The Experts below are selected from a list of 279 Experts worldwide ranked by ideXlab platform
Alexios-leandros Skaltsounis - One of the best experts on this subject based on the ideXlab platform.
-
cytotoxic prenylated Acetophenone dimers from acronychia pedunculata
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurall...
-
Cytotoxic prenylated Acetophenone dimers from Acronychia pedunculata.
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:: Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.
-
Cytotoxic Prenylated Acetophenone Dimers from Acronychia pedunculata
2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Sangkil Nam, Hamid A. Hadi, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC50 values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively
Dunming Zhu - One of the best experts on this subject based on the ideXlab platform.
-
molecular basis for the high activity and enantioselectivity of the carbonyl reductase from sporobolomyces salmonicolor toward α haloAcetophenones
ACS Catalysis, 2018Co-Authors: Xi Chen, Hongliu Zhang, Jinhui Feng, Dunming ZhuAbstract:In an effort to develop a practical method for the synthesis of optically pure 2,2,2-trifluoro-1-phenylethanol, we found that the carbonyl reductase (SSCR) from Sporobolomyces salmonicolor showed excellent activity and enantioselectivity toward the halogenated Acetophenones. Especially, SSCR exhibited more than 1000 times higher activity toward α,α,α-trifluoroAcetophenone than unsubstituted Acetophenone, a strikingly different observation from the previously well-studied alcohol dehydrogenase (LBADH) from Lactobacillus brevis. Enzyme–substrate docking and site-directed mutagenesis studies revealed the molecular basis for the high enzyme activity and enantioselectivity of SSCR toward the α-halogenated Acetophenones. The hydrogen bond of the Asn207 side chain with the substrate halogen atom and the XH/π interaction of the substrate phenyl group with the side chains of Ser222/Thr223 resulted in the formation of the highly reactive conformation of α-halogenated Acetophenones in the active site of the enzyme. ...
-
Molecular Basis for the High Activity and Enantioselectivity of the Carbonyl Reductase from Sporobolomyces salmonicolor toward α‑HaloAcetophenones
2018Co-Authors: Xi Chen, Hongliu Zhang, Jinhui Feng, Dunming ZhuAbstract:In an effort to develop a practical method for the synthesis of optically pure 2,2,2-trifluoro-1-phenylethanol, we found that the carbonyl reductase (SSCR) from Sporobolomyces salmonicolor showed excellent activity and enantioselectivity toward the halogenated Acetophenones. Especially, SSCR exhibited more than 1000 times higher activity toward α,α,α-trifluoroAcetophenone than unsubstituted Acetophenone, a strikingly different observation from the previously well-studied alcohol dehydrogenase (LBADH) from Lactobacillus brevis. Enzyme–substrate docking and site-directed mutagenesis studies revealed the molecular basis for the high enzyme activity and enantioselectivity of SSCR toward the α-halogenated Acetophenones. The hydrogen bond of the Asn207 side chain with the substrate halogen atom and the XH/π interaction of the substrate phenyl group with the side chains of Ser222/Thr223 resulted in the formation of the highly reactive conformation of α-halogenated Acetophenones in the active site of the enzyme. (S)-2,2,2-Trifluoro-1-phenylethanol was prepared in excellent isolated yield and enantiomeric excess from the reduction of α,α,α-trifluoroAcetophenone with mutant T209A. These results suggest that tuning the interactions between the halogen atoms/phenyl group of the substrate and the amino acid residues of the enzyme would lead to valuable mutants for the practical synthesis of β-haloalcohols
-
enzymatic ketone reduction mapping the substrate profile of a short chain alcohol dehydrogenase ymr226c from saccharomyces cerevisiae
Tetrahedron-asymmetry, 2007Co-Authors: Yan Yang, Dunming Zhu, Timothy J Piegat, Ling HuaAbstract:Abstract A short-chain alcohol dehydrogenase (YMR226c) from Saccharomyces cerevisiae was cloned and expressed in Escherichia coli, and the encoded protein was purified. The activity and enantioselectivity of this recombinant enzyme were evaluated with a series of ketones. The alcohol dehydrogenase (YMR226c) was found to effectively catalyze the enantioselective reductions of aryl-substituted Acetophenones, α-chloroAcetophenones, aliphatic ketones, and α- and β-ketoesters. While the enantioselectivity for the reduction of β-ketoesters was moderate, the Acetophenone derivatives, aromatic α-ketoesters, some substituted α-chloroAcetophenones, and aliphatic ketones were reduced to the corresponding chiral alcohols with excellent enantioselectivity. The enantiopreference of this enzyme generally followed Prelog’s rule for the simple ketones. The ester functionality played some role in determining the enzyme’s enantiopreference for the reduction of α- and β-ketoesters. The present study serves as a valuable guidance for the future applications of this versatile biocatalyst.
Eirini Kouloura - One of the best experts on this subject based on the ideXlab platform.
-
cytotoxic prenylated Acetophenone dimers from acronychia pedunculata
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurall...
-
Cytotoxic prenylated Acetophenone dimers from Acronychia pedunculata.
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:: Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.
-
Cytotoxic Prenylated Acetophenone Dimers from Acronychia pedunculata
2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Sangkil Nam, Hamid A. Hadi, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC50 values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively
Joerg Bohlmann - One of the best experts on this subject based on the ideXlab platform.
-
In vivo function of Pgβglu-1 in the release of Acetophenones in white spruce
PeerJ, 2017Co-Authors: Melissa H. Mageroy, Denis Lachance, Sharon Jancsik, Geneviève J. Parent, Armand Séguin, John Mackay, Joerg BohlmannAbstract:Eastern spruce budworm (Choristoneura fumiferiana Clemens) (ESBW) is a major forest pest which feeds on young shoots of white spruce (Picea glauca) and can cause landscape level economic and ecological losses. Release of Acetophenone metabolites, piceol and pungenol, from their corresponding glycosides, picein and pungenin, can confer natural resistance of spruce to ESBW. A beta-glucosidase gene, Pgβglu-1, was recently discovered and the encoded enzyme was characterized in vitro to function in the release of the defensive Acetophenone aglycons. Here we describe overexpression of Pgβglu-1 in a white spruce genotype whose metabolome contains the glucosylated Acetophenones, but no detectable amounts of the aglycons. Transgenic overexpression of Pgβglu-1 resulted in release of the Acetophenone aglycons in planta. This work provides in vivo evidence for the function of Pgβglu-1.
-
a conifer udp sugar dependent glycosyltransferase contributes to Acetophenone metabolism and defense against insects
Plant Physiology, 2017Co-Authors: Melissa H. Mageroy, Sharon Jancsik, John Mackay, Macaire M S Yuen, Michael Fischer, Stephen G Withers, Christian Paetz, Bernd Schneider, Joerg BohlmannAbstract:Acetophenones are phenolic compounds involved in the resistance of white spruce (Picea glauca) against spruce budworm (Choristoneura fumiferiana), a major forest pest in North America. The Acetophenones pungenol and piceol commonly accumulate in spruce foliage in the form of the corresponding glycosides, pungenin and picein. These glycosides appear to be inactive against the insect but can be cleaved by a spruce β-glucosidase, PgβGLU-1, which releases the active aglycons. The reverse glycosylation reaction was hypothesized to involve a family 1 UDP-sugar dependent glycosyltransferase (UGT) to facilitate Acetophenone accumulation in the plant. Metabolite and transcriptome profiling over a developmental time course of white spruce bud burst and shoot growth revealed two UGTs, PgUGT5 and PgUGT5b, that glycosylate pungenol. Recombinant PgUGT5b enzyme produced mostly pungenin, while PgUGT5 produced mostly isopungenin. Both UGTs also were active in vitro on select flavonoids. However, the context of transcript and metabolite accumulation did not support a biological role in flavonoid metabolism but correlated with the formation of pungenin in growing shoots. Transcript levels of PgUGT5b were higher than those of PgUGT5 in needles across different genotypes of white spruce. These results support a role of PgUGT5b in the biosynthesis of the glycosylated Acetophenone pungenin in white spruce.
Khalijah Awang - One of the best experts on this subject based on the ideXlab platform.
-
cytotoxic prenylated Acetophenone dimers from acronychia pedunculata
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurall...
-
Cytotoxic prenylated Acetophenone dimers from Acronychia pedunculata.
Journal of Natural Products, 2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Hamid A Hadi, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Alexios-leandros SkaltsounisAbstract:: Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC(50) values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively.
-
Cytotoxic Prenylated Acetophenone Dimers from Acronychia pedunculata
2012Co-Authors: Eirini Kouloura, Richard Jove, Khalijah Awang, Maria Halabalaki, Marc Litaudon, Mariechristine Lallemand, Sangkil Nam, Hamid A. Hadi, Alexios-leandros SkaltsounisAbstract:Three new Acetophenone dimers or Acronychia-type Acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known Acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the Acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated Acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC50 values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively
