoids (13-18), two triterpenoids (19 and 20), one sterol (21), and one tannin (22) were isolated from the flower buds of Syzygium aromaticum (cloves). The structure of the new compound 1 was determined by spectroscopic analyses including 1D-, 2D-NMR and HRMS interpretation. Among the isolates, one acetophenone (2), three phenylpropanoids (10 - 12), and one sesquiterpenoid (13) were isolated from the flower buds of S. aromaticum for the first time in this study. All the isolates (1 - 22) were evaluated for their cytotoxicity against human ovarian cancer cells (A2780) using MU assays. Some of the isolates (5, 6, 9, 15, 17, 19, 20, and 21) showed either moderate or weak cytotoxidty on A2780 cells. (C) 2016 Elsevier B.V. All rights reserved.</P>