41 results on '"Song, SJ"'
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2. Aromatic glycosides and lignans glycosides with their acetylcholinesterase inhibitory activities from the leaves of Picrasma quassioides.
- Author
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Jia Q, Yang PY, Zhang X, Song SJ, and Huang XX
- Subjects
- Molecular Structure, Acetylcholinesterase, Butyrylcholinesterase, Glycosides pharmacology, Molecular Docking Simulation, Cholinesterase Inhibitors pharmacology, Circular Dichroism, Lignans pharmacology, Picrasma chemistry
- Abstract
In this study, eight new natural products were isolated from the leaves of Picrasma quassioides. Spectroscopic techniques were used for the elucidation of their planar structures. Their absolute configurations were elucidated on the basis of electron circular dichroism (ECD) techniques combined with the P/M helicity rule for the 2,3-dihydrobenzofuran chromophore, and saccharide hydrolysis. Cholinesterase inhibitors are often used as Alzheimer's disease inhibitors.Thus, acetylcholinesterase and butyrylcholinesterase inhibitory activity of these eight compounds were tested, and results showed that only compound 6 showed weakly acetylcholinesterase inhibitory activity. In particular, molecular docking was used to illustrate the bindings between compound 6 and the active sites of AChE., Competing Interests: Declaration of Competing Interest The authors declare that there is no conflict of interest., (Copyright © 2023. Published by Elsevier B.V.)
- Published
- 2024
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3. Four pair of enantiomeric benzofuran lignans from the fruits of Crataegus pinnatifida bunge.
- Author
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Zhang DD, Zhao P, Huang SW, Song SJ, and Huang XX
- Subjects
- Fruit chemistry, Stereoisomerism, Molecular Structure, Lignans chemistry, Crataegus chemistry, Benzofurans analysis
- Abstract
Phytochemical investigation of the fruits of Crataegus pinnatifida Bunge led to the isolation of four pairs enantiomeric benzofuran lignans ( 1a / 1b - 4a / 4b ) including four undescribed compounds ( 1a , 2b , 3b and 4b ). Their structures were determined by extensive spectroscopic methods and the absolute configurations were further determined by the comparison of experimental and calculated ECD spectra. All the enantiomeric lignans were evaluated for their inhibitory activities to tyrosinase. Among them, compound 4a showed moderate inhibition activity (IC
50 = 0.54 mM).- Published
- 2023
- Full Text
- View/download PDF
4. Insight into tetrahydrofuran lignans from Isatis indigotica fortune with neuroprotective and acetylcholinesterase inhibitor activity.
- Author
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Xi YF, Bai M, Zhang X, Hou ZL, Lin B, Yao GD, Lou LL, Wang XB, Song SJ, and Huang XX
- Subjects
- Humans, Acetylcholinesterase, Cholinesterase Inhibitors, Hydrogen Peroxide, Furans chemistry, Molecular Structure, Lignans chemistry, Isatis chemistry, Neuroblastoma
- Abstract
Nine tetrahydrofuran lignans, including three undescribed spiro-lignans, were isolated from Isatis indigotica Fortune (Brassicaceae). Extensive spectroscopic analyses achieved the structure elucidation of these tetrahydrofuran lignans, and quantum chemical calculation combined with the MAE
ΔΔδ parameter. Notably, isatispironeols A-B have a unique spiro[dienone-tetrahydrofuran] molecular core. These spiro[dienone-tetrahydrofuran] lignans showed comparable neuroprotective effects as the positive control in the H2 O2 -induced SH-SY5Y cells model. In addition, (-)-(7R,8S,1'R,7'R,8'R)-isatispironeol A possessed more significant AChE inhibitory activity, further interact sites were also predicted by the in silico assay., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)- Published
- 2023
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5. Chemical structures and anti-tyrosinase activity of the constituents from Elephantopus scaber L.
- Author
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Xu W, Bai M, Du NN, Song SJ, Lin B, and Huang XX
- Subjects
- Lactones, Molecular Docking Simulation, Molecular Structure, Sesquiterpenes, Germacrane, Alkaloids, Asteraceae chemistry, Lignans, Sesquiterpenes
- Abstract
Four undescribed compounds including one germacrane-type sesquiterpene lactones (1), alkaloid (2) along with two neolignans (3-4) were isolated from Elephantopus scaber L. Their structures and absolute configurations were elucidated unambiguously by means of 1D and 2D NMR spectroscopic data analysis, and quantum chemical electronic circular dichroism calculations, as well as single-crystal X-ray crystallography. Their anti-tyrosinase activities have been evaluated in vitro and compound 2 exhibited significant inhibitory activity. Furthermore, molecular docking was performed to study the interaction patterns between 2 and the tyrosinase., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. No potential conflict of interest was reported by the authors., (Copyright © 2022. Published by Elsevier B.V.)
- Published
- 2022
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6. Lignans with neuroprotective activity from the fruits of Crataegus pinnatifida.
- Author
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Xin BS, Zhao P, Qin SY, Yao GD, Huang XX, and Song SJ
- Subjects
- Fruit chemistry, Humans, Hydrogen Peroxide analysis, Molecular Structure, Crataegus chemistry, Lignans pharmacology, Neuroblastoma, Neuroprotective Agents chemistry, Neuroprotective Agents pharmacology
- Abstract
Seven lignans (1a/1b-2a/2b and 3-5), including six new compounds (1b, 2a/2b, 3-5), were isolated from the fruits of Crataegus pinnatifida. Their structures were elucidated by comprehensive spectroscopic analyses. Compounds 1b/1b-2a/2b were two pairs of enantiomers and the absolute configurations were determined by comparison of their experimental and calculated ECD spectra. Moreover, bioinformatics analysis suggested that more than a third of diseases were related to the nervous system. Therefore, all compounds were evaluated for neuroprotective effects toward human neuroblastoma SH-SY5Y cells injury induced by H
2 O2 . Among them, compound 1a exhibited moderate protective effect., (Copyright © 2022 Elsevier B.V. All rights reserved.)- Published
- 2022
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7. A new dilignan from the twigs and leaves of Archidendron clypearia .
- Author
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Wang YX, Duan ZK, Shi WY, Chang Y, Huang XX, and Song SJ
- Subjects
- Molecular Structure, Plant Extracts, Plant Leaves, Fabaceae, Lignans
- Abstract
Previous work has shown that the lignans from the twigs and leaves of Archidendron clypearia (Jack) I.C.N. possess anti- β -amyloid aggregation activity. Here we report a new dilignan, archidendronin A ( 1 ), along with one known sesquilignan ( 2 ). Their structures were determined by extensive spectroscopic methods, including UV, HRESIMS, 1 D and 2 D NMR data. The inhibitory activity on A β
1-42 aggregation was screened by ThT assay with curcumin as the positive control, and compounds 1 and 2 showed inhibition rate of 60.0% and 64.4% at 20 μ M, respectively.[Formula: see text].- Published
- 2021
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8. A new dineolignan with anti- β -amyloid aggregation activity from the fruits of crataegus pinnatifida bge.
- Author
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Zhao P, Lou LL, Zhang H, Guo R, Wang XB, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides metabolism, Fruit chemistry, Molecular Structure, Peptide Fragments metabolism, Plants, Medicinal chemistry, Protein Aggregates drug effects, Spectrometry, Mass, Electrospray Ionization, Amyloid beta-Peptides antagonists & inhibitors, Crataegus chemistry, Lignans chemistry, Peptide Fragments antagonists & inhibitors
- Abstract
A new dineolignan, crataeguslignan A ( 1 ), along with one known dineolignan ( 2) were isolated from the fruits of Crataegus pinnatifida Bge. Its chemical structure was identified by comprehensive spectroscopic analyses. All the isolated compounds were investigated with regard to their A β
1-42 inhibition activity. Among them, 1 displayed the most potent A β1-42 inhibitory ability with the inhibition rate of 85.2% at the concentration of 20 μM.- Published
- 2021
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9. Enantiomeric 8-O-4'-type neolignans from Crataegus pinnatifida exhibit cytotoxic effect via apoptosis and autophagy in Hep3B cells.
- Author
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Shang XY, Guo R, Yu XQ, Lin B, Huang XX, Yao GD, and Song SJ
- Subjects
- Antineoplastic Agents chemistry, Antineoplastic Agents isolation & purification, Cell Proliferation drug effects, Cell Survival drug effects, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Lignans chemistry, Lignans isolation & purification, Molecular Structure, Stereoisomerism, Structure-Activity Relationship, Tumor Cells, Cultured, Antineoplastic Agents pharmacology, Apoptosis drug effects, Autophagy drug effects, Crataegus chemistry, Lignans pharmacology
- Abstract
Crataegus pinnatifida has been famous for its nutritional purpose. However, systematic investigation on the bioactive constituents is still lacking, although this fruit has been reported for its cytotoxic effect before. In this study, two pairs of new lignan enantiomers (1a/1b, 2a/2b), which isolated using chiral chromatographic column from the fruits of C. pinnatifida were studied. The absolute configurations of enantiomers were determined by comparison between the experimental electronic circular dichroism (ECD) and calculated ECD spectra. Among them, 1a/1b exhibited a better cytotoxic effect in hepatocellular carcinoma Hep3B cells with an IC
50 value of 34.97 ± 2.74 and 17.42 ± 0.71 μM, respectively. In addition, 1b induced much more apoptotic, autophagic cells than 1a in Hep3B cells. Furthermore, the underlying mechanism was demonstrated that p38 activation could promote 1b-induced apoptosis and autophagy. Moreover, 1b-induced apoptosis was significantly decreased in the presence of autophagic inhibitor Bafilomycin A1 (Baf A1), suggesting that the induction of autophagy enhanced apoptotic cell death in 1b-treated cells. In general, these findings provide a valuable basis for further understanding the effect of 8-O-4' lignans in C. pinnatifida on cytotoxic effect., (Copyright © 2020 Elsevier Inc. All rights reserved.)- Published
- 2020
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10. Chiral-phase resolution of sesquilignans from raspberries (Rubus idaeus L.) and their neuroprotective effects.
- Author
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Lu LW, Le-Zhou, Hou ZL, Jie-Wang, Yao GD, Lin B, Huang XX, and Song SJ
- Subjects
- Cell Line, Tumor, China, Fruit chemistry, Humans, Lignans isolation & purification, Molecular Structure, Neuroblastoma, Neuroprotective Agents isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Lignans pharmacology, Neuroprotective Agents pharmacology, Rubus chemistry
- Abstract
Two pairs of diastereoisomers (1/2 and 3/4) were isolated from the fruits of Rubus idaeus L. (Rosaceae). Their structures were elucidated on the basis of extensive spectroscopic analyses. Then chiral-phase HPLC resolution gave 1a/1b-4a/4b. Their absolute configurations were determined by comparison of the experimental ECD with the calculated data. Moreover, all isolated compounds were investigated for the neuroprotective effects against H
2 O2 -induced neurotoxicity in human neuroblastoma SH-SY5Y cells, and 2a (66.04%) exhibited moderate neuroprotective effects, better than trolox (60.54%) at the concentration of 25 μM., Competing Interests: Declaration of Competing Interest The authors declare that there are no conflicts of interest., (Copyright © 2020 Elsevier B.V. All rights reserved.)- Published
- 2020
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11. Lignans and neolignans with isovaleroyloxy moiety from Solanum lyratum Thunb.: Chiral resolution, configurational assignment and neuroprotective effects.
- Author
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Li SS, Hou ZL, Yao GD, Guo R, Wang YX, Lin B, Huang XX, and Song SJ
- Subjects
- Humans, Hydrogen Peroxide, Molecular Structure, Lignans, Neuroprotective Agents, Solanum
- Abstract
Eight pairs of enantiomeric lignans and neolignans including thirteen undescribed compounds, along with an undescribed meso compound, were isolated from the herbs of Solanum lyratum Thunb.(Solanaceae). Their structures and relative configurations were determined by extensive spectroscopic analyses of HRESIMS and nuclear magnetic resonance. The absolute configurations of the pure isomers were established based on the cooperative comparison between the experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR). It is interesting that we obtained several naturally occurring stereoisomers with the identical gross structure possessing several stereogenic carbons from S. lyratum. Additionally, all isolates were assessed for neuroprotective effects toward human neuroblastoma SH-SY5Y cells injury induced by H
2 O2 ., (Copyright © 2020 Elsevier Ltd. All rights reserved.)- Published
- 2020
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12. Chiral resolution and bioactivity of enantiomeric furofuran lignans from Juglans mandshurica Maxim.
- Author
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Wang J, Zhou L, Cheng ZY, Wang YX, Yan ZY, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides metabolism, Juglans drug effects, Lignans chemistry, Molecular Docking Simulation, Molecular Dynamics Simulation, Molecular Structure, Peptide Fragments metabolism, Stereoisomerism, Dioxoles chemistry, Furans isolation & purification, Juglans chemistry, Lignans isolation & purification, Optical Rotation
- Abstract
Enantiomers have generally been reported mostly for racemic mixtures with a 1:1 ratio, as in that case there were weak Cotton effects in the ECD spectrum and negligible optical rotations. A furofuran lignan (sesamin), with a remarkable rotation and significant Cotton effects, was isolated from Juglans mandshurica Maxim. Subsequently, sesamin was resolved by chiral HPLC to afford a pair of enantiomers, (+)-sesamin ( a ) and (-)-sesamin ( b ), in a ratio of approximately 1:3. Their absolute configurations were determined by computational analysis of their electronic circular dichroism (ECD) spectrum. In addition, the pair of enantiomers were evaluated for the inhibition of self-induced A β aggregation. Interestingly, (+)-sesamin ( a ) (67.7%) and (-)-sesamin ( b ) (80.6%) exhibited different degrees of anti-A β aggregation activity. The different inhibition profiles were further explained by molecular dynamics and docking simulation study.
- Published
- 2020
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13. Sesquineolignans derivatives with neuroprotective activity from the fruits of Crataegus pinnatifida.
- Author
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Zhao P, Qiu S, Hou ZL, Xue XB, Yao GD, Huang XX, and Song SJ
- Subjects
- Cell Line, Tumor, Cell Survival drug effects, China, Humans, Lignans isolation & purification, Molecular Structure, Neuroblastoma, Neuroprotective Agents isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Crataegus chemistry, Fruit chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology
- Abstract
Ten undescribed sesquineolignans (1-10), including four sesqui-norlignans (1-4), were isolated from the fruits of Crataegus pinnatifida. Their structures were determined by comprehensive spectroscopic analyses. All compounds were examined for their neuroprotective activities against H
2 O2 -induced cell injury in human neuroblastoma SH-SY5Y cells. Among them, 6 and 8 showed comparable protective effect with 79.36% and 80.72% cell viability compared with the positive control Trolox (78.64%) at 25 μM., Competing Interests: Declaration of Competing Interest The authors declare that there are no conflicts of interest., (Copyright © 2020 Elsevier B.V. All rights reserved.)- Published
- 2020
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14. Anti- β -amyloid aggregation activity of enantiomeric furolactone-type lignans from Archidendron clypearia (Jack) I.C.N.
- Author
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Wang YX, Lin B, Zhou L, Yan ZY, Zhang H, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides drug effects, Circular Dichroism, Lignans isolation & purification, Lignans pharmacology, Molecular Docking Simulation, Molecular Structure, Phytochemicals pharmacology, Phytochemicals therapeutic use, Protein Aggregation, Pathological prevention & control, Stereoisomerism, Fabaceae chemistry, Lignans chemistry, Phytochemicals analysis, Protein Aggregation, Pathological drug therapy
- Abstract
The phytochemical investigation on the twigs and leaves of Archidendron clypearia (Jack) I.C.N. led to the isolation of three pairs of furolactone-type lignans enantiomers, including a pair of new compounds (1 R ,5 S ,6 S )-Kachiranol ( 1a ) and (1 S ,5 R ,6 R )-Kachiranol ( 1b ) and four known compounds ( 2a / 2b and 3a / 3b ). Separation of the furolactone-type lignans enantiomeric mixtures was achieved using chiral HPLC for the first time. Their structures were determined by spectroscopic analysis and comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. All optical pure compounds were evaluated for their inhibitory effects on β -amyloid aggregation by ThT assay. Among them, the inhibitory activity of the compound 1b (71.1%) was higher than the positive control (61.0%) and other compounds. In addition, molecular dynamics and molecular docking were employed to explore the binding relationship between the ligand and the receptor.
- Published
- 2020
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15. Enantiomeric 8,4'-type oxyneolignans from the root barks of Ailanthus altissima (Mill.) Swingle and their neuroprotective effects against H 2 O 2 -induced SH-SY5Y cells injury.
- Author
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Du YQ, Lin B, Yan ZY, Hou ZL, Guo R, Bai M, Zhou L, Huang XX, and Song SJ
- Subjects
- Cell Line, Tumor, China, Humans, Hydrogen Peroxide, Lignans isolation & purification, Molecular Structure, Neuroblastoma, Neuroprotective Agents isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Plant Bark chemistry, Plant Roots chemistry, Stereoisomerism, Ailanthus chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology, Oxidative Stress drug effects
- Abstract
Ailanthus altissima Swingle is a deciduous tree, belonging to the Simaroubaceae family. Phytochemical investigation of the root barks of A. altissima showed the presence of eight pairs of enantiomeric 8,4'-type oxyneolignans (1a/1b-8a/8b) including nine undescribed compounds (1b, 2a, 3a/3b, 4a/4b, 5b, 7b, 8a). Their structures were elucidated by comprehensive spectroscopic analyses, and their absolute configurations were determined by comparison of the experimental and quantum chemical calculations of electronic circular dichroism (ECD) curves. In addition, their neuroprotective effects against H
2 O2 -induced oxidative stress in human neuroblastoma SH-SY5Y cells were investigated. Among them, 4a, 4b, and 8b exhibited moderate neuroprotective activity., (Copyright © 2019 Elsevier B.V. All rights reserved.)- Published
- 2019
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16. Two new sesquineolignans from the seeds of Crataegus pinnatifida and their β -amyloid aggregation inhibitory activitiy.
- Author
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Guo R, Zhou L, Zhao P, Wang XB, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides metabolism, Cell Line, Drug Evaluation, Preclinical methods, Humans, Hydrogen Peroxide toxicity, Magnetic Resonance Spectroscopy, Molecular Structure, Neurons drug effects, Neurons metabolism, Neuroprotective Agents chemistry, Peptide Fragments metabolism, Seeds chemistry, Spectrometry, Mass, Electrospray Ionization, Amyloid beta-Peptides antagonists & inhibitors, Crataegus chemistry, Lignans chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology, Peptide Fragments antagonists & inhibitors
- Abstract
Two new sesquineolignans, hawthornsesquinins K and L ( 1 and 2 ), were isolated from the seeds of Crataegus pinnatifida . Their structures were determined by spectroscopic analyses, including 1D, 2D NMR and HRESIMS data. All isolated compounds were tested for their β -amyloid aggregation inhibitory activity and neuroprotective effects against H
2 O2 -induced damage in SH-SY5Y cells. The results indicated that compound 1 showed prominent inhibition of A β1-42 aggregation and significant neuroprotective effect on H2 O2 -induced cellular damage in SH-SY5Y cells.- Published
- 2019
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17. Racemic neolignans from Crataegus pinnatifida: Chiral resolution, configurational assignment, and cytotoxic activities against human hepatoma cells.
- Author
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Guo R, Lv TM, Shang XY, Yao GD, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- Antineoplastic Agents, Phytogenic isolation & purification, China, Hep G2 Cells, Humans, Lignans isolation & purification, Molecular Structure, Phytochemicals isolation & purification, Phytochemicals pharmacology, Stereoisomerism, Antineoplastic Agents, Phytogenic pharmacology, Apoptosis drug effects, Crataegus chemistry, Fruit chemistry, Lignans pharmacology
- Abstract
Phytochemical investigation of the fruit of Crataegus pinnatifida led to the isolation of four pairs of dihydrobenzofuran neolignan enantiomers (1a/1b-4a/4b) including six new compounds (1a/1b, 2a/2b, 3a and 4a). The enantioseparations of the racemates were achieved successfully by chiral chromatographic column. Their structures were established by comprehensive spectroscopic analyses and the absolute configurations were determined by quantum mechanical calculation of electronic circular dichroism (ECD) spectra. All compounds were evaluated in vitro for their cytotoxicity using human hepatocellular carcinoma Hep3B and HepG2 cells. Among them, it was found that 2a had a selective cytotoxicity against Hep3B cells with IC
50 value of 25.47 μM, while the IC50 value of its enantiomer 2b on Hep3B cells was 59.37 μM. These results implied that the absolute configurations of 2a and 2b possessed remarkable influences on their cytotoxicity. Further flow cytometry analysis indicated that 2a performed more significant effect on cell apoptosis compared with its enantiomer 2b., (Copyright © 2019 Elsevier B.V. All rights reserved.)- Published
- 2019
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18. Discovery of cycloneolignan enantiomers from Isatis indigotica Fortune with neuroprotective effects against MPP + -induced SH-SY5Y cell injury.
- Author
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Xi YF, Liu SF, Hong W, Song XY, Lou LL, Zhou L, Yao GD, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- 1-Methyl-4-phenylpyridinium pharmacology, Cell Survival drug effects, Dose-Response Relationship, Drug, Humans, Lignans chemistry, Lignans isolation & purification, Molecular Structure, Neuroprotective Agents chemistry, Neuroprotective Agents isolation & purification, Plant Leaves chemistry, Stereoisomerism, Structure-Activity Relationship, Tumor Cells, Cultured, 1-Methyl-4-phenylpyridinium antagonists & inhibitors, Drug Discovery, Isatis chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology
- Abstract
A pair of new cycloneolignan enantiomers (1a and 1b) were isolated from the leaves of Isatis indigotica Fortune. Their structures were elucidated by extensive spectroscopic data analysis, including 1D and 2D NMR, HRESIMS, MS/MS analysis, together with theoretical electronic circular dichroism (ECD) calculations. Compounds 1a and 1b were then evaluated for their neuroprotective effects against MPP
+ -induced SH-SY5Y cell injury. As a result, compounds 1a (77.64%) and 1b (78.62%) exhibited moderate neuroprotective activity at the concentration of 12.5 µM compared with that of MPP+ treated group (62.00% at 1 mM) by MTT assay. Furthermore, Annexin V-FITC/PI analysis showed that apoptosis ratios of 1a and 1b were reduced to 10.99% and 9.31%, respectively., (Copyright © 2019 Elsevier Inc. All rights reserved.)- Published
- 2019
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19. Chiral resolution and neuroprotective activities of enantiomeric 8-O-4' neolignans from the fruits of Crataegus pinnatifida Bge.
- Author
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Zhao P, Zhang H, Han FY, Guo R, Huang SW, Lin B, Huang XX, and Song SJ
- Subjects
- Cell Line, Tumor, Humans, Lignans isolation & purification, Molecular Structure, Neuroprotective Agents isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Stereoisomerism, Crataegus chemistry, Fruit chemistry, Lignans pharmacology, Neuroblastoma pathology, Neuroprotective Agents pharmacology, Oxidative Stress drug effects
- Abstract
Five pairs of enantiomeric 8-O-4' neolignans (1a/1b-5a/5b), including seven new compounds (1a/1b, 2a, 3a, 4a/4b and 5b), were obtained from the fruits of Crataegus pinnatifida Bge. Their structures were determined by comprehensive spectroscopic analyses. The absolute configurations of the enantiomers were determined by comparison of the experimental ECD with the calculated data. Additionally, all the enantiomeric neolignans were evaluated for their neuroprotective activity against H
2 O2 -induced cell injury in human neuroblastoma SH-SY5Y cells, and most of them showed potent selective neuroprotective activity. Especially, 3b (72.98%) showed the best protective effect, better than 3a (63.49%) and trolox (62.86%) at 25 μM., (Copyright © 2019 Elsevier B.V. All rights reserved.)- Published
- 2019
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20. Characterization of enantiomeric lignanamides from Solanum nigrum L. and their neuroprotective effects against MPP + -induced SH-SY5Y cells injury.
- Author
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Li CX, Song XY, Zhao WY, Yao GD, Lin B, Huang XX, Li LZ, and Song SJ
- Subjects
- 1-Methyl-4-phenylpyridinium pharmacology, Amides chemistry, Apoptosis drug effects, Cell Survival drug effects, Dose-Response Relationship, Drug, Humans, Lignans chemistry, Molecular Structure, Neuroprotective Agents chemistry, Stereoisomerism, Structure-Activity Relationship, Amides pharmacology, Lignans pharmacology, Neuroprotective Agents pharmacology, Solanum nigrum chemistry
- Abstract
Five pairs of enantiomeric lignanamides including nine undescribed compounds along with a known one were obtained from Solanum nigrum L. (Solanaceae). Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses and quantum chemical calculations of electronic circular dichroism (ECD) curves. Additionally, all isolates were evaluated for their neuroprotective activity against MPP
+ (1-methyl-4-phenylpyridinium)-induced SH-SY5Y cells injury. Among them, cannabisin F showed the most significant neuroprotective effects at different concentrations (12.5, 25, 50 μM). Further studies by Hoechst 33258 staining, monodansylcadaverine (MDC) staining and Annexin V/PI analysis demonstrated that cannabisin F could induce protective autophagy to protect SH-SY5Y cells from MPP+ -induced apoptosis., (Copyright © 2019 Elsevier Ltd. All rights reserved.)- Published
- 2019
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21. Chiral resolution and neuroprotective activities of enantiomeric dihydrobenzofuran neolignans from the fruit of Crataegus pinnatifida.
- Author
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Guo R, Lv TM, Han FY, Lin B, Yao GD, Wang XB, Huang XX, and Song SJ
- Subjects
- Apoptosis drug effects, Benzofurans isolation & purification, Cell Line, Tumor, Cell Survival drug effects, Humans, Hydrogen Peroxide pharmacology, Lignans isolation & purification, Neuroprotective Agents isolation & purification, Oxidative Stress drug effects, Stereoisomerism, Benzofurans pharmacology, Crataegus chemistry, Fruit chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology
- Abstract
Three pairs of enantiomeric dihydrobenzofuran neolignans (1a/1b-3a/3b) including four new compounds (1a/1b and 2a/2b) were isolated from the fruit of Crataegus pinnatifida. Their structures including the absolute configurations were elucidated by extensive spectroscopic analyses and comparison between the experimental measurements of electronic circular dichroism (ECD) and the calculated ECD spectra. Additionally, all the enantiomeric neolignans were investigated for their neuroprotective activities against H
2 O2 -induced cell injury in human neuroblastoma SH-SY5Y cells. It was found that enantiomers 1a and 1b displayed different degrees of neuroprotective activities, and the results showed enantioselectivity, in which that 1b exhibited noticeable neuroprotective activity, while its enantiomer 1a only exhibited obvious protective effect at lower concentration. Further study demonstrated that the potential protective activities of compounds appeared to be mediated via suppressing cell apoptosis., (Copyright © 2019 Elsevier Inc. All rights reserved.)- Published
- 2019
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22. Seven new neuroprotective sesquineolignans isolated from the seeds of Crataegus pinnatifida.
- Author
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Cheng ZY, Lou LL, Yang PY, Song XY, Wang XB, Huang XX, and Song SJ
- Subjects
- Cell Line, Tumor, Humans, Hydrogen Peroxide, Lignans isolation & purification, Neuroblastoma drug therapy, Neuroprotective Agents isolation & purification, Phytochemicals isolation & purification, Phytochemicals pharmacology, Plant Extracts chemistry, Crataegus chemistry, Lignans pharmacology, Neuroprotective Agents pharmacology, Seeds chemistry
- Abstract
The investigation of the ethanol extract of the seeds of Crataegus pinnatifida led to the isolation of seven new 8-O-4' type sesquineolignans crasesquineolignan A-G (1-7), along with a reported analogue, leptolepisol B (8). The chemical structures of these compounds were elucidated based on complex analysis of their MS, 1D and 2D NMR data. All the isolated compounds were tested for their neuroprotective effects against the damage of human neuroblastoma SH-SY5Y cells induced by H
2 O2 , and most of them showed significant neuroprotective activity. Among them, compound 4 (77.58%) showed the best protective effect, even better than the positive control (69.26%) at 25 μM., (Copyright © 2019 Elsevier B.V. All rights reserved.)- Published
- 2019
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23. Phenylpropanoids and lignans from Prunus tomentosa seeds as efficient β-amyloid (Aβ) aggregation inhibitors.
- Author
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Liu Q, Wang J, Lin B, Cheng ZY, Bai M, Shi S, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides metabolism, Binding Sites, Humans, Lignans metabolism, Lignans pharmacology, Molecular Docking Simulation, Peptide Fragments antagonists & inhibitors, Peptide Fragments metabolism, Propanols metabolism, Propanols pharmacology, Protein Aggregates drug effects, Protein Structure, Tertiary, Prunus chemistry, Seeds chemistry, Seeds metabolism, Amyloid beta-Peptides antagonists & inhibitors, Lignans chemistry, Propanols chemistry, Prunus metabolism
- Abstract
Alzheimer's disease (AD) is characterized by the progressive accumulation of extracellular β-amyloid (Aβ) aggregates. Recently, lignans and phenylpropanoids are attracting increasing attention to discovery useful agents of inhibition on Aβ aggregation. In the present study, to develop potential agents for slowing the progression of AD, Prunus tomentosa seeds were selected as a raw material for bioactive compounds, which led to the separation of two pairs of new enantiomeric lignans and phenylpropanoids using chiral HPLC. The planar structures of these compounds were elucidated by spectroscopic data analyses. And their absolute configurations were determined by comparing of experimental and calculated electronic circular dichroism (ECD). The biosynthesis pathway was also discussed. Additionally, the inhibitory activity on Aβ aggregation of all optical pure compounds was tested by thioflavin T (ThT) assay. The isolates (1a, 1b, 2a and 2b) showed more potent inhibitory activity than positive control curcumin with inhibitory rate of 73.89 ± 3.41% 78.69 ± 1.50%, 63.25 ± 2.68%, and 67.13 ± 0.90% at 20 μM, respectively. More importantly, the inhibition profiles were explained by molecular dynamics and docking simulation studies., (Copyright © 2018 Elsevier Inc. All rights reserved.)
- Published
- 2019
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24. Neolignans from Red Raspberry ( Rubus idaeus L.) Exhibit Enantioselective Neuroprotective Effects against H 2 O 2 -Induced Oxidative Injury in SH-SY5Y Cells.
- Author
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Zhou L, Yao GD, Lu LW, Song XY, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- Apoptosis, Cell Line, Tumor, Fruit chemistry, Humans, Hydrogen Peroxide, Lignans isolation & purification, Membrane Potential, Mitochondrial, Mitochondria drug effects, Molecular Structure, Neuroprotective Agents isolation & purification, Oxidative Stress, Phytochemicals isolation & purification, Phytochemicals pharmacology, Reactive Oxygen Species metabolism, Lignans pharmacology, Neuroprotective Agents pharmacology, Rubus chemistry
- Abstract
Red raspberry has been well-known for its nutritional purpose. Although this fruit has been reported for its potent antioxidant activity and health-promoting properties, systematic studies responsible for the bioactive constituents were still insufficient. In the current study, three pairs of dihydrobenzofuran-type enantiomeric neolignans (1a/1b-3a/3b), including two new compounds (1b and 2a), were isolated from the fruit of Rubus idaeus. The structures of these enantiomers were determined through spectroscopic methods and quantum mechanical calculations. Biologically, enantiomers 2a and 2b exhibited significant enantioselective protective effects against H
2 O2 -induced neurotoxicity at 50 μM (2a, 86.72 ± 1.17%; 2b, 69.70 ± 1.59%). The underlying mechanism study demonstrated that enantiomer 2a is able to attenuate H2 O2 -induced apoptosis, reactive oxygen species (ROS) generation, and mitochondrial dysfunction in SH-SY5Y cells. Overall, these findings provide a valuable foundation for the understanding of neuroprotective activities of red raspberry and further investigation on its potential application values.- Published
- 2018
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25. Discovery of dihydrobenzofuran neolignans from Rubus ideaus L. with enantioselective anti-Aβ 1-42 aggregation activity.
- Author
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Zhou L, Wang J, Guo R, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides antagonists & inhibitors, Binding Sites, Circular Dichroism, Fruit chemistry, Fruit metabolism, Lignans isolation & purification, Lignans metabolism, Magnetic Resonance Spectroscopy, Molecular Conformation, Molecular Docking Simulation, Peptide Fragments antagonists & inhibitors, Plant Extracts chemistry, Protein Structure, Tertiary, Rubus metabolism, Stereoisomerism, Amyloid beta-Peptides metabolism, Benzofurans chemistry, Lignans chemistry, Peptide Fragments metabolism, Rubus chemistry
- Abstract
Four new dihydrobenzofuran neolignans 1a/1b and 2a/2b were isolated from the fruit of Rubus ideaus. 1a/1b and 2a/2b as two pairs of enantiomers were separated on a chiral chromatographic column. Their structures were determined using a suite of techniques including 1D and 2D NMR, HRESIMS, together with theoretical electronic circular dichroism (ECD) calculation. All compounds were evaluated for their inhibition of self-induced Aβ
1-42 aggregation. Compounds 1b and 2a exhibited optimal Aβ1-42 aggregation inhibition capability, with an inhibition potency of 81.6% and 83.4% at 20 μM, respectively. Additionally, molecular docking was performed to identify the possible factor responsible for the enantioselectivity in the anti-Aβ1-42 aggregation activity., (Copyright © 2018 Elsevier Inc. All rights reserved.)- Published
- 2018
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26. Lignans from the seeds of Chinese hawthorn (Crataegus pinnatifida var. major N.E.Br.) against β-amyloid aggregation.
- Author
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Huang XX, Xu Y, Bai M, Zhou L, Song SJ, and Wang XB
- Subjects
- Amyloid beta-Peptides antagonists & inhibitors, Amyloid beta-Peptides chemistry, Drug Evaluation, Preclinical methods, Humans, Magnetic Resonance Spectroscopy, Molecular Docking Simulation, Molecular Structure, Peptide Fragments antagonists & inhibitors, Peptide Fragments chemistry, Seeds chemistry, Amyloid beta-Peptides metabolism, Crataegus chemistry, Lignans chemistry, Lignans pharmacology, Peptide Fragments metabolism
- Abstract
Phytochemical investigation on the seeds of hawthorn (Crataegus spp.) led to the isolation of a new compound, (7'R, 8'R, 8S)-isolariciresinol (1), along with six known compounds (2-7). The structures of all compounds were determined based on spectroscopic data interpretation. The Aβ
1-42 inhibition activity of all isolated compounds was evaluated in vitro. As a result, compounds 5 and 6 showed stronger inhibition of Aβ1-42 aggregation than curcumin, with inhibition rates of 70.59 and 68.14% at 20 μM. The possible mechanism of interaction between Aβ1-42 and the active compounds 5 and 6 was also investigated by molecular docking.- Published
- 2018
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27. Chiral resolution and bioactivity of enantiomeric benzofuran neolignans from the fruit of Rubus ideaus L.
- Author
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Zhou L, Xi YF, Wang W, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides chemistry, Cell Line, Tumor, Circular Dichroism, Free Radical Scavengers chemistry, Humans, Magnetic Resonance Spectroscopy, Molecular Structure, Peptide Fragments chemistry, Stereoisomerism, Benzofurans chemistry, Fruit chemistry, Lignans chemistry, Rubus chemistry
- Abstract
Rubus ideaus L., a member of the Rosaceae family, is popular for its distinctive flavor and attractive red color. In order to explore the functional factors possibly presented in the fruit, seven new benzofuran neolignans (1a/1b-3a/3b and 4b), together with one known neolignan 4a, were isolated from the fruit of R. ideaus. Compounds 1a/1b-4a/4b as four pairs of enantiomers were separated on a chiral chromatographic column. Their structures including absolute configurations were elucidated by extensive spectroscopic data analyses, including UV, IR, HRESIMS, NMR, and comparing their experimental electronic circular dichroism (ECD) spectra with calculated ECD spectra. Additionally, all these enantiomeric compounds were evaluated for their antioxidant, neuroprotective, and anti-Aβ
1-42 aggregation activities., (Copyright © 2018 Elsevier B.V. All rights reserved.)- Published
- 2018
- Full Text
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28. Enantiomeric neolignans from Picrasma quassioides exhibit distinctive cytotoxicity on hepatic carcinoma cells through ROS generation and apoptosis induction.
- Author
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Lou LL, Yao GD, Wang J, Zhao WY, Wang XB, Huang XX, and Song SJ
- Subjects
- Antineoplastic Agents chemistry, Antineoplastic Agents isolation & purification, Cell Line, Tumor, Humans, Lignans chemistry, Lignans isolation & purification, Phenols chemistry, Phenols isolation & purification, Plant Stems chemistry, Stereoisomerism, Antineoplastic Agents pharmacology, Apoptosis drug effects, Lignans pharmacology, Phenols pharmacology, Picrasma chemistry, Reactive Oxygen Species metabolism
- Abstract
Three pairs of enantiomeric neolignans 1a/1b-3a/3b were isolated from the stems of Picrasma quassioides, and separated successfully by chiral-phase HPLC. Their structures were established by comprehensive spectroscopic analyses as well as ECD spectroscopy. The in vitro cytotoxicity of the isolates was evaluated against human hepatocellular carcinoma HepG2 and Hep3B cells. Among them, 1 and its enantiomers 1a/1b, 3 and 3a/3b displayed similar cytotoxicity in pair-wise comparison against HepG2 and Hep3B cells, and the similar effects of 2 and 2a/2b were found in Hep3B cells. Interestingly, 2a and 2b had different cytotoxic activities on HepG2 cells with IC
50 values of 35.6 μM and 104.4 μM, respectively. In addition, 2 exerted middle cytotoxicity against HepG2 cells with an IC50 value of 78.6 μM. The different cytotoxicity between enantiomers 2a and 2b attracted our interest. To investigate the underlying mechanisms responsible for the distinct cytotoxicity, we further assessed the effects of 2a and 2b on cell cycle distribution, cell apoptosis and reactive oxygen species (ROS) generation. The results indicated that 2a had more significant effect than 2b on apoptosis induction and ROS generation, but both had no obvious effect on cell cycle of HepG2 cells. It is concluded that the different configurations of 2a/2b determined the enantioselective cytotoxicity on HepG2 cells through apoptosis induction and ROS generation., (Copyright © 2018 Elsevier Ltd. All rights reserved.)- Published
- 2018
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29. Enantiomeric lignans with anti-β-amyloid aggregation activity from the twigs and leaves of Pithecellobium clypearia Benth.
- Author
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Wang YX, Zhou L, Wang J, Lin B, Wang XB, Huang XX, and Song SJ
- Subjects
- Amyloid beta-Peptides metabolism, Benzothiazoles chemistry, Dose-Response Relationship, Drug, Fluorescent Dyes chemistry, Humans, Lignans chemistry, Lignans isolation & purification, Models, Molecular, Molecular Structure, Plant Leaves chemistry, Plant Stems chemistry, Protein Aggregates drug effects, Stereoisomerism, Structure-Activity Relationship, Amyloid beta-Peptides antagonists & inhibitors, Fabaceae chemistry, Lignans pharmacology
- Abstract
To develop potential agents for slowing the progression of Alzheimer's disease, two pairs of new enantiomeric lignans, including a couple of rarely 8',9'-dinor-3',7-epoxy-8,4'-oxyneolignanes named (7S, 8S)- and (7R, 8R)-pithecellobiumin A (1a/1b) and a pair of 2',9'-epoxy-arylnaphthalenes named (7R, 8R, 8'R)- and (7S, 8S, 8'S)-pithecellobiumin B (2a/2b) were separated by chiral high performance liquid chromatography (HPLC). Their planar structures were elucidated by spectroscopic data analyses. The absolute configurations were determined by comparing of experimental and calculated electronic circular dichroism (ECD). The inhibitory activity on Aβ aggregation of all optical pure compounds was tested by ThT assay. Interestingly, enantiomeric inhibitors 1a (62.1%) and 1b (81.6%) exhibited different degrees of anti-Aβ aggregation activity. However, 2a (65.4%) and 2b (68.4%) showed similar inhibition rate. The different inhibition profiles were explained by molecular dynamics and docking simulation studies., (Copyright © 2018 Elsevier Inc. All rights reserved.)
- Published
- 2018
- Full Text
- View/download PDF
30. Seven new sesquineolignans isolated from the seeds of hawthorn and their neuroprotective activities.
- Author
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Huang XX, Ren Q, Song XY, Zhou L, Yao GD, Wang XB, and Song SJ
- Subjects
- Apoptosis, Cell Line, Tumor, Humans, Lignans pharmacology, Molecular Structure, Neuroblastoma, Neuroprotective Agents pharmacology, Crataegus chemistry, Lignans isolation & purification, Neuroprotective Agents isolation & purification, Seeds chemistry
- Abstract
Seven new sesquineolignans (1-7) were isolated from the 70% ethanolic extract of the hawthorn seeds. Their structures were established by comprehensive spectroscopic analyses including 1D, 2D NMR, CD and HRESIMS data. The neuroprotective activity of the isolated sesquilignans towards H
2 O2 -induced damage in human neuroblastoma SH-SY5Y cells was investigated. All of these sesquineolignans exhibited significant neuroprotective activity towards damaged SH-SY5Y cells, compared with the positive control (Trolox). Among them, 6 displayed the most potent neuroprotective ability with the survival rate of 90.74% at the concentration of 50μM. Moreover, Hoechst 33258 staining and Annexin V/PI analysis proved that 6 could protect damaged SH-SY5Y cells through inhibiting cellular apoptosis., (Copyright © 2017 Elsevier B.V. All rights reserved.)- Published
- 2018
- Full Text
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31. Antioxidant and cytotoxic lignans from the roots of Bupleurum chinense.
- Author
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Li DQ, Wang D, Zhou L, Li LZ, Liu QB, Wu YY, Yang JY, Song SJ, and Wu CF
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antioxidants chemistry, Benzothiazoles chemistry, Biphenyl Compounds pharmacology, Cell Line, Tumor, Drug Screening Assays, Antitumor, Fluorouracil pharmacology, Humans, Inhibitory Concentration 50, Lignans chemistry, MCF-7 Cells, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Picrates pharmacology, Plant Roots chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Antioxidants isolation & purification, Antioxidants pharmacology, Bupleurum chemistry, Lignans isolation & purification, Lignans pharmacology
- Abstract
In the search for biologically active compounds from the roots of Bupleurum chinense D C., phytochemical investigation of its ethanol extract led to the isolation and identification of a new 8-O-4' neolignan glucoside, saikolignanoside A (1), along with eight known lignans (2-9). Their structures were determined on the basis of IR, UV, HRESIMS, and NMR spectroscopic analyses. The antioxidant and cytotoxic effects of isolated compounds were evaluated in vitro. The isolated compounds (IC
50 > 200 μM) did not display 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity. Whereas compounds 1-2, 5, 7, and 9 exhibited potent 2, 2'-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging properties with IC50 values ranging from 8.34 to 15.24 μM, while compounds 3-4, 6, 8 showed moderate properties. In addition, all compounds were evaluated for cytotoxicities against A549, HepG2, U251, Bcap-37, and MCF-7 cell lines. Compounds 5 and 9 (IC50 < 51.62 μM) possessed stronger cytotoxic activities against all the tested tumor cell lines, compared with the positive control 5-Fluorouracil.- Published
- 2017
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32. Antioxidant and anti-inflammatory neolignans from the seeds of hawthorn.
- Author
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Peng Y, Lou LL, Liu SF, Zhou L, Huang XX, and Song SJ
- Subjects
- Animals, Anti-Inflammatory Agents isolation & purification, Antioxidants isolation & purification, Benzothiazoles chemistry, Biphenyl Compounds chemistry, Lignans isolation & purification, Mice, Nitric Oxide antagonists & inhibitors, Picrates chemistry, Plant Extracts chemistry, Plant Extracts pharmacology, RAW 264.7 Cells, Seeds chemistry, Sulfonic Acids chemistry, Tumor Necrosis Factor-alpha antagonists & inhibitors, Anti-Inflammatory Agents chemistry, Anti-Inflammatory Agents pharmacology, Antioxidants chemistry, Antioxidants pharmacology, Crataegus chemistry, Lignans chemistry, Lignans pharmacology
- Abstract
Seven new neolignans (1-2, 7-11) and five known compounds (3-6, 12) were isolated from the 70% EtOH extract of hawthorn seeds. Their structures were determined by spectroscopic analyses. The antioxidant and anti-inflammatory activities of all the isolates were investigated. Most of the isolates showed moderate radical scavenging activity in the DPPH assay and significant activities in the ABTS and FRAP assays. Furthermore, compounds 7-12 exhibited marked nitric oxide (NO) inhibition and compounds 1-4 had a potent necrosis factor-α (TNF-α) inhibitory effect. The results we obtained showed that hawthorn seeds can be regarded as a potential new and cheap source of antioxidants and inflammation inhibitors., (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Published
- 2016
- Full Text
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33. Bioactive norditerpenoids and neolignans from the roots of salvia miltiorrhiza.
- Author
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Li LZ, Liang X, Sun X, Qi XL, Wang J, Zhao QC, and Song SJ
- Subjects
- Benzothiazoles chemistry, Biphenyl Compounds chemistry, Cell Line, Microglia drug effects, Microglia metabolism, Models, Molecular, Molecular Conformation, Nitric Oxide biosynthesis, Picrates chemistry, Sulfonic Acids chemistry, Diterpenes chemistry, Diterpenes pharmacology, Free Radical Scavengers chemistry, Free Radical Scavengers pharmacology, Lignans chemistry, Plant Roots chemistry, Salvia miltiorrhiza chemistry
- Abstract
Two new norditerpenoids, miltiolactones A and B (1a, 1b); seven new neolignans, miltiolignanolides A-G (2a, 2b and 3a, 3b and 4a, 4b, and 5) were obtained from the root extract of Salvia miltiorrhiza. Using HPLC separation with a chiral column, compounds 1-4 were found to exist as four pairs of enantiomers. Compounds 2-5 are novel neolignans with a dibenzocycloheptatriene ring system, which form an unprecedented 6/7/6 carbon skeleton. The structures were established via extensive spectroscopic analysis, and experimental and calculated electronic circular dichroism (ECD) spectra, and compound 1 was also elucidated by X-ray diffraction experiments. Compounds 2a and 2b significantly increased the viability of H9c2 cells from H
2 O2 -induced cell death, and 3a showed significant antioxidant activity in an ABTS assay. In addition, compounds 2a, 2b and 3a, 3b display moderate inhibitory effects on nitric oxide (NO) production in LPS-induced microglial cells.- Published
- 2016
- Full Text
- View/download PDF
34. 3, 3'-Neolignans from Pithecellobium clypearia Benth and their anti-inflammatory activity.
- Author
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Lou LL, Li LG, Liu QB, Li DQ, Liu ZX, Huang XX, and Song SJ
- Subjects
- Animals, Anti-Inflammatory Agents isolation & purification, Free Radical Scavengers chemistry, Free Radical Scavengers isolation & purification, Lignans isolation & purification, Mice, Molecular Structure, Nitric Oxide metabolism, Plant Extracts chemistry, RAW 264.7 Cells, Anti-Inflammatory Agents chemistry, Fabaceae chemistry, Lignans chemistry
- Published
- 2016
- Full Text
- View/download PDF
35. Food Byproducts as a New and Cheap Source of Bioactive Compounds: Lignans with Antioxidant and Anti-inflammatory Properties from Crataegus pinnatifida Seeds.
- Author
-
Huang XX, Bai M, Zhou L, Lou LL, Liu QB, Zhang Y, Li LZ, and Song SJ
- Subjects
- Animals, Anti-Inflammatory Agents pharmacology, Antioxidants pharmacology, Lignans pharmacology, Macrophages drug effects, Macrophages immunology, Mice, Plant Extracts pharmacology, RAW 264.7 Cells, Seeds chemistry, Tumor Necrosis Factor-alpha genetics, Tumor Necrosis Factor-alpha immunology, Anti-Inflammatory Agents analysis, Antioxidants analysis, Crataegus chemistry, Lignans analysis, Plant Extracts analysis, Waste Products analysis
- Abstract
During the process of manufacturing hawthorn (Crataegus pinnatifida) juice and jam, a significant quantity of byproducts (leaves, seeds) is generated. The antioxidant and anti-inflammatory bioassay-guided fractionation of the extract of hawthorn seeds has led to the isolation of eight new lignans, hawthornnins A-H (1-8), and seven known analogues (9-15). Their structures were elucidated by spectroscopic techniques, including 1D and 2D NMR and CD spectra. The radical-scavenging effects of all isolated compounds were investigated. 1-6 and 8 showed moderate activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH), whereas 1-6 and 14 displayed good 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radical-scavenging activities that were even more potent than that of trolox. In addition, all isolates were evaluated for their anti-inflammatory activities by detecting the nitric oxide (NO) and tumor necrosis factor α (TNF-α) production by the LPS-induced murine macrophage cell line RAW264.7, and compounds 1-7, 13, and 14 exhibited potent inhibition of NO and TNF-α production. The structure-activity relationships of isolated lignans were also examined, and the results obtained show that C. pinnatifida seeds can be regarded as a potential new and cheap source of antioxidants and inflammation inhibitors.
- Published
- 2015
- Full Text
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36. A new cyclolignan glycoside from the tubers of Pinellia ternata.
- Author
-
Wu YY, Huang XX, Wu J, Zhou L, Li DQ, Liu QB, Li LZ, Yan XJ, and Song SJ
- Subjects
- Agaricales drug effects, Agaricales enzymology, Antioxidants chemistry, Antioxidants pharmacology, Drugs, Chinese Herbal chemistry, Drugs, Chinese Herbal pharmacology, Glycosides chemistry, Glycosides pharmacology, Lignans chemistry, Lignans pharmacology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Tubers chemistry, Antioxidants isolation & purification, Drugs, Chinese Herbal isolation & purification, Glycosides isolation & purification, Lignans isolation & purification, Monophenol Monooxygenase antagonists & inhibitors, Pinellia chemistry
- Abstract
A new 2,7'-type cyclolignan glycoside, cyclolignanyingoside A (1), together with six known compounds (2-7) were isolated from the tubers of Pinellia ternata (Thunb.) Breit. The structure of 1 was elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MS, and CD spectrometry. The cytotoxic, antioxidant and tyrosinase-inhibiting activities of all the isolates were determined. However, all the isolates exhibited no activity on the selected cell lines (Hep-3B, Bcap-37, and MCF-7). In addition, compounds 1-3 and 7 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, and compounds 2 and 4 showed a moderate mushroom tyrsinase inhibitory activity.
- Published
- 2015
- Full Text
- View/download PDF
37. Antioxidant and tyrosinase inhibitory effects of neolignan glycosides from Crataegus pinnatifida seeds.
- Author
-
Huang XX, Liu QB, Wu J, Yu LH, Cong Q, Zhang Y, Lou LL, Li LZ, and Song SJ
- Subjects
- Drug Evaluation, Preclinical methods, Enzyme Inhibitors chemistry, Magnetic Resonance Spectroscopy, Molecular Structure, Monophenol Monooxygenase metabolism, Seeds chemistry, Structure-Activity Relationship, Antioxidants pharmacology, Crataegus chemistry, Enzyme Inhibitors pharmacology, Glycosides chemistry, Lignans chemistry, Monophenol Monooxygenase antagonists & inhibitors
- Abstract
In our efforts to find an inhibitor of melanin formation and develop potential depigmenting agents for skin-protecting cosmetics and medicinal products from natural resources, we focused on the seeds of Crataegus pinnatifida which showed antioxidant and tyrosinase-inhibiting activities. By activity-guided fractionation of an extract of C. pinnatifida seeds, four new neolignan glycosides, pinnatifidaninsides A-D (1-4), along with two known compounds (5-6), were isolated. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The antioxidant and tyrosinase-inhibiting activities of all isolates were assayed. Compound 6 showed good activity against 2,2-diphenyl-1-pikrylhydrazyl, while compounds 1, 2, 5, and 6 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, being as effective as, or even more effective than the positive control Trolox. Moreover, compounds 5 and 6 displayed a moderate mushroom tyrosinase inhibitory activity., (Georg Thieme Verlag KG Stuttgart · New York.)
- Published
- 2014
- Full Text
- View/download PDF
38. Antioxidant and anti-inflammatory active dihydrobenzofuran neolignans from the seeds of Prunus tomentosa.
- Author
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Liu QB, Huang XX, Bai M, Chang XB, Yan XJ, Zhu T, Zhao W, Peng Y, and Song SJ
- Subjects
- Animals, Anti-Inflammatory Agents pharmacology, Antioxidants pharmacology, Benzofurans chemistry, Benzofurans pharmacology, Cell Line, Lignans chemistry, Lignans pharmacology, Mice, Microglia, Molecular Structure, Plant Extracts chemistry, Anti-Inflammatory Agents analysis, Antioxidants analysis, Benzofurans analysis, Lignans analysis, Prunus chemistry, Seeds chemistry
- Abstract
Prunus tomentosa seeds were researched for antioxidant and anti-inflammatory constituents. By activity-guided fractionation of P. tomentosa seed extract, six new dihydrobenzofuran neolignans, prunustosanans AI-IV (1-4) and prunustosanansides AI and AII (5 and 6), together with 10 known compounds (7-16) were isolated from bioactive fraction. The structures were determined by spectroscopic analyses, especially NMR, HRESIMS, and CD spectra. The antioxidant activity was greatest for 5, 10, and 12 against DPPH radical and for 8, 9, and 13 against ABTS radical. Moreover, compounds 7 and 11 exhibited much stronger inhibitory activity on nitric oxide (NO) production in murine microglia BV-2 compared with positive control minocycline (IC50 = 19.7 ± 1.5 μM). The results show that P. tomentosa seeds can be regarded as a potential source of antioxidants and inflammation inhibitors.
- Published
- 2014
- Full Text
- View/download PDF
39. Three new lignan glycosides from the fruits of Forsythia suspense.
- Author
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Yan XJ, Peng Y, Liu ZX, Wen J, Liu QB, Li LZ, and Song SJ
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Drug Screening Assays, Antitumor, Drugs, Chinese Herbal chemistry, Drugs, Chinese Herbal pharmacology, Fruit chemistry, Glycosides chemistry, Glycosides pharmacology, HL-60 Cells, Humans, KB Cells, Lignans chemistry, Lignans pharmacology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Antineoplastic Agents, Phytogenic isolation & purification, Drugs, Chinese Herbal isolation & purification, Forsythia chemistry, Glycosides isolation & purification, Lignans isolation & purification
- Abstract
Two new lignan glycosides forsythiayanoside A (1) and forsythiayanoside B (2), one new stereoisomer of lignan glycoside (+)-8-hydroxyepipinoresinol-4-O-β-D-glucopyranoside (3), together with seven known compounds (4-10), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. Compounds 4 and 10 were isolated from this species for the first time. The structures of 1-3 were elucidated on the basis of chemical and spectral analyses, including 1D and 2D NMR data and HR-ESI-MS. The absolute configurations were determined by the circular dichroism method. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). In particular, compound 3 showed significant cytotoxicity with IC50 values of 9.48, 7.75, 0.59, 4.06, and 38.38 μM, respectively.
- Published
- 2014
- Full Text
- View/download PDF
40. Cytotoxic and antioxidant dihydrobenzofuran neolignans from the seeds of Crataegus pinnatifida.
- Author
-
Huang XX, Zhou CC, Li LZ, Peng Y, Lou LL, Liu S, Li DM, Ikejima T, and Song SJ
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Antioxidants chemistry, Antioxidants isolation & purification, Antioxidants pharmacology, Benzofurans chemistry, Benzofurans isolation & purification, Benzofurans pharmacology, Benzothiazoles metabolism, Biphenyl Compounds metabolism, Cell Line, Tumor, Humans, Inhibitory Concentration 50, Lignans chemistry, Lignans isolation & purification, Lignans pharmacology, Molecular Structure, Picrates metabolism, Plant Extracts chemistry, Plant Extracts pharmacology, Plant Extracts therapeutic use, Seeds chemistry, Sulfonic Acids metabolism, Antineoplastic Agents, Phytogenic therapeutic use, Antioxidants therapeutic use, Benzofurans therapeutic use, Crataegus chemistry, Lignans therapeutic use, Neoplasms drug therapy, Phytotherapy
- Abstract
Eight new dihydrobenzofuran neolignans, pinnatifidanin C I-VIII (1-8), together with two known analogs (9-10) were isolated from the seeds of Crataegus pinnatifida. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The cytotoxic activities of all isolates against human cancer cell lines were assayed, and most interestingly, compound 10 revealed preferred cytotoxicity on the HT-1080 cell line and displayed much stronger inhibitory activity (IC50=8.86 μM) compared with positive control 5-fluorouracil (IC50=35.62 μM). Meanwhile, antioxidant activities of all the isolates were evaluated using 2,2-diphenyl-1-pikrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays, and the results showed that most of the isolates exhibited potent antioxidant activity., (© 2013.)
- Published
- 2013
- Full Text
- View/download PDF
41. The cytotoxicity of 8-O-4' neolignans from the seeds of Crataegus pinnatifida.
- Author
-
Huang XX, Zhou CC, Li LZ, Li FF, Lou LL, Li DM, Ikejima T, Peng Y, and Song SJ
- Subjects
- Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic toxicity, Cell Line, Tumor, Cell Survival drug effects, Circular Dichroism, Crataegus metabolism, Drug Screening Assays, Antitumor, Humans, Lignans isolation & purification, Lignans toxicity, Magnetic Resonance Spectroscopy, Molecular Conformation, Seeds chemistry, Seeds metabolism, Antineoplastic Agents, Phytogenic chemistry, Crataegus chemistry, Lignans chemistry
- Abstract
Nine new 8-O-4' neolignans, named pinnatifidanin B I-IX (1-9), together with 9 known analogs (10-18) were isolated from the seeds of Crataegus pinnatifida. The structures of 1-18 were determined by spectroscopic methods, including 1D, 2D NMR, CD and HRESIMS analysis. Compounds 8-11, 17 and 18 displayed potent cytotoxic activities against human cancer cell lines, and most interestingly, none of the 6 compounds displayed inhibitory activity against human lung cell line (Mrc5). The 6 cytotoxic compounds are considered to be potential as antitumor agents, which could significantly inhibit the cancer cell growth in a dose-dependent manner and are probably safer than positive control drug., (Copyright © 2013 Elsevier Ltd. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
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