Panax ginseng is a traditional Chinese medicine with significant pharmaceutical effects and wide application. Through orientational modification and transformation of ginsenoside glycosyl, rare ginsenosides with high antitumor activities can be generated. Traditional chemical methods cannot be applied in clinic. because of extremely complex preparation technologies and very high cost Transformations using microorganisms and their enzymatic systems provide the most feasible methods for solving the main problems. At present, the key problems in enzymatic synthesis of ginsenosides include low specific enzyme activities, identity of enzymes involved in the enzymatic synthesis, and their catalytic mechanisms, as well as nonsystematic studies on structural bioinformatics; specificity of enzymatic hydrolysis for saponin glycosyl has been rarely studied. Many reviews have been reported on glycosidase molecular recognition, immobilization, and biotransformation in ionic liquids (ILs), whereas ginsenoside transformation and application have not been systematically studied. To evaluate theoretical and applied studies on ginsenoside-oriented biotransformation, by reviewing the latest developments in related fields and evaluating the widely applied biocatalytic strategy, this review aims to evaluate the ginsenoside-oriented transformation method with improved product specificity, increased biocatalytic efficiency, and industrial application prospect based on the designed transformations of enzyme and solvent engineering of ILs. Therefore, useful theoretical and experimental evidence can be obtained for the development of ginsenoside anticancer drugs, large-scale preparation, and clinical applications in cancer therapy.
Biocatalysis ; Ginsenosides ; Glycoside Hydrolases ; Panax ; Saponins

The root of Panax ginseng, is a Korea traditional medicine, which is used in both raw and processed forms due to their different pharmacological activities. As part of a continued chemical investigation of ginseng, the focus of this research is on the isolation and identification of compounds from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, semi-preparative-high performance liquid chromatography, Fast atom bombardment mass spectrometric, and nuclear magnetic resonance. Dammarane-type triterpenoid saponins were isolated from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, and semi-preparative-high performance liquid chromatography. Their structures were identified as protopanaxadiol ginsenosides [gypenoside-V (1), ginsenosides-Rb1 (2), -Rb2 (3), -Rb3 (4), -Rc (5), and -Rd (6)], protopanaxatriol ginsenosides [20(S)-notoginsenoside-R2 (7), notoginsenoside-Rt (8), 20(S)-O-glucoginsenoside-Rf (9), 6-O-[alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl]-20-O-beta-D-glucopyranosyl-3beta,12beta, 20(S)-dihydroxy-dammar-25-en-24-one (10), majoroside-F6 (11), pseudoginsenoside-Rt3 (12), ginsenosides-Re (13), -Re5 (14), -Rf (15), -Rg1 (16), -Rg2 (17), and -Rh1 (18), and vinaginsenoside-R15 (19)], and oleanene ginsenosides [calenduloside-B (20) and ginsenoside-Ro (21)] through the interpretation of spectroscopic analysis. The configuration of the sugar linkages in each saponin was established on the basic of chemical and spectroscopic data. Among them, compounds 1, 8, 10, 11, 12, 19, and 20 were isolated for the first time from P. ginseng root.
Chromatography ; Chromatography, Liquid ; Ginsenosides ; Magnetic Resonance Spectroscopy ; Medicine, Korean Traditional ; Panax* ; Saponins*

OBJECTIVETo develop a reliable method to assess the stability of xinyue capsules containing Panax quinquefolius saponins according to European quality standards.

METHODSAn efficient high-performance liquid chromatography ultraviolet (HPLC-UV) method was established to analyse six main ginsenosides (Rb1, Rb2, Rc, Rd, Re and Rg1) in six different batches (120 capsules/batch) from the same lot of xinyue capsules and in one batch measured six times within one day. The six ginsenosides were separated on a Hypersil BDS-C18 column (3 μm, 100 mm×3 mm) at a flow rate of 0.5 mL/min. Gradient elution was performed using a mobile phase gradient of acetonitrile-water modified with 0.01% formic acid. The HPLC chromatograms were analyzed with "LC data comparison" using Lab Solutions software.

RESULTSThe HPLC peaks were identified by comparing their retention times (Rg1: 23.44 min, Re: 23.77 min, Rb1: 35.24 min, Rc: 36.18 min, Rb2: 38.55 min and Rd: 40.88 min) with those of the standards under the same chromatographic conditions, which showed similar results among the samples of six different batches and among the samples from one batch detected six times within one day.

CONCLUSIONSXinyue capsules have good drug intra-day consistency at room temperature and exhibit a consistent quality between different batches. This study established a reliable method to assess the stability of xinyue capsules, which is suitable for further qualitative analysis and may assist in promoting the safe and effective use of Chinese herbal medicine.

The relationship between saponin content of in different parts of the organization and expression of ginsenoside biosynthesis related gene was obtained by the correlation analysis between saponin content and gene expression. The 14 tissue parts of were studied, six saponins in Samples (ginsenoside Rg₁, Re, Rb₁, Rc, Rb₂ and Rd), group saponins and total saponins were determined by high performance liquid chromatography and vanillin-sulfuric acid colorimetric method. Simultaneously, the expression levels of 7 ginsenoside biosynthesis related genes ( and ) in different tissues of were determined by Real-time fluorescence quantitative PCR. Although 7 kinds of ginsenoside biosynthesis related enzyme gene in the involved in ginsenoside synthesis, the expression of and P450 genes had no significant effect on the content of monosodium saponins, grouping saponins and total saponins, and had significant or extremely significant on the contents of single saponins Re, Rg1, Rb1, Rd, group saponin PPD and PPT, total saponin TMS and total saponin TS (<0.05 or <0.01). The biosynthesis of partial saponins, grouping saponins and total saponins in was affected by the interaction of multiple enzyme genes in the saponin synthesis pathway, the content of saponins in different tissues of was determined by the differences in the expression of key enzymes in the biosynthetic pathway. Therefore, this study further clarified that and was the key enzyme to control the synthesis of saponins in by correlation analysis, the biosynthesis of ginsenosides in was regulated by these five kind of enzymes in cluster co-expression of interaction mode.
Biosynthetic Pathways ; Chromatography, High Pressure Liquid ; Ginsenosides ; biosynthesis ; genetics ; Panax ; genetics ; Plant Roots ; Saponins ; biosynthesis ; genetics

This project is to investigate the chemical constituents of ginsenosides from the flower buds of Panax ginseng. The compounds were isolated by using a variety of chromatographic methods including Diaion HP-20,silica gel,MCI gel and semi-preparative HPLC chromatography. Their structures were identified by NMR,and MS data. As a result,32 compounds were isolated from the extract of P. ginseng flower buds,and identified as ginsenoside Rk_3( 1),ginsenoside Rh_4( 2),ginsenoside Rh_8( 3),pseudoginsenoside Rc_1( 4),ginsenoside Rc( 5),ginsenoside Rb_2( 6),ginsenoside Rg_6( 7),20( E)-ginsenoside F_4( 8),ginsenoside Rb_1( 9),vinaginsenoside R_(16)( 10),ginsenoside Rh_6( 11),vinaginsenoside R_3( 12),5,6-didehydro-ginsenoside Rd( 13),vinaginsenoside R_4( 14),vinaginsenoside R_8( 15),ginsenoside Rf( 16),notoginsenoside E( 17),ginsenoside Ⅲ( 18),3-O-β-D-glucopyranosyl-3β,7β,12β,20 S-tetrahydroxydammar-5( 6),24-diene-20-O-β-D-glucopyranoside( 19),20( S)-ginsenoside Rg_2( 20),20( R)-ginsenoside Rg_2( 21),notoginsenoside R_2( 22),ginsenoside F_2( 23),quinquenoside I( 24),ginsenoside M_1( 25),quinquenoside L_(10)( 26),ginsenoside Rh_5( 27),ginsenoside Rg_5( 28),ginsenoside Rk_1( 29),20( R)-ginsenoside Rg_3( 30),oleanolic acid 3-O-β-D-glucopyranosyl-( 1→2)-β-D-( 6'-methyl ester)-glucuronopyranoside( 31) and ginsenoside MC( 32). Among them,compounds 10,12,13,15,19,22,24,31 and 32 were isolated from P. ginseng for the first time,and compound 19 was a genuine ginsenoside firstly obtained by separation and identification,with NMR data that were also reported. Compounds 1-3,7,8,23,25-30 were isolated from P. ginseng flower buds for the first time.
Chromatography, High Pressure Liquid ; Flowers ; chemistry ; Ginsenosides ; analysis ; Magnetic Resonance Spectroscopy ; Panax ; chemistry ; Saponins ; analysis

Here, we designed to examine the anti-inflammatory effects on RAW264.7 cells and the immunosuppressive effects by evaluating interleukin-2 (IL-2) production in Jurkat T cells using a MeOH extract of Panax notoginseng roots. The results showed that the MeOH extract inhibited the synthesis of nitric oxide (NO) in a dose-dependent manner (IC₅₀ value of 7.08 µg/mL) and displayed effects on T cell activation at a concentration of 400 µg/mL. In efforts to identify the potent compounds, bioactivity-guided fractionation of the MeOH extract and chemical investigation of its active CH₂Cl₂-, EtOAc-, and butanol-soluble fractions led to the successful isolation and identification of eleven compounds, including two polyacetylenes (1, 2), a steroid saponin (3), seven dammarane-type ginsenosides (4 – 10), and an oleanane-type ginsenoside (11). Among them, compound 11 was isolated from this plant for the first time. Compound 2 exhibited potent inhibitory effects on NO synthesis and an immunosuppressive effect with IC₅₀ values of 2.28 and 65.57 µM, respectively.
Ginsenosides ; Interleukin-2 ; Nitric Oxide ; Panax notoginseng ; Panax ; Plants ; Polyacetylenes ; Saponins ; T-Lymphocytes

Ginsenoside Rh_2,firstly isolated from red ginseng,is protopanaxadiol type of steroidal saponin. Rh_2 possessed variety of activities,but bioavailability of oral administration Rh_2 was extremely low due to poor absorption. Moreover,ginsenoside Rh_2 exhibited toxicity on human normal cells. Therefore,to improve stronger anti-tumor activity and attenuate toxicity,it was essential to design and optimize chemical structure of ginsenoside Rh_2. Through n-octanoylchloride modifications,a novel ester derivative of ginsenoside Rh_2 named caprylic acid monoester of Rh_2( C-Rh_2) was designed and synthesized. Structure of novel ginsenoside derivative was identified by1 D and 2 D NMR,as well as ESI-MS analyses. Anti-tumor effect of C-Rh_2 was tested on H22 tumor bearing mice. C-Rh_2 displayed certain anti-tumor activities and exhibited less toxicity than Rh_2. In the present study,C-Rh_2 as ester form of ginsenoside Rh_2 showed better anti-tumor activity and less toxicity,but the specific mechanism needs further investigation.
Animals ; Caprylates ; Ginsenosides ; chemical synthesis ; pharmacology ; Mice ; Molecular Structure ; Neoplasms, Experimental ; drug therapy ; Saponins

Panax quinquefolium, as a common precious medicinal plant, has complex chemical components and unique pharmacological activities, which can play a healthcare role in the human body. With the deepening of research, the application of P. quinquefolium has become increasingly extensive. This paper summarized the research progress of the saponins isolated and identified from diffe-rent parts of P. quinquefolium, the structural classification and pharmacological activities of the saponins, and the quality control of Panacis Quinquefolii Radix. Further, this paper put forward the urgent problems to be solved in the development of P. quinquefolium. It is hoped to lay a foundation for the further study and provide reference for the research direction of P. quinquefolium.
Ginsenosides ; Humans ; Panax/chemistry* ; Plants, Medicinal/chemistry* ; Quality Control ; Saponins/pharmacology*

The present study quickly identified the ginsenosides in fresh Panax ginseng and specified the effects of different drying methods(50 ℃-drying, 80 ℃-drying, and-70 ℃ freeze-drying) on ginsenosides.Three P.ginseng products by different drying methods were prepared, and the UHPLC-Q-Exactive Orbitrap high-resolution liquid mass spectrometry(MS) technique was applied to perform gradient elution using water-acetonitrile as the mobile phase, and the data collected in the negative ion mode were analyzed using X Calibur 2.2.The results showed that 57 saponins were identified from fresh P.ginseng.As revealed by the comparison with the fresh P.ginseng, in terms of the loss of ginsenosides, the dried products were ranked as the dried product at 50 ℃, freeze-dried products at-70 ℃, and the dried product at 80 ℃ in the ascending order.This study elucidated the effects of different drying methods on the types and relative content of ginsenosides, which can provide references for the processing of P.ginseng in the producing areas.
Ginsenosides/analysis* ; Chromatography, High Pressure Liquid/methods* ; Panax ; Mass Spectrometry/methods* ; Saponins

With the improvement of living standards and changes in working style, the prevalence of abnormal glucose and lipid metabolism in humans is increasing in modern society. Clinically, the related indicators are often improved by changing the lifestyle and/or taking hypoglycemic and lipid-lowering drugs, but there are no therapeutic drugs for disorders of glucose and lipid metabolism at present. Hepatitis C virus core protein binding protein 6(HCBP6) is a newly discovered target that can regulate triglyceride and cholesterol content according to level oscillations in the body, thereby regulating abnormal glucose and lipid metabolism. Relevant studies have shown that ginsenoside Rh_2 can significantly up-regulate the expression of HCBP6, but there are few studies on the effect of Chinese herbal medicines on HCBP6. Moreover, the three-dimensional structural information of HCBP6 has not been determined and the discovery of potential active components acting on HCBP6 is not rapidly advanced. Therefore, the total saponins of eight Chinese herbal medicines commonly used to regulate abnormal glucose and lipid metabolism were selected as the research objects to observe their effect on the expression of HCBP6. Then, the three-dimensional structure of HCBP6 was predicted, followed by molecular docking with saponins in eight Chinese herbal medicines to quickly find potential active components. The results showed that all total saponins tended to up-regulate HCBP6 mRNA and protein expression, where gypenosides showed the optimum effect on up-regulating HCBP6 mRNA and ginsenosides showed the optimum effect on up-regulating HCBP6 protein expression. Reliable protein structures were obtained after the prediction of protein structures using the Robetta website and the evaluation of the predicted structures by SAVES. The saponins from the website and literature were also collected and docked with the predicted protein, and the saponin components were found to have good binding activity to the HCBP6 protein. The results of the study are expected to provide ideas and methods for the discovery of new drugs from Chinese herbal medicines to regulate glucose and lipid metabolism.
Humans ; Glucose ; Lipid Metabolism ; Molecular Docking Simulation ; Drugs, Chinese Herbal/pharmacology* ; Ginsenosides ; Proteins ; Saponins ; RNA, Messenger