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Chemical constituents of water extracts of Asplenium ruprechtii were investigated. Five compounds were isolated by silica gel, Sephadex LH-20 gel column chromatographies and preparative HPLC, and their structures were identified by various spectral analyses as aspleniumside G(1), trans-p-coumaric acid(2), trans-p-coumaric acid 4-O-β-D-glucoside(3), cis-p-coumaric acid 4-O-β-D-glucoside(4), and(E)-ferulic acid-4-O-β-D-glucoside(5). Among them, compound 1 is a new 9,19-cycloartane glycoside.
Subject(s)
Chromatography, High Pressure Liquid , Glucosides , Glycosides , TriterpenesABSTRACT
Glycyrrhizae Radix et Rhizoma, a traditional Chinese herbal medicine, mainly contains triterpenoids, flavonoids, polysaccharides, coumarins and volatile oils with many pharmacological activities such as anti-tumor, anti-bacterial, anti-viral, anti-inflammatory, immune regulatory and anti-fibrotic effects. The widespread applications of Glycyrrhizae Radix et Rhizoma in food, medicine and chemical industries make its demand increase gradually. Therefore, the quality guarantee of the medicinal is of great value. Starting from the elaboration of chemical components and pharmacological effects of Glycyrrhizae Radix et Rhizoma and the introduction to the concept of quality marker(Q-marker), this study analyzed the Q-markers of Glycyrrhizae Radix et Rhizoma from the aspects of plant phylogene-tics, chemical component specificity, traditional efficacy, traditional medicinal properties, absorbed components, different processing methods and so on, which provides reference for quality evaluation, development and utilization of Glycyrrhizae Radix et Rhizoma.
Subject(s)
Drugs, Chinese Herbal/pharmacology , Glycyrrhiza , Rhizome , TriterpenesABSTRACT
Dammarane-type triterpenoid saponins are regarded as the main active constituents of Gynostemma longipes C.Y.Wu. By using MCI and silica gel column chromatography, as well as preparative HPLC, we isolated four new dammarane-type triterpenoid saponins from the polar saponin fraction of G. longipes C.Y.Wu. Their structures were determined by comprehensive analyses of NMR and MS data and identified as (20S)-3β,20,21-trihydroxydammar-19-oxo-24-ene-3-O-{[α-L-rhamnopyranosyl(1→2)]-[β-D-xylopyranosyl(1→3)]-α-L-arabinopyranosyl}-21-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (1), (20S)-3β,20,21-trihydroxydammar-24-ene-19-oxo-3-O-[α-L-rhamnopyranosyl(1→2)]-[β-D-xylopyranosyl(1→3)]-α-L-arabinopyranosyl-21-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside (2), (20S)-3β,19,20,21-terahydroxydammar-24-ene-3-O-{[α-L-rhamnopyranosyl(1→2)]-[β-D-xylopyranosyl(1→3)]-α-L-arabinopyranosyl}-21-O-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside (3), (20S)-3β,20,21-trihydroxydammar-24-ene-3-O-{[α-L-rhamnopyranosyl(1→2)]-[β-D-glucopyranosyl(1→3)]-β-D-glucopyranosyl}-21-O-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside (4). Compounds 1-4 are new dammarane-type triterpenoid saponins which contain five glycosyl residues.
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Seven new triterpenoid saponins, including five ursane-type saponins, ilexchinenosides R-V (1-5), and two oleanane-type saponins, ilexchinenosides W-X (6-7), with four known triterpenoid saponins (8-11) were isolated from the leaves of Ilex chinensis. Their structures were elucidated by comprehensive spectroscopic 1D and 2D NMR and HR-ESI-MS data. Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization. Compounds 1, 2, 4, 9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell injury in vitro.
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Two new triterpenoid saponins, ardisicrenoside R and S (1 and 2), and one new phenylpropanoid glycoside, ardicrephenin (3), along with five known compounds (4-8), were isolated from roots of Ardisia crenata. Their structures were elucidated on the basis of NMR spectroscopic data and chemical methods. Compounds 2-7 were evaluated for their cytotoxic activities against A549, MCF-7, HepG2 and MDA-MB-231 cell lines by MTT assay. Ardicrenin (6) showed significant cytotoxicity, with IC
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Objective: To investigate the enzymatic hydrolysis of gypenosides by β-glucanase 26130 CN to prepare some hydrolyzed secondary saponins, so as to provide material basis for further biological studies. Methods: Using β-glucanase 26130 CN, the total saponins from Herba Gynostemmatis were hydrolyzed with the enzyme catalysis, and the hydrolytic products were analyzed by ultra high- performance liquid chromatography coupled with quadrupole time- of- flight mass spectrometry(UHPLC- Q- TOF/MSE)to identify the converted products. Then, the main components of Herba Gynostemmatis, gypenosides XLIX and A, were used as substrates of the β-glucanase 26130 CN for convertsion to secondary saponin products. The products were separated by preparative highperformance liquid chromatography(HPLC)and identified by NMR and MS. Results: Twenty eight triterpenoid saponins were identified in the total saponin hydrolysate on the basis of their high-resolution MS data, by comparison with the data in the literature, and seven of them were validated to be the converted products. It was found that the β-glucanase 26130 CN could hydrolyze the glycosidic bond of terminal glucose or xylose in the molecule of gypenosides. By the enzymatic hydrolysis of gypenoside XLIX and gypenoside A, gypenoside I(the one glucosyl-lost gypenoside XLIX)and gypenoside UL1(the one xylosyl-lost gypenoside A)were obtained via the preparative HPLC separation of the gypenoside XLIX and gypenoside A hydrolysates, respectively. Conclusion: β-glucanase 26130 CN could effectively catalyze the hydrolysis of terminal glucosyl and xylosyl groups in gypenosides, with a relatively high hydrolytic conversion rate, which could be used to prepare some secondary saponins or aglycones.
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In recent years, biosynthesis of triterpenoid saponins in medicinal plants has been widely studied because of their active ingredients with diverse pharmacological activities. Various oxidosqualene cyclases, cytochrome P450 monooxygenases, uridine diphosphate glucuronosyltransferases, and transcription factors related to triterpenoid saponins biosynthesis have been explored and identified. In the biosynthesis of triterpenoid saponins, the progress of gene mining by omics-based sequencing, gene screening, gene function verification, catalyzing mechanism of key enzymes and gene regulation are summarized and discussed. By the progress of the biosynthesis pathway of triterpenoid saponins, the large-scale production of some triterpenoid saponins and aglycones has been achieved through plant tissue culture, transgenic plants and engineered yeast cells. However, the complex biosynthetic pathway and structural diversity limit the biosynthesis of triterpenoid saponins in different system. Special focus can further be placed on the systematic botany information of medicinal plants obtained from omics large dataset, and triterpenoid saponins produced by synthetic biology strategies, gene mutations and gene editing technology.
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Traditional Chinese medicine (TCM) has been paid much attentions due to the prevention and treatment of steroid hormone disorders. Ginseng, the root of Panax ginseng C. A. Meyer (Araliaceae), is one of the most valuable herbs in complementary and alternative medicines around the world. A series of dammarane triterpenoid saponins, also known as phytosteroids, were reported as the primary ingredients of Ginseng, and indicated broad spectral pharmacological actions, including anti-cancer, anti-inflammation and anti-fatigue. The skeletons of the dammarane triterpenoid aglycone are structurally similar to the steroid hormones. Both in vitro and in vivo studies showed that Ginseng and its active ingredients have beneficial hormone-like role in hormonal disorders. This review thus summarizes the structural similarities between hormones and dammarane ginsenosides and integrates the analogous effect of Ginseng and ginsenosides on prevention and treatment of hormonal disorders published in recent twenty years (1998-2018). The review may provide convenience for anticipate structure-function relationship between saponins structure and hormone-like effect.
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Due to lack of reference substances,the content of triterpenoid saponins in traditional Chinese medicines is usually characterized by colorimetric determination of total saponins. However,the specificity of colorimetric method is poor,and the determination result is not accurate enough. So,in this paper,the content determination method of total triterpenoid saponins was studied by taking Akebiae Caulis saponins as an example. The contents of three main saponin aglycones,including arjunolic acid,hederagenin and oleanolic acid,were determined by HPLC method. Referring to the content determination method of total flavonol glycosides in Ginkgo biloba leaves in the 2015 edition of Chinese Pharmacopoeia,the content of Akebiae Caulis saponins was obtained by multiplying the total content of the three above-mentioned aglycones with conversion coefficient. LC-MS/MS analysis results showed that mutongsaponin C and aponin PJIwere the two main triterpene saponins in Akebiae Caulis,and they shared the same molecular formula. So,the average value of the ratios of the molecular weight between mutongsaponin C and the three aglycones was defined as the conversion coefficient.The three aglycones were separated on an ACE Excel 3 C18-AR column( 4. 6 mm×150 mm,3 μm),and methanol-water( containing0. 04% glacial acetic acid and 0. 02% triethylamine) was used as mobile phase with gradient elution. The detection wavelength was set at 210 nm,and the flow rate was 0. 5 m L·min-1. The results showed that there was a good linearity among the ranges of 1. 053-16. 84,0. 200-3. 200 and 1. 515-24. 24 μg for arjunolic acid,hederagenin and oleanolic acid,respectively. Their average recoveries were97. 90%,97. 50% and 100. 5%,with RSD of 2. 0%,2. 9% and 2. 9%,respectively. The results of methodological investigation met the requirements of content determination. The conversion coefficient was 2. 31. This method is simple and reliable,and can be used for the determination of total triterpenoid saponins in Akebiae Caulis. The assay strategy can be used for the determination of total triterpenoid saponins in other traditional Chinese medicines.
Subject(s)
Chromatography, High Pressure Liquid , Chromatography, Liquid , Drugs, Chinese Herbal , Medicine, Chinese Traditional , Phytochemicals , Ranunculales , Chemistry , Saponins , Tandem Mass Spectrometry , TriterpenesABSTRACT
Ziziphi Spinosae Semen (ZSS) is the first choice for traditional Chinese medicine in the treatment of insomnia. The saponins are the main active ingredient of ZSS. At present, 51 kinds of saponin components have been obtained from ZSS, which are mainly classified into tetracyclic triterpenes and pentacyclic triterpenoid saponins according to the aglycon structure. With the deep research on the saponins from ZSS, it has been found that it has a wide range of pharmacological effects, such as calming, anti-anxiety, anti-depression, anti-tumor, and myocardial protection. In view of the increasingly serious harm to human health caused by nervous system diseases and the important role of ZSS in the prevention and treatment of nervous system diseases, this study focused on systematically summarizing the structural types of ZSS saponins and the pharmacological effects in the nervous system to provide a scientific reference for the development and utilization of ZSS saponins.
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Objective: To study the minor triterpenoid saponins from the roots of Panax notoginseng, which provided basis for the systematic research, quality control and safety evaluation of P. notoginseng. Methods The compounds were isolated and purified by MCI resin, ODS, along with Preparative-HPLC, and the structures were identified by spectroscopic analysis, and comparing with the pubished literature values. Results: Twelve monomeric compounds isolated from the roots of P. notoginseng, were identified as notoginsenoside P1 (1), notoginsenoside T5 (2), ginsenoside Rk3 (3), ginsenoside Rh4 (4), notoginsenoside T3 (5), 20(S)-protopanaxatriol (6), dammar 20 (21),24-diene-3β,6α,12β-triol (7), ginsenoside Rg3 (8), gypenoside XIII (9), ginsenoside Rk1 (10), ginsenoside Rg5 (11), and 20 (S)-ginsenoside Rh2 (12). Conclusion: Compound 1 is a new dammarane-type triterpenoid saponin
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Anemone flaccida Fr. Schmidt is a perennial medicinal herb that contains pentacyclic triterpenoid saponins as the major bioactive constituents. In China, the rhizomes are used as treatments for a variety of ailments including arthritis. However, yields of the saponins are low, and little is known about the plant's genetic background or phytohormonal responsiveness. Using one-quarter of the 454 pyrosequencing information from the Roche GS FLX Titanium platform, we performed a transcriptomic analysis to identify 157 genes putatively encoding 26 enzymes involved in the synthesis of the bioactive compounds. It was revealed that there are two biosynthetic pathways of triterpene saponins in A. flaccida. One pathway depends on β-amyrin synthase and is similar to that found in other plants. The second, subsidiary ("backburner") pathway is catalyzed by camelliol C synthase and yields β-amyrin as minor byproduct. Both pathways used cytochrome P450-dependent monooxygenases (CYPs) and family 1 uridine diphosphate glycosyltransferases (UGTs) to modify the triterpenoid backbone. The expression of CYPs and UGTs were quite different in roots treated with the phytohormones methyl jasmonate, salicylic acid and indole-3-acetic acid. This study provides the first large-scale transcriptional dataset for the biosynthetic pathways of triterpene saponins and their phytohormonal responsiveness in the genus Anemone.
Subject(s)
Anemone , Genetics , Metabolism , Biosynthetic Pathways , Genetics , Cytochrome P-450 Enzyme System , Genetics , Metabolism , Gene Expression Profiling , Gene Expression Regulation, Plant , Glycosyltransferases , Genetics , Metabolism , Oleanolic Acid , Metabolism , Plant Growth Regulators , Pharmacology , Plant Proteins , Genetics , Metabolism , Plants, Medicinal , Rhizome , Genetics , Metabolism , Saponins , Metabolism , Triterpenes , MetabolismABSTRACT
Saponins are important components in traditional Chinese medicine (TCM) with significant biological activities, which could be divided into triterpenoid saponins and steroidal saponins according to structures of the aglycone skeletons. This article reviews the in vivo metabolic pathways of some typical natural saponins such as ginsenosides, licorice saponins, saikosaponins, timosaponins and diosgenin glycosides. Saponins often show poor absorbance after oral administration. The in vivo metabolism of saponins generally contain two steps. These compounds usually undergo hydrolysis in stomach and gut. Then they are absorbed into blood and metabolized in liver. The secondary glycosides and the aglycones produced in gastrointestinal tract often show higher bioavailability and better bioactivity, while downstream metabolites in liver are mainly produced by phase I metabolism. Clarification of the in vivo metabolism of bioactive saponins is helpful for the understanding of the effective ingredients in TCM, as well as the discovery of new drugs from natural products.
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To explore the effects of shading and the expression of key enzyme genes on the synthesis and accumulation of Panax japonicus var. major saponins, different shading treatments (0%, 30%,50%) of potted P. japonicus var. major were used as test materials, the expression of three key enzyme genes(CAS,DS,-AS) of leaves and rhizomes in different growth periods of P. japonicus var. major was determined by real-time quantitative PCR, the content of total saponins was determined by ultraviolet spectrophotometry. The results indicated that, in flowering stage, CAS,DS,-AS were highly expressed in the aerial parts of P. japonicus var. major, 30% shading treatment significantly inhibited the expression of CAS in leaves and promoted the expression of DS and -AS in stems, leaves and flowers, it was speculated that the main part of saponin synthesis was leaf in this stage. Both the expression levels of DS and -AS and changes in the content of total saponins in leaves showed a tendency of low-high-low throughout the growth cycle, correlation coefficient analysis showed that there was a positive correlation between them. Compared with control, the expression levels of DS and -AS and the content of total saponins were greatly enhanced under shading treatment, 30% shading treatment significantly promoted the accumulation of total saponins. Therefore, it is suggested that 30% shading treatment should be applied to the artificial cultivation of P. japonicus var. major, which is beneficial to the accumulation and quality improvement of saponins.
Subject(s)
Gene Expression Regulation, Plant , Light , Panax , Genetics , Radiation Effects , Plant Leaves , Genetics , Rhizome , Genetics , SaponinsABSTRACT
Triterpenoid saponins is an important secondary metabolites in medicinal plants, and the tetracyclic triterpenoid saponins, as one of the main categories, have very high medicinal value and market demand. However, there is no systematic review on the research. Thus, the elucidation of the biosynthetic pathway and metabolism of the medicinal plant tetracyclic triterpenoid saponins has important theoretical significance and broad application prospects.In this review, the biosynthetic pathway and metabolic regulation of medicinal plant of tetracyclic triterpenoid saponins were discussed. My focus in this paper was to introduce the research development of several metabolic biosynthetic pathways of tetracyclic triterpenoid saponins centered on dammarane type, and the gene improvement by methods such as metabolic pathway and other technological methods. This study provides references on secondary metabolic framework of medicinal plants of tetracyclic triterpenoid saponins, accurately locating secondary metabolism and its key enzymes, and promoting the sustainable uses of medicinal plant resources.
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Radix Codonopsis is a traditional tonic medicine commonly used in traditional Chinese medicine. It contains sugar, alkaloids, polyynes, glycosides, terpenoids, and other chemical constituents. It has the functions of regulating blood sugar, promoting hematopoietic function, anti-hypoxia, anti-stress, alleviating fatigability, enhancing the body immunity, anti-aging, regulating gastric contraction, anti-ulcer, and other pharmacological activities. This paper summarized the literature on the chemical composition and their pharmacological activities of Codonopsis and provided the basis for the further development and utilization of Codonopsis resources.
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Objective: To study the chemical constituents of transformed products by Sphingomonas yabuuchiae GTC 868T (AB071955) and Pectinex Ultra AFP from the saponin of Ardisia gigantifolia. Methods: Transformation products separated by the process of silica gel column, compounds were identified and elucidated by spectral and chemical methods. Their cytotoxicity activities were tested by Cell Counting Kit 8 colorimetric assay. Results: Five triterpenoid saponins were obtained, including 3β-O-{α-L-rhamnopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl}-cyclamiretin A (1), 3β-O-{β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside}-cyclamiretin A (2), 3β-O-{β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside}-cyclamiretin A (3), 3-O-α-L-arabinopyranosyl cyclamiretin A (4), and cyclamiretin A (5). Conclusion: Compounds 2-5 are obtained by biotransformation for the first time. Some of the compounds showed certain antitumor activity, among them, compound 2 shows more cytotoxicity activity than Ag3 and positive control.
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Objective: To study the triterpenoids from the leaves of Ilex chinensis. Methods: The constituents were isolated and purified by various chromatographic methods, and the structures were elucidated by spectroscopic analysis. Results: Thirteen triterpenoid saponins were isolated from 70% ethanol extracts in the leaves of I. chinensis and identified as 3β, 23-dihydroxyurs-12-en-28-oic acid 28-O-β-D-glucopyranoside (1), quadranoside IV (2), mussaendoside R (3), monepaloside F (4), ilexoside XXVII (5), ilexoside XXXVII (6), ilexoside XXXVIII (7), ilexoside XLI (8), niga-ichigoside F1 (9), kalidiumoside D (10), chikusetsusaponin Iva (11), oblonganoside M (12), and 23-hydroxy-betulinic acid-28-O-β-D-glucopyranoside (13). Conclusion: Compounds 1, 10, and 13 are isolated from the genus Ilex for the first time. Compounds 2-8, 11, and 12 are isolated from this plant for the first time.
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Objective: To analyze the main chemical constituents of traditional Chinese medicine compound Chenxiang Huaqi Pills by using UPLC-Q-TOF/MS technology. Methods: The separation was performed on Phenomenex Kinetex C18 column (100 mm×4.6 mm, 2.7 μm), and the gradient elution of acetonitrile-0.1% formic acid was used as mobile phase at a flow rate of 0.8 mL/min. The data was collected by the positive and negative ion modes using Q-TOF/MS and ESI source. The main chemical constituents of Chenxiang Huaqi Pills were identified according to the exact molecular mass, the cleavage fragments of MS/MS, the literature data, and the reference control. Results: A total of 73 chemical components were separated and identified in Chenxiang Huaqi Pills, including 36 flavonoids, 16 2-(2-phenylethyl) chromones, 7 triterpenoid saponins, 2 sesquiterpene lactones, and 12 other components. Conclusion: This study showed that UPLC-Q-TOF/MS technology provided a simple, rapid, and accurate method for the identification of chemical constituents in Chenxiang Huaqi Pills, which provided a new technology method for the pharmacological basis and quality control of Chenxiang Huaqi Pills.
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The present study was designed to investigate the chemical constituents of the roots of Cyathula officinalis. Compounds were isolated by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. Their structures were determined on the basis of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. One new oleanane-type triterpenoid saponin, 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl-(1→3)-β-D-glucopyranosyl] hederagenin (1), was isolated from the roots of Cyathula officinalis. The anti-inflammatory activities of the isolates were evaluated for their inhibitory effects against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages cells. Compounds 2, 4, and 6 exhibited moderate anti-inflammatory activities.