The configurations of C-20 in derivatives of novel 5α-adynerin type,co-existing glycoside in pair,were identified with the calculated chemical shifts of carbon at the B3LYP/6-311＋G（2d,p）level.These glycosides are ...The configurations of C-20 in derivatives of novel 5α-adynerin type,co-existing glycoside in pair,were identified with the calculated chemical shifts of carbon at the B3LYP/6-311＋G（2d,p）level.These glycosides are unusual cardic aglycones without the common olefin bond in ring E.展开更多
Fusagerins A–F(1–6),six new alkaloids including a unique one with the rare a-(N-formyl)carboxamide moiety(1),a hydantoin(imidazolidin-2,4-dione)derivative(2),and four fungerin analogues(3–6),were isolated from the ...Fusagerins A–F(1–6),six new alkaloids including a unique one with the rare a-(N-formyl)carboxamide moiety(1),a hydantoin(imidazolidin-2,4-dione)derivative(2),and four fungerin analogues(3–6),were isolated from the crude extract of the fungus Fusarium sp.,together with the known compound fungerin(7).Compound 2 was isolated as a racemate and further separated into two enantiomers on a chiral HPLC column.The structures of 1–6 were determined mainly by NMR experiments,and the absolute configuration of 1 and 2 was assigned by electronic circular dichroism(ECD)calculations.Compound 7 showed antibacterial activity against Staphylococcus aureus and Streptococcus pneumoniae,and weak cytotoxicity against the T24 cells.展开更多
Michael addition of the chiral alpha,beta -unsaturated ester 2 with furyl lithium proceeded in syn manner with excellent diastereoselectivity. The diastereoselectivity was not affected by the configuration of the doub...Michael addition of the chiral alpha,beta -unsaturated ester 2 with furyl lithium proceeded in syn manner with excellent diastereoselectivity. The diastereoselectivity was not affected by the configuration of the double bond in 2.展开更多
A phytochemical investigation on the seeds of Sophora alopecuroides led to obtaining fourteen structurally diverse matrine-based alkaloids(1-14),including eight new ones(1,6,8-12,14).Notably,alopecuroide F(1)represent...A phytochemical investigation on the seeds of Sophora alopecuroides led to obtaining fourteen structurally diverse matrine-based alkaloids(1-14),including eight new ones(1,6,8-12,14).Notably,alopecuroide F(1)represents the first dimeric matrine-type skeleton assembled via unprecedent C-13-C-12'connection.The new structures were determined through extensive spectroscopic data(UV,OR,HRESIMS,1D,and 2D NMR),ECD calculations,and three instances,verified by X-ray crystallography.Biologically,all alkaloids were evaluated for cytotoxicity against four human cancer cell lines(HepG2,A549,THP-1,and MCF-7)and anti-inflammatory activities for two pro-inflammatory cytokines(TNF-αand IL-6).Alopecuroide F(1)can inhibit TNF-αand IL-6 productions in a dose-dependent manner with IC50 values of 35.6±0.5 and 41.7±0.8μmol/L,respectively.展开更多
A rare highly fused racemic merosesquiterpenoid,9-epi-verrubenzospirolactone(1),six new asteriscane-type sesquiterpenoids,sinuhumesins A-F(4-9),and two related known ones(10 and 11)were isolated from Hainan soft coral...A rare highly fused racemic merosesquiterpenoid,9-epi-verrubenzospirolactone(1),six new asteriscane-type sesquiterpenoids,sinuhumesins A-F(4-9),and two related known ones(10 and 11)were isolated from Hainan soft coral Sinularia humesi.Compound 1 was further separated by chiral HPLC resolution to one pair of enantiomers[(+)-1 and(-)-1],respectively.The full structures of the new compounds were unambiguously determined by extensive spectroscopic analysis,chemical computation approaches,modified Mosher's method and/or X-ray diffract!on analysis,as well as comparison with previously reported data of related model compounds.展开更多
A detailed chemical study on the Hainan soft coral Sinularia crass has resulted in the isolation and characterization of eleven cas-bane-type diterpenoids,named sinucrassins A-K(1-11),along with six known related ones...A detailed chemical study on the Hainan soft coral Sinularia crass has resulted in the isolation and characterization of eleven cas-bane-type diterpenoids,named sinucrassins A-K(1-11),along with six known related ones(12-17).Their structures were elucidated by extensive spectroscopic analyses and comparison with the reported data.The absolute configurations of new compounds were determi ned by the X-ray diffracti on analysis and computer-assisted structural elucidati on in eluding 13C NMR data calculati on and time-dependent density functional theory/electronic circular dichroism calculation.展开更多
Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South Ch...Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells.展开更多
Comprehensive Summary Seven new kalihinene diterpenoids,kalihioxepanes A-G(1-7)bearing a rare oxepane ring,were isolated from sponge Acanthella cavernosa collected from the South China Sea.The structures and absolute ...Comprehensive Summary Seven new kalihinene diterpenoids,kalihioxepanes A-G(1-7)bearing a rare oxepane ring,were isolated from sponge Acanthella cavernosa collected from the South China Sea.The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis,single crystal X-ray diffraction,and quantum chemical calculation methods.Kalihioxepane A(1)displayed strong cytotoxicity against H69 and K562 tumor cells,while kalihioxepane B(2)showed moderate cytotoxicity against K562 cells.展开更多
Main observation and conclusion Two new bis-quinolizidine alkaloids,neopetrosiasins A(1)and B(2),possessing cis-and trans-quinolizidine nuclei,one known related analogue petrosin(3)and three known xestospongins(4-6),w...Main observation and conclusion Two new bis-quinolizidine alkaloids,neopetrosiasins A(1)and B(2),possessing cis-and trans-quinolizidine nuclei,one known related analogue petrosin(3)and three known xestospongins(4-6),were isolated from the South China Sea sponge Neopetrosia chaliniformis.展开更多
Five unreported and oxygenated ent-rosane diterpenoids(ent-RDs),Euphomillanols A—E(1—5),were isolated from Euphorbia milii.Among them,compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5,10-seco-ent-RDs and p...Five unreported and oxygenated ent-rosane diterpenoids(ent-RDs),Euphomillanols A—E(1—5),were isolated from Euphorbia milii.Among them,compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5,10-seco-ent-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10),5-diene moiety,while 3 is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A.Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods,X-ray crystallography,and ECD calculation.Putative biosynthetic pathways for compounds 1—3 are proposed.All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes,and the most potent compound 4 showed an EC_(50)value of 3.92μmol/L with low cytotoxicity(IC_(50)>89.54μmol/L).展开更多
基金Supported by the Hundred Talents Program of Chinese Academic of Sciences the Science and Technology Committee ofYunnan Province,China.
文摘The configurations of C-20 in derivatives of novel 5α-adynerin type,co-existing glycoside in pair,were identified with the calculated chemical shifts of carbon at the B3LYP/6-311＋G（2d,p）level.These glycosides are unusual cardic aglycones without the common olefin bond in ring E.
基金the National Natural Science Foundation of China(81273395)the National Program of Drug Research and Development(2012ZX09301-003).
文摘Fusagerins A–F(1–6),six new alkaloids including a unique one with the rare a-(N-formyl)carboxamide moiety(1),a hydantoin(imidazolidin-2,4-dione)derivative(2),and four fungerin analogues(3–6),were isolated from the crude extract of the fungus Fusarium sp.,together with the known compound fungerin(7).Compound 2 was isolated as a racemate and further separated into two enantiomers on a chiral HPLC column.The structures of 1–6 were determined mainly by NMR experiments,and the absolute configuration of 1 and 2 was assigned by electronic circular dichroism(ECD)calculations.Compound 7 showed antibacterial activity against Staphylococcus aureus and Streptococcus pneumoniae,and weak cytotoxicity against the T24 cells.
基金This work was partially supported by the National Natural Science Foundation of China.
文摘Michael addition of the chiral alpha,beta -unsaturated ester 2 with furyl lithium proceeded in syn manner with excellent diastereoselectivity. The diastereoselectivity was not affected by the configuration of the double bond in 2.
基金This project was supported financially by grants from the National Natural Science Foundation of China(Nos.81803376,82074116,81973190)the Guangdong Basic and Applied Basic Research Foundation(No.2020B1515020033)+4 种基金the Natural Science Foundation of Guangdong Province(No.2018B030311020)the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program(No.2017BT01Y036)Guangdong Basic and Applied Basic Research Foundation-Regional Joint Fund(Youth Fund Project,No.2020A1515110415)Pearl River S&T Nova Program of Guangzhou(No.201906010069)We thank the High Performance Public Computing Service Platform of Jinan University for the help of theoretical ECD calculations.
文摘A phytochemical investigation on the seeds of Sophora alopecuroides led to obtaining fourteen structurally diverse matrine-based alkaloids(1-14),including eight new ones(1,6,8-12,14).Notably,alopecuroide F(1)represents the first dimeric matrine-type skeleton assembled via unprecedent C-13-C-12'connection.The new structures were determined through extensive spectroscopic data(UV,OR,HRESIMS,1D,and 2D NMR),ECD calculations,and three instances,verified by X-ray crystallography.Biologically,all alkaloids were evaluated for cytotoxicity against four human cancer cell lines(HepG2,A549,THP-1,and MCF-7)and anti-inflammatory activities for two pro-inflammatory cytokines(TNF-αand IL-6).Alopecuroide F(1)can inhibit TNF-αand IL-6 productions in a dose-dependent manner with IC50 values of 35.6±0.5 and 41.7±0.8μmol/L,respectively.
基金supported by the National Key Research and Developme nt Program of China(No.2018YFC0310903)the Natural Science Foundation of China(No.81991521)the SKLDR/SIMM Projects(No.SIMM2103ZZ-06)。
文摘A rare highly fused racemic merosesquiterpenoid,9-epi-verrubenzospirolactone(1),six new asteriscane-type sesquiterpenoids,sinuhumesins A-F(4-9),and two related known ones(10 and 11)were isolated from Hainan soft coral Sinularia humesi.Compound 1 was further separated by chiral HPLC resolution to one pair of enantiomers[(+)-1 and(-)-1],respectively.The full structures of the new compounds were unambiguously determined by extensive spectroscopic analysis,chemical computation approaches,modified Mosher's method and/or X-ray diffract!on analysis,as well as comparison with previously reported data of related model compounds.
基金supported by the National Natural Science Foundation of China(No.81991521)the National Key Research and Development Program of China(No.2018YFC0310903)the SKLDR/SIMM Project(No.SIMM2103ZZ-06)。
文摘A detailed chemical study on the Hainan soft coral Sinularia crass has resulted in the isolation and characterization of eleven cas-bane-type diterpenoids,named sinucrassins A-K(1-11),along with six known related ones(12-17).Their structures were elucidated by extensive spectroscopic analyses and comparison with the reported data.The absolute configurations of new compounds were determi ned by the X-ray diffracti on analysis and computer-assisted structural elucidati on in eluding 13C NMR data calculati on and time-dependent density functional theory/electronic circular dichroism calculation.
基金financially supported by the National Natural Science Foundation of China(Nos.81991521,41776093)the National Key Research and Development Program of China(No.2018YFC0310903)+2 种基金the Key Research and Development Project of Hainan Province(ZDYF2021SHFZ107)Financial Fund of the Ministry of Agriculture and Rural Affairs,P.R.China(NFZX2021)the SKLDR/SIMM Project(No.SIMM2103ZZ-06).
文摘Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells.
基金This work was supported by the National Natural Science Foundation of China(Nos.U2006204,41776136,2181101213,81991522,and 41876161)。
文摘Comprehensive Summary Seven new kalihinene diterpenoids,kalihioxepanes A-G(1-7)bearing a rare oxepane ring,were isolated from sponge Acanthella cavernosa collected from the South China Sea.The structures and absolute configurations were elucidated by comprehensive spectroscopic analysis,single crystal X-ray diffraction,and quantum chemical calculation methods.Kalihioxepane A(1)displayed strong cytotoxicity against H69 and K562 tumor cells,while kalihioxepane B(2)showed moderate cytotoxicity against K562 cells.
基金This research work was financially supported by the National Natural Science Foundation of China(Nos.81991521,82022069,42076099,41830535)the Shanghai Rising-Star Program(No.20QA1411100)+1 种基金the National Key Research and Development Program of China(No.2018YFC0310903)the Taishan Scholars Program,China.Bao Chen is thankful for the financial support of Syngenta-OUC-PhD Studentship Project.
文摘Main observation and conclusion Two new bis-quinolizidine alkaloids,neopetrosiasins A(1)and B(2),possessing cis-and trans-quinolizidine nuclei,one known related analogue petrosin(3)and three known xestospongins(4-6),were isolated from the South China Sea sponge Neopetrosia chaliniformis.
基金Financial support from the National Natural Science Foundation of China(No.82122062)the 145 Programs(XTBG-145)of Xishuangbanna Tropical Botanical Garden,Chinese Academy of Sciences(CAS)the Program of CAS Key Laboratory of Tropical Plant Resources and Sustainable Use(No.20228012802)is highly acknowledged.
文摘Five unreported and oxygenated ent-rosane diterpenoids(ent-RDs),Euphomillanols A—E(1—5),were isolated from Euphorbia milii.Among them,compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5,10-seco-ent-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10),5-diene moiety,while 3 is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A.Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods,X-ray crystallography,and ECD calculation.Putative biosynthetic pathways for compounds 1—3 are proposed.All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes,and the most potent compound 4 showed an EC_(50)value of 3.92μmol/L with low cytotoxicity(IC_(50)>89.54μmol/L).
