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The purpose of this study is to investigate the effect of Reduning injection (RI) on influenza A virus (IAV) and its mechanism. We evaluated the cytotoxicity of RI in A549 and MDCK cells by cell counting kit-8 (CCK-8) assay. Western blot and cytopathic effect (CPE) assays were applied to test the effects of RI on viral protein, CPE and virus virulence to evaluate its inhibitory effect. The proteins level of heme oxygenase 1 (HO-1), nuclear factor erythroid 2-related factor 2 (Nrf2), phosphorylation of P38 mitogen-activated protein kinases (MAPK) and extracellular signal-regulated kinases 1/2 (ERK1/2) were detected by Western blot. Real-time fluorescence quantitative PCR (qRT-PCR) was used to detect the RNA expression of interferon-α/β (IFN-α/β). The relative luciferase reporter assay was used to analyze the promoter activity and transcriptional regulation of Nrf2. The results indicated that RI inhibited IAV-induced MDCK cytopathies in a dose-dependent manner, decreased M2 protein of influenza virus and viral titer, indicating that it has definite effect on inhibiting IAV. RI promotes the phosphorylation of P38 MAPK and ERK1/2, activates the activity of Nrf2 nuclear transcription factor, increases the expression of Nrf2 protein in the nucleus, thus up-regulates the expression of HO-1 protein, and ultimately increases the IFN-α/β mRNA level. In summary, our results demonstrated that RI inhibits the replication of IAV by activating MAPK/Nrf2/HO-1 signaling pathway, revealing a new mechanism of RI against influenza virus, and providing theoretical basis for clinical treatment of influenza virus.
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OBJECTIVE@#To investigate the anti-coronavirus potential and the corresponding mechanisms of the two ingredients of Reduning Injection: quercetin and luteolin.@*METHODS@#A pseudovirus system was designed to test the efficacy of quercetin and luteolin to inhibit SARS-CoV-2 infection and the corresponding cellular toxicity. Luteolin was tested for its activities against the pseudoviruses of SARS-CoV-2 and its variants. Virtual screening was performed to predict the binding sites by Autodock Vina 1.1.230 and PyMol. To validate docking results, surface plasmon resonance (SPR) was used to measure the binding affinity of the compounds with various proteins of the coronaviruses. Quercetin and luteolin were further tested for their inhibitory effects on other coronaviruses by indirect immunofluorescence assay on rhabdomyosarcoma cells infected with HCoV-OC43.@*RESULTS@#The inhibition of SARS-CoV-2 pseudovirus by luteolin and quercetin were strongly dose-dependent, with concentration for 50% of maximal effect (EC50) of 8.817 and 52.98 µmol/L, respectively. Their cytotoxicity to BHK21-hACE2 were 177.6 and 405.1 µmol/L, respectively. In addition, luetolin significantly blocked the entry of 4 pseudoviruses of SARS-CoV-2 variants, with EC50 lower than 7 µmol/L. Virtual screening and SPR confirmed that luteolin binds to the S-proteins and quercetin binds to the active center of the 3CLpro, PLpro, and helicase proteins. Quercetin and luteolin showed over 99% inhibition against HCoV-OC43.@*CONCLUSIONS@#The mechanisms were revealed of quercetin and luteolin inhibiting the infection of SARS-CoV-2 and its variants. Reduning Injection is a promising drug for COVID-19.
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Humans , SARS-CoV-2 , COVID-19 , Luteolin , QuercetinABSTRACT
ObjectiveTo compare and observe the effect of Reduning injection （mainly clearing heat）， Shenfu injection （mainly warming Yang） combined with gefitinib on the proliferation， apoptosis， stemness characteristics and metabolism of lung cancer cells. MethodDifferent non-small cell lung cancer （NSCLC） cell lines were selected and intervened with gefitinib （5， 10， 20 μmol·L-1）， Reduning injection （0.6%， 0.9%）， Shenfu injection （0.6%， 0.9%）， gefitinib combined with Reduning injection， and gefitinib combined with Shenfu injection. Cell proliferation in each group was detected by cell counting kit-8 （CCK-8） assay， and cell apoptosis was detected by flow cytometry. The mRNA and protein expressions of lung cancer stem cell markers sex determining region Y-box 2 （Sox2） and aldehyde dehydrogenase family 1 member A1 （ALDH1A1） were determind by real-time quantitative polymerase chain reaction （Real-time PCR） and Western blot， respectively. The redox ratio of lung cancer cells was observed by femtosecond label-free imaging （FLI） and energy metabolism instrument was used to determine the glycolysis level in cells. ResultCompared with the blank group， Reduning injection reduced the survival rate of lung cancer cells （P<0.05）， increased the apoptosis rate （P<0.05）， down-regulated the mRNA and protein expressions of Sox2 and ALDH1A1 （P<0.05）， and up-regulated the redox ratio of cells （P<0.05）， while Shenfu injection exerted no remarkable effect on the above indexes. In addition， compared with gefitinib alone， Reduning injection combined with gefitinib inhibited the survival rate of lung cancer cells （P<0.05）， promoted the cell apoptosis （P<0.05）， down-regulated the mRNA and protein expressions of Sox2 and ALDH1A1 （P<0.05）， up-regulated the redox ratio of cells （P<0.05）， and lowered the proton efflux rate of glycolysis （P<0.05）， while Shenfu injection combined with gefitinib failed to affect these indexes of lung cancer cells significantly. ConclusionReduning injection may inhibit stemness characteristics of tumor cells by regulating their metabolism to enhance the proliferation-inhibiting and pro-apoptotic effects of gefitinib on lung cancer cells， while Shenfu injection had no significant enhancing effect on gefitinib. This indicates that epidermal growth factor receptor tyrosine kinase inhibitors （EGFR-TKIs） should be used in combination with heat-clearing Chinese medicines.
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Objective: To elucidate the anti-inflammatory mechanism of Reduning Injection (RDN) by analyzing the potential biomarkers and metabolic pathways of the carrageenan-induced inflammatory model from the overall metabolic level. Methods: Rat inflammatory model was established by carrageenan. UPLC-Q-TOF/MS was used to detect and analyze changes of endogenous metabolites in the serum and urine of carrageenan-induced inflammatory rats. Combined with multivariate analysis and databases analysis, inflammatory-related potential biomarkers were screened and identified to analyze possible metabolic pathways. The reliability and biological significance of these biomarkers was verified by metabolic network analysis and correlation analysis with pharmacodynamic indicators. Results: A total of 16 potential biomarkers were screened and identified by multivariate analysis and metabolite databases, among which 13 species could be adjusted by RDN. The metabolism pathway analysis revealed that histidine metabolism, sphingolipid metabolism, and tyrosine metabolism were greatly disturbed. Their biomarkers involved urocanic acid, sphingosine, and norepinephrine, all of which showed a callback trend after RDN treatment. The three biomarkers had a certain correlation with some known inflammatory-related small molecules (histamine, arachidonic acid, Leukotriene B4, and PGE
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This study employed Box-Behnken design combined with flux attenuation to explore the nanofiltration conditions for separation of alcohol precipitation liquid during the preparation of Reduning Injection and discussed the applicability of nanofiltration in the separation of the liquid with high-concentration ethanol. The effects of nanofiltration molecular weight cut-off(MWCO) and pH on the rejection of chlorogenic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid were consistent with the principles of pore size sieving and charge effect, respectively. The rejection of the three phenolic acids was reduced by concentration polarization effect caused by trans-membrane pressure(TMP). The swelling of membrane surface decreased the pore size and membrane flux for effective separation. Chlorogenic acid and 4,5-dicaffeoylquinic acid were more sensitive to pH and ethanol concentration than 3,5-dicaffeoylquinic acid. A certain correlation existed between the compound structure and the separation factors of nanofiltration, and the separation rules were associated with the comprehensive effect of charge effect, pore size sieving, concentration polarization, steric hindrance and so on.
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Chlorogenic Acid , Drugs, Chinese Herbal/chemistry , Ethanol , InjectionsABSTRACT
Enterovirus 71 (EV71) infection is more likely to cause hand, foot and mouth disease (HFMD) in children, which can lead to neurogenic complications and higher mortality. As a commonly used clinical medicine, Reduning injection (RDN) helps to shorten the symptoms of patients with HFMD and facilitate the early recovery of children. However, the regulatory mechanism of RDN on the HFMD immune system disorder caused by EV71 remains to be discussed. This study collected detailed treatment data of 56 children with HFMD who entered the affiliated Children's Hospital of Nanjing Medical University during 2019. Retrospective analysis of clinical data showed that the symptoms of the RDN treatment group were improved compared with the untreated group. To explore its mechanism, the relevant detection indicators were detected by flow cytometry, enzyme-linked immunosorbent assay and real-time quantitative PCR. It was found that the number and function of innate immune (ILCs) and adaptive immunity (Th1, Th2 and secreted cytokines) were reduced, suggesting that RDN plays a role by regulating cellular immunity. The in vitro differentiation inhibition test further confirmed that RDN affected Th1 differentiation by inhibiting the expression of transcription factors on the basis of Th1 cell differentiation in vitro.
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Objective: To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model. The chemical constituents were isolated by chromatography on HP-20 macroporous adsorptive resins, silica gel, ODS columns and reverse phase MPLC and HPLC repeatedly, and their structures were elucidated based on spectroscopic analysis (HR-ESI-MS, NMR, ECD) and chemical methods. Meanwhile, we evaluated the anti-inflammatory activities of the isolates by measuring their inhibitory effects on TNF-α production in LPS stimulated RAW 264.7 macrophages. Results: The 95% ethanol eluate of RDN Injection by the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of this injection. A novel iridoid, named jasminoide A (1), and a new guaiane sesquiterpenoid, named (1R,7R,8S,10R)-7,8,11-trihydroxy-4-guaien-3-one (2), were isolated from Reduning injection, and compound 2 can inhibit TNF-α production with IC50 values of 72.24 µmol/L. Conclusion: In this study, two new terpenoids were isolated from Reduning Injection, and compound 2 showed inhibitory activity against LPS-activated TNF-α production in RAW 264.7 cells in vitro.
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OBJECTIVE: To evaluate the safety and rationality of Reduning injection in the treatment of COVID-19. METHODS: Through consulting, summarizing and analyzing literatures, the rapid HTA evaluation of Reduning was carried out, and its pharmacological rationality and drug monitoring for COVID-19 were discussed. RESULTS: Literature analysis indicated that COVID-19 belongs to the pestilence of TCM. It was characterized by “dampness, heat, deficiency, toxin and stasis”, and its clinical manifestations involved inflammatory factor storm, immune system damage, etc. Reduning injection was approved to the treatment of influenza, cough and respiratory tract infections caused by exopathic wind-heat, and a typical drug for heat-clearing and detoxifying. CONCLUSION: The rapid HTA evaluation showed that Reduning injection has good safety, effectiveness and economy. The mechanisms of Reduning in antipyretic and anti-inflammatory, immune regulation and anti-virus suggest the rationality of Reduning in treating COVID-19, but drug monitoring should be done well in the use process.
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Objective: To identify the key process parameters of the Chinese materia medica (CMM) production process by using grey relation analysis (GRA) method. Methods: Taking Lonicerae Japonicae Flos and Artemisiae Annuae Herba extraction section of Reduning Injection as an example, GRA was adopted to calculate and compare the influence of the process parameters on the quality index. Meanwhile, analytic hierarchy process (AHP) combined with Spearman rank correlation analysis was used to validate mutually. Results: According to GRA Results:, the relative importance of process parameters was ranked as follows: average volume flow rate of extraction (X4) > pH after acid adjustment (X2) > the paste temperature of extracting concentration (X7) > alcohol precipitation concentrated extract weight (X1) > hydrochloric acid weight (X3) > extraction time (X6) > relative standard deviation of flow rate (X5). The correlation coefficient between the order by GRA and that by AHP was 0.893. According to the importance of process parameters, the average volume flow rate of extraction, the pH after acid adjustment, and the paste temperature of extracting concentration were identified as the key process parameters. Conclusion: The Results: obtained in this study show the feasibility of GRA in selecting key process parameters, which can provide theoretical reference for the establishment of prediction model as well as online feedback regulation.
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Objective: To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the LPS-induced mouse endotoxin shock model. The chemical constituents were isolated by chromatography on HP-20 macroporous resin, silica gel, MCI, ODS, reverse MPLC, and HPLC repeatedly, and their structures were identified by spectral data and physicochemical property. Taking PGE2 as the evaluating indicator, the model of LPS-induced RAW264.7 cells was used to evaluare the in vitro anti-inflammatory activity of these compounds. Results: The 95% ethanol eluate of RDN Injection on the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of RDN Injection. A total of 24 compounds were isolated and identified as (4aS,7aS,7bS)-4,4a,7a,7b-tetrahydro-2H-1,7-dioxacyclopent [cd] indene-5-carboxylic acid methyl ester (1), (4aS,7aS)-1,4a,5,7a- tetrahydro-7-(hydroxymethyl)-cyclopenta [c] pyran-4-carboxy licacid methyl ester (2), 3α,5α-tetrahydrodeoxycordifoline lactam (3), R-(Z)-4-methyl-5-[(2',6',6'-trimethyl-4'-oxo-2'-cyclohexen-1'-yl) methylene]-2(5H)-furanone (4), (1α,2α,3β,4β)-2,4-bis(4-hydroxy-3- methoxyphenyl)-1,3-cyclobutanedicarboxylic acid (5), 4-[(6-O-benzoyl-β-D-glucopyranosyl) oxy]-3-methoxybenzoic acid (6), syringaresinol (7), E-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl) dihydrofuran-2-one (8), 6,7-dimethoxy coumarin (9), 7-hydroxy-6-methoxy coumarin (10), salicylic acid (11), syringaldehyde (12), phenylacetic acid (13), vanillin (14), caffeic acid (15), aceto-vanillone (16), 3,5-di-O-caffeoylquinic acid (17), 4,5-di-O-caffeoylquinic acid (18), 3,4-di-O-caffeoylquinic acid methyl ester (19), 3,5-di-O-caffeoylquinic acid methyl ester (20), 4,5-di-O-caffeoylquinic acid methyl ester (21), 5-O-caffeoylquinic acid ethyl ester (22), 3,5-di-O-caffeoylquinic acid ethyl ester (23), and 4,5-di-O-caffeoylquinic acid ethyl ester (24). Among them, compounds 1, 10, and 14-24 significantly inhibited PGE2 expression in RAW 246.7 cells stimulated by LPS. Conclusion: Compounds 1-9, 11-13, and 22-24 are isolated from RDN Injection for the first time; And organic acids may be one of the main pharmacodynamic substances of RDN injection for antipyresis and anti-inflammation.
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This study was designed to determine the metabolites of Renduining injection in rats. The ultra-high performance liquid chromatography-LTQ Orbitrap mass spectrometric (UHPLC-LTQ-Orbitrap-MS) and mass defect filter techniques were applied to analyze the metabolites of Reduning injection in rat plasma, bile, urine and feces. As a result, we determined 14 metabolites of geniposide, including oxidation, dehydration, hydroxymethylene loss, hydrolysis, ring-opened, cysteine conjugation and glucuronidation conjugation of aglycone; 9 metabolites of geniposidic acid, consisting of dehydration, ring-opened, double-bond reduction and cysteine conjugation; 6 metabolites of secoxylogain including hydrolysis, hydroxymethylene loss, hydroxylation and ethylation; 12 metabolites of chlorogenic acid, containing decarboxylation, hydrolysis, methylation, acetylation, cysteinylglycine conjugation and glutathione conjugation. It provided information for the therapeutic effect of Reduning in vivo.
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Objective To investigate the effect of Reduning Injection on Vero cells and suckling mice infected by EV71 virus and its mechanism in vitro and in vivo. Methods The anti-virus ability was exhibited in Vero cells which were infected by 33 TCID50 and 25 TCID50 titers of EV71 in vitro. Meanwhile, the antiviral activity in vivo was evaluated on suckling mice model, in which suckling mice were intraperitoneal injected with EV71 at 100 μL. After 2 h infection, Reduning Injection 2.60, 1.30, and 0.65 g/kg and ribavirin 10 mg/kg were followed for treatment. To further understand the antiviral effects of Reduning Injection, weigh of suckling mice, clinical symptoms, expression of IL-1β, IL-6, MCP-1, and TNF-α in skeletal muscle were recorded. Moreover, histological examination of skeletal muscle was examined. Results The results demonstrated that Reduning Injection 5.0 mg/mL could obviously inhibit Vero cells lesion induced by EV71 in vitro. Compared with the model group, suckling mouse model results showed the high and middle dose of Reduning Injection could reduce clinical manifestations scores, increase the weight and improve living conditions of model mice, decrease the expression of IL-1β, IL-6, TNF-α, and MCP-1 in skeletal muscle of suckling mice (P<0.05, 0.01). Histological damages in skeletal muscle were also alleviated with Reduning Injection treatment. Conclusion In a suckling mouse model, Reduning Injection can reduce mortality and obviously prolong the survival time of suckling mice caused by EV71 infection. It can alleviate clinical symptoms and growth inhibition caused by the EV71 virus. Inhibition of IL-1β, IL-6, TNF-α, and MCP-1 levels may be the important mechanism of Reduning Injection in the treatment of hand-foot-and-mouth disease.
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Objective To investigate the effect of Reduning Injection (RI) combined with spleen aminopeptide oral solution on children with hand-foot-and-mouth disease and its regulative effect on myocardial enzyme and inflammatory level.Methods Totally 184 cases treated in Children's Hospital of Kaifeng City from September,2014 to September,2016 were randomly divided into observation group and control group with each group of 92 cases.Control group was given conventional therapy,on the basis of which,observation group was given RI combined with spleen aminopeptide oral solution.Clinical effect and levels of inflammatory cytokine and myocardial enzyme were compared between the two groups.Results The total effective rate in observation group was 93.48％,which was significantly higher than that in control group (80.43％) (P ＜ 0.05).After therapy,the levels ofhs-cTnT,CK-MB,CK,TNF-α,IL-6,CRP,CD3+,CD4+,CD8+,IgA,IgM,and IgG in observation group showed no statistical difference compared with healthy group.Index mentioned above of control group were significantly improved,however there were still statistical difference compared with healthy group (P ＜ 0.05).Conclusion RI combined with spleen aminopeptide oral solution could effectively decrease the levels of inflammatory cytokine as well as myocardial enzyme,which deserves clinical expansion.
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Objective: The calibration models were developed in the concentration of alcohol precipitation proee for Artemisiae Annuae Herba (AAH) and Lonicerae Flos (LF) in Reduning Injection (RI) to realize the on-line monitoring of production process. Methods: Based on the near infrared reflectance spectroscopy (NIRS), partial least regression (PLS) models were developed to fast measure the contents of neochlorogenic acid, chlorogenic acid, and 4-O-caffeoylquinic acid in the concentration of the alcohol precipitation proee for AAH and LF. Results: In the quantitative models of neochlorogenic acid, chlorogenic acid, and 4-O-caffeoylquinic acid, the coefficient of determination (R2) of cross validation sets were 0.954 5, 0.975 2, and 0.969 1; The root mean square errors of calibration (RMSEC) were 0.213, 0.676, and 0.225; The root mean square errors of cross-validation (RMSECV) were 0.233, 0.692, and 0.258. When the established models were applied to on-line monitoring, the coefficient of determination of neochlorogenic acid, chlorogenic acid, and 4-O-caffeoylquinic acid were 0.984 2, 0.983 7, and 0.987 0, the residual predictive deviation (RPD) were 4.77, 5.29, and 4.37; The relative standard errors of prediction (RSEP) were 3.519%, 3.778%, and 3.895%. Conclusion: The models above are proved to fast measure the contents of neochlorogenic acid, chlorogenic acid, and 4-O-caffeoylquinic acid in the concentration of alcohol precipitation proee for AAH and LF in RI.
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Objective: To establish the quality standards of Reduning Injection (RI) based on UV fingerprint, and improve the quality standards of RI. Methods: Full wavelength UV-vis spectrophotometer was used to scan the 15 batches of RI, a reference fingerprint was established, correlation coefficient method was used to calculate RI sample fingerprint and control fingerprint similarity, and the 14 batches of samples were verified. Results: The five batches of RI were within the validity period, their UV fingerprints were in line with the requirements, similarity was all above 0.902, while the absorbance values were in the ranges of 0.693-0.781 (323 nm), 0.323-0.370 (267 nm), 0.957-1.067 (236 nm), 0.902-1.013 (226 nm), 0.953-1.075 (218 nm), and 0.926-1.052 (211 nm); In addition the expired nine batches of RI, similarity is less than 0.902 or the absorbance value does not meet the standard. Conclusion: UV fingerprint method can be used as a simple and accurate method of quality evaluation for the quality control of RI.
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Reduning Injection (RI) has the effects of clearing heat, dispelling wind, and detoxification. It has been proved to be widely used for the treatment of wind-heat cold, cough, fever, upper respiratory tract infection, and acute bronchitis with good therapeutic effect and high security in clinical practice. Main chemical composition of RI includes iridoids, lignans, coumarins, sesquiterpenoids, flavonoids, coffee acyl quinine acids, phenolic acids, etc. This paper reviews domestic and foreign researches about RI in recent years and summarizes the chemical constituents, pharmacological action, and clinical application.
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Objective: An ultra high performance liquid chromatography coupled to triple quadrupole mass spectrometry (UPLC- QqQ-MS/MS) method has been established to simultaneously determine the contents of six bioactive constituents [japonicaside A (JA), L-phenylalanion secologanin B (PSB), luteolin, scopolamine, (1S,6R,7R,10R)-6-carboxy-10-methyl-α-methylene-1-(1- oxobutyl)-cyclohexane acrylic acid (CMCA), and 3α,5α-tetrahydrodeoxycordifoline lactam (TL)] from Reduning Injection. Methods: This chromatographic separation was performed on an Agilent Zorbax SB-Aq C18 (150 mm × 2.1 mm, 3.5 μm) column with the mobile phase consisting of 0.1% formic acid water (A) and methanol (B) in a gradient elution (0.01-2.00 min, 5% B; 2.00-4.00 min, 5%-40% B; 4.00-11.00 min, 40%-95% B; 11.00-13.00 min, 95% B; 13.00-13.10 min, 95%-5% B; 13.10-14.00 min, 5% B) at a flow rate of 0.5 mL/min and the colunm temperature was set at 20℃. The analytes were detected using electrospray ionization (ESI) source by positive and negative ion monitoring mode. A triple quadrupole mass spectrometer was operated by ESI source in positive and negative ionization mode with multiple reaction monitoring for the detection of the six compounds. In the positive ion monitoring mode, the flow rate of Collision Gas (CAD) was 8 mL/min, the flow rate of Curtain Gas (CUR) was 20 mL/min, the temperature (TEM) was 500℃ and the Ion Spray Voltage (IS) was 4 500 V. In the negative ion monitoring mode, the flow rate of Collision Gas (CAD) was 8 mL/min, the flow rate of Curtain Gas (CUR) was 20 mL/min, the temperature (TEM) was 500℃ and the Ion Spray Voltage (IS) was -4 500 V. Results: All calibration curves of the six components showed excellent linear regressions (r ≥ 0.999 0) within the test range. The average recoveries were 78.93%, 114.65%, 101.99%, 90.98%, 98.08%, and 115.58%, and the average contents of six bioactive constituents in 16 batches of Reduning Injection were 2.00, 26.63, 52.63, 5.29, 34.64, and 9.69 μg/mL, respectively. Conclusion: The established method is rapid, accurate, and has high repeatability, which could provide scientific evidences for the quality control of Reduning Injection.
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Objective: To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning Injection (RI). Methods: The active fraction of RI was screened by the LPS-induced mouse endotoxin shock model. The chemical constituents were isolated by chromatography on silica gel, ODS, Sephadex LH-20, Toyopearl HW-40 columns, reverse phase MPLC, and HPLC repeatedly, and their structures were identified by spectral data and physicochemical property. Results: The 95% ethanol eluate of RI on the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of RI. Fourteen compounds were isolated and identified as dibutyl phthalate (1), isovanillic acid (2), acetovanillone (3), phenylpropionic acid (4), geniposide (5), jasmigeniposide B (6), geniposidic acid (7), genipin-1-β-D-gentiobioside (8), 6″-O-trans-p-coumaroylgenipin gentiobioside (9), 6″-O-trans-feruloylgenipin gentiobioside (10), 6″-O-trans-sinapoylgenipin gentiobioside (11), jasmigeniposide A (12), 6″-O-trans-cinnamoylgenipin gentiobioside (13), and 2'-O-trans-caffeoylgardoside (14). Conclusion: Compounds 1-4 and 13 are reported from RI for the first time; And UPLC analyses and literature data showe that compounds 5 and 7-13 are originated from Gardenia jasminoides.