1.Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara.
Yu-Peng LI ; Kang YANG ; Hui MENG ; Tao SHEN ; Hua ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2022;20(4):301-308
Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.
Animals
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Flowers/chemistry*
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Glucosides/pharmacology*
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Mice
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Sesquiterpenes/pharmacology*
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Sesquiterpenes, Eudesmane/pharmacology*
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Tussilago/chemistry*
2.A new eudesmane type sesquiterpene from cultivated Clerodendranthus spicatus in Hainan.
Hui-Qin CHEN ; Rong-Rong ZHANG ; Wen-Li MEI ; Cai-Hong CAI ; Cui-Juan GAI ; Xu-Dong YU ; Hao-Fu DAI
China Journal of Chinese Materia Medica 2019;44(1):95-99
Six compounds were isolated from the aerial part of cultivated Clerodendranthus spicatus in Hainan with various chromatographic techniques,and their structures were determined as:1-dehydroxy-1-oxo-rupestrinol(1),N-trans-feruloyltyramine(2),methyl 3,4-dihydroxyphenyllactate(3),caffein acid(4),methyl caffeate(5) and ethyl caffeate(6),via analysis of physicochemical properties and spectroscopic evidence.Compound 1 was a new compound,while compounds 2 and 3 were isolated from C.spicatus for the first time.Biological activity results showed that compounds 2-4 exhibited α-glucosidase inhibitory activity with different inhibition ratio.
China
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Glycoside Hydrolase Inhibitors
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isolation & purification
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pharmacology
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Lamiaceae
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chemistry
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Molecular Structure
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Phytochemicals
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isolation & purification
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pharmacology
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Sesquiterpenes, Eudesmane
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isolation & purification
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pharmacology
3.New eudesmane sesquiterpenoids from Atractylodis Macrocephalae Rhizoma and their inhibitory activities against SREBPs.
Rui-Zhu XU ; Xuan ZHAO ; Yue-Yue DU ; Meng-Sha XU ; Xin-Guang LIU ; Zhi-Shen XIE ; Song GAO ; Jiang-Yan XU ; Pan WANG
China Journal of Chinese Materia Medica 2022;47(2):428-432
Three sesquiterpenoids were isolated and purified from the 95% ethanol extract of Atractylodis Macrocephalae Rhizoma by column chromatography on silica gel, Sephadex LH-20, ODS, and high-performance liquid chromatography(HPLC). Their chemical structures were identified on the basis of spectroscopic analysis and physiochemical properties as(7Z)-8β,13-diacetoxy-eudesma-4(15),7(11)-diene(1), 7-oxo-7,8-secoeudesma-4(15),11-dien-8-oic acid(2), and guai-10(14)-en-11-ol(3). Compounds 1 and 2 are new compounds and compound 3 was obtained from Compositae family for the first time. Compounds 1, 2, and 3 showed weak inhibitory activities against sterol regulatory element-binding proteins(SREBPs).
Atractylodes/chemistry*
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Drugs, Chinese Herbal/chemistry*
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Rhizome/chemistry*
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Sesquiterpenes, Eudesmane/pharmacology*
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Sterol Regulatory Element Binding Proteins/antagonists & inhibitors*
4.Effect of Alantolactone on Proliferation of RPMI-8226 Cells and Its Possible Mechnism.
Yao YAO ; Yue-Yue SUN ; Dan-Dan XIA ; Ming-Shan NIU ; Kai ZHAO ; Zhen-Yu LI ; Ling-Yu ZENG ; Kai-Lin XU
Journal of Experimental Hematology 2015;23(5):1336-1340
OBJECTIVETo investigate the effect of alantolactone on perliferation and apoptosis of multiple myeloma (MM) RPMI-8226 cells, and to explore its possible mechism in vitro and in vivo.
METHODSThe RPMI-8226 cells were treated with alantolactone (1, 2.5, 5, 7.5 and 10 µmol/L) for 48 h, cell viability was detected by CCK-8 assay and the value of IC50 was calculated; The RPMI-8226 cells were treated with alantolactone (2.5, 5 and 7.5 µmol/L) for 48 h, the apoptotic rate was detected by flow cytmetry with Annexin V/PI staining; the expression level of cleaved caspase-3 and phosphorylation of ERK were measured by Western blot; the nude mice was used to further confirm the proapoptotic effect of alantolactone on MM cells in vivo.
RESULTSThe alantolactone inhibited RPMI-8226 cell viability remarkably with a dose-dependent manner; the IC50 value of RPMI-8226 cells at 48 h was 4.32 ± 0.15 µmol/L; the apoptotic rate increased observably with a dose-dependent manner; the levels of cleaved-caspase-3 increased and the phosphorylation of ERK decreased significantly; as compared to control, the volum of tumor was much smaller, the expression levels of Ki67 and p-ERK decreased.
CONCLUSIONThe alantolactone can efficiently inhibit the proliferation and induce the apoptosis of multiple myeloma RPMI-8226 cells in vitro and in vivo through inhibiting the activation of ERK signal pathway.
Animals ; Apoptosis ; Caspase 3 ; metabolism ; Cell Line, Tumor ; drug effects ; Cell Proliferation ; drug effects ; Humans ; Lactones ; pharmacology ; Mice ; Mice, Nude ; Multiple Myeloma ; pathology ; Sesquiterpenes, Eudesmane ; pharmacology ; Signal Transduction
5.Advances in studies on chemical constituents of Senecio.
China Journal of Chinese Materia Medica 2003;28(2):97-100
The large cosmopolitan genus Senecio, a perennial medicinal herb of the family compositae, has been utilized as a anthmicrobial agent. A variety of pyrrolizidine alkaloids and furanoeremophilanes are widespread in the genus Senecio, which are responsible for the hepatotoxic and carchnogenic effects. Some of them have been screened for anti-tumour activity, but their liver toxicity renders their use in chemotherapy. This article reviews the recent advances in chemical constituents, identification methods and pharmacological activities of it.
Animals
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Anti-Bacterial Agents
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pharmacology
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Antineoplastic Agents, Phytogenic
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pharmacology
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Chromatography, High Pressure Liquid
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methods
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Humans
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Molecular Structure
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Plants, Medicinal
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chemistry
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Pyrrolizidine Alkaloids
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chemistry
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isolation & purification
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pharmacology
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Senecio
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chemistry
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Sesquiterpenes
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chemistry
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isolation & purification
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pharmacology
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Sesquiterpenes, Eudesmane
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chemistry
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isolation & purification
6.Inhibitory effect of alantolactone on the proliferation of K562/ADR cells and its mechanism.
Chunhui YANG ; Hong CAI ; Jiangzhou YAN ; Jingbo YANG ; Meiyan SUN ; Xiuxiang MENG ; Tonghui MA
Chinese Journal of Hematology 2014;35(6):515-518
OBJECTIVETo explore the inhibitory effect of alantolactone on the proliferation of adriamycin-resistant human chronic myelogenous leukemia cell line K562/ADR cells and its mechanism.
METHODSK562/ADR cells were treated with various concentrations of alantolactone (0, 1, 2, 4, 6, 8, and 10 μmol/L) for different time points. Cell viability was analyzed with MTT assay. The effect of alantolactone on the apoptosis of K562/ADR cells was measured by flow cytometry. The expression of apoptosis-related proteins after treatment with alantolactone was analyzed using Western blot.
RESULTSAlantolactone could effectively inhibit the proliferation of K562/ADR cells in dose- and time- dependent manner, the IC50 value of alantolactone treatment of K562/ADR cells for 24 h was 4.7 μmol/L (P<0.05). Flow cytometric analysis displayed that the apoptotic rates were 1.35%, 16.91%, 29.61% and 46.26%, respectively, after treatment with alantolactone at 0, 2.5, 5 and 7.5 μmol/L. Meanwhile, the expression of Bcl-2 and BCR-ABL proteins were significantly decreased and that of Bax, cytochrome C, cleaved-caspase-9, cleaved-caspase-3 and cleaved-PARP increased by alantolactone treatment.
CONCLUSIONAlantolactone had obvious inhibitory effect on the proliferation of K562/ADR cells through the caspase dependent mitochondrial(or intrinsic)apoptotic pathway.
Apoptosis ; Caspase 3 ; metabolism ; Caspase 9 ; metabolism ; Cell Proliferation ; drug effects ; Fusion Proteins, bcr-abl ; metabolism ; Humans ; K562 Cells ; Lactones ; pharmacology ; Proto-Oncogene Proteins c-bcl-2 ; metabolism ; Sesquiterpenes, Eudesmane ; pharmacology ; bcl-2-Associated X Protein ; metabolism