[Objectives]This study was conducted to explore the action mechanism of limonoids against Alzheimer s disease(AD)based on network pharmacology and molecular docking techniques.[Methods]Limonoid compounds were obtained...[Objectives]This study was conducted to explore the action mechanism of limonoids against Alzheimer s disease(AD)based on network pharmacology and molecular docking techniques.[Methods]Limonoid compounds were obtained through literature research(January 1942 to January 2021).Active components and potential targets of limonoids were retrieved from PubChem,TCMSP,and Swiss Target Prediction databases.AD-related targets were obtained from the GeneCards database,and intersecting targets were identified using Venny 2.1.0 to obtain the action targets of limonoids against AD.The protein-protein interaction(PPI)network was constructed using the String platform,and key targets were screened and visualized via network topology analysis with Cytoscape software.GO and KEGG pathway enrichment analyses were performed using the Metascape database,and a"drug-component-target-pathway-disease"network diagram was constructed using Cytoscape.AutoDock was empolyed for molecular docking to predict the binding properties of limonoid active components and their targets.[Results]A total of 60 limonoid compounds were obtained from literature research.Network pharmacology analysis showed 58 effective active components and 134 common targets between limonoids and AD.Key targets included AKT1(serine/threonine-protein kinase 1),TNF(tumor necrosis factor),STAT3(signal transducer and activator of transcription 3),BCL2(B-cell lymphoma 2),and EGFR(epidermal growth factor receptor).KEGG enrichment analysis revealed key signaling pathways such as pathways in cancer,Kaposi sarcoma-associated herpesvirus infection,PI3K-Akt signaling pathway,lipid and atherosclerosis,proteoglycans in cancer,MAPK signaling pathway,and Ras signaling pathway.Molecular docking results indicated that aphanamixoid A,obacunol,cipadesin C,harpertrioate A,xylogranatin A,11-oxocneorin G,evodulone,methyl angolensate,harrpemoid B and khivorin may be key components of limonoids against AD.[Conclusions]Limonoids exert anti-Alzheimer s effects through a multi-molecule,multi-target and multi-pathway mechanism.展开更多
Two new limonoid-type triterpenoids, named 12-o-ethyl-l-deacetylnimbolinin B and 1-o-tigloyl-1-o-debenzoylohchinal, have been isolated from the fruit of Melia toosendan Sieb. et Zucc. Their structures were elucidated ...Two new limonoid-type triterpenoids, named 12-o-ethyl-l-deacetylnimbolinin B and 1-o-tigloyl-1-o-debenzoylohchinal, have been isolated from the fruit of Melia toosendan Sieb. et Zucc. Their structures were elucidated by spectral methods, including 2D-NMR spectra.展开更多
Two new limonoids, 12-ethoxynimbolinins G and H(compounds 1 and 2), and one known compound, toosendanin(Chuanliansu)(compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spe...Two new limonoids, 12-ethoxynimbolinins G and H(compounds 1 and 2), and one known compound, toosendanin(Chuanliansu)(compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin(3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.展开更多
In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin(1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin(2), together with other four known limonoids(3-6)...In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin(1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin(2), together with other four known limonoids(3-6), were isolated from the fruits of Melia toosendan. Their structures were elucidated by means of extensive spectroscopic analyses(NMR and ESI-MS) and comparisons with the data reported in the literature. The isolated compounds were evaluated for their antibacterial activities. Compound 4 exhibited significant antibacterial activity against an oral pathogen, Porphyromonas gingivalis ATCC 33277, with an MIC value of 15.2 μg·m L-1. Compound 2 was also active against P. gingivalis ATCC 33277, with an MIC value of 31.25 μg·m L-1. In conlcusion, our resutls indicate that these compounds may provide a basis for future development of novel antibiotics.展开更多
Six new trichilin-type limonoids(1-6)with C-19/29 lactol or acetal bridge and a new ring intact limonoid(7)were isolated from the desiccative ripe fruits of Trichilia sinensis.Their structures were determined by exten...Six new trichilin-type limonoids(1-6)with C-19/29 lactol or acetal bridge and a new ring intact limonoid(7)were isolated from the desiccative ripe fruits of Trichilia sinensis.Their structures were determined by extensive spectroscopic methods including 1 H NMR,13 C NMR,HSQC,HMBC,ROESY experiments as well as HRESI-MS data.All isolated compounds were evaluated for toxicities against human pulmonary carcinoma A549 and Hela cell lines by sulforhodamine B(SRB)method.Compound 7 showed weak inhibitory activity in Hela cell line at 40μmol·L^-1.展开更多
Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Mun...Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Munronia unifoliolata.Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),X-ray crystallography,electronic circular dichroism(ECD)calculations and NMR calculations with DP4+analyses.The unprecedented ethyl group of 1 was hypothesized to be derived from methyl migration and ring reduction rearrangement of ring A-seco limonoid 4.Compounds 2 and 4 showed significant multidrug resistance(MDR)reversal activities in MCF-7/DOX cells with reversal fold(RF)values of 13.1 and 8.0,respectively.展开更多
Two new limonoids,1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12α-ethoxyl nimbolinin（1） and lα-benzoyloxy-3α-acetoxyl-7α- hydroxyl-12α-ethoxyl nimbolinin（2）,were isolated from the fruits of Melia toosendan.Their...Two new limonoids,1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12α-ethoxyl nimbolinin（1） and lα-benzoyloxy-3α-acetoxyl-7α- hydroxyl-12α-ethoxyl nimbolinin（2）,were isolated from the fruits of Melia toosendan.Their structures were established on the basis of various NMR spectroscopic analyses,including 2D-NMR techniques（HSQC,HMBC,NOESY） and HR-ESI-MS.展开更多
Five new mexicanolide-type limonoids,heytrijunolides A-E(1-5)were isolated from the branches and leaves of Heynea trijuga.The structures of these new compounds were elucidated on the basis of extensive spectroscopic a...Five new mexicanolide-type limonoids,heytrijunolides A-E(1-5)were isolated from the branches and leaves of Heynea trijuga.The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis.Compound 3 showed weak cytotoxicity against HL-60,SMMC-7721 and A-549 human tumor cell lines with the IC50 values of 21.88,20.66 and 12.70μM,respectively.展开更多
A new trijugin-type limonoid,cipatrijugin G(1),together with the related known cipatrijugin A(2),were isolated from the aerial parts of Cipadessa cinerascens.The structure of the new compound was determined by extensi...A new trijugin-type limonoid,cipatrijugin G(1),together with the related known cipatrijugin A(2),were isolated from the aerial parts of Cipadessa cinerascens.The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature.Compound 1 showed cytotoxicity against tumor cell line A549 with an IC_(50) value of 9.78μM.This is the first report of a trijugin-type limonoid bearing aγ-hydroxybutenolide unit,in comparison to the common furan unit as ring E.展开更多
A new cytotoxic salannin-class limonoid alkaloid, azadiramide A（1）,was isolated from seeds of Azadirachta indica A. Juss. Its structure was elucidated by extensive analysis of spectroscopic data and quantum chemical...A new cytotoxic salannin-class limonoid alkaloid, azadiramide A（1）,was isolated from seeds of Azadirachta indica A. Juss. Its structure was elucidated by extensive analysis of spectroscopic data and quantum chemical calculation. Compound 1 is a rare salannin-class limonoid alkaloid. To our best knowledge, only two compounds belonging to this type were so far found. It showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC_（50） value of 2.70±0.63 μmol/L.展开更多
Two new highly oxygenated limonoids,flexuosoids A(1)and B(2),and three new arylnaphthalene lignan glycosides,phyllanthusmins D–F(3–5),were isolated from the roots of Phyllanthus flexuosus,in addition to three known ...Two new highly oxygenated limonoids,flexuosoids A(1)and B(2),and three new arylnaphthalene lignan glycosides,phyllanthusmins D–F(3–5),were isolated from the roots of Phyllanthus flexuosus,in addition to three known lignans,phyllanthusmin C,arabelline,and(?)-diasyringaresinol.Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods.Compounds 1 and 2,two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1,C-2,C-3,C-7,C-11,C-17,and C-30,represent the second example of limonoids in the Euphorbiaceae family.Most of the isolates were tested for their antifeedant,anti-herpes simplex virus 1,and cytotoxic activities.The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua)with EC50 values of 25.1 and 17.3 lg/cm2,respectively.In addition,both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line,along with the known lignan glycoside,phyllanthusmin C,with the IC50 values of 11.5(1),8.5(2),and 7.8(phyllanthusmin C)lM,respectively.展开更多
Two new phragmalin-type limonoids orthoesters, encandollens A and B(1 and 2), were isolated from the stem barks of Entandrophragma candollei collected in Ghana. The structures of these compounds were elucidated on the...Two new phragmalin-type limonoids orthoesters, encandollens A and B(1 and 2), were isolated from the stem barks of Entandrophragma candollei collected in Ghana. The structures of these compounds were elucidated on the basis of HR-ESI-MS, ~1 H and ^(13) C NMR, HSQC, HMBC, and ROESY data. Compound 1 was a rare C-15 enolic acyl phragmalin-type limonoid orthoester. Compounds 1 and 2 exhibited weak inhibitory effects on NO production in lipopolysaccharide(LPS)-induced RAW 264.7 cells.展开更多
Three new compounds,including two diterpenoids,nemoralisins H and I(1 and 2),and a limonoid,2-methoxy khayseneganin E(3),along with four known constituents(4-7),were isolated from the leaves and twigs of Swietenia mah...Three new compounds,including two diterpenoids,nemoralisins H and I(1 and 2),and a limonoid,2-methoxy khayseneganin E(3),along with four known constituents(4-7),were isolated from the leaves and twigs of Swietenia mahagoni.Their chemical structures were elucidated by means of spectroscopic analysis.The cytotoxities of these isolated constituents were assayed.展开更多
Two new furan fragment isomerized limonoids, meliazedalides A and B(compounds 1 and 2), were isolated from the fruits of Melia azedarach Linn.. Their chemical structures were elucidated on the basis of HR-ESI-MS and 1...Two new furan fragment isomerized limonoids, meliazedalides A and B(compounds 1 and 2), were isolated from the fruits of Melia azedarach Linn.. Their chemical structures were elucidated on the basis of HR-ESI-MS and 1D and 2D NMR data, which belonged to nimbolinin-and trichilin-class, respectively. Compound 2 exhibited weak inhibitory effect on NO production in lipopolysaccharide(LPS)-activated RAW 264.7 macrophages with IC_(50) being 37.41 μmol·L^(–1).展开更多
A new limonoid named rohituka-15 1, with a known limonoid dregeana-1 2, was isolated from the seed of Aphanamixis polystachya (Meliaceae). The 13C NMR data assignment of dregeana-1 2 and the structural elucidation of...A new limonoid named rohituka-15 1, with a known limonoid dregeana-1 2, was isolated from the seed of Aphanamixis polystachya (Meliaceae). The 13C NMR data assignment of dregeana-1 2 and the structural elucidation of the new compound 1 were based on spectral analysis including 1H-1H COSY, HMQC and HMBC experiments.展开更多
Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D(1-4),and one new furan ring degraded limonoid walsurobustone E(5)together with one known compound toonapubesic acid B(6)were isolated...Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D(1-4),and one new furan ring degraded limonoid walsurobustone E(5)together with one known compound toonapubesic acid B(6)were isolated from the leaves of Walsura robusta.Their structures were elucidated by NMR and MS data.Especially,the absolute configuration of toonapubesic acid B(6)was confirmed by X-ray diffraction study.Compounds 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60,SMMC-7721,A-549,MCF-7,and SW480.展开更多
Four new limonoids,dysohainanins A-D(1-4),and two new triterpenoids,dysohainanins E and F(5 and 6),together with seven known ones were isolated from the twigs and leaves of Dysoxylum hainanense Merr.The structures of ...Four new limonoids,dysohainanins A-D(1-4),and two new triterpenoids,dysohainanins E and F(5 and 6),together with seven known ones were isolated from the twigs and leaves of Dysoxylum hainanense Merr.The structures of the new compounds were determined by a variety of spectroscopic methods.The cytotoxic activities of these compounds were evaluated,and the known compound ent-19-nor-4,16,18-trihydroxy-8(14)-pomaren-15-one(13)showed in vitro cytotoxicity against HL-60,A-549,MCF-7,and SW480 cells,with IC50 values of 24.3,28.1,30.7,and 22.5mM,respectively.Compounds 2 and 3 were tested their insecticidal activities using brine shrimp and both of them were inactive.展开更多
A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the me...A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.展开更多
Four new limonoids,toonayunnanaes F−I(1−4),and six known compounds(5−10)were isolated from the barks of Toona ciliata.Their structures were elucidated by thoroughly analyzing of NMR and HRMS data,and single-crystal X-...Four new limonoids,toonayunnanaes F−I(1−4),and six known compounds(5−10)were isolated from the barks of Toona ciliata.Their structures were elucidated by thoroughly analyzing of NMR and HRMS data,and single-crystal X-ray diffraction of 1.The oxetane ring moiety in 1 was rare in limonoids and other natural products.Compound 1 showed nitric oxide(NO)inhibitory effect with an IC5038.45±0.41μM in lipopolysaccharide(LPS)-activated RAW 264.7 macrophages.展开更多
The high morbidity generated by the infection caused by parasites of the genus Leishmania, make of this infection into one of the vector-borne infectious diseases most relevant worldwide, which added to the fact that ...The high morbidity generated by the infection caused by parasites of the genus Leishmania, make of this infection into one of the vector-borne infectious diseases most relevant worldwide, which added to the fact that the drugs used for its treatment are far from be optimal and considering that prophylactic approaches (such as the development of a vaccine) still seems far from being achieved, make of the search for new therapeutic alternatives for safe and effective treatment of this disease one of the most accurate approaches to the control of this disease. In this study we evaluated the antileishmanial and immunomodu- latory activity of the compound 11α,19β-dihydroxy- 7-acetoxy-7-deoxoichangin (a seco-limonid molecule) through: 1) evaluation of its cytotoxicity over promastigotes and axenic amastigotes of L. (V) panamensis, 2) determination of its ability to induce the control of in vitro infection, using infected murine cells (J774.2) and human dendritic cells (hDCs), 3) quantifying the levels of pro-inflammatory cytokines, (iv) evaluating the expression of cell markers associated with hDCs maturation, and (v) determinating the production of nitric oxide free radicals (NO). In this regard, this seco-limonoid exhibited an antileishmanial activity represented in the reduction of in vitro infection in J774.2 cells and hDCs, with a EC50 of 7.9 μM (4.48 μg/mL) and 25.5 μM (14.39 μg/mL), respectively, and additionally, we observed an increase on the production of IL-12p70, TNF-α and NO, as also, in the number of hDCs HLA-DR-positive in treated infected hDCs. These findings suggest that anti-lei- shmanial activity of this compound could be associated with the potential “reactivation” of phagocytic cell that is “paralyzed” by the infection, generating an immune phenotype associated with protection.展开更多
基金Supported by Science and Technology Fund of Guizhou health and Health Committee(gzwkj2024-240)Anshun City Science and Technology Bureau(ASKS[2024]01).
文摘[Objectives]This study was conducted to explore the action mechanism of limonoids against Alzheimer s disease(AD)based on network pharmacology and molecular docking techniques.[Methods]Limonoid compounds were obtained through literature research(January 1942 to January 2021).Active components and potential targets of limonoids were retrieved from PubChem,TCMSP,and Swiss Target Prediction databases.AD-related targets were obtained from the GeneCards database,and intersecting targets were identified using Venny 2.1.0 to obtain the action targets of limonoids against AD.The protein-protein interaction(PPI)network was constructed using the String platform,and key targets were screened and visualized via network topology analysis with Cytoscape software.GO and KEGG pathway enrichment analyses were performed using the Metascape database,and a"drug-component-target-pathway-disease"network diagram was constructed using Cytoscape.AutoDock was empolyed for molecular docking to predict the binding properties of limonoid active components and their targets.[Results]A total of 60 limonoid compounds were obtained from literature research.Network pharmacology analysis showed 58 effective active components and 134 common targets between limonoids and AD.Key targets included AKT1(serine/threonine-protein kinase 1),TNF(tumor necrosis factor),STAT3(signal transducer and activator of transcription 3),BCL2(B-cell lymphoma 2),and EGFR(epidermal growth factor receptor).KEGG enrichment analysis revealed key signaling pathways such as pathways in cancer,Kaposi sarcoma-associated herpesvirus infection,PI3K-Akt signaling pathway,lipid and atherosclerosis,proteoglycans in cancer,MAPK signaling pathway,and Ras signaling pathway.Molecular docking results indicated that aphanamixoid A,obacunol,cipadesin C,harpertrioate A,xylogranatin A,11-oxocneorin G,evodulone,methyl angolensate,harrpemoid B and khivorin may be key components of limonoids against AD.[Conclusions]Limonoids exert anti-Alzheimer s effects through a multi-molecule,multi-target and multi-pathway mechanism.
文摘Two new limonoid-type triterpenoids, named 12-o-ethyl-l-deacetylnimbolinin B and 1-o-tigloyl-1-o-debenzoylohchinal, have been isolated from the fruit of Melia toosendan Sieb. et Zucc. Their structures were elucidated by spectral methods, including 2D-NMR spectra.
基金supported by National Natural Science Foundation of China(No.31440027)Natural Science Foundation of Shanxi Province,China(No.201601D011123)+1 种基金Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi(No.2014133)Science and Technology Innovation Found of Shanxi Medical University(No.C01201008)
文摘Two new limonoids, 12-ethoxynimbolinins G and H(compounds 1 and 2), and one known compound, toosendanin(Chuanliansu)(compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin(3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.
基金supported by National Natural Science Foundation of China(No.31440027)the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi(No.2014133)+2 种基金Natural Science Foundation for Young Scientists of Shanxi Province,China(No.2011021007-3)the Science and Technology Innovation Found of Shanxi Medical University(No.C01201008)the Program for the Top Science and Technology Innovation Teams of Higher Learning Institutions of Shanxi Province,China
文摘In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin(1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin(2), together with other four known limonoids(3-6), were isolated from the fruits of Melia toosendan. Their structures were elucidated by means of extensive spectroscopic analyses(NMR and ESI-MS) and comparisons with the data reported in the literature. The isolated compounds were evaluated for their antibacterial activities. Compound 4 exhibited significant antibacterial activity against an oral pathogen, Porphyromonas gingivalis ATCC 33277, with an MIC value of 15.2 μg·m L-1. Compound 2 was also active against P. gingivalis ATCC 33277, with an MIC value of 31.25 μg·m L-1. In conlcusion, our resutls indicate that these compounds may provide a basis for future development of novel antibiotics.
基金supported by the National Natural Science Foundation of China(No.31470416)the Outstanding Youth Fund of the Basic Research Program of Jiangsu Province(No.BK20160077)the Program for Changjiang Scholars and Innovative Research Team in University(No.IRT_15R63)
文摘Six new trichilin-type limonoids(1-6)with C-19/29 lactol or acetal bridge and a new ring intact limonoid(7)were isolated from the desiccative ripe fruits of Trichilia sinensis.Their structures were determined by extensive spectroscopic methods including 1 H NMR,13 C NMR,HSQC,HMBC,ROESY experiments as well as HRESI-MS data.All isolated compounds were evaluated for toxicities against human pulmonary carcinoma A549 and Hela cell lines by sulforhodamine B(SRB)method.Compound 7 showed weak inhibitory activity in Hela cell line at 40μmol·L^-1.
基金supported by the National Natural Science Foundation of China(No.31470416)the 111 Project from Ministry of Education of China and the State Administration of Foreign Export Affairs of China(No.B18056).ll supported in part by SciGrid,Chinese Academy of Sciences。
文摘Mufolinin A(1),a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton,together with three new potential precursors(ring A-seco limonoids,2–4)were isolated from Munronia unifoliolata.Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR),high resolution electrospray ionization mass spectroscopy(HRESIMS),X-ray crystallography,electronic circular dichroism(ECD)calculations and NMR calculations with DP4+analyses.The unprecedented ethyl group of 1 was hypothesized to be derived from methyl migration and ring reduction rearrangement of ring A-seco limonoid 4.Compounds 2 and 4 showed significant multidrug resistance(MDR)reversal activities in MCF-7/DOX cells with reversal fold(RF)values of 13.1 and 8.0,respectively.
文摘Two new limonoids,1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12α-ethoxyl nimbolinin（1） and lα-benzoyloxy-3α-acetoxyl-7α- hydroxyl-12α-ethoxyl nimbolinin（2）,were isolated from the fruits of Melia toosendan.Their structures were established on the basis of various NMR spectroscopic analyses,including 2D-NMR techniques（HSQC,HMBC,NOESY） and HR-ESI-MS.
基金supported by grants from the National Basic Research Program of China(973 Program,2009CB522300 and 2009CB940900)National Natural Science Funding of China(31170332)the Young Academic and Technical Leader Raising Foundation of Yunnan Province(2010CI047).
文摘Five new mexicanolide-type limonoids,heytrijunolides A-E(1-5)were isolated from the branches and leaves of Heynea trijuga.The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis.Compound 3 showed weak cytotoxicity against HL-60,SMMC-7721 and A-549 human tumor cell lines with the IC50 values of 21.88,20.66 and 12.70μM,respectively.
基金This research work was financially supported by the National Marine‘863’Projects(No.2013AA092902)the Natural Science Foundation of China(Nos.21021063,81273430,and 2107224)was partially funded by the EU 7th Framework Programme-IRSES Project(No.246987).
文摘A new trijugin-type limonoid,cipatrijugin G(1),together with the related known cipatrijugin A(2),were isolated from the aerial parts of Cipadessa cinerascens.The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature.Compound 1 showed cytotoxicity against tumor cell line A549 with an IC_(50) value of 9.78μM.This is the first report of a trijugin-type limonoid bearing aγ-hydroxybutenolide unit,in comparison to the common furan unit as ring E.
基金supported by grants from Thousand Young Talents Program of China and the National Natural Science Foundation of China (No. 81673530)
文摘A new cytotoxic salannin-class limonoid alkaloid, azadiramide A（1）,was isolated from seeds of Azadirachta indica A. Juss. Its structure was elucidated by extensive analysis of spectroscopic data and quantum chemical calculation. Compound 1 is a rare salannin-class limonoid alkaloid. To our best knowledge, only two compounds belonging to this type were so far found. It showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC_（50） value of 2.70±0.63 μmol/L.
基金the NSFC 21002105,the 973 Program of Science and Technology of P.R.China(2011CB915503)the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province(Min XU,2011CI044)。
文摘Two new highly oxygenated limonoids,flexuosoids A(1)and B(2),and three new arylnaphthalene lignan glycosides,phyllanthusmins D–F(3–5),were isolated from the roots of Phyllanthus flexuosus,in addition to three known lignans,phyllanthusmin C,arabelline,and(?)-diasyringaresinol.Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods.Compounds 1 and 2,two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1,C-2,C-3,C-7,C-11,C-17,and C-30,represent the second example of limonoids in the Euphorbiaceae family.Most of the isolates were tested for their antifeedant,anti-herpes simplex virus 1,and cytotoxic activities.The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua)with EC50 values of 25.1 and 17.3 lg/cm2,respectively.In addition,both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line,along with the known lignan glycoside,phyllanthusmin C,with the IC50 values of 11.5(1),8.5(2),and 7.8(phyllanthusmin C)lM,respectively.
基金supported by the National Natural Science Foundation of China(Nos.31470416 and 81430092)the Program for New Century Excellent Talents in University(No.NCET-2013-1035)+1 种基金the Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD)the Program for Changjiang Scholars and Innovative Research Team in University(IRT_15R63)
文摘Two new phragmalin-type limonoids orthoesters, encandollens A and B(1 and 2), were isolated from the stem barks of Entandrophragma candollei collected in Ghana. The structures of these compounds were elucidated on the basis of HR-ESI-MS, ~1 H and ^(13) C NMR, HSQC, HMBC, and ROESY data. Compound 1 was a rare C-15 enolic acyl phragmalin-type limonoid orthoester. Compounds 1 and 2 exhibited weak inhibitory effects on NO production in lipopolysaccharide(LPS)-induced RAW 264.7 cells.
基金supported financially by the National Special Program of Basic Research(SB2007FY400)the Knowledge Innovation Program of CAS(Grant No.Qian-2011,KSCX2-YW-G-038)+1 种基金Foundation of Yunnan Tobacco Industry Group(2010-2012)State Key Laboratory of Phytochemistry and Plant Resources in West China.
文摘Three new compounds,including two diterpenoids,nemoralisins H and I(1 and 2),and a limonoid,2-methoxy khayseneganin E(3),along with four known constituents(4-7),were isolated from the leaves and twigs of Swietenia mahagoni.Their chemical structures were elucidated by means of spectroscopic analysis.The cytotoxities of these isolated constituents were assayed.
基金supported by the National Natural Science Foundation of China(No.81573550)the Outstanding Youth Fund of the Basic Research Program of Jiangsu Province(BK20160077)
文摘Two new furan fragment isomerized limonoids, meliazedalides A and B(compounds 1 and 2), were isolated from the fruits of Melia azedarach Linn.. Their chemical structures were elucidated on the basis of HR-ESI-MS and 1D and 2D NMR data, which belonged to nimbolinin-and trichilin-class, respectively. Compound 2 exhibited weak inhibitory effect on NO production in lipopolysaccharide(LPS)-activated RAW 264.7 macrophages with IC_(50) being 37.41 μmol·L^(–1).
文摘A new limonoid named rohituka-15 1, with a known limonoid dregeana-1 2, was isolated from the seed of Aphanamixis polystachya (Meliaceae). The 13C NMR data assignment of dregeana-1 2 and the structural elucidation of the new compound 1 were based on spectral analysis including 1H-1H COSY, HMQC and HMBC experiments.
基金the National Natural Science Foundation of China(U1812403 to X.-J.Hao and 22177050 to M.Cao)Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(2022YKZY001)+1 种基金Foundation of Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences(CAM202103,China)Youth Innovation Promotion Association CAS to M.Cao(2022-2026).
文摘Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D(1-4),and one new furan ring degraded limonoid walsurobustone E(5)together with one known compound toonapubesic acid B(6)were isolated from the leaves of Walsura robusta.Their structures were elucidated by NMR and MS data.Especially,the absolute configuration of toonapubesic acid B(6)was confirmed by X-ray diffraction study.Compounds 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60,SMMC-7721,A-549,MCF-7,and SW480.
基金supported by grants from the Ministry of Science and Technology(2009CB522300 and 2009CB940900).
文摘Four new limonoids,dysohainanins A-D(1-4),and two new triterpenoids,dysohainanins E and F(5 and 6),together with seven known ones were isolated from the twigs and leaves of Dysoxylum hainanense Merr.The structures of the new compounds were determined by a variety of spectroscopic methods.The cytotoxic activities of these compounds were evaluated,and the known compound ent-19-nor-4,16,18-trihydroxy-8(14)-pomaren-15-one(13)showed in vitro cytotoxicity against HL-60,A-549,MCF-7,and SW480 cells,with IC50 values of 24.3,28.1,30.7,and 22.5mM,respectively.Compounds 2 and 3 were tested their insecticidal activities using brine shrimp and both of them were inactive.
基金the Natural Science Foundation of China(81225024)the National Science and Technology Support Program of China(2013BAI11B02)。
文摘A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.
基金supports for this study were from the National Natural Science Foundation of China(31470416)the National New Drug Innovation Major Project(2018ZX09711-001-007)+1 种基金the National Key R&D Program of China(2018YFC1707105)the"Double First-Class"University project(CPU2018GY08,China).
文摘Four new limonoids,toonayunnanaes F−I(1−4),and six known compounds(5−10)were isolated from the barks of Toona ciliata.Their structures were elucidated by thoroughly analyzing of NMR and HRMS data,and single-crystal X-ray diffraction of 1.The oxetane ring moiety in 1 was rare in limonoids and other natural products.Compound 1 showed nitric oxide(NO)inhibitory effect with an IC5038.45±0.41μM in lipopolysaccharide(LPS)-activated RAW 264.7 macrophages.
文摘The high morbidity generated by the infection caused by parasites of the genus Leishmania, make of this infection into one of the vector-borne infectious diseases most relevant worldwide, which added to the fact that the drugs used for its treatment are far from be optimal and considering that prophylactic approaches (such as the development of a vaccine) still seems far from being achieved, make of the search for new therapeutic alternatives for safe and effective treatment of this disease one of the most accurate approaches to the control of this disease. In this study we evaluated the antileishmanial and immunomodu- latory activity of the compound 11α,19β-dihydroxy- 7-acetoxy-7-deoxoichangin (a seco-limonid molecule) through: 1) evaluation of its cytotoxicity over promastigotes and axenic amastigotes of L. (V) panamensis, 2) determination of its ability to induce the control of in vitro infection, using infected murine cells (J774.2) and human dendritic cells (hDCs), 3) quantifying the levels of pro-inflammatory cytokines, (iv) evaluating the expression of cell markers associated with hDCs maturation, and (v) determinating the production of nitric oxide free radicals (NO). In this regard, this seco-limonoid exhibited an antileishmanial activity represented in the reduction of in vitro infection in J774.2 cells and hDCs, with a EC50 of 7.9 μM (4.48 μg/mL) and 25.5 μM (14.39 μg/mL), respectively, and additionally, we observed an increase on the production of IL-12p70, TNF-α and NO, as also, in the number of hDCs HLA-DR-positive in treated infected hDCs. These findings suggest that anti-lei- shmanial activity of this compound could be associated with the potential “reactivation” of phagocytic cell that is “paralyzed” by the infection, generating an immune phenotype associated with protection.
