An efficient synthetic route to muurolane type sesquiterpenes starting from （R）-carvone, employing allylic diazene rearrangement and the ring closing methesis （RCM） reaction as key steps, is described. The first a...An efficient synthetic route to muurolane type sesquiterpenes starting from （R）-carvone, employing allylic diazene rearrangement and the ring closing methesis （RCM） reaction as key steps, is described. The first asymmetric total synthesis of （-）-10α- hydroxy-4-muurolen-3-one 11 and （-）-10β-hydroxy-4-muurolen-3-one C was accomplished. Through the total synthesis, the absolute configurations of the natural products A, B and C were established.展开更多
A facile synthesis of the analog of curcumin. 1,7-bis (4-hydroxyphenyl)-3-hydroxy-1.3-heptadien-5-one 1 was achieved. The key step was completed through the regioselective condensation of ketone 5 and acyl chloride 7.
The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.
<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="fo...<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one with </span><span style="font-family:Verdana;">iron(III), cobat(III) and chromium(III) were synthesized with M:L (1:2)</span><span style="font-family:Verdana;">. Mixed ligand coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and 1,2-diaminocyclohexane using the same metal ions were also synthesized </span><b><span style="font-family:Verdana;">M:L1</span></b><span style="font-family:Verdana;">:</span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> (1:1:1) where </span><b><span style="font-family:Verdana;">L1</span></b><span style="font-family:Verdana;"> is 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and </span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> is 1,2-diaminocyclohexane. The coordination compounds obtained were characterized using electronic and infrared spectral analyses, magnetic susceptibility and percentage metal analysis. They were also evaluated for their cytotoxic and antioxidant activities. The result obtained suggested that octahedral geometry was obtained for all the compounds, as a result of additional two molecules of the solvent coordinated to the metal ions. Both the primary and secondary ligands coordinated in a bidentate fashion. The synthesized compounds exhibited moderate cytotoxicity, although none was as active as the standard. The cobalt(III) mixed ligand complex elicited the highest activity. The synthesized compounds all exhibited good to moderate antioxidant activity.</span>展开更多
A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions o...A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.展开更多
The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized...The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.展开更多
Three compounds were obtained from the mycelia of an endophytic fungus Gliocladium sp. (designated as strain F) of Taxus chinensis (Pilg.) Rehd. growing in Fujian Province, China. Their structures were determined on t...Three compounds were obtained from the mycelia of an endophytic fungus Gliocladium sp. (designated as strain F) of Taxus chinensis (Pilg.) Rehd. growing in Fujian Province, China. Their structures were determined on the basis of spectral analysis. (20S,22S)-4a-homo-22-hydroxy-4-oxaergosta-7,24(28)-dien-3-one was a novel compound. 4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone was firstly isolated from the genus ofGliocladium and 6,9-epoxyergosta-7,22-dien-3-ol was firstly obtained from the strain F.展开更多
A new halogenated biindole and a new apo-carotenone have been isolated from the ethanolic extract of the green alga Chaetomorpha basiretorsa Sethcell. On the basis of chemical and spectroscopic methods including 2D NM...A new halogenated biindole and a new apo-carotenone have been isolated from the ethanolic extract of the green alga Chaetomorpha basiretorsa Sethcell. On the basis of chemical and spectroscopic methods including 2D NMR technique, their structures have been elucidated as 4,4′-dichloro-5,5′-dibromo-7,7′-dimethoxy-2,2′-bi-1H-indole and 1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′- trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien-2-one, respectively.展开更多
Two pairs of unusual scalemic enantiomers with a dimethoxyphenyl）ethyl]-2-methoxyindolin-3-one, novel carbon skeleton of 2-[1′-（4＂-hydroxy-3＂,5＂- named isatidifoliumindolinones A-D （1-4）, were isolated from an...Two pairs of unusual scalemic enantiomers with a dimethoxyphenyl）ethyl]-2-methoxyindolin-3-one, novel carbon skeleton of 2-[1′-（4＂-hydroxy-3＂,5＂- named isatidifoliumindolinones A-D （1-4）, were isolated from an aqueous extract of lsatis indigotica leaves （da qing ye）. Their structures including absolute configurations were determined by spectroscopic data analysis combined with comparison of their experimental CD and calculated ECD spectra. Validity of the ECD spectra calculation to assign the absolute configurations is discussed. Plausible biosynthetic pathways of 1-4 are proposed. Stereochemistry-dependent activity against LPS-induced NO production in BY2 cells was observed, and among the stereoisomers compound 4 is most active.展开更多
Objective:To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning(RDN)Injection.Methods:In this study,the active fraction of RDN Injection was screened by the LPS-induced mouse...Objective:To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning(RDN)Injection.Methods:In this study,the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model.The chemical constituents were isolated by chromatography on HP-20 macroporous adsorptive resins,silica gel,ODS columns and reverse phase MPLC and HPLC repeatedly,and their structures were elucidated based on spectroscopic analysis(HR-ESI-MS,NMR,ECD)and chemical methods.Meanwhile,we evaluated the anti-inflammatory activities of the isolates by measuring their inhibitory effects on TNF-αproduction in LPS stimulated RAW 264.7 macrophages.Results:The 95%ethanol eluate of RDN Injection by the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of this injection.A novel iridoid,named jasminoide A(1),and a new guaiane sesquiterpenoid,named(1 R,7 R,8 S,10 R)-7,8,11-trihydroxy-4-guaien-3-one(2),were isolated from Reduning injection,and compound 2 can inhibit TNF-αproduction with IC50 values of 72.24μmol/L.Conclusion:In this study,two new terpenoids were isolated from Reduning Injection,and compound 2 showed inhibitory activity against LPS-activated TNF-αproduction in RAW 264.7 cells in vitro.展开更多
基金the financial supports from the National Natural Science Foundation of China (No.20272021).
文摘An efficient synthetic route to muurolane type sesquiterpenes starting from （R）-carvone, employing allylic diazene rearrangement and the ring closing methesis （RCM） reaction as key steps, is described. The first asymmetric total synthesis of （-）-10α- hydroxy-4-muurolen-3-one 11 and （-）-10β-hydroxy-4-muurolen-3-one C was accomplished. Through the total synthesis, the absolute configurations of the natural products A, B and C were established.
文摘A facile synthesis of the analog of curcumin. 1,7-bis (4-hydroxyphenyl)-3-hydroxy-1.3-heptadien-5-one 1 was achieved. The key step was completed through the regioselective condensation of ketone 5 and acyl chloride 7.
基金This work was financially supported by the National Natural Science Foundation of China （No 20272021）.
文摘The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.
文摘<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one with </span><span style="font-family:Verdana;">iron(III), cobat(III) and chromium(III) were synthesized with M:L (1:2)</span><span style="font-family:Verdana;">. Mixed ligand coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and 1,2-diaminocyclohexane using the same metal ions were also synthesized </span><b><span style="font-family:Verdana;">M:L1</span></b><span style="font-family:Verdana;">:</span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> (1:1:1) where </span><b><span style="font-family:Verdana;">L1</span></b><span style="font-family:Verdana;"> is 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and </span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> is 1,2-diaminocyclohexane. The coordination compounds obtained were characterized using electronic and infrared spectral analyses, magnetic susceptibility and percentage metal analysis. They were also evaluated for their cytotoxic and antioxidant activities. The result obtained suggested that octahedral geometry was obtained for all the compounds, as a result of additional two molecules of the solvent coordinated to the metal ions. Both the primary and secondary ligands coordinated in a bidentate fashion. The synthesized compounds exhibited moderate cytotoxicity, although none was as active as the standard. The cobalt(III) mixed ligand complex elicited the highest activity. The synthesized compounds all exhibited good to moderate antioxidant activity.</span>
文摘A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.
文摘The two diarylheptanoids (E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl) hept-4-en-3-one 1 (Gingerenone C) and (±)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4- hydroxyphenyl)-3-heptanone 2 were synthesized from vanillin 3 and 4-hydroxybenzaldehyde 9.
文摘Three compounds were obtained from the mycelia of an endophytic fungus Gliocladium sp. (designated as strain F) of Taxus chinensis (Pilg.) Rehd. growing in Fujian Province, China. Their structures were determined on the basis of spectral analysis. (20S,22S)-4a-homo-22-hydroxy-4-oxaergosta-7,24(28)-dien-3-one was a novel compound. 4,8,12,16-tetramethyl-1,5,9,13-tetraoxacyclohexadecane-2,6,10,14-tetraone was firstly isolated from the genus ofGliocladium and 6,9-epoxyergosta-7,22-dien-3-ol was firstly obtained from the strain F.
基金supported by national 863 project(Grant No.2004AA625030,2001AA620503)NNSFC(Grant No.20432030)Key Innovative Project of the Academy(Grant No.KZCX3-SW-215).
文摘A new halogenated biindole and a new apo-carotenone have been isolated from the ethanolic extract of the green alga Chaetomorpha basiretorsa Sethcell. On the basis of chemical and spectroscopic methods including 2D NMR technique, their structures have been elucidated as 4,4′-dichloro-5,5′-dibromo-7,7′-dimethoxy-2,2′-bi-1H-indole and 1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′- trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien-2-one, respectively.
基金Financial support from the National Natural Science Foundation of China (NNSFCNos.81630094,81373287,and 30825044)
文摘Two pairs of unusual scalemic enantiomers with a dimethoxyphenyl）ethyl]-2-methoxyindolin-3-one, novel carbon skeleton of 2-[1′-（4＂-hydroxy-3＂,5＂- named isatidifoliumindolinones A-D （1-4）, were isolated from an aqueous extract of lsatis indigotica leaves （da qing ye）. Their structures including absolute configurations were determined by spectroscopic data analysis combined with comparison of their experimental CD and calculated ECD spectra. Validity of the ECD spectra calculation to assign the absolute configurations is discussed. Plausible biosynthetic pathways of 1-4 are proposed. Stereochemistry-dependent activity against LPS-induced NO production in BY2 cells was observed, and among the stereoisomers compound 4 is most active.
基金supported by the National Standard Research of Traditional Chinese Medicine for Reduning Injection(ZYBZHC-JS-31)National Standard Research of Traditional Chinese Medicine for Guzhi Fuling Capsule(ZYBZH-C-JS-28)grant from the National Natural Science Foundation of China(No.81602984)。
文摘Objective:To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning(RDN)Injection.Methods:In this study,the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model.The chemical constituents were isolated by chromatography on HP-20 macroporous adsorptive resins,silica gel,ODS columns and reverse phase MPLC and HPLC repeatedly,and their structures were elucidated based on spectroscopic analysis(HR-ESI-MS,NMR,ECD)and chemical methods.Meanwhile,we evaluated the anti-inflammatory activities of the isolates by measuring their inhibitory effects on TNF-αproduction in LPS stimulated RAW 264.7 macrophages.Results:The 95%ethanol eluate of RDN Injection by the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of this injection.A novel iridoid,named jasminoide A(1),and a new guaiane sesquiterpenoid,named(1 R,7 R,8 S,10 R)-7,8,11-trihydroxy-4-guaien-3-one(2),were isolated from Reduning injection,and compound 2 can inhibit TNF-αproduction with IC50 values of 72.24μmol/L.Conclusion:In this study,two new terpenoids were isolated from Reduning Injection,and compound 2 showed inhibitory activity against LPS-activated TNF-αproduction in RAW 264.7 cells in vitro.
