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1.
Article in Chinese | WPRIM | ID: wpr-906468

ABSTRACT

Objective:In order to systematically clarify the chemical composition of Jiechangyan Qixiao granules, the main chemical components in this preparation were rapidly identified and assigned by ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF/MS<sup>E</sup>). Method:ACQUITY UPLC BEH C<sub>18</sub> column (2.1 mm×100 mm, 1.8 μm) was employed for UPLC analysis with the mobile phase of 0.1% formic acid aqueous solution (A)-acetonitrile (B) for gradient elution (0-2 min, 5%B; 2-16 min, 5%-21%B; 16-30 min, 21%-95%B; 30-33 min, 95%B; 33-34 min, 95%-5%B; 34-37 min, 5%B). The flow rate was 0.3 mL·min<sup>-1</sup>, the column temperature was 30 ℃, and the volume of sample injection was 2 μL. Electrospray ionization (ESI) was applied for scanning under positive and negative ion modes with the scanning range of <italic>m</italic>/<italic>z</italic> 60-1 200. MS<sup>E</sup> mode was used to collect mass spectral data. The ion peaks were identified by comparing with the information of control substances, literature references and self-built database. Result:A total of 102 chemical components were separated and identified in Jiechangyan Qixiao granules, including organic acids, flavonoids and its glycosides, triterpenes, phenylethanoid glycosides, tannins, iridoid glycosides and other components, among which flavonoids and its glycosides were from Drynariae Rhizoma and Crataegi Fructus, phenylethanoid glycosides and iridoid glycosides were from Plantaginis Semen, triterpenoids and tannins were from Crataegi Fructus and Chebulae Fructus. Among the identified chemical constituents, there were 28 from Drynariae Rhizoma, 31 from Plantaginis Semen, 53 from Chebulae Fructus and 58 ingredients from Crataegi Fructus. Conclusion:The established UPLC-Q-TOF/MS<sup>E</sup> can comprehensively and rapidly analyze the chemical constituents in Jiechangyan Qixiao granules, and preliminarily elucidates the chemical composition profile of this granules, which can lay a foundation for further research on the pharmacodynamic material basis and quality control of Jiechangyan Qixiao granules.

2.
Article in Chinese | WPRIM | ID: wpr-906183

ABSTRACT

Objective:To investigate the antioxidant activity and chemical composition of 75% ethanol extract of <italic>Rosa cymosa</italic> roots and its different polar parts. Method:The 75% ethanol extract of <italic>R. cymosa</italic> roots was divided into dichloromethane, ethyl acetate, <italic>n</italic>-butanol and water parts by organic solvent extraction. <italic>In vitro</italic> antioxidant activity of each fraction was determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging assays, as well as ferric reducing antioxidant power (FRAP) test. The contents of total triterpenes, total phenols, total tannins and condensed tannins in each fraction were determined by spectrophotometry. SPSS 24.0 software was used to conduct Pearson correlation analysis between the antioxidant activity of each fraction and the content of the main components, and then the main active fraction and the main active components were determined. The chemical constituents of the active fraction was analyzed by ultra performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS), and the structures of the main chromatographic peaks were predicted. Result:Each fraction of <italic>R. cymosa</italic> roots had certain antioxidant activity, and there was a significant dose-effect relationship within a certain concentration range, but the antioxidant activity of different polar parts was different. In DPPH and ABTS free radical scavenging tests, the antioxidant activity of each fraction and vitamin C (VC, the positive drug) was ranked as ethyl acetate fraction>VC><italic>n</italic>-butanol fraction>ethanol extract>water fraction>dichloromethane fraction. In FRAP test, the activity of ethyl acetate fraction was weaker than that of VC, and the other order was unchanged. The contents of total triterpenes, total phenols, total tannins and condensed tannins in ethyl acetate fraction were 3.81%, 50.33%, 3.32%, and 39.79%, in <italic>n</italic>-butanol fraction were 0.88%, 41.42%, 2.25% and 23.55%, in ethanol extract were 2.90%, 41.95%, 3.43% and 20.14%, in water fraction were 0, 26.80%, 16.90% and 7.57%, and in dichloromethane fraction were 21.23%, 12.90%, 1.59%, and 6.17%, respectively. Correlation analysis results showed that the contents of total phenols and condensed tannins were positively correlated with the antioxidant activity, the contents of total triterpenes were negatively correlated with the antioxidant activity, and the correlation between total tannins and antioxidant activity was not obvious. A total of 26 compounds were identified from the ethyl acetate fraction by UPLC-Q-TOF-MS/MS, including 11 condensed tannins, 4 hydrolysable tannins, 6 triterpenes, 3 flavonoids, 1 benzoic acid derivative and 1 chlorogenic acid analogue. Conclusion:Ethyl acetate fraction is the main antioxidant active site of <italic>R. cymosa</italic> roots, and phenols mainly composed of condensed tannins are the main active components. The results can provide experimental basis for the development of natural antioxidants.

3.
Article in Chinese | WPRIM | ID: wpr-883503

ABSTRACT

Alismatis Rhizoma(AR)is widely used in Chinese medicine,and its major bioactive components,tri-terpenes,reportedly possess various pharmacological activities.Therefore,it is very important to study the metabolism of triterpenes in vivo.However,the metabolism of AR triterpene extract has not been comprehensively elucidated due to its complex chemical components and metabolic pathways.In this study,an ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry method,which was based on the characteristic ions from an established database of known triterpenes,was used to analyze the major metabolites in rats following the oral administration of Alismatis Rhizoma extracts(ARE).As a result,a total of 233 constituents,with 85 prototype compounds and 148 metabo-lites,were identified for the first time.Hydrogenation,oxidation,sulfate and glucuronidation conjugation were the major metabolic pathways for triterpenes in AR.In addition,the mutual in vivo transformation of known ARE triterpenes was discovered and confirmed for the first time.Those results provide comprehensive insights into the metabolism of AR in vivo,which will be useful for future studies on its pharmacodynamics and pharmacokinetics.Moreover,this established strategy may be useful in meta-bolic studies of similar compounds.

4.
China Pharmacy ; (12): 201-206, 2021.
Article in Chinese | WPRIM | ID: wpr-862644

ABSTRACT

OBJECTIVE:To establish fingerprint of Paliurus ramosissimus total triterpenes ,and to conduct cluster analysis and principal component analysis ,and to determine the content of the main component paliurusene. METHODS :HPLC method was adopted. The determination was performed on Agilent PheHex column with mobile phase consisted of methanol- 0.05% phosphoric acid solution (gradient eluetion ) at the flow rate of 1 mL/min. The detection wavelength was set at 320 nm,and column temperature was 30 ℃. The sample size was 5 μL. Using paliurusene as reference,HPLC fingerprints of 10 batches of P. ramosissimus total triterpenes were drawn. Similarity evaluation was performed by using TCM Chromatographic Fingerprint Similarity Evaluation System (2012 edition),and the common peaks were confirmed. Cluster analysis and principle component analysis were performed by using SPSS 26.0 software. The content of paliurusene was determined by same HPLC method. RESULTS:There were totally 6 common peaks in HPLC fingerprint of 10 batches of P. ramosissimus total triterpenes. The similarity was more than 0.990;one of six common peaks was identified as paliurusene. The results of cluster analysis showed that 10 batches of samples could be clustered into 4 categories,including S 1,S2,S3-S6 and S 7-S10. The results of principal component analysis showed that the accumulative variance contribution rate of primary 2 principal components was 99.430%. Comprehensive score ranking was S 1>S9>S8>S7>S10>S2>S3>S5>S6>S4. The linear range of paliurusene concentration was 33.7-844.0 μg/mL(r=0.999 9). RSDs of precision ,reproducibility and stability (24 h)tests were all lower than 2%. Average recovery was 99.75%(RSD=1.13%,n=6). The average contents of paliurusene in 10 batches of P. ramosissimus total triterpenes was 0.576%-0.712%. CONCLUSIONS :Established HPLC fingerprint and content d etermination method are reliable and stable , and can be used for the quality control of P. ramosissimus .

5.
China Pharmacy ; (12): 46-50, 2021.
Article in Chinese | WPRIM | ID: wpr-862264

ABSTRACT

OBJECTIVE:To optimize the extraction technology for total triterpenes from the leaves of Cornus officinalis . METHODS:Based on the full swelling of the leaves of C. officinalis ,total triterpenes was extracted with heating reflux method. The effects of ethanol concentration ,liquid-solid ratio ,extraction time and extraction times on the contents of total triterpenes from the leaves of C. officinalis were investigated by single factor test. Using oleanolic acid as control ,the contents of total triterpenes were detected by UV spectrometry. On the basis of single factor test ,fixing the times of extraction a s 3 times,taking the contents of total triterpenes as response value ,using ethanol volume fraction ,solid-liquid ratio and extraction time as factors , Box-Behnken design-response methodology was used to optimize the extraction technology of total triterpenes from the leaves of C. officinalis,and the optimized extraction technology was validated. RESULTS :The optimal extraction technology of total triterpenes from the leaves of C. officinalis were as follows as ethanol concentration of 73%,liquid-to-material ratio of 38 ∶ 1(mL/g), extraction time of 60 min. Results of 3 validation tests showed that the contents of total triterpenes from the leaves of C. officinalis were 6.92%,6.91%,6.84%;the average content was 6.89%(RSD=0.63%),relative error of which with the predicted value (7.28%)was 5.36%. CONCLUSIONS :The optimized technology is stable and reliable ,and can be used for the extraction of total triterpenes from leaves of C. officinalis .

6.
Article in English | WPRIM | ID: wpr-880990

ABSTRACT

The genus Chrysobalanus is one of the classes of medicinal plants used in the treatment and management of several diseases. This study is aimed at providing up-to-date information on the phytochemical composition and pharmacological uses of Chrysobalanus icaco. Current literature on the Chrysobalanus species was obtained by searching electronic databases such as PubMed, Google Scholar and Web of Science. Of the species in this genus, four have been reported in the literature, but only one (C. icaco) has been extensively studied. C. icaco is rich in several minerals, including potassium, magnesium, calcium and sodium. The plant also contains a host of phytochemicals, such as flavonoids, diterpenes and triterpenes, which have been shown to have pharmacological activity. It can be concluded that C. icaco is a good source of phytochemicals that contribute to its therapeutic uses. However, bioassay-guided isolation of its bioactive compounds is necessary for promoting the development of drugs from this medicinal plant.

7.
Braz. J. Pharm. Sci. (Online) ; 56: e17666, 2020. tab, graf
Article in English | LILACS-Express | LILACS | ID: biblio-1089217

ABSTRACT

Cancer is one of the most prevalent diseases worldwide and the natural products could be a source of bioactive compounds. Passiflora mucronata (PM) belongs to a very known vegetal genus, although, there are no studies about cytotoxic activity or isolated compounds. Different extracts from PM were obtained by liquid-liquid partition (P), Soxhlet (Sox) and supercritical fluid (SFE1-5) extraction techniques, being compared concerning their yields, chemical profile and cytotoxicity. The Sox extracts showed the highest yields (6.03%: hexane; 2.51%: dichloromethane) followed by SFE (from 4.34 to 1.63%) and partitions (1.06 and 2.26%). The hexane partition (HP) showed the best cytotoxic activity against K562 cell line (IC50 = 18.72 µg.mL-1). From HP, the following compounds were identified and analysed its cytotoxic activities: β-amyrin (IC50 = 3.92 µg.mL-1), β-sitosterol (IC50 = 3.37 µg.mL-1), stigmasterol (IC50 = 3.31 µg.mL-1) and oleanolic acid. Stigmasterol induced about 75% of K562 total apoptosis. The compounds were tested against MA-104 cell line and the selective index (SI) attributed (SI >10 for all compounds). This indicates good selectivity to K562 cell line at the expense of MA-104. This is the first time, identifying those compounds to PM .

8.
Chinese Herbal Medicines ; (4): 118-124, 2020.
Article in Chinese | WPRIM | ID: wpr-842031

ABSTRACT

Botanical pentacyclic triterpenes possessed a broad range of pharmacological activities such as anti-oxidant, anti-tumor, anti-microbial and anti-inflammatory activities. It is believed that the mechanisms involved in these bioactivities are due to the modulation of immune system. Recently, the pharmacological validation on immunomodulatory of pentacyclic triterpenes derived from higher plants is very limited and several existence review papers related for this group of compound have not been focused for this activity. In this review, we have highlighted several studies on immunomodulatory potential of botanical pentacyclic triterpenes isolated from wide array of different species of medicinal plants and herbs based on various preclinical in vitro and animal models. This review also attempts to discuss on bioactivities of compouns related with their structure-activity relationship. Hence, the evaluation of pentacyclic triterpenes offers a great opportunity to discover adjuvants and novel therapeutic agents that presented beneficial immunomodulatory properties.

9.
Article in Chinese | WPRIM | ID: wpr-846614

ABSTRACT

Objective: To investigate the chemical constituents of the leaves of Phyllanthus acidus. Methods: All compounds were isolated by silica gel and Sephadex LH-20 gel column chromatographies as well as semi-preparative HPLC, and their structures were elucidated on the basis of physicochemical properties and spectral data. Results: Ten compounds were isolated and identified as 3α-cinnamoyloxyurs-20(29)-en-18β-ol (1), phyllanthol (2), maslinic acid (3), ovoideal E (4), quercetin-3-rhamnoside (5), 4-hydroxybenzoic acid (6), methyl 4-hydroxyphenylacetate (7), 4-O-(β-glucopyranosyloxy)-benzoic acid (8), thioacetic anhydride (9), L-pyroglutamic acid (10). Conclusion: Compound 1 is a new compound named as phyllanacidol B, and compounds 3-10 are obtained from P. acidus for the first time.

10.
Article in Chinese | WPRIM | ID: wpr-846503

ABSTRACT

Paeoniae Radix Alba (PRA) is a clinically commonly used drug for tonifying blood and regulating meridians, which was listed as one of the highest grade herb in Shengnong's Classic of Materia Medica. The main chemical constituents of PRA are monoterpenes, triterpenes and flavonoids, and its processing methods are cleansing, cutting, adding auxiliary materials, etc. At present, the mainstream processing methods are stir-frying or stir-frying with wine. Modern studies have shown that PRA has the effects of protecting cardiovascular, anti-inflammatory and anti-oxidant. In this paper, we consulted with the ancient Chinese materia medica and ancient Chinese medical book, analyzed the local traditional Chinese medicine slices processing norms and modern pharmacopoeia. Meanwhile, we reviewed the history of PRA in function and processing, and discussed the modern processing technology, chemical composition and pharmacological research in some extent. We hope it can be helpful for some related research of PRA.

11.
Article in Chinese | WPRIM | ID: wpr-846420

ABSTRACT

Poria cocos is a traditional Chinese medicine with homology of medicine and food in China. It has the effects of promoting diuresis, eliminating dampness, invigorating spleen, calming heart and so on. It is widely used in medicine, food and health care products. With the in-depth study of P. cocos, its triterpenes, polysaccharides and other major chemical components, as well as its wide range of pharmacological effects and application development research have attracted much attention. This paper systematically reviewed the chemical components and pharmacological effects of P. cocos, according to the concept of quality markers, the quality markers of P. cocos were predicted and analyzed from the aspects of the biosynthetic approach and specificity of chemical components, traditional medicinal efficacy, traditional medicinal properties, measurable components, different processing methods and so on, which provides a scientific basis for quality evaluation and product development of P. cocos.

12.
Article in Chinese | WPRIM | ID: wpr-873256

ABSTRACT

Objective::To study on the content change and transformation rule of eight main characteristic components in stir-frying process of Glycyrrhizae Radix et Rhizoma. Method::The contents of liquiritin apioside, liquiritin, isoliquiritin apioside, isoliquiritin, liquiritigenin, isoliquiritigenin, glycyrrhizic acid and glycyrrhetinic acid in Glycyrrhizae Radix et Rhizoma were determined simultaneously by HPLC. The chromatographic conditions were Waters Symmetry® C18 column (4.6 mm×250 mm, 5 μm), and the mobile phase of acetonitrile (A)-0.05%phosphoric acid solution (B) for gradient elution (0-9 min, 19%-25%A; 9-18 min, 25%-34%A; 18-38 min, 34%-51%A; 38-58 min, 51%-89%A), the flow rate of 1 mL·min-1, the detection wavelengths at 320 nm (0-16 min), 276 nm (16-25 min), 370 nm (25-28 min), 254 nm (28-58 min), the injection volume of 10 μL and the column temperature at 30 ℃. Result::After stir-frying, the total content of three components with dihydroflavone as mother nucleus was decreased, while the total content of three components with chalcone as mother nucleus showed an upward trend, the content change of glycyrrhizic acid was not obvious, but glycyrrhetinic acid content showed a slight upward trend. When the monomer heating temperature reached 130 ℃, dihydroflavones and chalcones could be isomerized with each other, and with the increase of temperature, the isomerization became more obvious. When the heating temperature rose to 180 ℃ (isoliquiritin apioside was 130 ℃), in addition to the isomerization, the glucosidic bond of flavonoid glycosides began to break and gradually transformed into the corresponding secondary glycosides or aglycones. Glucosidic bond of glycyrrhizic acid could also be broken to form glycyrrhetinic acid, which was detected at 150 ℃. Conclusion::The change of chemical composition is complex during stir-frying process of Glycyrrhizae Radix et Rhizoma, in addition to the isomerization and glucosidic bonds breaking observed in this experiment, there may be other complex reactions. The content of one compound in the herb is affected by many factors during its processing, such as the time and temperature of frying, the stability of the compound itself and so on.

13.
Article in Chinese | WPRIM | ID: wpr-846306

ABSTRACT

Objective: To screen the upstream regulatory transcription factors of farnesyl diphosphate synthase (FPS) in the triterpenoid synthesis pathway in Ganoderma lucidum. Methods: In this study, the FPS promoter was cloned and connected to the pAbAi plasmid to construct bait vector pAbAi-FPS, which was transformed into Y1H yeast competent cells to construct bait yeast. The yeast one-hybrid cDNA library was constructed by using SMART technology, then the purified ds-cDNA and pGADT7-Rec were co-transformed into bait yeast strain to screen the upstream transcriptional regulatory factors of PFS. Results: The bait vector containing pAbAi-FPS was constructed and the bait strain was screened, the cDNA library was constructed and transformed to the bait strain. A total of 37 positive clones were screened and sequenced. The sequences of conserved domain were predicted and performed blast search against the whole-genome database to identify their function. As a result, a total of 18 upstream regulatory factors were screened out including three transcription factors, five ribosomal proteins, and 10 other transcription regulators. Conclusion: The results indicated that transcription factors GlSNF2, GlMHR, and GlZn2Cys6 were candidate genes for regulating the expression of FPS, and this study offered data for further study on the regulation mechanism of FPS expression.

14.
Article in Chinese | WPRIM | ID: wpr-846280

ABSTRACT

As a traditional Chinese medicine, Melia toosendan is widely used as a natural deworming agent. M. toosendan is rich in chemical components, incluing limonoid-type triterpenes, lignans, flavonoids, steroids, organic acids and so on. Its pharmacological activities are mainly anti-tumor, anti-oxidation, anti-bacterial, anti-inflammatory and analgesic effects, antiviral, deworming. The application of M. toosendan is limited due to its hepatotoxicity, pregnancy toxicity and so on. In this paper, the chemical constituents, pharmacological activities and toxicity of M. toosendan were reviewed, which will provide scientific basis for its further development research and clinical application.

15.
Article in Chinese | WPRIM | ID: wpr-846140

ABSTRACT

Objective: To study triterpenes and their anti-inflammatory activity from the ethanol extract of Centipeda minima. Methods: The compounds were isolated and purified by silica gel, Sephadex LH-20, MCI, ODS and RP-HPLC gel column chromatography, and their structures were elucidated by NMR and MS spectroscopic techniques. The inhibitory activity of the compound on the release of inflammatory mediators NO from mouse macrophages (RAW264.7) induced by lipopolysaccharide (LPS) was determined by Griess method, and then the anti-inflammatory activity of the compounds was evaluated Results: A total of 17 compounds were isolated and identified as: 20-oxo-30-nortaraxastan-3β-yl acetate (1), 3β-acetoxytaraxaster-20-en-30-al (2), 3β-hydroxytaraxaster-20-en-30-al (3), taraxasterol (4), arnidiol (5), 3β,21β-dihydroxy-20(30)-en-taraxastane (6), faradiol (7), pseudotaraxasteryl acetate (8), taraxast-20-ene-3β,30-diol (9), 18α-olean-12-ene-3,11-dione (10), maniladiol (11), 3β- hydroxyolean-12-en-11-one (12), coflodiol (13), lupeol (14), 3β,16β-dihydroxylup-20(29)-ene (15), 16β-hydroxylupa-20(29)- en-3-one (16) and garcinielliptone Q (17). Compounds 2, 5-6, 8-10, 12-13, 15-17 displayed moderate inhibitory activity on theoverproduction of NO in LPS-activated RAW 264.7 mouse macrophage cell lines, IC50 values ranging from 11.9 to 27.1 μmol/L. Conclusion: Compound 1 is a new natural product, and its 1H-NMR and 13C-NMR data was first completely assigned on the basis of 1D and 2D NMR spectroscopic evidence. Compounds 2, 3, 6, 8-10, 12, 13, 15 and 16 are isolated from C. minima for the first time. This work provided theoretical basis for clinical application of C. minima

16.
Article in Chinese | WPRIM | ID: wpr-846100

ABSTRACT

Objective: To study the chemical constituents of Artemisia argyi. Methods: The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Result Thirty-one compounds were isolated from A. argyi with the structures identified as (E)-β-farnesene (1), β-amyrin acetate (2), cycloartenol acetate (3), lupelo acetate (4), n-triacontanol (5), docosanoic acid (6), octadecanoic acid (7), tetracosanoic acid (8), (2R,4aR,8aR)-3,4,4a,8a-tetrahydro-4a-hydroxy-2,6,7,8a-tetramethyl-2-(4,8,12-trimethyl)-chromene-5,8-dione (9), α-spinasterol (10), monopalmitin (11), 12β,20β-dihydroxyldamar-23-en-3-ketone (12), monostearin (13), monolinolenin (14), monolinolein (15), monoolein (16), 3-(3-methyl-2-butenyl)acetophenone-4-O-β-D-glucoside (17), (-)cis-chrysan-thenol-β-D-glucoside (18), artemisioside (19), (1S,2S,4R)-p-menthane-1,2,8-triol-2-O-glucoside (20), (2E,6R)-2,6-dimethyl-2,7-octadiene-6-hydroxy-1-O- glycoside (21), ampelopsisionoside (22), 4-hydroxy acetophenone-4-O-β-D-glucoside (23), skimmin (24), scopoletin (25), dendanthemoside B (26), (4R)-p-menth-1-ene-7,8-diol-7-O-β-D-glucoside (27), (4R)-p-menthane-7,8-diol-7-O-β-D-glucoside (28), isorhoifolin (29), 1,3-dicaffeoylquinic acid (30) and pinitol (31). Conclusion: Compounds 1, 9, 17, 20, 21, 26, 28 are separated from Artemisia genus for the first time. Compounds 11, 12, 14-16, 18, 19, 23, 24, 27, 30, 31 are isolated from A. argyi for the first time.

17.
Article in Chinese | WPRIM | ID: wpr-846096

ABSTRACT

Coicis Semen is a common traditional Chinese medicine for medicine and food homology, with high nutritional value, known as "the King of Gramineae". It contains fatty acids and esters, polysaccharides, flavonoids, triterpenes, alkaloids, sterols, lactams, starch and other compounds, which exerts different effects in the treatment of diseases of Coicis Semen to achieve the purpose of treatment. Recent research has found that Coicis Semen not only has a good effect of removing dampness and diuresis in the theory of traditional Chinese medicine, but also can treat a variety of cancers, hypertension, hyperlipidemia, fatty liver, rheumatoid arthritis and other diseases. Furthermore, it can enhance immunity and regulate intestinal flora. It also can be used as the treatment for medicinal diet auxiliary diseases, and the clinical adverse reactions are less, and the medication is safer. Kanglaite injection with Coicis Semen oil as the main raw material has been widely used in the clinical treatment of a variety of cancers, and many health foods and medicinal diets are also under development. This paper mainly discusses the research progress on the chemical constituents and pharmacological effects of Coicis Semen, hoping to provide reference for the further study of Coicis Semen.

18.
Acta Pharmaceutica Sinica ; (12): 283-288, 2020.
Article in Chinese | WPRIM | ID: wpr-789015

ABSTRACT

Eight triterpenes were isolated from the methanol extract of Galbanum by various chromatographic methods including silica gel, ODS opening column, recrystallization and semi-preparative HPLC. Their structures were determined by spectroscopic methods and physicochemical properties as 3β,19α,21α-trihydroxyl-12-en-28-oic acid (1), sumaresinolic acid (2), 3β,19α-dihydroxyl-12-en-28-oic acid (3), oleanolic acid (4), 3β,6β,19α-trihydroxyl-12-en-28-oic acid (5), 19α-hydroxy oleanonic acid (6), 6α-hydroxy oleanonic acid (7), and (11R,12R)-3α,6α-dihydroxy-epoxyolean-28α,13α-olide (8). Among them, compound 1 is a new compound, while compounds 2-8 were newly isolated from the Apiaceae family. The ability of compounds 1-8 to inhibit cholinesterase was determined with an improved Ellman method. Compound 1 showed strong inhibitory activity against butyrylcholinesterase. The molecular docking results indicated that Trp82, His438, Phe329 and Ala328 played an important role in the binding of compound 1 to butyrylcholinesterase.

19.
Vitae (Medellín) ; 27(2): 1-11, 2020. Ilustraciones
Article in English | LILACS, COLNAL | ID: biblio-1120320

ABSTRACT

Background: Passiflora quadrangularis L. has antihypertensive and anxiolytic properties observed in experimental models. Objectives: The aim of this work was to establish the vascular effects exerted by two known monodesmosidic triterpene saponins, 3-O-ß-D-glucopyranosyloleanolic acid (Compound 1) (not previously described for this plant) and, 3-O-[ß-D-glucopyranosyl-(1→2)-ß-D-glucopyranosyl] oleanolic acid (Compound 2), isolated from the ethanolic extract of Passiflora quadrangularis L. leaves. Methods: The structural elucidation was achieved by Nuclear Magnetic Resonance (NMR) experiments and High-Resolution Mass Spectrometry (HRMS). Aortic rings from Wistar rats, previously stimulated with phenylephrine (PE, 1µM) and washed, were exposed to cumulatively concentrations of compound 1 and compound 2 (10 to 400 µM). Ethanolic extract from leaves of P. quadrangularis L. (10 to 320 µg/ mL) and clonidine (1nM to 100µM) were also used for comparison. Concentration response curves of compounds 1 and 2 were examined in presence and absence of: endothelium, the alpha-2 antagonist yohimbine (1 and 100 µM), the alpha non selective antagonist phentolamine (1µM), the alpha-1 antagonist prazosin (1µM) and the calcium channel blocker verapamil (10 and 100 µM). In addition, cumulatively response curve of acetylcholine (ACh, 10nM to 10µM) and sodium nitroprusside (SNP, 1nM to 100µM) were assayed in rings precontracted with compounds 1 and 2 (400 µM). Results: Compounds 1 and 2 elicited a vasoconstriction response in intact aorta rings in similar way (pEC50: 3.92±0.01 and 4.09±0.01, respectively), effect that did not change in denuded rings (pEC50: 3.90±0.01 and 4.11±0.01). The potency order (pEC50) of compounds 1 and 2 decreased according to the following: verapamil (3.53±0.01 and 3.90±0.02; p<0.05) < yohimbine (3.65±0.01 and 3.94±0.02; p<0.05) < prazosin (3.86±0.01 and 4.30±0.02) < phentolamine (4.05±0.02 and 4.05±0.01). SNP but not ACh, was able to decrease the vasopressor effect of compounds 1 and 2 (pIC50: 8.61±0.01 and 8.24 ± 0.15, respectively). Conclusions: Compounds 1 and 2 are key metabolites responsible for the ex vivo vasoconstrictor response induced by P. quadrangularis L. Activation of voltage-dependent calcium channels and/or α2-adrenergic receptors stimulation could be mechanisms implicated.


Antecedentes: Passiflora quadrangularis L. tiene propiedades antihipertensivas y ansiolíticas observadas en modelos animales. Objetivos: El objetivo de este trabajo fue establecer los efectos vasculares ejercidos por dos conocidas saponinas triterpénicas monodesmosídicas: el ácido 3-O-ß-D glucopiranosiloleanólico (Compuesto 1) (no descrito previamente para esta especie vegetal) y el ácido 3-O-[ß-D-glucopiranosil- (1→2)-ß-D-glucopiranosil]oleanólico (Compuesto 2), aisladas del extracto etanólico de las hojas de Passiflora quadrangularis L. Métodos: La elucidación estructural se llevó a cabo mediante experimentos de Resonancia Magnética Nuclear (NMR) y determinaciones de Espectrometría de Masas de Alta Resolución (HRMS). Los anillos aórticos de ratas Wistar, previamente estimulados con fenilefrina (PE, 1 µM) y lavados, fueron expuestos a concentraciones acumulativas del compuesto 1 y compuesto 2 (10 a 400 µM). El extracto etanólico de las hojas de P. quadrangularis L. (10 a 320 µg / ml) y clonidina (1 nM a 100 µM) se utilizaron para la comparación. Las curvas de concentración respuesta de los compuestos 1 y 2 se examinaron en presencia y ausencia de: endotelio, el antagonista alfa-2 yohimbina (1 y 100 µM), el antagonista alfa no selectivo fentolamina (1 µM), el antagonista alfa-1 prazosina (1 µM) y el bloqueador de canales de calcio verapamilo (10 y 100 µM). Además, la curva de concentraciones acumulativas de acetilcolina (ACh, 10 nM a 10 µM) y nitroprusiato de sodio (SNP, 1 nM a 100 µM) se ensayó en anillos pre-contraídos con los compuestos 1 y 2 (400 µM). Resultados: Los compuestos 1 y 2 provocaron una respuesta de vasoconstricción en los anillos de aorta intactos de manera similar (pEC50: 3.92 ± 0.01 y 4.09 ± 0.01, respectivamente), este efecto no cambió en los anillos denudados (pEC50: 3.90 ± 0.01 y 4.11 ± 0.01). El orden de potencia (pEC50) de los compuestos 1 y 2 disminuyó de la siguiente manera: verapamilo (3.53 ± 0.01 y 3.90 ± 0.02; p <0.05) < yohimbina (3.65 ± 0.01 y 3.94 ± 0.02; p <0.05) < prazosina (3.86 ± 0.01 y 4.30 ± 0.02)

Subject(s)
Humans , Saponins , Vasoconstriction , Passiflora , Oleanolic Acid , Antihypertensive Agents
20.
Article | IMSEAR | ID: sea-209841

ABSTRACT

Genus Nicotiana (Solanaceae) includes 76 species, among which only Nicotiana tabacum L. (common tobacco) isrecognized as economically important. Nicotiana species synthesize various secondary metabolites with biological orecological activities, but many of them still have not been sufficiently studied. The objective of current study was todetermine the content of selected groups of metabolites (e.g., phenolic acids, flavonoids, and triterpenes) in the leavesand extracts of three Nicotiana species (Nicotiana alata Link and Otto, Nicotiana rustica L., and N. tabacum L.),grown side by side. The results from the high-performance liquid chromatography identification of polyphenols andtriterpenes in leaves and extracts showed considerable variations between the species. All of them, however, werecharacterized as plant materials containing various specialized and bioactive metabolites, which substantiate theirconsideration as a valuable source for obtaining different phytoproducts. In terms of the studied groups of bioactivemetabolites, the results from the study suggest that 50% and 70% ethanol are the most suitable solvent concentrationsfor the extraction of N. alata, N. rustica, and N. tabacum leaves. The high content of polyphenols and triterpenesin the extracts provides grounds for their use in various cosmetic and pharmaceutical products, which could be thesubject of future research.

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