AIM: To study the chemical constituents of the solid culture of the endophyte Phomopsis sp. IFB-E060 in Vatica mangachapoi. METHOD: Isolation and purification were performed through silica gel column chromatography, g...AIM: To study the chemical constituents of the solid culture of the endophyte Phomopsis sp. IFB-E060 in Vatica mangachapoi. METHOD: Isolation and purification were performed through silica gel column chromatography, gel filtration over Sephadex LH-20, ODS column chromatography, and HPLC. Structures of the isolated compounds were elucidated by a combination of spectroscopic analyses(UV, CD, IR, MS, 1D, and 2D NMR). The cytotoxicity of the isolates was evaluated in vitro by the MTT method against the human hepatocarcinoma cell line SMMC-7721. RESULTS: Five compounds were isolated from the solid culture of the endophyte Phomopsis sp. IFB-E060 and their structures were identified as 18-methoxy cytochalasin J(1), cytochalasin H(2),(22E, 24S)-cerevisterol(3), ergosterol(4), and nicotinic acid(5). Compound 1 had an inhibition rate of 24.4% at 10 μg·mL-1 and 2 had an IC50 value of 15.0 μg·mL-1, while a positive control 5-fluorouracil had an inhibition rate of 28.7% at 10 μg·mL-1. CONCLUSION: 18-Methoxy cytochalasin J(1), produced by endophytic Phomopsis sp. IFB-E060, is a new cytochalasin with weak cytotoxicity to the human hepatocarcinoma cell line SMMC-7721.展开更多
Vercytochalasins A(1) and B(2), two biosynthetically related cytochalasins featuring novel structure and substituents, were isolated from the endozoic fungus Curvularia verruculosa which was associated with the deep-s...Vercytochalasins A(1) and B(2), two biosynthetically related cytochalasins featuring novel structure and substituents, were isolated from the endozoic fungus Curvularia verruculosa which was associated with the deep-sea squat lobster Shinkaia crosnieri collected from the cold seep environment in South China sea. Their structures were elucidated by detailed interpretation of NMR spectroscopic and mass spectrometric data. The absolute configurations were confirmed by NOESY experiments as well as by DP4+ and ECD calculations. Differed from common cytochalasins, compound 1 is an uncommon secocytochalasin featuring the ester group cleaved between C-9 and C-23, and incorporating an additional oxygenated C4 unit which coupled with C-20 and C-22 to form a new substituted cyclohexenone moiety, while compound 2 contains an unusual 2–hydroxy-3-oxobutan-2-yl unit at C-22. Both compounds are distinctive from the commonly described cytochalasins. Compound 1 exhibited potent activity against angiotensinI-converting enzyme(ACE) whereas compound 2 showed antibacterial activity. Molecular docking simulations were performed to explore the intermolecular interaction of compounds 1 and 2 with ACE.展开更多
Three previously undescribed cytochalasins,named xylariasins A‒C(1‒3),together with six known ones(4‒9)were iso-lated from Xylaria sp.CFL5,an endophytic fungus of Cephalotaxus fortunei.The chemical structures of all n...Three previously undescribed cytochalasins,named xylariasins A‒C(1‒3),together with six known ones(4‒9)were iso-lated from Xylaria sp.CFL5,an endophytic fungus of Cephalotaxus fortunei.The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation,as well as optical rotation calculation.Biological activities of compounds 1,4‒9 were evaluated,including cytotoxic,LAG3/MHC II binding inhibition and LAG3/FGL1 binding inhibition activities.Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5μM,with inhibition rates of 94%and 64%,respectively.In addition,all tested isolates,except compound 6,exhibited obvious inhibitory activity against the interaction of both LAG3/MHC II and LAG3/FGL1.Compounds 1,5,7,and 8 inhibited LAG3/MHC II with IC50 values ranging from 2.37 to 4.74μM.Meanwhile,the IC50 values of compounds 1,7,and 8 against LAG3/FGL1 were 11.78,4.39,and 7.45μM,respectively.展开更多
Cytochalasin B (cytoB) loaded nanoparticles (NPs) and microspheres (MSs) were formed using an emulsification / solvent evaporation technique.Biodegradable poly(lactic co glycolic acid)(PLGA) and poly(L lactic acid)(PL...Cytochalasin B (cytoB) loaded nanoparticles (NPs) and microspheres (MSs) were formed using an emulsification / solvent evaporation technique.Biodegradable poly(lactic co glycolic acid)(PLGA) and poly(L lactic acid)(PLLA)were used as carrier and were compared in terms of drug release rate and initial burst.The PLGA nanoparticles and microparticles of graded diameter,150 nm,500 nm,1 μm,5 μm,10 μm and 20 μm,is formulated.Nanoparticles of 150 500 nm diameter were obtained by high energy sonication,whereas larger size particles were obtained by normal homogenization.The degree of initial burst release varied depending on particle size and polymer matrix.For the PLGA matrix,about 50% of the entrapped drug released from the 150 nm nanoparticles,whereas only 10% released from the 20 μm particles within the first 24 hours.On the other hand,cytoB release from 150 nm PLLA nanoparticles was much slower and showed less burst effect than the PLGA ones with same size.The results suggest that desired release profile can be achieved by properly selecting the matrix material and particle size.展开更多
Objective:To investigate whether eytochalasin D can induce antitumor activities in a tumor model.Methods:Murine CT26 colorectal carcinoma cells were cultured hi vitro and cytochalasin D was used as a cytotoxic agent t...Objective:To investigate whether eytochalasin D can induce antitumor activities in a tumor model.Methods:Murine CT26 colorectal carcinoma cells were cultured hi vitro and cytochalasin D was used as a cytotoxic agent to detect its capabilities of inhibiting CT26 cell proliferation and inducing cell apoptosis by MTT and a TUNEL-based apoptosis assay.Murine CT26 tumor model was established to observe the tumor growth and survival time.Tumor tissues were used to detect the mierovessel density by immunohistochemistry.In addition,alginate encapsulated tumor cell assay was used to quantify the tumor angiogenesis in vivo.Results:Cytochalasin D inhibited CT26 tumor cell proliferation in lime and dose dependent manner and induced signiflcanl CT26 cell apoptosis,which almost reached the level induced by the positive control nuclease.The optimum effective dose of cytochalasin D for in vivo therapy was about 50 mg/kg.Cytochalasin D in vivo treatment significandy inhibited tumor growth and prolonged the survival times in CT26 tumor-bearing mice.The results of immunohistochemistry analysis and alginate encapsulation assay indicated that the cytochalasin D could effectively inhibited tumor angiogenesis. Conclusions:Cytochalasin D inhibits CT26 tumor growth potentially through inhibition of cell proliferation,induction of cell apoptosis and suppression of tumor angiogenesis.展开更多
Feartilized eggs of Penaeus chinensis were treated with cytochalasin B (C. B ) to induce triploid.A number of them were cultured to the stage of on larvae. The C. B concentrations employed were 0. 1～2. 5 mg/dm3. The...Feartilized eggs of Penaeus chinensis were treated with cytochalasin B (C. B ) to induce triploid.A number of them were cultured to the stage of on larvae. The C. B concentrations employed were 0. 1～2. 5 mg/dm3. The treatments started at 5～20 min after fertilization and lasted for various periods of time from 10 to 40 min. The highest inducing rate was 62. 5%.It was obvious that haaer C. B concentration gave stronger inhibition on the releas of polar bodies,and the higher the C. B concentration was, the more abnormal and aneuploid embryos were obtained. The success in inducing tripled in P.chinensis provided a posibility of polyploid breding of this species.展开更多
Diacylglycerol (DG) and cAMP, two intracellular second messengers, play importantroles in responding to the stimulation of extracellular signal. DG activates protein kinaseC (PKC), and cAMP activates protein kinase A ...Diacylglycerol (DG) and cAMP, two intracellular second messengers, play importantroles in responding to the stimulation of extracellular signal. DG activates protein kinaseC (PKC), and cAMP activates protein kinase A (PKA). Activation of these展开更多
Cytochalasin B(CB)was a depolymeriziner agent of F-aetin.Therefore a lot of plant cell motilities related to action,such as cytoplasmic streaming,pollen
The interphase nuclei of parenchyma cells and epidermal cells of garlic ( Allium sativum L.) clove were labelled with rabbit anti_actin antibody and FITC_conjugated goat anti_rabbit IgG antibody. The authors observ...The interphase nuclei of parenchyma cells and epidermal cells of garlic ( Allium sativum L.) clove were labelled with rabbit anti_actin antibody and FITC_conjugated goat anti_rabbit IgG antibody. The authors observed results with fluorescence microscopy and confocal laser scanning microscopy. The nuclei showed prominent green_yellow fluorescence, indicating the presence of actin in the nuclei. Fluorescence examination with TRITC_phalloidin showed distinctive red fluorescence in the nuclei, indicating that F_actin is present in the nuclei. Confocal laser scanning microscopy indicated the presence of F_actin containing network structures in the nuclei, but the network structures were absent and the nuclei still showed red fluorescence when the cells were treated with cytochalasin D before fixation; the red fluorescence in the nuclei was hard to be observed when the cells were treated with unlabelled phalloidin before the cells were stained with TRITC_phalloidin. These results indicate that F_actin is in the nuclei and forms network structures in the nuclei of garlic cells.展开更多
A new ceramide, (2S,3S,4R, 10E)-2-[(2'R)-2'-hydroxytetracosanoyl amino]-10-octadecene-1, 3,4-triol (1), together with twelve known compounds, cerebroside A, cerebroside B, cerebroside D, cytochalasin D, epoxyc...A new ceramide, (2S,3S,4R, 10E)-2-[(2'R)-2'-hydroxytetracosanoyl amino]-10-octadecene-1, 3,4-triol (1), together with twelve known compounds, cerebroside A, cerebroside B, cerebroside D, cytochalasin D, epoxycytochalasin D, cytochalasin C, loganin, cerevisterol, ergosta-7,22-dien-3beta, 5alpha, 6alpha-triol, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol peroxide and ergosta-5,7,22-trien-3-ol, was isolated from ethyl acetate fraction of Engleromyces goetzei P. Henn. The structure of new ceramide (1) was elucidated by spectral data and chemical method, especially by 2D-NMR techniques. All of the compounds except cytochalasin D were first obtained from this fungus.展开更多
基金supported by the Natural Science Foundation of China(Nos.81121062,30701045,21132004&21072092)the Natural Science Foundation of Jiangsu Province(No.BK2009010)the Social Development Project of Yangzhou(No.YZ2011097)
文摘AIM: To study the chemical constituents of the solid culture of the endophyte Phomopsis sp. IFB-E060 in Vatica mangachapoi. METHOD: Isolation and purification were performed through silica gel column chromatography, gel filtration over Sephadex LH-20, ODS column chromatography, and HPLC. Structures of the isolated compounds were elucidated by a combination of spectroscopic analyses(UV, CD, IR, MS, 1D, and 2D NMR). The cytotoxicity of the isolates was evaluated in vitro by the MTT method against the human hepatocarcinoma cell line SMMC-7721. RESULTS: Five compounds were isolated from the solid culture of the endophyte Phomopsis sp. IFB-E060 and their structures were identified as 18-methoxy cytochalasin J(1), cytochalasin H(2),(22E, 24S)-cerevisterol(3), ergosterol(4), and nicotinic acid(5). Compound 1 had an inhibition rate of 24.4% at 10 μg·mL-1 and 2 had an IC50 value of 15.0 μg·mL-1, while a positive control 5-fluorouracil had an inhibition rate of 28.7% at 10 μg·mL-1. CONCLUSION: 18-Methoxy cytochalasin J(1), produced by endophytic Phomopsis sp. IFB-E060, is a new cytochalasin with weak cytotoxicity to the human hepatocarcinoma cell line SMMC-7721.
基金financially supported by the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDA22050401)the National Natural Science Foundation of China (Nos. U2006203 and 42076090)+3 种基金the Senior User Project of RV KEXUE (No. KEXUE2020GZ02)the Shandong Provincial Natural Science Foundation (No. ZR2021ZD28)the Basic Applied Research program of Qingdao (No. 19–6–2–40-cg)the support of the RV KEXUE of the National Major Science and Technology Infrastructure from the Chinese Academy of Sciences (for sampling) and the Oceanographic Data center at IOCAS (for CPU time)。
文摘Vercytochalasins A(1) and B(2), two biosynthetically related cytochalasins featuring novel structure and substituents, were isolated from the endozoic fungus Curvularia verruculosa which was associated with the deep-sea squat lobster Shinkaia crosnieri collected from the cold seep environment in South China sea. Their structures were elucidated by detailed interpretation of NMR spectroscopic and mass spectrometric data. The absolute configurations were confirmed by NOESY experiments as well as by DP4+ and ECD calculations. Differed from common cytochalasins, compound 1 is an uncommon secocytochalasin featuring the ester group cleaved between C-9 and C-23, and incorporating an additional oxygenated C4 unit which coupled with C-20 and C-22 to form a new substituted cyclohexenone moiety, while compound 2 contains an unusual 2–hydroxy-3-oxobutan-2-yl unit at C-22. Both compounds are distinctive from the commonly described cytochalasins. Compound 1 exhibited potent activity against angiotensinI-converting enzyme(ACE) whereas compound 2 showed antibacterial activity. Molecular docking simulations were performed to explore the intermolecular interaction of compounds 1 and 2 with ACE.
基金supported financially by the National Natural Science Foundation of China(No.21778027)the Natural Science Foundation of Gansu Province(No.18JR4RA003).
文摘Three previously undescribed cytochalasins,named xylariasins A‒C(1‒3),together with six known ones(4‒9)were iso-lated from Xylaria sp.CFL5,an endophytic fungus of Cephalotaxus fortunei.The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation,as well as optical rotation calculation.Biological activities of compounds 1,4‒9 were evaluated,including cytotoxic,LAG3/MHC II binding inhibition and LAG3/FGL1 binding inhibition activities.Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5μM,with inhibition rates of 94%and 64%,respectively.In addition,all tested isolates,except compound 6,exhibited obvious inhibitory activity against the interaction of both LAG3/MHC II and LAG3/FGL1.Compounds 1,5,7,and 8 inhibited LAG3/MHC II with IC50 values ranging from 2.37 to 4.74μM.Meanwhile,the IC50 values of compounds 1,7,and 8 against LAG3/FGL1 were 11.78,4.39,and 7.45μM,respectively.
文摘Cytochalasin B (cytoB) loaded nanoparticles (NPs) and microspheres (MSs) were formed using an emulsification / solvent evaporation technique.Biodegradable poly(lactic co glycolic acid)(PLGA) and poly(L lactic acid)(PLLA)were used as carrier and were compared in terms of drug release rate and initial burst.The PLGA nanoparticles and microparticles of graded diameter,150 nm,500 nm,1 μm,5 μm,10 μm and 20 μm,is formulated.Nanoparticles of 150 500 nm diameter were obtained by high energy sonication,whereas larger size particles were obtained by normal homogenization.The degree of initial burst release varied depending on particle size and polymer matrix.For the PLGA matrix,about 50% of the entrapped drug released from the 150 nm nanoparticles,whereas only 10% released from the 20 μm particles within the first 24 hours.On the other hand,cytoB release from 150 nm PLLA nanoparticles was much slower and showed less burst effect than the PLGA ones with same size.The results suggest that desired release profile can be achieved by properly selecting the matrix material and particle size.
基金partially funded by National Basie Research Program of China(2010CB534909)National Natural Seience Foundation of China (30960411 and 81160288)Hainan Provincial Key Scientific Project(061009)
文摘Objective:To investigate whether eytochalasin D can induce antitumor activities in a tumor model.Methods:Murine CT26 colorectal carcinoma cells were cultured hi vitro and cytochalasin D was used as a cytotoxic agent to detect its capabilities of inhibiting CT26 cell proliferation and inducing cell apoptosis by MTT and a TUNEL-based apoptosis assay.Murine CT26 tumor model was established to observe the tumor growth and survival time.Tumor tissues were used to detect the mierovessel density by immunohistochemistry.In addition,alginate encapsulated tumor cell assay was used to quantify the tumor angiogenesis in vivo.Results:Cytochalasin D inhibited CT26 tumor cell proliferation in lime and dose dependent manner and induced signiflcanl CT26 cell apoptosis,which almost reached the level induced by the positive control nuclease.The optimum effective dose of cytochalasin D for in vivo therapy was about 50 mg/kg.Cytochalasin D in vivo treatment significandy inhibited tumor growth and prolonged the survival times in CT26 tumor-bearing mice.The results of immunohistochemistry analysis and alginate encapsulation assay indicated that the cytochalasin D could effectively inhibited tumor angiogenesis. Conclusions:Cytochalasin D inhibits CT26 tumor growth potentially through inhibition of cell proliferation,induction of cell apoptosis and suppression of tumor angiogenesis.
文摘Feartilized eggs of Penaeus chinensis were treated with cytochalasin B (C. B ) to induce triploid.A number of them were cultured to the stage of on larvae. The C. B concentrations employed were 0. 1～2. 5 mg/dm3. The treatments started at 5～20 min after fertilization and lasted for various periods of time from 10 to 40 min. The highest inducing rate was 62. 5%.It was obvious that haaer C. B concentration gave stronger inhibition on the releas of polar bodies,and the higher the C. B concentration was, the more abnormal and aneuploid embryos were obtained. The success in inducing tripled in P.chinensis provided a posibility of polyploid breding of this species.
基金Project supported by the National Natural Science Foundation of China.
文摘Diacylglycerol (DG) and cAMP, two intracellular second messengers, play importantroles in responding to the stimulation of extracellular signal. DG activates protein kinaseC (PKC), and cAMP activates protein kinase A (PKA). Activation of these
文摘Cytochalasin B(CB)was a depolymeriziner agent of F-aetin.Therefore a lot of plant cell motilities related to action,such as cytoplasmic streaming,pollen
文摘The interphase nuclei of parenchyma cells and epidermal cells of garlic ( Allium sativum L.) clove were labelled with rabbit anti_actin antibody and FITC_conjugated goat anti_rabbit IgG antibody. The authors observed results with fluorescence microscopy and confocal laser scanning microscopy. The nuclei showed prominent green_yellow fluorescence, indicating the presence of actin in the nuclei. Fluorescence examination with TRITC_phalloidin showed distinctive red fluorescence in the nuclei, indicating that F_actin is present in the nuclei. Confocal laser scanning microscopy indicated the presence of F_actin containing network structures in the nuclei, but the network structures were absent and the nuclei still showed red fluorescence when the cells were treated with cytochalasin D before fixation; the red fluorescence in the nuclei was hard to be observed when the cells were treated with unlabelled phalloidin before the cells were stained with TRITC_phalloidin. These results indicate that F_actin is in the nuclei and forms network structures in the nuclei of garlic cells.
文摘A new ceramide, (2S,3S,4R, 10E)-2-[(2'R)-2'-hydroxytetracosanoyl amino]-10-octadecene-1, 3,4-triol (1), together with twelve known compounds, cerebroside A, cerebroside B, cerebroside D, cytochalasin D, epoxycytochalasin D, cytochalasin C, loganin, cerevisterol, ergosta-7,22-dien-3beta, 5alpha, 6alpha-triol, ergosta-4,6,8(14),22-tetraen-3-one, ergosterol peroxide and ergosta-5,7,22-trien-3-ol, was isolated from ethyl acetate fraction of Engleromyces goetzei P. Henn. The structure of new ceramide (1) was elucidated by spectral data and chemical method, especially by 2D-NMR techniques. All of the compounds except cytochalasin D were first obtained from this fungus.
