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1.
Article in English | WPRIM | ID: wpr-929262

ABSTRACT

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.


Subject(s)
Animals , Flowers/chemistry , Glucosides/pharmacology , Mice , Sesquiterpenes/pharmacology , Sesquiterpenes, Eudesmane/pharmacology , Tussilago/chemistry
2.
Article in Chinese | WPRIM | ID: wpr-927985

ABSTRACT

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).


Subject(s)
Atractylodes/chemistry , Drugs, Chinese Herbal/chemistry , Rhizome/chemistry , Sesquiterpenes, Eudesmane/pharmacology , Sterol Regulatory Element Binding Proteins/antagonists & inhibitors
3.
Article in Chinese | WPRIM | ID: wpr-771512

ABSTRACT

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.


Subject(s)
China , Glycoside Hydrolase Inhibitors , Pharmacology , Lamiaceae , Chemistry , Molecular Structure , Phytochemicals , Pharmacology , Sesquiterpenes, Eudesmane , Pharmacology
4.
Article in Chinese | WPRIM | ID: wpr-304827

ABSTRACT

Chemical constituents from the acetone extract of twigs of Manglietia hookeri were isolated and purified by various column chromatographic methods over silica gel and sephadex LH-20, and preparative TLC. The structures of these compounds were identified on the basis of physicochemical properties and spectral analysis, including NMR and MS spectra. Six eudesmane sesquiterpenes were obtained and their structures were identified as trans-eudesmane-4, 11-diol(1), β-eudesmol(2), (-) -10-epi-5β-hydroxy-β-eudesmol (3), epi-carrisone (4), 6-hydroxy-eudesm-4(14) -ene(5) and gynurenol(6). All the compounds were isolated from this plant for the first time. Furthermore, the 13C-NMR data of compound 3 were reported for the first time.


Subject(s)
Drugs, Chinese Herbal , Chemistry , Magnetic Resonance Spectroscopy , Magnolia , Chemistry , Molecular Structure , Plant Stems , Chemistry , Sesquiterpenes, Eudesmane , Chemistry , Spectrometry, Mass, Electrospray Ionization
5.
Journal of Experimental Hematology ; (6): 1336-1340, 2015.
Article in Chinese | WPRIM | ID: wpr-274040

ABSTRACT

<p><b>OBJECTIVE</b>To 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.</p><p><b>METHODS</b>The 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.</p><p><b>RESULTS</b>The 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.</p><p><b>CONCLUSION</b>The 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.</p>


Subject(s)
Animals , Apoptosis , Caspase 3 , Metabolism , Cell Line, Tumor , Cell Proliferation , Humans , Lactones , Pharmacology , Mice , Mice, Nude , Multiple Myeloma , Pathology , Sesquiterpenes, Eudesmane , Pharmacology , Signal Transduction
6.
Chinese Journal of Hematology ; (12): 515-518, 2014.
Article in Chinese | WPRIM | ID: wpr-238769

ABSTRACT

<p><b>OBJECTIVE</b>To explore the inhibitory effect of alantolactone on the proliferation of adriamycin-resistant human chronic myelogenous leukemia cell line K562/ADR cells and its mechanism.</p><p><b>METHODS</b>K562/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.</p><p><b>RESULTS</b>Alantolactone 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.</p><p><b>CONCLUSION</b>Alantolactone had obvious inhibitory effect on the proliferation of K562/ADR cells through the caspase dependent mitochondrial(or intrinsic)apoptotic pathway.</p>


Subject(s)
Apoptosis , Caspase 3 , Metabolism , Caspase 9 , Metabolism , Cell Proliferation , 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
7.
Article in Chinese | WPRIM | ID: wpr-267042

ABSTRACT

<p><b>OBJECTIVE</b>To study chemical constituents from the roots of Saussurea lappa.</p><p><b>METHOD</b>Chemical constituents were separated and purified by various techniques such as silica gel column chromatography, Sephadex LH-20 and reversed phase RP-18 column chromatography. Their structures were identified on the basis of spectral data.</p><p><b>RESULT</b>Seventeen compounds were separated and identified as ascleposide E(1), (+)-1-hydroxypinoresinol-4"-O-methyl ester-4'-beta-D-glucopyranoside (2), (+)-1 -hydroxypinoresinol-4"-O-beta-D-glucopyranoside(3), (+)-1-hydroxypinoresinol-1-O-P-D-glucopyranoside (4), phenyl-beta-D-glucopyranoside (5), benzyl-beta-D-glucopyranoside (6), n-butyl-beta-D-glucopyranoside (7), ilicic alcohol (8), beta-cyclocostunolide (9), reynosin (10), 11beta, 13-dihydroreynosin (11), arbusculin A(12), 1beta-hydroxy-arbusculin A (13), santamarin (14), dehydrocostuslactone (15), 11beta, 13-dihydro-3-epizaluzanin C(16)and costunolide (17).</p><p><b>CONCLUSION</b>Compounds 1-2 were separated from this genus for the first time,and compounds 3,5-7 were separated from this plant for the first time.</p>


Subject(s)
Ethanol , Chemistry , Glucosides , Chemistry , Lactones , Chemistry , Plant Roots , Chemistry , Saussurea , Chemistry , Sesquiterpenes , Chemistry , Sesquiterpenes, Eudesmane , Chemistry
8.
Article in Chinese | WPRIM | ID: wpr-281729

ABSTRACT

<p><b>OBJECTIVE</b>To develop a GC method for simultaneous determination of 4 compounds (atractylone, hinesol, beta-eudesmol and atractylodin) in Atractylodes lancea.</p><p><b>METHOD</b>A HP-1 capillary column (0.25 mm x 30 m, 0.25 microm) was used. The detector was FID:Inlet temperature was 250 degrees C. The detector temperature was 250 degrees C. The column temperature was set at 145 degrees C and held for 25 min after injection, then programmed at 10 degrees C x min(-1) to 250 degrees C and held for 10 min at the temperature. The carrying gas was nitrogen, split ratio was 40:1. Injection volume was 2 microL, Cluster analysis was performed by SPSS13.0 software.</p><p><b>RESULT</b>The linear ranges for atractylone, hinesol, beta-eudesmol and atractylodin were 0.0122. 32 (r = .9998), 0.008-1.68 (r = 0.9998), 0.009-1.76 (r = 0.9999), 0.016-3.20 g x L(-1) (r = 0.9997), respectively. The average recoveries (n = 3) of atractylone, hinesol, beta-eudesmol and atractylodin were 98.0%-99.0%, 97.7%-99.4%, 98.4%-99.2%, 97.8%-99.7%, respectively. The samples analyzed were divided into two classes.</p><p><b>CONCLUSION</b>This method is simple, specific, repeatable and stable. It can be applied for the simultaneous determination of 4 compounds (atractylone, hinesol, beta-eudesmol and atractylodin) in A. lancea, which will provide the basis for the quality control of A. lancea. The contents of 4 active compounds were significantly different between geo-authentic and non-authentic producing areas.</p>


Subject(s)
Atractylodes , Chemistry , Chromatography, High Pressure Liquid , Methods , Cluster Analysis , Drugs, Chinese Herbal , Furans , Plant Extracts , Chemistry , Plant Oils , Quality Control , Sesquiterpenes , Sesquiterpenes, Eudesmane , Spiro Compounds
9.
Article in Chinese | WPRIM | ID: wpr-324363

ABSTRACT

<p><b>OBJECTIVE</b>To develop a RP-HPLC method for determination of beta-eudesmol in rhizome of Atractylodes lancea, and to provide valuble data for quality control of A. lancea.</p><p><b>METHOD</b>The samples were separated on an Inertsil ODS-3 (4.6 mm x 250 mm, 5 microm) column with the mobile phase of acetonitrile-water (68:32). Flow rate was 1.0 mL x min(-1). The detection wavelength was set at 200 nm. Column temperature was 25 degrees C.</p><p><b>RESULT</b>The contents of beta-eudesmol determinated was 0.833-4.466 mg x g(-1), The linear range of beta-eudesmol was 0.048-1.200 microg (r = 0.999 9), the average recovery was 99.3%, RSD was 1.4% (n = 9).</p><p><b>CONCLUSION</b>The method for quantitation of beta-eudesmol in A. lancea was accurate and reliable, which can be used to evaluate the quality of rhizome of A. lancea.</p>


Subject(s)
Atractylodes , Chemistry , Chromatography, High Pressure Liquid , Methods , Plants, Medicinal , Chemistry , Quality Control , Reproducibility of Results , Rhizome , Chemistry , Sesquiterpenes, Eudesmane , Reference Standards
10.
Acta Pharmaceutica Sinica ; (12): 968-972, 2007.
Article in Chinese | WPRIM | ID: wpr-268545

ABSTRACT

To study the fingerprint of the volatile oil of Atractylodes lancea (Thunb.) DC., and to offer the characteristic data for the quality evaluation, GC-MS analysis was performed for 17 samples of different areas used as Atractylodes lancea (Thunb.) DC. Nine kinds of same components were selected. TIC profiles were evaluated by "Computer Aided Similarity Calculation". The characteristic peaks in chromatograms were identified by comparing mass data with literatures. Hierarchical clustering analysis was performed by SPSS based on the relative peak area (RPA) of identified peak to atractydin in 17 samples. The mutual mode fingerprint plots of genuine Atractylodes lancea (Thunb.) DC. have been established, the matching of active components was characteristic that atractylon, hinesol, beta-eudesmol, atractydin as (0.89 - 1.12): (0.11 - 0.15) : (0.48 - 0.61) : 1. The difference of resemblance of not genuine samples with genuine samples was remarkable. Two categorizations were clustered. Atractylodes lancea (Thunb.) DC. from genuine and Tangshan and Nanshan, Jiangsu Prov. were in a group, while those from Anhui and Hubei Prov. were in another group. The characteristic fingerprint of genuine Atractylodes lancea (Thunb.) DC. combined with the study of the matching of active components for the quality control and the resemblance calculation of fingerprints and SPSS hierarchical clustering analysis provided a new analytic method for the quality evaluation and discrimination of Atractylodes lancea (Thunb.) DC.


Subject(s)
Atractylodes , Chemistry , Cluster Analysis , Ecosystem , Gas Chromatography-Mass Spectrometry , Oils, Volatile , Chemistry , Plant Oils , Chemistry , Plants, Medicinal , Chemistry , Quality Control , Rhizome , Chemistry , Sesquiterpenes , Sesquiterpenes, Eudesmane , Spiro Compounds
11.
Acta Pharmaceutica Sinica ; (12): 1062-1065, 2007.
Article in English | WPRIM | ID: wpr-268232

ABSTRACT

The aim of the study was to investigate the sesquiterpene constituents from the rhizomes of Curcuma wenyujin Y. H. Chen et C. Ling. The isolation and purification of the constituents from the 50% EtOH extracts of the rhizomes were performed with repeated column chromatography over sillica gel and macroporous resin. Eight sesquiterpenes were obtained and identified as wenyujinlactone A (1), neolitamone A (2), zedoarondiol (3), isozedoarondiol (4), aerugidiol (5), curcumol (6), curdione (7) and (1R, 10R)-epoxy-(-)-1, 10-dihydrocurdine (8) by means of spectral analysis. Among them, compound 1 was found to be a new eudesmane sesquiterpene lactone, whilst compounds 2-5 were obtained from this plant for the first time.


Subject(s)
Curcuma , Chemistry , Molecular Structure , Plants, Medicinal , Chemistry , Rhizome , Chemistry , Sesquiterpenes, Eudesmane , Chemistry
12.
An. acad. bras. ciênc ; 78(1): 17-21, Mar. 2006. tab
Article in English | LILACS | ID: lil-422257

ABSTRACT

O estudo fitoquímico de Salzmmania nitida D.C. (Rubiaceae) conduziu ao isolamento e identificação de dois novos terpenoides, (+)-3-oxo-thermarol e 11-acetoxi-4alfa-metil-5alfa-eudesmanol além do (+)-termarol. As estruturas foram estabelecidas com base na análise de espectros de IV, Massas e RMN de 1H e 13C (1D e 2D).


Subject(s)
Abietanes/chemistry , Diterpenes/chemistry , Rubiaceae/chemistry , Sesquiterpenes, Eudesmane/chemistry , Abietanes/isolation & purification , Diterpenes/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes, Eudesmane/isolation & purification
13.
Article in Chinese | WPRIM | ID: wpr-350981

ABSTRACT

Laggera plants are traditionally used as folk medicine to treat bacterial infection, inflammation and fever in China. Three species, Laggera alata, L. intermedia and L. pterodonta, grow in China. Modem clinical studies show that L. pterodonta is a good medicine against inflammation. More than 100 compounds were obtained from these plants. In order to assist in medicinal application of this species of plants, progresses made in this field are systemically reviewed in this article.


Subject(s)
Asteraceae , Chemistry , Classification , Flavonols , Chemistry , Molecular Structure , Plants, Medicinal , Chemistry , Classification , Sesquiterpenes, Eudesmane , Chemistry
14.
Article in Chinese | WPRIM | ID: wpr-266812

ABSTRACT

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.


Subject(s)
Animals , Anti-Bacterial Agents , Pharmacology , Antineoplastic Agents, Phytogenic , Pharmacology , Chromatography, High Pressure Liquid , Methods , Humans , Molecular Structure , Plants, Medicinal , Chemistry , Pyrrolizidine Alkaloids , Chemistry , Pharmacology , Senecio , Chemistry , Sesquiterpenes , Chemistry , Pharmacology , Sesquiterpenes, Eudesmane , Chemistry
15.
Article in Chinese | WPRIM | ID: wpr-271802

ABSTRACT

<p><b>OBJECTIVE</b>To find the chemical diversity and characteristics of A. lancea on two levels--individuals and populations, and to discover the chemical essentials for forming geoherbs.</p><p><b>METHOD</b>47 rhizomes of A. lancea were collected in 7 populations, and 6 naphtha components (1. elemol, 2. hinesol, 3. beta-eudesmol, 4. atractylone, 5. atractylodin, 6. atractylenolid I) in the rhizomes were determined by GC-MS combination. Principal Component Analysis and Cluster Analysis were carried out by SPSS.</p><p><b>RESULT</b>Cluster Analysis of the 6 main components indicated that the chemical components of geoherbs were different from those of the non-geonerbs of A. lancea. Other analysis showed as follows: 1. The general oil of geoberbs were lower than that of non-geoherbs(P < 0.01), but components yielding more than 1% (% of the total oil) were more than non-geoherbs(P < 0.01); 2. Hinesol mixing beta-eudesmol was more in non-geoherbs, which atractylodin mixing atractylone was more in geoherbs(P < 0.001); 3. Principal Component Analysis implied that atractylone was the most important component to discriminate geoherbs and non-geoherbs of A. Lancea.</p><p><b>CONCLUSION</b>The naphtha composing characteristics of geoherbs was the special proportionment sale, viz. atractylone: hinesol: beta-eudesmol: atractylodin being(0.70~2.00):(0.04~0.35):(0.09~0.40):1.</p>


Subject(s)
Atractylodes , Chemistry , Classification , Ecosystem , Furans , Gas Chromatography-Mass Spectrometry , Oils, Volatile , Chemistry , Plant Extracts , Plants, Medicinal , Chemistry , Classification , Sesquiterpenes , Sesquiterpenes, Eudesmane , Spiro Compounds , Terpenes
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