Prostatic carcinoma(PCa)has become one of the most common cancers among men worldwide,with both incidence and mortality rates steadily rising.Although current treatments are effective in the early stages of PCa,many c...Prostatic carcinoma(PCa)has become one of the most common cancers among men worldwide,with both incidence and mortality rates steadily rising.Although current treatments are effective in the early stages of PCa,many cases eventually progress to castration-resistant prostate cancer(CRPC),and led to treatment failure.To develop new therapeutic strategies to ameliorate the survival of PCa patients then has pressed the need on medicinal researchers.Of traditional Chinese medicinal herbs,Angelica gigas Naka(AGN),and its major pyranocoumarins were broadly reported on the effect of anti-PCa.However,existing reviews mainly focus on decursin(D),decursinol angelate(DA),and decursinol(DOH),without fully exploring other coumarins in AGN.Moreover,most reviews discuss general anticancer effects,with limited emphasis on PCa specifically.This review made a comprehensive summary of the coumarin components of AGN,and depicted the anti-PCa effects and mechanisms,giving a solid research support for drug discovery and development.This review also featured pharmacokinetic advantages and therapeutic potential of DOH,in order to suggest possibilities to overcome the in vivo transformation limitations of D and DA,and shed light on CRPC treatment.We also recommend future studies focus on more in vivo evidence,safety and toxicity evaluation,and clinical validation in humans.展开更多
A photocatalyst-free photoinduced radical difluoromethylation approach for the convenient synthesis of 3-CF_(2)H-coumarins from alkynoates by difluoromethyl phenoxathiinium salt(PT-CF_(2)H^(+)BF_(4)^(-))was developed....A photocatalyst-free photoinduced radical difluoromethylation approach for the convenient synthesis of 3-CF_(2)H-coumarins from alkynoates by difluoromethyl phenoxathiinium salt(PT-CF_(2)H^(+)BF_(4)^(-))was developed.This transformation in-volves radical difluoromethylation/5-exo spirocyclization/ester migration rearrangement cascade process and features mild reaction conditions,broad substrate scope and good functional groups tolerance.Using this method,a wide range of alkynoates was successfully converted to desired 3-CF_(2)H-coumarins in moderate to good yields.展开更多
Background Coumarins are toxic phytochemicals found in a variety of plants and are known to limit microbial degradation and interfere with nutrient cycling.While the degradation of coumarins by fungi has been studied ...Background Coumarins are toxic phytochemicals found in a variety of plants and are known to limit microbial degradation and interfere with nutrient cycling.While the degradation of coumarins by fungi has been studied in an environmental context,little is known about their degradation in the gastrointestinal system of herbivores after ingestion.Results In this study,we investigated in vitro fermentation by microbial enrichment,transcriptome sequencing,and high-resolution mass spectrometry to evaluate the ability of rumen anaerobic fungi to degrade coumarins.The results showed that despite the low abundance of anaerobic fungi in the rumen microbiota,they were able to effectively degrade coumarins.Specifically,Pecoramyces ruminantium F1 could tolerate coumarin concentrations up to 3 mmol/L and degrade it efficiently via metabolic pathways involving alpha/beta hydrolases and NAD(P)H oxidoreductases within the late growth phase.The fungus metabolized coumarin to less toxic compounds,including o-coumaric acid and melilotic acid,highlighting the detoxification potential of anaerobic fungi.Conclusions This study is the first to demonstrate the ability of rumen anaerobic fungi to degrade coumarin,providing new insights into the use of anaerobic fungi in sustainable agricultural practices and environmental detoxification strategies.展开更多
TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succini- midyl selenide as the selenium source. This catalytic process provides an efficient method for th...TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succini- midyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumar- ins and coumarins in good yields and purifies.展开更多
Two new coumarins, named marminal (13) and 7' O methylmarmin (15), along with nineteen known compounds: ( sitosteryl pentadecanoate (1), 4 methoxy 1 methyl 2 quinolone (2), aurapten (3), 4 sitosten 3 on...Two new coumarins, named marminal (13) and 7' O methylmarmin (15), along with nineteen known compounds: ( sitosteryl pentadecanoate (1), 4 methoxy 1 methyl 2 quinolone (2), aurapten (3), 4 sitosten 3 one (4), lupeol (5), imperatorin (6), xanthotoxin (7), dictamnine (8), (+) epoxyaurapten (9), ( sitosterol (10), ( fagarine (11), skimmianine (12), scoparone (14), umbelliferone (16), scopoletin (17), decursinol (18), marmesin (19), marmin (20), and integriquinolone (21) were isolated from the methanolic extract of the roots of Aegle marmelos Corr. (family Rutaceae).展开更多
Oxalic acid was found to be an efficient catalyst for Pechmann condensation, which includes the reaction between phenols and β-keto esters leading to formation of coumarin derivatives. The advantages of present metho...Oxalic acid was found to be an efficient catalyst for Pechmann condensation, which includes the reaction between phenols and β-keto esters leading to formation of coumarin derivatives. The advantages of present methods are the use of cheap and easy available catalyst, solvent-free reaction conditions, better yields and shorter reaction time.展开更多
Pharmaceutical research has focused on the discovery and development of anticancer drugs. Clinical application of chemotherapy drugs is limited due to their severe side effects. In this regard, new naturally occurring...Pharmaceutical research has focused on the discovery and development of anticancer drugs. Clinical application of chemotherapy drugs is limited due to their severe side effects. In this regard, new naturally occurring anticancer drugs have gained increasing attention because of their potential effectiveness and safety. Fruits and vegetables are promising sources of anticancer remedy. Clausena(family Rutaceae) is a genus of flowering plants and includes several kinds of edible fruits and vegetables. Phytochemical and pharmacological studies show that carbazole alkaloids and coumarins from Clausena plants exhibit anticancer activity. This review summarizes research progresses made in the anticancer properties of plants belonging to Clausena; in particular, compounds with direct cytotoxicity, cell cycle arrest, apoptosis induction, and immune potentiation effects are discussed. This review reveals the potential use of plants from Clausena in preventing and treating cancer and provides a basis for development of relevant therapeutic agents.展开更多
Objective: To use structure-activity analysis to study the anti-Alzheimer's disease(anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaries, along with one purchased couma...Objective: To use structure-activity analysis to study the anti-Alzheimer's disease(anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaries, along with one purchased coumarin(daphnetin). Methods: Umbelliferone, umbelliferone 6-carboxylic acid, scopoletin, isoscopoletin, 7-methoxy coumarin, scoparone, scopolin, and esculetin have been previously isolated; however 2'-isopropyl psoralene was isolated from Angelica decursiva for the first time to evaluate their inhibitory effects against acetylcholinesterase(ACh E), butyrylcholinesterase(BCh E), and β-site amyloid precursor protein cleaving enzyme 1(BACE1) enzyme activity. We scrutinized the potentials of coumarins as cholinesterase and BACE1 inhibitors via enzyme kinetics and molecular docking simulation. Results: Among the test compounds, umbelliferone 6-carboxylic acid, esculetin and daphnetin exhibited potent inhibitory activity against ACh E, BCh E and BACE1. Both esculetin and daphnetin have a catechol group and exhibit significant anti-AD activity against ACh E and BCh E. In contrast, presence of a sugar moiety and methoxylation markedly reduced the anti-AD activity of the coumarins investigated in this study. With respect to BACE1 inhibition, umbelliferone 6-carboxylic acid, esculetin and daphnetin contained carboxyl or catechol groups, which significantly contributed to their antiAD activities. To further investigate these results, we generated a 3D structure of BACE1 using Autodock 4.2 and simulated binding of umbelliferone 6-carboxylic acid, esculetin and daphnetin. Docking simulations showed that different residues of BACE1 interacted with hydroxyl and carboxylic groups, and the binding energies of umbelliferone 6-carboxylic acid, esculetin and daphnetin were negative(-4.58,-6.25 and-6.37 kcal/mol respectively). Conclusions: Taken together, our results suggest that umbelliferone 6-carboxylic acid, esculetin and daphnetin have anti-AD effects by inhibiting ACh E, BCh E and BACE1, which might be useful against AD.展开更多
The effect of L-proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild...The effect of L-proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild reaction conditions and achieved high yields. Moreover, the ionic liquid containing L-proline could be recycled and reused for several times without noticeably decreasing in productivity. The results show that the L-proline-[emim]BF4 system has a potential in contribution to the development of environmentally friendly and inexpensive processes in organic syntheses.展开更多
Four new coumarins named qianhucoumarins A, B, C, D have been isolated from traditional Chinese medicine-the root of Peucedanum praeruptorum. Their structures were elucidated by chemical evidences and spectral analysis.
Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ ...Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ in good to high yields.展开更多
We reported the discovery of six novel coumarins, toddasirins A–F ( 1 – 6 ), each endowed with modified isoprenyl or geranyl side chains, derived from the roots of Toddalia asiatica. Comprehensive structural elucida...We reported the discovery of six novel coumarins, toddasirins A–F ( 1 – 6 ), each endowed with modified isoprenyl or geranyl side chains, derived from the roots of Toddalia asiatica. Comprehensive structural elucidation was achieved through multispectroscopic analyses, single-crystal X-ray diffraction experiments, and advanced quantum mechanical electronic circular dichroism (ECD) calculations. Furthermore, the anti-inflammatory activity of these compounds was assessed. Notably, compounds 1 – 3 and 6 demonstrated notable inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells, with 50% inhibitory concentration (IC50) values of 3.22, 4.78, 8.90, and 4.31 μmol·L^(−1), respectively.展开更多
The resin of Ferula sinkiangensis has been traditionally utilized for treating gastrointestinal disorders,inflammation,tumors,various cancers,and alopecia areata.The primary bioactive constituents,sesquiterpene coumar...The resin of Ferula sinkiangensis has been traditionally utilized for treating gastrointestinal disorders,inflammation,tumors,various cancers,and alopecia areata.The primary bioactive constituents,sesquiterpene coumarins,have demonstrated notable therapeutic potential against neuroinflammation.In this study,a structure-guided fractionation method was used to isolate nine novel sesquiterpene coumarins from the resin of F.sinkiangensis.These compounds were characterized and structurally elucidated using comprehensive physicochemical and spectroscopic techniques,including calculated electronic circular dichroism(ECD).Anti-neuroinflammatory assays revealed that compounds 2,3,and 6 significantly inhibited nitric oxide(NO)production in lipopolysaccharide(LPS)-stimulated BV2 microglial cells,with IC_(50)values ranging from 1.63 to 12.25μmol·L^(−1).展开更多
Two new coumarins,4'-hydroxycolumbianetin named angelidiol(A)and 6- [(?)(R),2(S)-3-trihydroxy-3-methylbutyl]-7-methoxycoumarin named angelitriol(B),were isolated from the EtOAc-soluble fraction of the 80% EtOH ext...Two new coumarins,4'-hydroxycolumbianetin named angelidiol(A)and 6- [(?)(R),2(S)-3-trihydroxy-3-methylbutyl]-7-methoxycoumarin named angelitriol(B),were isolated from the EtOAc-soluble fraction of the 80% EtOH extract and structurally eluciated on the basis of spectral analyses.展开更多
Three new coumarins,integmarins A–C(1–3),and a new coumarin glycoside,integmaside A(4)were isolated from the leaves and stems of Micromelum integerrimum.Their structures were elucidated on the basis of 1 D and 2 D N...Three new coumarins,integmarins A–C(1–3),and a new coumarin glycoside,integmaside A(4)were isolated from the leaves and stems of Micromelum integerrimum.Their structures were elucidated on the basis of 1 D and 2 D NMR and MS data,and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data.Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position;compound 3 is a novel coumarin with a highly oxidized prenyl group,and compound 4 is a rare bisdihydrofuranocoumarin glycoside.展开更多
Melamine-formaldehyde resin supported H~＋ is used as an efficient catalyst in the Pechmann condensation reaction of phenols withβ-ketoesters,in solvent-free media leading to the formation of coumarin derivatives usi...Melamine-formaldehyde resin supported H~＋ is used as an efficient catalyst in the Pechmann condensation reaction of phenols withβ-ketoesters,in solvent-free media leading to the formation of coumarin derivatives using conventional heating and microwave irradiation in excellent yields with good purity.展开更多
Different hydroxy substituted coumarins were successfully phosphorylated with diisopropylphophite （DIPPH） by the Atherton-Todd reaction in 76-89% yields. Moreover, the reaction activities of different hydroxys of th...Different hydroxy substituted coumarins were successfully phosphorylated with diisopropylphophite （DIPPH） by the Atherton-Todd reaction in 76-89% yields. Moreover, the reaction activities of different hydroxys of the coumarins in the Atherton-Todd reaction were studied.展开更多
Silica-bonded S-sulfonic acid （SBSSA） was prepared by the reaction of 3-mercaptopropylsilica （MPS） and chlorosulfonic acid in chloroform. This solid acid has been employed as a recyclable catalyst for the synthesi...Silica-bonded S-sulfonic acid （SBSSA） was prepared by the reaction of 3-mercaptopropylsilica （MPS） and chlorosulfonic acid in chloroform. This solid acid has been employed as a recyclable catalyst for the synthesis of coumarins from phenols and β-keto- esters at 80 ℃ under solvent-free conditions.展开更多
Tetracyclic coumarins are a class of important compounds with diverse and superior pharmacolog‐ical activities.However,a direct stereoselective method from simple and readily‐made coumarins derivatives remains chall...Tetracyclic coumarins are a class of important compounds with diverse and superior pharmacolog‐ical activities.However,a direct stereoselective method from simple and readily‐made coumarins derivatives remains challenging due to the inertness of coumarins as dienophiles.Herein,we de‐velop a decarboxylative asymmetric[4+2]cycloaddition of 3‐cyanocoumarins with vinyl benzoxa‐zinones,affording the coumarin‐derived condensed rings bearing three continuous stereocenters in high yields with excellent diastereoselectivities(>20/1 d.r.)and enantioselectivities(up to 99%ee).This direct enantioselective reaction was achieved by a Pd(0)/Cu(I)bimetallic catalytic system.The mechanism studies indicated that the synergistic activation effect,in which chiral Cu(I)as an availa‐ble Lewis acid catalyst activates 3‐cyanocoumarin and chiral Pd(0)complex activates benzoxazi‐none by the formation ofπ‐allyl‐palladium intermediate,plays an important role on the stereoselec‐tive control.The current work provides a new activation modes of Cu catalyst in the Pd/Cu bimetal‐lic catalytic system.展开更多
基金supported by the Natural Science Foundation of Guangdong Province(grant number 2021A1515011485)the Traditional Chinese Medicine Multidisciplinary Innovation Team Program of Liaoning Province(grant number LNZYYCXTD-JCCX-002)+1 种基金the Key Laboratory foundation of Ministry of Education for TCM Viscera State Theory and Applications of Liaoning University of Traditional Chinese Medicine(grant number.zyzx1807)“Three levels”Talent Construction Projects in Zhuhai College of Science and Technology.
文摘Prostatic carcinoma(PCa)has become one of the most common cancers among men worldwide,with both incidence and mortality rates steadily rising.Although current treatments are effective in the early stages of PCa,many cases eventually progress to castration-resistant prostate cancer(CRPC),and led to treatment failure.To develop new therapeutic strategies to ameliorate the survival of PCa patients then has pressed the need on medicinal researchers.Of traditional Chinese medicinal herbs,Angelica gigas Naka(AGN),and its major pyranocoumarins were broadly reported on the effect of anti-PCa.However,existing reviews mainly focus on decursin(D),decursinol angelate(DA),and decursinol(DOH),without fully exploring other coumarins in AGN.Moreover,most reviews discuss general anticancer effects,with limited emphasis on PCa specifically.This review made a comprehensive summary of the coumarin components of AGN,and depicted the anti-PCa effects and mechanisms,giving a solid research support for drug discovery and development.This review also featured pharmacokinetic advantages and therapeutic potential of DOH,in order to suggest possibilities to overcome the in vivo transformation limitations of D and DA,and shed light on CRPC treatment.We also recommend future studies focus on more in vivo evidence,safety and toxicity evaluation,and clinical validation in humans.
文摘A photocatalyst-free photoinduced radical difluoromethylation approach for the convenient synthesis of 3-CF_(2)H-coumarins from alkynoates by difluoromethyl phenoxathiinium salt(PT-CF_(2)H^(+)BF_(4)^(-))was developed.This transformation in-volves radical difluoromethylation/5-exo spirocyclization/ester migration rearrangement cascade process and features mild reaction conditions,broad substrate scope and good functional groups tolerance.Using this method,a wide range of alkynoates was successfully converted to desired 3-CF_(2)H-coumarins in moderate to good yields.
基金supported by National Key Research and Development Program of China(2021YFD1300302)the National Natural Science Foundation of China(U23A20216 and 32372905)。
文摘Background Coumarins are toxic phytochemicals found in a variety of plants and are known to limit microbial degradation and interfere with nutrient cycling.While the degradation of coumarins by fungi has been studied in an environmental context,little is known about their degradation in the gastrointestinal system of herbivores after ingestion.Results In this study,we investigated in vitro fermentation by microbial enrichment,transcriptome sequencing,and high-resolution mass spectrometry to evaluate the ability of rumen anaerobic fungi to degrade coumarins.The results showed that despite the low abundance of anaerobic fungi in the rumen microbiota,they were able to effectively degrade coumarins.Specifically,Pecoramyces ruminantium F1 could tolerate coumarin concentrations up to 3 mmol/L and degrade it efficiently via metabolic pathways involving alpha/beta hydrolases and NAD(P)H oxidoreductases within the late growth phase.The fungus metabolized coumarin to less toxic compounds,including o-coumaric acid and melilotic acid,highlighting the detoxification potential of anaerobic fungi.Conclusions This study is the first to demonstrate the ability of rumen anaerobic fungi to degrade coumarin,providing new insights into the use of anaerobic fungi in sustainable agricultural practices and environmental detoxification strategies.
基金the National Natural Science Foundation of China(Nos.20802063,21162032)the Foundation of the Key Laboratory of Medicinal Chemistry of Natural Resource(Yunnan University),Ministry of Education,China
文摘TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succini- midyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumar- ins and coumarins in good yields and purifies.
文摘Oxalic acid was found to be an efficient catalyst for Pechmann condensation, which includes the reaction between phenols and β-keto esters leading to formation of coumarin derivatives. The advantages of present methods are the use of cheap and easy available catalyst, solvent-free reaction conditions, better yields and shorter reaction time.
基金supported by the Macao Science and Technology Development Fund(No.120/2013/A3)the Research Fund of University of Macao(Nos.MYRG2015-00153-ICMS-QRCM and MYRG2017-00109-ICMS)
文摘Pharmaceutical research has focused on the discovery and development of anticancer drugs. Clinical application of chemotherapy drugs is limited due to their severe side effects. In this regard, new naturally occurring anticancer drugs have gained increasing attention because of their potential effectiveness and safety. Fruits and vegetables are promising sources of anticancer remedy. Clausena(family Rutaceae) is a genus of flowering plants and includes several kinds of edible fruits and vegetables. Phytochemical and pharmacological studies show that carbazole alkaloids and coumarins from Clausena plants exhibit anticancer activity. This review summarizes research progresses made in the anticancer properties of plants belonging to Clausena; in particular, compounds with direct cytotoxicity, cell cycle arrest, apoptosis induction, and immune potentiation effects are discussed. This review reveals the potential use of plants from Clausena in preventing and treating cancer and provides a basis for development of relevant therapeutic agents.
基金supported by the Basic Science Research Program through the National Research Foundation of Koreafunded by the Ministry of Science,ICT&Future Planning(grant No.2014R1A1A3051684 and 2012R1A6A1028677)
文摘Objective: To use structure-activity analysis to study the anti-Alzheimer's disease(anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaries, along with one purchased coumarin(daphnetin). Methods: Umbelliferone, umbelliferone 6-carboxylic acid, scopoletin, isoscopoletin, 7-methoxy coumarin, scoparone, scopolin, and esculetin have been previously isolated; however 2'-isopropyl psoralene was isolated from Angelica decursiva for the first time to evaluate their inhibitory effects against acetylcholinesterase(ACh E), butyrylcholinesterase(BCh E), and β-site amyloid precursor protein cleaving enzyme 1(BACE1) enzyme activity. We scrutinized the potentials of coumarins as cholinesterase and BACE1 inhibitors via enzyme kinetics and molecular docking simulation. Results: Among the test compounds, umbelliferone 6-carboxylic acid, esculetin and daphnetin exhibited potent inhibitory activity against ACh E, BCh E and BACE1. Both esculetin and daphnetin have a catechol group and exhibit significant anti-AD activity against ACh E and BCh E. In contrast, presence of a sugar moiety and methoxylation markedly reduced the anti-AD activity of the coumarins investigated in this study. With respect to BACE1 inhibition, umbelliferone 6-carboxylic acid, esculetin and daphnetin contained carboxyl or catechol groups, which significantly contributed to their antiAD activities. To further investigate these results, we generated a 3D structure of BACE1 using Autodock 4.2 and simulated binding of umbelliferone 6-carboxylic acid, esculetin and daphnetin. Docking simulations showed that different residues of BACE1 interacted with hydroxyl and carboxylic groups, and the binding energies of umbelliferone 6-carboxylic acid, esculetin and daphnetin were negative(-4.58,-6.25 and-6.37 kcal/mol respectively). Conclusions: Taken together, our results suggest that umbelliferone 6-carboxylic acid, esculetin and daphnetin have anti-AD effects by inhibiting ACh E, BCh E and BACE1, which might be useful against AD.
文摘The effect of L-proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild reaction conditions and achieved high yields. Moreover, the ionic liquid containing L-proline could be recycled and reused for several times without noticeably decreasing in productivity. The results show that the L-proline-[emim]BF4 system has a potential in contribution to the development of environmentally friendly and inexpensive processes in organic syntheses.
文摘Four new coumarins named qianhucoumarins A, B, C, D have been isolated from traditional Chinese medicine-the root of Peucedanum praeruptorum. Their structures were elucidated by chemical evidences and spectral analysis.
文摘Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ in good to high yields.
基金supported financially by the National Natural Science Foundation of China(No.82104014 and 82003605)the Key Laboratory Project of Colleges and Universities in Guangdong Province(No.2019KSYS005)the Guangdong Province Science and Technology Plan International Cooperation Project(No.2020A0505100052)。
文摘We reported the discovery of six novel coumarins, toddasirins A–F ( 1 – 6 ), each endowed with modified isoprenyl or geranyl side chains, derived from the roots of Toddalia asiatica. Comprehensive structural elucidation was achieved through multispectroscopic analyses, single-crystal X-ray diffraction experiments, and advanced quantum mechanical electronic circular dichroism (ECD) calculations. Furthermore, the anti-inflammatory activity of these compounds was assessed. Notably, compounds 1 – 3 and 6 demonstrated notable inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells, with 50% inhibitory concentration (IC50) values of 3.22, 4.78, 8.90, and 4.31 μmol·L^(−1), respectively.
基金supported by the National Natural Science Foundation of China(No.U1903122)the Scientific Research Fund of Liaoning Province Education Department(No.LJKZ0945)the Natural Science Foundation of Liaoning Province(No.2022-MS-242).
文摘The resin of Ferula sinkiangensis has been traditionally utilized for treating gastrointestinal disorders,inflammation,tumors,various cancers,and alopecia areata.The primary bioactive constituents,sesquiterpene coumarins,have demonstrated notable therapeutic potential against neuroinflammation.In this study,a structure-guided fractionation method was used to isolate nine novel sesquiterpene coumarins from the resin of F.sinkiangensis.These compounds were characterized and structurally elucidated using comprehensive physicochemical and spectroscopic techniques,including calculated electronic circular dichroism(ECD).Anti-neuroinflammatory assays revealed that compounds 2,3,and 6 significantly inhibited nitric oxide(NO)production in lipopolysaccharide(LPS)-stimulated BV2 microglial cells,with IC_(50)values ranging from 1.63 to 12.25μmol·L^(−1).
基金Project supported by the National Natural Science Foundation of China
文摘Two new coumarins,4'-hydroxycolumbianetin named angelidiol(A)and 6- [(?)(R),2(S)-3-trihydroxy-3-methylbutyl]-7-methoxycoumarin named angelitriol(B),were isolated from the EtOAc-soluble fraction of the 80% EtOH extract and structurally eluciated on the basis of spectral analyses.
基金supported by the National Natural Sciences Foundation of China(Nos.81973199,81773864 and81473106)the Drug Innovation Major Project of China(No.2018ZX09711001-008-003)。
文摘Three new coumarins,integmarins A–C(1–3),and a new coumarin glycoside,integmaside A(4)were isolated from the leaves and stems of Micromelum integerrimum.Their structures were elucidated on the basis of 1 D and 2 D NMR and MS data,and their absolute configurations were assigned according to the ECD data of the in situ formed transition metal complexes and comparison of experimental and calculated ECD data.Compounds 1 and 2 are two rare coumarins with butyl and propyl moieties at the C-6 position;compound 3 is a novel coumarin with a highly oxidized prenyl group,and compound 4 is a rare bisdihydrofuranocoumarin glycoside.
文摘Melamine-formaldehyde resin supported H~＋ is used as an efficient catalyst in the Pechmann condensation reaction of phenols withβ-ketoesters,in solvent-free media leading to the formation of coumarin derivatives using conventional heating and microwave irradiation in excellent yields with good purity.
基金The authors thank the financial supports from the National Natural Science Foundation of China(No.20132020)the Ministry of Science and Technology,the Chinese Ministry of Education and Zhengzhou University.
文摘Different hydroxy substituted coumarins were successfully phosphorylated with diisopropylphophite （DIPPH） by the Atherton-Todd reaction in 76-89% yields. Moreover, the reaction activities of different hydroxys of the coumarins in the Atherton-Todd reaction were studied.
文摘Silica-bonded S-sulfonic acid （SBSSA） was prepared by the reaction of 3-mercaptopropylsilica （MPS） and chlorosulfonic acid in chloroform. This solid acid has been employed as a recyclable catalyst for the synthesis of coumarins from phenols and β-keto- esters at 80 ℃ under solvent-free conditions.
文摘Tetracyclic coumarins are a class of important compounds with diverse and superior pharmacolog‐ical activities.However,a direct stereoselective method from simple and readily‐made coumarins derivatives remains challenging due to the inertness of coumarins as dienophiles.Herein,we de‐velop a decarboxylative asymmetric[4+2]cycloaddition of 3‐cyanocoumarins with vinyl benzoxa‐zinones,affording the coumarin‐derived condensed rings bearing three continuous stereocenters in high yields with excellent diastereoselectivities(>20/1 d.r.)and enantioselectivities(up to 99%ee).This direct enantioselective reaction was achieved by a Pd(0)/Cu(I)bimetallic catalytic system.The mechanism studies indicated that the synergistic activation effect,in which chiral Cu(I)as an availa‐ble Lewis acid catalyst activates 3‐cyanocoumarin and chiral Pd(0)complex activates benzoxazi‐none by the formation ofπ‐allyl‐palladium intermediate,plays an important role on the stereoselec‐tive control.The current work provides a new activation modes of Cu catalyst in the Pd/Cu bimetal‐lic catalytic system.
