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ABSTRACT: The pre-harvest residue limit (PHRL) of abamectin (abamectin B1a and B1b) in Perilla frutescens leaves grown under greenhouse conditions were investigated using high-performance liquid chromatography with a fluorescence detector. Samples were extracted with acetonitrile. The extract was purified through a solid phase extraction procedure. Then the purified extract was derivatized with trifluoroacetic anhydride and N-methylimidazole to form a strong stable fluorescent derivative of abamectin. Finally, derivatized abamectins were conveyed to the detector via an Atlantis C18 column, with water and methanol as a mobile phase. Calibration curves were linear over the calibration ranges with coefficients of determinants r (2) ≥ 0.999. The limits of detection and quantification were 0.0033 and 0.01 mg kg(-1) for abamectin B1a and B1b, respectively. Recovery was assessed in a control matrix at two different fortification concentrations, with three replicates for each concentration. Good recoveries were obtained for the target analytes and ranged from 82.11 to 93.03 %, with relative standard deviations of less than 8 %. The rate of disappearance of total abamectin on perilla leaves for recommended and double the recommended doses was described as first-order kinetics with a half-life of 0.7 days. Using the PHRL curve, we could predict the residue level of total abamectin to be 0.92 mg kg(-1) at 7 days before harvest or 0.26 mg kg(-1) at 4 days before harvest, which would be below the provisional MRL designed by the Korea Food and Drug Administration.
Environmental Monitoring and Assessment 06/2013; · 1.40 Impact Factor
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ABSTRACT: Chelidonium majus L. is an herbal plant that is commonly used in Western phytotherapy and traditional Chinese medicine for diuretic, antitussive, eye-regenerative, anti-osteoporotic, and radioprotective purposes. In this study, we purified 6-acetonyl-5,6-dihydrosanguinarine (ADS) from C. majus and investigated its immune-stimulatory effect. We found that ADS has the potential to induce the inflammatory cytokines TNF-α, IL-6, and IL-8 in macrophages and dendritic cells (DCs), that NFκB activation is a critical mediator of ADS-induced cytokine production, and that the activation of NFκB was dependent on reactive oxygen species (ROS). ADS induced phosphorylation of ERK and JNK, which was also associated with NFκB activation; phosphorylarion and cytokine production were inhibited by ROS scavenger and by specific MAPK inhibitors. Taken together, the results suggest that ADS from C. majus, as a positive immune modulator, induces inflammatory cytokines that might improve immunity, via the ROS-ERK/JNK-NFκB pathway.
Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 05/2013; · 2.99 Impact Factor
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ABSTRACT: The aim of this study was to investigate the protective effect of 2,3-dehydrosilybin (DHS) against carbon tetrachloride (CCl(4))-induced liver injury in rats. Administration of DHS significantly attenuated the levels of serum aspartate aminotransferase, alanine aminotransferase, and liver lipid peroxidation in CCl(4)-treated rats. Moreover, we showed that DHS prevented DNA damage and decreased the protein levels of γ-H2AX, which is a specific DNA damage marker, in CCl(4)-treated rat livers. DHS also markedly increased the activity of antioxidant enzymes, such as superoxide dismutase, catalase, glutathione peroxidase, and glutathione reductase in CCl(4)-treated rat livers. Furthermore, we found that DHS significantly inhibited the production of serum nitric oxide as well as the levels of serum IL-6, IFN-γ, and TNF-α in CCl(4)-treated rats. Additionally, DHS significantly suppressed iNOS expression on the protein levels in CCl(4)-treated rat livers. Collectively, the present study suggests that DHS protects the liver from CCl(4)-induced hepatic damage via antioxidant and anti-inflammatory mechanisms.
Food Chemistry 05/2013; 138(1):107-15. · 3.65 Impact Factor
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ABSTRACT: SARS-CoV papain-like protease (PLpro) is an important antiviral target due to its key roles in SARS virus replication. The MeOH extracts of the fruits of the Paulownia tree yielded many small molecules capable of targeting PLpro. Five of these compounds were new geranylated flavonoids, tomentin A, tomentin B, tomentin C, tomentin D, tomentin E (1-5). Structure analysis of new compounds (1-5) by NMR showed that they all contain a 3,4-dihydro-2H-pyran moiety. This chemotype is very rare and is derived from cyclization of a geranyl group with a phenol functionality. Most compounds (1-12) inhibited PLpro in a dose dependent manner with IC50's raging between 5.0 and 14.4μM. All new compounds having the dihydro-2H-pyran group showed better inhibition than their parent compounds (1 vs 11, 2 vs 9, 4 vs 12, 5 vs 6). In kinetic studies, 1-12 emerged to be reversible, mixed inhibitors.
Bioorganic & medicinal chemistry 03/2013; · 2.82 Impact Factor
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ABSTRACT: Abstract Severe acute respiratory syndrome coronavirus (SARS-CoV) papain-like protease (PLpro) is a key enzyme that plays an important role in SARS virus replication. The ethanol extract of the seeds of Psoralea corylifolia showed high activity against the SARS-CoV PLpro with an IC(50) of value of 15 µg/ml. Due to its potency, subsequent bioactivity-guided fractionation of the ethanol extract led to six aromatic compounds (1-6), which were identified as bavachinin (1), neobavaisoflavone (2), isobavachalcone (3), 4'-O-methylbavachalcone (4), psoralidin (5) and corylifol A (6). All isolated flavonoids (1-6) inhibited PLpro in a dose-dependent manner with IC(50) ranging between 4.2 and 38.4 µM. Lineweaver-Burk and Dixon plots and their secondary replots indicated that inhibitors (1-6) were mixed inhibitors of PLpro. The analysis of K(I) and K(IS) values proved that the two most promising compounds (3 and 5) had reversible mixed type I mechanisms.
Journal of Enzyme Inhibition and Medicinal Chemistry 01/2013; · 1.62 Impact Factor
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ABSTRACT: The present research was the first to investigate phenolic compound profiles and antioxidant properties in the seeds of various perilla (Perilla frutescens) cultivars. The 80% methanol extract (50μg/ml) of this species showed potent antioxidant activities against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals. Phenolic compounds were characterised by nuclear magnetic resonance (NMR) spectroscopy, and ultra performance liquid chromatography with photodiode array detector and electrospray ionisation/mass (UPLC-PDA-ESI/MS) analysis. Nine compounds were elucidated as caffeic acid-3-O-glucoside (1), caffeic acid (2), luteolin-7-O-glucoside (3), apigenin-7-O-glucoside (4), rosmarinic acid-3-O-glucoside (5), rosmarinic acid (6), luteolin (7), apigenin (8), and chrysoeriol (9). The individual and total phenolic contents were remarkably different, especially rosmarinic acid-3-O-glucoside (5) and rosmarinic acid (6) which were the predominant compounds (>95%) in all perilla cultivars. Additionally, Yeupsil cultivar exhibited the highest phenolic content (5029.0μg/g) and antioxidant activity, whereas the lowest was shown by Dasil (2138.7μg/g). Therefore, these results suggest that antioxidant effects of perilla seeds are correlated with phenolic contents.
Food Chemistry 01/2013; 136(2):843-52. · 3.65 Impact Factor
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ABSTRACT: Bacterial neuraminidase (NA) is a lynch pin enzyme in the formation of biofilms. Thus NA continues to be one of the key enzymes targeted by bacterial infection. The purpose of this manuscript is to communicate four new naturally derived inhibitors of neuraminidase (IC50s 3.7-24.4 μM). All these active species (1-4) contained a resveratrol chemotype, however resveratrol itself was inactive (IC50 > 100 μM). 1-4 were isolated from the 60% aqueous ethanol extract of seeds of paeonia lactiflora, which exhibited potent neuraminidase inhibition. Purification of the extracts yielded four chiral polyphenols, suffruticosol A (1), suffruticosol B (2), trans-ε-viniferin (3), and trans-gnetin H (4). Mechanistic analysis of 1-4's inhibition showed that they were all reversible, noncompetitive inhibitors. Trans-ε-viniferin (3) underwent trans-cis isomerization, which led to a reduction in inhibition potency. This correlates with the fact that the cis-isomer is a weaker inhibitor of neuraminidase than the trans-isomer. Importantly, significantly different optical rotations ([α]D) compared to previous reports were found for suffruticosols A (+95 vs -34) and B (+136 vs +13). These two species are the most important standard metabolites in the whole paeoniaceae family and therefore correction of this error is important.
Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association 01/2013; · 2.99 Impact Factor
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Woo Duck Seo,
Heung Joo Yuk,
Marcus J Curtis Long,
Ki Chang Jang,
Jin Hwan Lee,
Sang-Ik Han,
Hang Won Kang,
Min Hee Nam,
Sung-Joon Lee,
Ji Hae Lee, Ki Hun Park
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ABSTRACT: AMPK is an intracellular sensor that modulates the energy balance within the cell. AMPK was activated significantly by the hexane extract of barley sprouts. This AMPK activation emerges across the growth stages of the sprout, becoming most significant (three times above the initial stages) 10 days after seeding. After this time, the activation decreased between 13 days to 20 days post sprouting. Analysis of the hexane extracts by GC-MS, showed the amounts of policosanols (C20-30) in the plant dramatically increased between 5 days (109.7 mg/100g) to 10 days (343.7 mg/100g) post sprouting, and then levels fell back down, reaching 76.4 mg/100g 20 days post sprouting. This trend is consistent with policosanols being the active ingredient in the barley plants. We validate this by showing that hexacosanol is an activator of AMPK. The richest cultivar for PCs was found to be Daejin cultivar. Cultivars had a significant effect on total PC content (113.2 to 183.5 mg/100g) within the plant up to 5 days post sprouting. However this dependence on cultivar was not so apparent at peak stages of PC production (10 days post sprouting). The most abundant policosanol in barley sprout, hexacosanol contributed 62-80% of the total PC content at every stage. These results are valuable to determine the optimal times of harvest to ensure that policosanols from barley sprouts are within the required limits.
Journal of Agricultural and Food Chemistry 01/2013; · 2.82 Impact Factor
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Oisun Jung,
Suyong Choi,
Sun-Bok Jang,
Sin-Ae Lee,
Ssang-Taek Lim,
Yoon-Ju Choi,
Hye-Jin Kim,
Do-Hee Kim,
Tae Kyoung Kwak,
Hyeonjung Kim, [......],
Mi-Sook Lee,
Sook Young Park,
Jihye Ryu,
Doyoung Jeong,
Hae-Kap Cheong,
Hyun Jeong Kim, Ki Hun Park,
Bong-Jin Lee,
David D Schlaepfer,
Jung Weon Lee
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ABSTRACT: Transmembrane 4 L six family member 5 (TM4SF5) plays an important role in migration. Focal adhesion kinase (FAK) activity is essential for homeostatic and pathological migration of adherent cells. However, it is unclear how TM4SF5 signaling mediates the activation of cellular migration machinery and how FAK is activated during cell adhesion. Here we showed that TM4SF5 directly and adhesion-dependently bound FAK, causing a structural alteration possibly to release the inhibitory intramolecular interaction, which activated FAK at the leading edges of cells to promote migration/invasion and in vivo metastasis. TM4SF5-mediated FAK activation occurred during integrin-mediated cell adhesion. TM4SF5 was localized at the leading peripheries together with FAK and actin-organizing molecules, indicating a signaling link between TM4SF5/FAK and actin reorganization machinery. Impaired interactions between TM4SF5 and FAK attenuated FAK phosphorylation, the signaling link to actin organization machinery, and the metastatic potential. Our findings demonstrate that TM4SF5 directly binds to and activates FAK in an adhesion-dependent manner to regulate cell migration and invasion, suggesting that TM4SF5 is a promising target in the treatment of metastatic cancer.
Journal of Cell Science 10/2012; · 6.11 Impact Factor
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ABSTRACT: Celastrol has been reported to possess anticancer effects in various cancers; however, the precise mechanism underlying ROS-mediated mitochondria-dependent apoptotic cell death triggered by celastrol treatment in melanoma cells remains unknown. We showed that celastrol effectively induced apoptotic cell death and inhibited tumor growth using tissue culture and in vivo models of B16 melanoma. In addition to apoptotic cell death in B16 cells, several apoptotic events such as PARP cleavage and activation of caspase were confirmed. Pretreatment with caspase inhibitor modestly attenuated the celastrol-induced increase in PARP cleavage and sub-G1 cell population, implying that caspases play a partial role in celastrol-induced apoptosis. Moreover, ROS generation was detected following celastrol treatment. Blocking of ROS accumulation with ROS scavengers resulted in inhibition of celastrol-induced Bcl-2 family-mediated apoptosis, indicating that celastrol-induced apoptosis involves ROS generation as well as an increase in the Bax/Bcl-2 ratio leading to release of cytochrome c and AIF. Importantly, silencing of AIF by transfection of siAIF into cells remarkably attenuated celastrol-induced apoptotic cell death. Moreover, celastrol inhibited the activation of PI3K/AKT/mTOR signaling cascade in B16 cells. Our data reveal that celastrol inhibits growth and induces apoptosis in melanoma cells via the activation of ROS-mediated caspase-dependent and -independent pathways and the suppression of PI3K/AKT signaling.
Apoptosis 10/2012; · 4.07 Impact Factor
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ABSTRACT: The papain-like protease (PL(pro)), which controls replication of the severe acute respiratory syndrome (SARS) coronavirus, has been identified as a potential drug target for the treatment of SARS. An intensive hunt for effective anti-SARS drugs has been undertaken by screening for natural product inhibitors that target SARS-CoV PL(pro). In this study, diarylheptanoids 1-9 were isolated from Alnus japonica, and the inhibitory activities of these compounds against PL(pro) were determined. Of the isolated diarylheptanoids, hirsutenone (2) showed the most potent PL(pro) inhibitory activity, with an IC(50) value of 4.1 µM. Structure-activity analysis showed that catechol and α,β-unsaturated carbonyl moiety in the molecule were the key requirement for SARS-CoV cysteine protease inhibition.
Biological & Pharmaceutical Bulletin 09/2012; · 1.66 Impact Factor
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ABSTRACT: In the search for anti-SARS-CoV, tanshinones derived from Salvia miltiorrhiza were found to be specific and selective inhibitors for the SARS-CoV 3CL(pro) and PL(pro), viral cysteine proteases. A literature search for studies involving the seven isolated tanshinone hits showed that at present, none have been identified as coronaviral protease inhibitors. We have identified that all of the isolated tanshinones are good inhibitors of both cysteine proteases. However, their activity was slightly affected by subtle changes in structure and targeting enzymes. All isolated compounds (1-7) act as time dependent inhibitors of PL(pro), but no improved inhibition was observed following preincubation with the 3CL(pro). In a detail kinetic mechanism study, all of the tanshinones except rosmariquinone (7) were identified as noncompetitive enzyme isomerization inhibitors. However, rosmariquinone (7) showed a different kinetic mechanism through mixed-type simple reversible slow-binding inhibition. Furthermore, tanshinone I (5) exhibited the most potent nanomolar level inhibitory activity toward deubiquitinating (IC(50)=0.7μM). Additionally, the inhibition is selective because these compounds do not exert significant inhibitory effects against other proteases including chymotrysin, papain, and HIV protease. These findings provide potential inhibitors for SARS-CoV viral infection and replication.
Bioorganic & medicinal chemistry 08/2012; 20(19):5928-35. · 2.82 Impact Factor
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ABSTRACT: Melanogenesis can be controlled by tyrosinase inhibition or by blocking the maturation processes of tyrosinase and its related proteins. Mangostenone F was isolated from the seedcases of Garcinia mangostana . Mangostenone F was shown to be inactive against tyrosinase (IC(50) > 200 μM) but was a potent α-glucosidase inhibitor in vitro (IC(50) = 21.0 μM). Mangostenone F was found to inhibit production of melanin in the mouse melanoma cell line B16F10. Importantly, unlike most glycosidase inhibitors, mangostenone F displayed very low cytotoxicity (EC(50) > 200 μM). The Western blot for expression levels of proteins involved in melanogenesis showed that mangostenone F down-regulated tyrosinase and TRP-2 expression. Treating B16F10 cells with mangostenone F significantly increased the susceptibility of tyrosinase to endoglycosidase H digestion, indicating that tyrosinase was unable to mature fully and pass to the trans-golgi apparatus. Consistent with these data, in lysate assays, mangostenone F was shown to be a better inhibitor of α-glucosidases than deoxynojirimycin, a representative glycosidase inhibitor.
Journal of Agricultural and Food Chemistry 07/2012; · 2.82 Impact Factor
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ABSTRACT: Four guaia-12,6-olide type sesquiterpene lactones, aguerin B (1), 8α-acetoxyzaluzanin C (2), cynaropicrin (3), and deacylcynaropicrin (4), were isolated from the flowers ofHemisteptia lyrata Bunge. It is the first report on the isolation of compounds1-4 from Hemisteptia species. All the isolates (1-4) were examined for their cytotoxic activity against SK-OV-3, LOX-IMVI, A549, MCF-7, PC-3, and HCT-15 human cancer cell lines.
Archives of Pharmacal Research 04/2012; 26(11):925-928. · 1.59 Impact Factor
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ABSTRACT: Alzheimer's disease is rapidly becoming one of the most prevalent human diseases. Inhibition of human acetylcholinestrase (hAChE) and butyrylcholinestrase (BChE) has been linked to amelioration of Alzheimer's symptoms and research into inhibitors is of critical importance. Purification of the methanol extract of Paulownia tomentosa fruits yielded potent hAChE and BChE inhibitory flavonoids (1-9). A comparative activity screen indicated that a geranyl group at C6 is crucial for both hAChE and BChE. For example, diplacone (8) showed 250-fold higher efficacy than its parent eriodictyol (12). IC(50)s of diplacone (8) were 7.2 μM for hAChE and 1.4 μM for BChE. Similar trends were also observed for 4'-O-methyldiplacone (4) (vs its parent, hesperetin 10) and mimulone (7) (vs its parent, naringenin 11). Representative inhibitors (1-8) showed mixed inhibition kinetics as well as time-dependent, reversible inhibition toward hAChE. The binding affinities of these compounds to hAChE were investigated by monitoring quenching of inherent enzyme fluorescence. The affinity constants (K(SA)) increased in proportion to inhibitory potencies.
Bioorganic & medicinal chemistry 03/2012; 20(8):2595-602. · 2.82 Impact Factor
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ABSTRACT: Sialidases are enzymes that catalyze the hydrolysis of sialic acid residues from various glycoconjugates, which are widely found in a number of viral and microbial pathogens. In this study, we investigated the biological evaluation of isolated six shikonins (1-6) and three shikonofurans (7-9) from Lithospermum erythrorhizon. The nine isolated compounds 1-9 showed strong and selective inhibition of glycosyl hydrolase (GH) 33 and -34 sialidases activities. In GH33 bacterial-sialidase inhibition assay, the inhibitory activities against GH33 siadliase of all shikonofuran derivatives (7-9) were greater than shikonin derivatives (1-6). Shikonofuran E (8) exhibited the most potent inhibitory activity toward GH33 sialidases (IC(50)=0.24μM). Moreover, our detailed kinetic analysis of these species unveiled that they are all competitive and simple reversible slow-binding inhibitors. Otherwise, they showed different inhibitory capacities and kinetic modes to GH34 viral-sialidase activity. All the naphthoquinone derivatives (1-6) were of almost equal efficiency with IC(50) value of 40μM and shikonofurans (7-9) did not show the significant inhibitory effect to GH34 sialidase. Kinetic analyses indicated that naphthoquinones acted via a noncompetitive mechanism.
Bioorganic & medicinal chemistry 03/2012; 20(5):1740-8. · 2.82 Impact Factor
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Hyun-Mee Oh,
Seung Woong Lee,
Mi Hye Park,
Mi Hwa Kim,
Young Bae Ryu,
Myo Sun Kim,
Ha-Hyun Kim, Ki Hun Park,
Woo Song Lee,
Su-Jin Park,
Mun-Chual Rho
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ABSTRACT: This study examined the effect of norkurarinol on the toll-like receptor 3 (TLR3)-mediated signaling pathways and rotavirus replication. Norkurarinol, a lavandulylated flavanone, was isolated from the roots of Sophora flavescens, which has been shown to have anti-inflammatory activity. Norkurarinol suppressed the NF-κB and AP-1 inducible secreted embryonic alkaline phosphatase (SEAP) activity induced by poly(I:C), TLR3 ligand, in THP1-Blue-CD14 cells with IC(50) values of 20.9 µM. Norkurarinol also significantly suppressed the mRNA expression of pro-inflammatory and adhesive molecules induced by poly(I:C) and rotavirus infection. Pretreatment of norkurarinol blocked the NF-κB and AP-1 signaling pathway and the phosphorylation of MAPKs induced by poly(I:C). On the other hand, norkurarinol increased the level of IRF3 phosphorylation and IFNβ expression in a dose-dependent manner. Moreover, norkurarinol inhibited the rotavirus-induced cytopathic effects. These results suggest that norkurarinol can modulate the TLR3-mediated inflammatory responses and rotavirus replication.
Journal of Pharmacological Sciences 02/2012; 118(2):161-70. · 2.08 Impact Factor
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ABSTRACT: Flavonoids, secondary plant metabolites which mainly have a polyphenolic structure, play an important role in plant-microbe communications for nitrogen-fixing symbiosis. Among 10 polyphenolic compounds isolated from soybean roots in our previous study, coumestrol showed the highest antioxidant activity. In this study, its effect on the soybean nodulation was tested. The soybean symbiont Bradyrhizobium japonicum USDA110 pretreated with 20 μM coumestrol enhanced soybean nodulation by increasing the number of nodules 1.7-fold compared to the control. We also tested the effect of coumestrol on B. japonicum biofilm formation. At a concentration of 2 μM, coumestrol caused a higher degree of biofilm formation than two major soybean isoflavonoids, genistein and daidzein, although no biofilm formation was observed at a concentration of 20 μM each compound. A genome-wide transcriptional analysis was performed to obtain a comprehensive snapshot of the B. japonicum response to coumestrol. When the bacterium was incubated in 20 μM coumestrol for 24 h, a total of 371 genes (139 upregulated and 232 downregulated) were differentially expressed at a 2-fold cutoff with a q value of less than 5%. No common nod gene induction was found in the microarray data. However, quantitative reverse transcription-PCR (qRT-PCR) data showed that incubation for 12 h resulted in a moderate induction (ca. 2-fold) of nodD1 and nodABC, indicating that soybean coumestrol is a weak inducer of common nod genes. In addition, disruption of nfeD (bll4952) affected the soybean nodulation by an approximate 30% reduction in the average number of nodules.
Applied and environmental microbiology 02/2012; 78(8):2896-903. · 3.69 Impact Factor
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ABSTRACT: The action of β-secretase (BACE1) is strongly correlated with the onset of Alzheimer's disease (AD). Aminochalcone derivatives were examined for their ability to inhibit BACE1. Parent aminochalcones showed two digit micromolar IC(50)s against BACE1. Potency was enhanced 10-fold or more by introducing benzenesulfonyl derivatives to the amino group: 1 (IC(50) = 48.2 μM) versus 4a (IC(50) = 1.44 μM) and 2 (IC(50) = 17.7 μM) versus 5a (IC(50) = 0.21 μM). The activity was significantly influenced by position and number of hydroxyl groups on the chalcone B-ring: 3,4-dihydroxy 5a (IC(50) = 0.21 μM) > 4-hydroxy 4a (IC(50) = 1.44 μM) > 2,4-dihydroxy 6 (IC(50) = 3.60 μM) > 2,5-dihydroxy 7 (IC(50) = 16.87 μM) > des hydroxy 4b (IC(50) = 168.7 μM). Lineweaver-Burk and Dixon plots and their secondary replots indicate that compound 5a was a mixed inhibitor with reversible and time-dependent behavior. Potent BACE1 inhibitors 4a,c,f, 5a-c showed moderate inhibition against two other enzymes implicated in AD pathogenesis, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with IC(50)s ranging between 56.1 ~ 95.8 μM and 19.5 ~ 79.0 μM, respectively.
Molecules 01/2012; 18(1):140-53. · 2.39 Impact Factor
