The work reports antibacterial and antifungal activity of some 3-(substituted phenyl) isocoumarins (1H-2-benzopyran-1-ones), isocarbostyrils 1(2H)-isoquinolones, the nitrogen analogues of isocoumarins and isocoumarin-...The work reports antibacterial and antifungal activity of some 3-(substituted phenyl) isocoumarins (1H-2-benzopyran-1-ones), isocarbostyrils 1(2H)-isoquinolones, the nitrogen analogues of isocoumarins and isocoumarin-1-thiones, the thio derivatives of isocoumarins. The antimicrobial activity was determined against ten different Gram positive and Gram negative bacterial strains and three fungal strains. The bacterial strains were Klebsiella pneumonae (ATCC 6633), Staphylococcus aureus (ATCC 29213), Micrococcus luteus (ATCC 9341), Pseudomonas aeruginosa (ATCC 33347), Escherichia coli (ATCC 25922), Salmonella typhi (ATCC 19430), Lactobacillus bulgaricus, (ATCC 25929), Pasteurella multocida A (ATCC 9150), Staphylococcus epidermidis (ATCC 29232) and Proteus vulgaris (ATCC 49565) and fungal strains were Aspergillus flavus, Aspergillus nigar and Aspergillus pterus. Agar well diffusion method was followed for antibacterial activity and poison plate method was adopted for antifungal assay. Chloramphenicol and fluconazole used as standard drugs for antibacterial and antifungal activity respectively. In general, these compounds exhibited high antibacterial potential than antifungal. Comparative study reveals that the 1-thio derivatives are more active than parent isocoumarins but 1(2H)-isoquinolones, are less active. Most of these compounds showed poor activity but some of these compounds exhibited moderate to good activity against Staphylococcus epidermidis, Klebsiella pneumonae, Escherichia coli and Proteus vulgaris, compared with the standard drug.展开更多
Ten novel isocoumarins,including four pairs of enantiomers,were isolated from Artemisia dubia var.subdigitata(Asteraceae).Compounds 1,2 and 3a/3b possessed a unique 6/6/6-tricyclic system comprising an unusual 1-(2-me...Ten novel isocoumarins,including four pairs of enantiomers,were isolated from Artemisia dubia var.subdigitata(Asteraceae).Compounds 1,2 and 3a/3b possessed a unique 6/6/6-tricyclic system comprising an unusual 1-(2-methylcyclohexyl)propan-1-one moiety fused with isocoumarin core skeleton.Compounds 4a/4b were characterized as an unexpected 2,5-dimethylcyclohexan-1-one scaffold,and compounds 5a/5b and 6a/6b were rare 1,2-seco-isocoumarin.Their structures and absolute configurations were elucidated through spectroscopic data,X-ray crystallography,ECD and NMR calculations with DP4+analyses.Plausible biosynthetic pathways were proposed from the naturally occurring isocoumarin.Network pharmacological analysis suggested that the targets of compound 1 were significantly enriched in the cell cycle and Pl3K-Akt signaling pathway.The molecular docking revealed that compound 1 had high binding affinity with CDK2(total score:6.8717).Furthermore,compounds 1 and 2 exhibited inhibitory activity on three human hepatoma cell lines,with inhibitory ratios of 85.1% and 84.5%(HepG2),88.2% and 87.3%(Huh7),and 69.2% and 69.1%(SK-Hep-1)at 200μmol·L^(-1),respectively.展开更多
3-Alkyl isocoumarins are provided by CuI/amino acid-catalyzed Sonogashira coupling reaction of o-bromo benzoic acids and terminal alkynes and the subsequent additive cyclization. This cascade process allows synthesis ...3-Alkyl isocoumarins are provided by CuI/amino acid-catalyzed Sonogashira coupling reaction of o-bromo benzoic acids and terminal alkynes and the subsequent additive cyclization. This cascade process allows synthesis of diverse isocoumarins by varying both coupling partners bearing a wide range of functional groups.展开更多
Four new compounds, asperisocoumarin G(1), asperisocoumarin H(2),(±)-asperisocoumarin I [(±)-3], along with the known pergillin(4) and penicisochroman L(5) were isolated from a mangrove endophytic fungus Asp...Four new compounds, asperisocoumarin G(1), asperisocoumarin H(2),(±)-asperisocoumarin I [(±)-3], along with the known pergillin(4) and penicisochroman L(5) were isolated from a mangrove endophytic fungus Aspergillus sp. 085242 by further chemical investigation. The structures of the new compounds, including their absolute configurations, were established by analysis of HR-ESI-MS and NMR spectroscopic data, and ECD calculation. Asperisocoumarins G-I(1-3) were new isocoumarins belonging to the class of furo[3, 2-h]isocoumarins which are rarely found in natural sources. All of the isolated compounds were evaluated for theirα-glucosidase inhibitory effects, and compounds 1 and 4 showed moderate α-glucosidase inhibitory activity, respectively. In an antimicrobial test, the racemate of 3 showed antibacterial activity against Salmonella.展开更多
Three new isocoumarin derivatives,(S)-6,8-dihydroxy-5-(methoxymethyl)-3,7-dimethylisochroman-1-one(1),(S)-6,8-dihydroxy-3,5,7-trimethyl-isochroman-1-one(2) and(R)-2-chloro-3-(8-hydroxy-6-methoxy-1-oxo-1 H-isochromen-3...Three new isocoumarin derivatives,(S)-6,8-dihydroxy-5-(methoxymethyl)-3,7-dimethylisochroman-1-one(1),(S)-6,8-dihydroxy-3,5,7-trimethyl-isochroman-1-one(2) and(R)-2-chloro-3-(8-hydroxy-6-methoxy-1-oxo-1 H-isochromen-3-yl) propyl acetate(3), along with four known compounds(4–7) were isolated from a mangrove endophytic fungus Penicillium sp. YYSJ-3. Their structures were established on the basis of the extensive spectroscopic data and HR-ESI-MS analysis. The absolute configurations of1–3 were further determined by X-ray diffraction analysis and optical rotations. Compounds 3, 6 and 7 showed promising inhibitory activity against α-glucosidase, which were stronger than that of the positive control 1-deoxynojirimycin(IC50 141.2 μmol·L-1).展开更多
Amicoumacin isocoumarin-type compounds are mainly derived from the secondary metabolites of Bacillus bacteria,and have potential biological activities such as antibacterial,anti-tumor,anti-inflammatory,and anti-ulcer....Amicoumacin isocoumarin-type compounds are mainly derived from the secondary metabolites of Bacillus bacteria,and have potential biological activities such as antibacterial,anti-tumor,anti-inflammatory,and anti-ulcer.In our previous research,three amicoumacin-type isocoumarin compounds,Paenicoumacin A,Paenicoumacin B,and Paenicoumacin C(B and C are novel),were isolated from an endophytic bacterium in Houttuynia cordata.In this study,network pharmacology and bioinformatics techniques were used to analyze the potential activities of amicoumacin compounds in the treatment of liver cancer.These compounds were found to mainly regulate cellular oxidative stress,cancer process,nucleic acid metabolism,nutritional metabolism and other pathways.The findings provide useful information for subsequent experimental verification.展开更多
Xylariaceae sp.QGS 01,an endophytic fungus isolated from the stem of Quercus gilva Blume showed high-glucosidase inhibitory activity.α-Glucosidase inhibitor have the role as one of carbohydrate-hydrolyzing enzymes to...Xylariaceae sp.QGS 01,an endophytic fungus isolated from the stem of Quercus gilva Blume showed high-glucosidase inhibitory activity.α-Glucosidase inhibitor have the role as one of carbohydrate-hydrolyzing enzymes to postpone absorption of glucose in the digestive organs.The α-glucosidase inhibitor constituents were isolated from the ethyl acetate extract of the mycellium of endophytic fungi Xylariaceae sp.QGS 01 using a bioassay-guided fractionation technique.Further separation and purification of the active fraction led to the isolation of constituents with strong inhibitory activities against-glucosidase:8-hydroxy-6,7-dimethoxy-3-methylisocoumarine(1)with inhibitory concentration(IC50)values against-glucosidase from Saccharomyces cerevisiae of 41.75μg/mL,while quercetin as the standard had an IC50 value of 4.80g/mL.The results of the present study showed that the endophytic fungus Xylariaceae sp.QGS 01 is potentially a rich source of antidiabetic medicine.展开更多
A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200℃ under catalyst and solvent free reaction conditi...A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200℃ under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient onepot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis.展开更多
Acid-controlled,chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(Ⅲ)-cataIyzed C—H activation.Diazo compounds act as a carbene precursor,and...Acid-controlled,chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(Ⅲ)-cataIyzed C—H activation.Diazo compounds act as a carbene precursor,and coupling occurs in one-pot process,where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.展开更多
Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives,setosphlides A-D(1-4),and four known analogues(5-8).Their planar s...Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives,setosphlides A-D(1-4),and four known analogues(5-8).Their planar structures and the relative configurations were elucidated by comprehensive spectroscopic methods.The absolute configurations of isocoumarin nucleus for 1-4 were elucidated by their ECD spectra.The C-10 relative configurations for the pair of C-10 epimers(1 and 2)were established by comparing the magnitude of the computed 13C NMR chemical shifts(Δδcalcd.)with the experimental 13C NMR values(Δδexp.)for the epimers.All of the isolated compounds(1-8)were evaluated for their cytotoxicities against four human tumor cell lines MCF-7,MGC-803,HeLa,and Huh-7.展开更多
3,5-Dimethoxyhomophthalic acid was synthesized in four steps from 3,5-dimethoxycinnamic acid via a series of reactions including cyclization of 3-（3＇,5＇-dimethoxyphenyl）propionic acid to 5,7-dimethoxy-1-indanone a...3,5-Dimethoxyhomophthalic acid was synthesized in four steps from 3,5-dimethoxycinnamic acid via a series of reactions including cyclization of 3-（3＇,5＇-dimethoxyphenyl）propionic acid to 5,7-dimethoxy-1-indanone and oxidative decomposition of methyl-2-hydroxy-2-[5,7-dimethyoxy-1-oxo-1H-inden-2（3H）-ylidene]acetate to 3,5-dimethoxyhomophthalic acid.The synthesized compounds were characterized by elemental analysis,IR,1H NMR,and MS.The biological evaluation experiments of 3,5-dimthoxyhomophthalic acid and the related synthesized compounds were also carried out.Naturally occurring biologically active isocoumarins were prepared in a single step by the condensation of the homophthalic acid with appropriate acid chlorides.展开更多
6,8-Dimethoxy-3-[2-（4-methoxyphenyl）ethyl]isocoumarin was synthesized by condensation of 5,7-dimethoxyhompophthalic acid with 3-（4-methoxyphenyl）propanoyl chloride. The structure of the synthesized compound was co...6,8-Dimethoxy-3-[2-（4-methoxyphenyl）ethyl]isocoumarin was synthesized by condensation of 5,7-dimethoxyhompophthalic acid with 3-（4-methoxyphenyl）propanoyl chloride. The structure of the synthesized compound was confirmed by its mass spectrometric studies. The synthesized compound serves as a model for synthesis of DL-agrimonolide.展开更多
文摘The work reports antibacterial and antifungal activity of some 3-(substituted phenyl) isocoumarins (1H-2-benzopyran-1-ones), isocarbostyrils 1(2H)-isoquinolones, the nitrogen analogues of isocoumarins and isocoumarin-1-thiones, the thio derivatives of isocoumarins. The antimicrobial activity was determined against ten different Gram positive and Gram negative bacterial strains and three fungal strains. The bacterial strains were Klebsiella pneumonae (ATCC 6633), Staphylococcus aureus (ATCC 29213), Micrococcus luteus (ATCC 9341), Pseudomonas aeruginosa (ATCC 33347), Escherichia coli (ATCC 25922), Salmonella typhi (ATCC 19430), Lactobacillus bulgaricus, (ATCC 25929), Pasteurella multocida A (ATCC 9150), Staphylococcus epidermidis (ATCC 29232) and Proteus vulgaris (ATCC 49565) and fungal strains were Aspergillus flavus, Aspergillus nigar and Aspergillus pterus. Agar well diffusion method was followed for antibacterial activity and poison plate method was adopted for antifungal assay. Chloramphenicol and fluconazole used as standard drugs for antibacterial and antifungal activity respectively. In general, these compounds exhibited high antibacterial potential than antifungal. Comparative study reveals that the 1-thio derivatives are more active than parent isocoumarins but 1(2H)-isoquinolones, are less active. Most of these compounds showed poor activity but some of these compounds exhibited moderate to good activity against Staphylococcus epidermidis, Klebsiella pneumonae, Escherichia coli and Proteus vulgaris, compared with the standard drug.
基金financially supported by the Key Program of the National Natural Science Foundation of China(22137008)the Xingdian Yingcai Project(YNWR-KJLJ-2019-002)+1 种基金the Youth Innovation Promotion Association,CAs(2020386)the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province(202105AC160021).
文摘Ten novel isocoumarins,including four pairs of enantiomers,were isolated from Artemisia dubia var.subdigitata(Asteraceae).Compounds 1,2 and 3a/3b possessed a unique 6/6/6-tricyclic system comprising an unusual 1-(2-methylcyclohexyl)propan-1-one moiety fused with isocoumarin core skeleton.Compounds 4a/4b were characterized as an unexpected 2,5-dimethylcyclohexan-1-one scaffold,and compounds 5a/5b and 6a/6b were rare 1,2-seco-isocoumarin.Their structures and absolute configurations were elucidated through spectroscopic data,X-ray crystallography,ECD and NMR calculations with DP4+analyses.Plausible biosynthetic pathways were proposed from the naturally occurring isocoumarin.Network pharmacological analysis suggested that the targets of compound 1 were significantly enriched in the cell cycle and Pl3K-Akt signaling pathway.The molecular docking revealed that compound 1 had high binding affinity with CDK2(total score:6.8717).Furthermore,compounds 1 and 2 exhibited inhibitory activity on three human hepatoma cell lines,with inhibitory ratios of 85.1% and 84.5%(HepG2),88.2% and 87.3%(Huh7),and 69.2% and 69.1%(SK-Hep-1)at 200μmol·L^(-1),respectively.
基金Supported by the National Natural Science Foundation of China (Grant Nos. 20621062 & 20872156)
文摘3-Alkyl isocoumarins are provided by CuI/amino acid-catalyzed Sonogashira coupling reaction of o-bromo benzoic acids and terminal alkynes and the subsequent additive cyclization. This cascade process allows synthesis of diverse isocoumarins by varying both coupling partners bearing a wide range of functional groups.
基金supported by the National Natural Science Foundation of China (No. 41876153)Guangdong Special Fund for Marine Economic Development (No. GDME-2018C004)the Natural Science Foundation of Guangdong Province (No.2017A030313088)。
文摘Four new compounds, asperisocoumarin G(1), asperisocoumarin H(2),(±)-asperisocoumarin I [(±)-3], along with the known pergillin(4) and penicisochroman L(5) were isolated from a mangrove endophytic fungus Aspergillus sp. 085242 by further chemical investigation. The structures of the new compounds, including their absolute configurations, were established by analysis of HR-ESI-MS and NMR spectroscopic data, and ECD calculation. Asperisocoumarins G-I(1-3) were new isocoumarins belonging to the class of furo[3, 2-h]isocoumarins which are rarely found in natural sources. All of the isolated compounds were evaluated for theirα-glucosidase inhibitory effects, and compounds 1 and 4 showed moderate α-glucosidase inhibitory activity, respectively. In an antimicrobial test, the racemate of 3 showed antibacterial activity against Salmonella.
基金the National Natural Science Foundation of China (No. 21877133)Guangdong MEPP Fund (No. GDOE-2019A21)the Key Project of Natural Science Foundation of Guangdong Province (No. 2016A040403091) for generous support。
文摘Three new isocoumarin derivatives,(S)-6,8-dihydroxy-5-(methoxymethyl)-3,7-dimethylisochroman-1-one(1),(S)-6,8-dihydroxy-3,5,7-trimethyl-isochroman-1-one(2) and(R)-2-chloro-3-(8-hydroxy-6-methoxy-1-oxo-1 H-isochromen-3-yl) propyl acetate(3), along with four known compounds(4–7) were isolated from a mangrove endophytic fungus Penicillium sp. YYSJ-3. Their structures were established on the basis of the extensive spectroscopic data and HR-ESI-MS analysis. The absolute configurations of1–3 were further determined by X-ray diffraction analysis and optical rotations. Compounds 3, 6 and 7 showed promising inhibitory activity against α-glucosidase, which were stronger than that of the positive control 1-deoxynojirimycin(IC50 141.2 μmol·L-1).
基金Natural Science Foundation of Liaoning(2019-ZD-0457)Foundation of Career Development Plan for young and middle-aged Teachers of Shenyang Pharmaceutical University(ZQN2018004).
文摘Amicoumacin isocoumarin-type compounds are mainly derived from the secondary metabolites of Bacillus bacteria,and have potential biological activities such as antibacterial,anti-tumor,anti-inflammatory,and anti-ulcer.In our previous research,three amicoumacin-type isocoumarin compounds,Paenicoumacin A,Paenicoumacin B,and Paenicoumacin C(B and C are novel),were isolated from an endophytic bacterium in Houttuynia cordata.In this study,network pharmacology and bioinformatics techniques were used to analyze the potential activities of amicoumacin compounds in the treatment of liver cancer.These compounds were found to mainly regulate cellular oxidative stress,cancer process,nucleic acid metabolism,nutritional metabolism and other pathways.The findings provide useful information for subsequent experimental verification.
文摘Xylariaceae sp.QGS 01,an endophytic fungus isolated from the stem of Quercus gilva Blume showed high-glucosidase inhibitory activity.α-Glucosidase inhibitor have the role as one of carbohydrate-hydrolyzing enzymes to postpone absorption of glucose in the digestive organs.The α-glucosidase inhibitor constituents were isolated from the ethyl acetate extract of the mycellium of endophytic fungi Xylariaceae sp.QGS 01 using a bioassay-guided fractionation technique.Further separation and purification of the active fraction led to the isolation of constituents with strong inhibitory activities against-glucosidase:8-hydroxy-6,7-dimethoxy-3-methylisocoumarine(1)with inhibitory concentration(IC50)values against-glucosidase from Saccharomyces cerevisiae of 41.75μg/mL,while quercetin as the standard had an IC50 value of 4.80g/mL.The results of the present study showed that the endophytic fungus Xylariaceae sp.QGS 01 is potentially a rich source of antidiabetic medicine.
基金supported by the Higher Education Commission (HEC),Govt.of Pakistan for financial support
文摘A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200℃ under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient onepot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis.
文摘Acid-controlled,chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(Ⅲ)-cataIyzed C—H activation.Diazo compounds act as a carbene precursor,and coupling occurs in one-pot process,where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
基金This work was funded by the National Natural Science Foundation of China(31672070)National Key Research and Development Program of China(2017YFD0201400 and 2017YFD0201401)the High Performance Computer Center of Hebei University.
文摘Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives,setosphlides A-D(1-4),and four known analogues(5-8).Their planar structures and the relative configurations were elucidated by comprehensive spectroscopic methods.The absolute configurations of isocoumarin nucleus for 1-4 were elucidated by their ECD spectra.The C-10 relative configurations for the pair of C-10 epimers(1 and 2)were established by comparing the magnitude of the computed 13C NMR chemical shifts(Δδcalcd.)with the experimental 13C NMR values(Δδexp.)for the epimers.All of the isolated compounds(1-8)were evaluated for their cytotoxicities against four human tumor cell lines MCF-7,MGC-803,HeLa,and Huh-7.
基金Supported by Higher Education Commission of Pakistan,the National Basic Research Program of China(No.2003CB114402)the National Natrual Science Foundation of China(No.20672062)the Tianjin Natural Science Foundation(No.07JCYBJC01200).
文摘3,5-Dimethoxyhomophthalic acid was synthesized in four steps from 3,5-dimethoxycinnamic acid via a series of reactions including cyclization of 3-（3＇,5＇-dimethoxyphenyl）propionic acid to 5,7-dimethoxy-1-indanone and oxidative decomposition of methyl-2-hydroxy-2-[5,7-dimethyoxy-1-oxo-1H-inden-2（3H）-ylidene]acetate to 3,5-dimethoxyhomophthalic acid.The synthesized compounds were characterized by elemental analysis,IR,1H NMR,and MS.The biological evaluation experiments of 3,5-dimthoxyhomophthalic acid and the related synthesized compounds were also carried out.Naturally occurring biologically active isocoumarins were prepared in a single step by the condensation of the homophthalic acid with appropriate acid chlorides.
文摘6,8-Dimethoxy-3-[2-（4-methoxyphenyl）ethyl]isocoumarin was synthesized by condensation of 5,7-dimethoxyhompophthalic acid with 3-（4-methoxyphenyl）propanoyl chloride. The structure of the synthesized compound was confirmed by its mass spectrometric studies. The synthesized compound serves as a model for synthesis of DL-agrimonolide.
