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
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
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
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
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 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
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
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
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
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
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
Twelve new limonoids(1—12),named trichilitins A—L,were isolated from the leaves and twigs of Trichilia connaroides,together with ten known compounds(13—22).The structures were elucidated by extensive spectroscopic ...Twelve new limonoids(1—12),named trichilitins A—L,were isolated from the leaves and twigs of Trichilia connaroides,together with ten known compounds(13—22).The structures were elucidated by extensive spectroscopic investigations,X-ray diffraction analyses,and ECD calculations.Compound 1,which belongs to a unique class of ring B-seco limonoid,has been identified as 6/7/6/5 tetracyclic due to a key Baeyer-Villiger oxidation.Compounds 2—7 were identified as ring intact limonoids,while compounds 8—10 were established as ring D-seco ones,and 11 and 12 were determined to be rearranged ones.All of the compounds were tested for cytotoxicity against three human tumor cell lines(HCT-116,NCl-H1975,and SH-SY5Y).Compounds 6,7,13,14,and 19 exhibited significant cytotoxic effects,especially 7 exhibited significant cytotoxic effects against HCT-116 with an IC_(50)value of 0.035μmol·L^(–1)and was more active than the positive control,doxorubicin with an IC_(50)value of 0.20μmol·L^(–1).Compound 7 effectively induced apoptosis of HCT-116,which was associated with S-phase cell cycle arrest.Furthermore,the Western blot analysis showed that compound 7 could induce cell cycle arrest by promoting the expression levels of p53 and p21.展开更多
[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
Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were i...Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were isolated from Munronia unifoliolata.Their structures including absolute configurations were elucidated by combination of NMR,HR-MS,single-crystal X-ray diffraction and calculations of ECD and NMR technologies.Compounds 24,25,33,34 could be significantly reversed the multidrug resistance of MCF-7/doxorubicin(DOX)cells,and the reversal fold(RF)was much higher than that of positive drug Verapamil.Compounds 24,28,and 29 exhibited significant anti-inflammatory activity with the IC50 values in the range of 17.7—39.4μmol/L.Furthermore,compound 29 could markedly inhibit the release of IL-1βby inhibiting the initiation and assembly of NLRP3 inflammasome,which demonstrates the great potential of limonoids as an anti-inflammatory agent.展开更多
Six new mexicanolide-type limonoids, dysoxylumasins A-F （1-6）, together with eight known compounds, namely litseagermacrane, 15-methoxyisodauc-3-ene-1β, 5α-diol, isodauc-6-ene-10β,14-diol, 4-epi-isodauc-6-ene- 10...Six new mexicanolide-type limonoids, dysoxylumasins A-F （1-6）, together with eight known compounds, namely litseagermacrane, 15-methoxyisodauc-3-ene-1β, 5α-diol, isodauc-6-ene-10β,14-diol, 4-epi-isodauc-6-ene- 10β,14-diol, 2a,3a,4β-trihydroxypregnan-16-one, 1,7-phenanthrenedimethanol, spicatin, and aurantiamide, were isolated from the leaves and twigs of Dysoxylum mollissimum B1. Their structures were established by the analyses of spectroscopic data.展开更多
Four new limonoids, named aphanagranins A-D （1-4）, were isolated from the fruits ofAphanamixis grandi- folia. The new structures were determined by spectroscopic methods especially 1D and 2D NMR analysis, Aphana- gr...Four new limonoids, named aphanagranins A-D （1-4）, were isolated from the fruits ofAphanamixis grandi- folia. The new structures were determined by spectroscopic methods especially 1D and 2D NMR analysis, Aphana- granin A （1） possessed a rare four membered oxygen heterocyclic ring and its absolute configurations were deter- mined on the basis of the signal crystal X-ray diffraction analysis. Furthermore, compounds 1 and 2 showed weak activity toward brine shrimp （Artemia salina）.展开更多
Three limonoids cipaferoids A-C （1-3） representing two different scaffolds were isolated from Cipadessa baccifera. Their structures were completely assigned by spectroscopic data, CD exciton chirality method, and X-...Three limonoids cipaferoids A-C （1-3） representing two different scaffolds were isolated from Cipadessa baccifera. Their structures were completely assigned by spectroscopic data, CD exciton chirality method, and X-ray crystallography. Compounds 2 and 3 exhibited moderate antimalarial activity with IC50 values of 9.3±0.1 and 14.7±4.8 μmol·L^-1, respectively.展开更多
Screening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery1. We hereby reported the isolation of seven new neotecleanin-type limo...Screening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery1. We hereby reported the isolation of seven new neotecleanin-type limonoids(1–7), seven new limonoids with 5-oxatricyclo[5.4.0.11,4]hendecane ring system(8–14), and two new precursors(15–16) together with four known limonoids(17–20) from the root barks of Walsura robusta. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR, ECD spectrum calculations and singlecrystal X-ray diffraction techniques. Compounds 2, 8, 9, 11, 13, 14, 18 showed significant anti-inflammatory activities in LPS-induced RAW 264.7 cell line, BV2 microglial cells, and Propionibacterium acnes-stimulated THP-1 human monocytic cells. Walrobsin M(11) exhibited anti-inflammatory activity with IC50 value of 7.9670.36 μmol/L, and down-regulated phosphorylation levels of ERK and p38 in a dose-dependent manner.展开更多
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 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 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(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.
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.
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 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).
基金Financial support for this study was provided by National Natural Science Foundation of China(82360687)Guizhou Provincial Science and Technology Project(ZK[2022]393)+1 种基金Key Research and Development Project of Yunnan Province(202203AC100009,202003AD150012)Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(2022YKZY001).
文摘Twelve new limonoids(1—12),named trichilitins A—L,were isolated from the leaves and twigs of Trichilia connaroides,together with ten known compounds(13—22).The structures were elucidated by extensive spectroscopic investigations,X-ray diffraction analyses,and ECD calculations.Compound 1,which belongs to a unique class of ring B-seco limonoid,has been identified as 6/7/6/5 tetracyclic due to a key Baeyer-Villiger oxidation.Compounds 2—7 were identified as ring intact limonoids,while compounds 8—10 were established as ring D-seco ones,and 11 and 12 were determined to be rearranged ones.All of the compounds were tested for cytotoxicity against three human tumor cell lines(HCT-116,NCl-H1975,and SH-SY5Y).Compounds 6,7,13,14,and 19 exhibited significant cytotoxic effects,especially 7 exhibited significant cytotoxic effects against HCT-116 with an IC_(50)value of 0.035μmol·L^(–1)and was more active than the positive control,doxorubicin with an IC_(50)value of 0.20μmol·L^(–1).Compound 7 effectively induced apoptosis of HCT-116,which was associated with S-phase cell cycle arrest.Furthermore,the Western blot analysis showed that compound 7 could induce cell cycle arrest by promoting the expression levels of p53 and p21.
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.
基金sponsored by the National Natural Science Foundation of China(31470416)the 111 Project from Ministry of Education of Chinathe State Administration of Foreign Export Affairs of China(B18056).
文摘Twenty-two new limonoids,mufolinoids A—V(1—22),including six rings A,B-seco limonoids(1—6),twelve ring A-seco limonoids(7—18),four ring-intact limonoids(19—22),together with thirteen known compounds(23—35)were isolated from Munronia unifoliolata.Their structures including absolute configurations were elucidated by combination of NMR,HR-MS,single-crystal X-ray diffraction and calculations of ECD and NMR technologies.Compounds 24,25,33,34 could be significantly reversed the multidrug resistance of MCF-7/doxorubicin(DOX)cells,and the reversal fold(RF)was much higher than that of positive drug Verapamil.Compounds 24,28,and 29 exhibited significant anti-inflammatory activity with the IC50 values in the range of 17.7—39.4μmol/L.Furthermore,compound 29 could markedly inhibit the release of IL-1βby inhibiting the initiation and assembly of NLRP3 inflammasome,which demonstrates the great potential of limonoids as an anti-inflammatory agent.
基金Acknowledgement Financial support by the National Science ＆ Tech- nology Major Project ＂Key New Drug Creation and Manufacturing Program＂ （No. 2011ZX09307-002-03）, and the National Natural Science Foundation （No. 21072203） of the People＇s Republic of China, are gratefully acknowledged. We thank Prof. Youkai Xu of Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, for the identification of the plant material.
文摘Six new mexicanolide-type limonoids, dysoxylumasins A-F （1-6）, together with eight known compounds, namely litseagermacrane, 15-methoxyisodauc-3-ene-1β, 5α-diol, isodauc-6-ene-10β,14-diol, 4-epi-isodauc-6-ene- 10β,14-diol, 2a,3a,4β-trihydroxypregnan-16-one, 1,7-phenanthrenedimethanol, spicatin, and aurantiamide, were isolated from the leaves and twigs of Dysoxylum mollissimum B1. Their structures were established by the analyses of spectroscopic data.
文摘Four new limonoids, named aphanagranins A-D （1-4）, were isolated from the fruits ofAphanamixis grandi- folia. The new structures were determined by spectroscopic methods especially 1D and 2D NMR analysis, Aphana- granin A （1） possessed a rare four membered oxygen heterocyclic ring and its absolute configurations were deter- mined on the basis of the signal crystal X-ray diffraction analysis. Furthermore, compounds 1 and 2 showed weak activity toward brine shrimp （Artemia salina）.
基金This work was financially supported by the National Natural Science Foundation （Nos. 21532007, 81273398, and 81321092） of the People＇s Republic of China.
文摘Three limonoids cipaferoids A-C （1-3） representing two different scaffolds were isolated from Cipadessa baccifera. Their structures were completely assigned by spectroscopic data, CD exciton chirality method, and X-ray crystallography. Compounds 2 and 3 exhibited moderate antimalarial activity with IC50 values of 9.3±0.1 and 14.7±4.8 μmol·L^-1, respectively.
基金Financial support for this study by the National Natural Science Foundation of China (31470416, China)the Outstanding Youth Fund of the Basic Research Program of Jiangsu Province (BK20160077, China)+1 种基金the Program for Changjiang Scholars and Innovative Research Team in University (IRT_15R63, China)the "Double First-Class" University project (CPU2018GY08, China)
文摘Screening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery1. We hereby reported the isolation of seven new neotecleanin-type limonoids(1–7), seven new limonoids with 5-oxatricyclo[5.4.0.11,4]hendecane ring system(8–14), and two new precursors(15–16) together with four known limonoids(17–20) from the root barks of Walsura robusta. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR, ECD spectrum calculations and singlecrystal X-ray diffraction techniques. Compounds 2, 8, 9, 11, 13, 14, 18 showed significant anti-inflammatory activities in LPS-induced RAW 264.7 cell line, BV2 microglial cells, and Propionibacterium acnes-stimulated THP-1 human monocytic cells. Walrobsin M(11) exhibited anti-inflammatory activity with IC50 value of 7.9670.36 μmol/L, and down-regulated phosphorylation levels of ERK and p38 in a dose-dependent manner.
