H.-B. Li’s research while affiliated with Jiangsu Kanion Pharmaceutical and other places

Objective: To study the main constituents from Gardenia jasminoides. Method In this study, the chemical constituents of enrichment fraction of iridoid glycosides were isolated by various chromatographic techniques and their structures were elucidated by spectroscopic analyses and comparison of NMR data with those reported in literatures. Results: The 60% ethanol extract of G. jasminoides was subjected to HP-20 macroporous adsorption resin CC to yield 30% ethanol fraction (GJ-2, UPLC-Q/TOF-MS method was used to identify the enrichment fraction of iridoid glycosides). Thirty-one compounds were obtained and characterized as 2'-O-trans-coumaroylgardoside (1), 6'-O-trans-sinapoylgardoside (2), 7-deoxygardoside (3), tarenninoside C (4), 2'-O-coumaroylmussaenosidic acid (5), 10-O-caffeoyl deacetyldaphylloside (6), 6'-O-trans-sinapoylgeniposide (7), genipin-1-O-β-D-gentiobioside (8), geniposide (9), 7-deoxy-8-epiloganicacid (10), secologanoside (11), gardenamide A (12), 6'-O-trans-sinapoyljasminoside B (13), epijasminoside A (14), jasminodiol (15), 6'-O-trans-sinapoyljasminoside L (16), 3-(β-D- glucopyranosyl-oxymethyl)-2,4,4-trimethyl-2-cyclohexen-1-one (17), jasminoside C (18), sinapinic acid (19), caffeic acid (20), methyl gallate (21), C-veratroylglucol (22), β-hydroxypropiosyringone (23), 3-hydroxy-1-(4-hydroxy-3-methoxyphenoyl) propan-1-one (24), threo-guaiacylglycerol-8'-vanillic acid ether (25), 1,2-bis-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (26), trans-2,3,5,4'-tetrahydroxystilbene-2-β-D-glucoside (27), 1-sinapoyl-β-D-glucopyranoside (28), 1,3,5-trimethoxybenzene (29), rutin (30), and glycyrrhisoflavone (31), respectively. Conclusion: Compounds 1-12are iridoid glycosides and 13-18are monoterpenoid glycosides. Compounds 6, 10, 22-29, and 31 were identified from Gardeniae Fructus for the first time. © 2020, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

As a commonly used Chinese materia medica, Artemisia annua mainly contains sesquiterpenoids, diterpenes, phenylpropionic acids, coumarins, flavonoids, volatile oil, and other chemical compositions. Its pharmacological activities are anti-malaria, anti-tumor, anti-microbial, anti-parasitic, antipyretic, anti-inflammatory, immunoregulation and so on. The significantly anti-malarial activity has led to its earlier use in the treatment of malaria. In this paper, the chemical constituents and pharmacological activities of A. annua in recent years are reviewed in order to provide a reference for the further development and rational utilization of this plant resource. © 2019, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

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. © 2017, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

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. © 2017, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

The aim of this study was to develop a simple, sensitive ultra performance liquid chromatography mass spectrometry (UPLC-MS/MS) method for the determination of syringaresinol, N-trans-feruloyltyramine, chelerythrine chloride, sinomenine, coptisine chloride, sanguinarine, chelidonine, magnolflorine, allocryptopine, protopine, farrerol, stylopine and dihydrosanguin-arine in Tong'an injection (TAI), which could be used for the quality control of TAI. The UPLC analysis was performed on Agilent Zorbax SB-Aq column (2.1 mm×150 mm,3.5 μm), with 0.1% formic acid solution (A) -acetonitrile (B) as the mobile phase for gradient elution (0.01-2 min, 5%B; 2-8 min, 5%-30%B; 8-11 min, 30%-95%B; 11-13 min, 95%B; 13-13.1 min, 95%-5%B; 13.1-14 min, 5%B). The flow rate was 0.5 mL•min⁻¹, and the column temperature was 25 ℃; multiple reaction monitoring (MRM) was performed in electrospray ion source positive ion mode for quantitative determination. The calibration curves for the above thirteen compounds showed good linear relationship in corresponding mass concentration range (r>0.999 0). The average recovery rate of the compounds ranged from 95.70% to 104.8%, with RSD of less than 1.9%. The contents of thirteen active components in 10 batches of TAI were 0.021 2-0.029 0, 0.001 7-0.002 3, 0.000 9-0.001 3, 5.952-6.205 2, 0.195 4-0.240 5, 0.002 0-0.002 9, 0.693-0.798 2, 0.069 3-0.078 2, 0.089 29-0.102 9, 0.386 5-0.420 1, 0.014 3-0.015 9, 0.755 3-0.842 1, and 0.008 2-0.011 2 g•L⁻¹ respectively. Methodology validation proved that this method was simple, rapid, sensitive and accurate, which can be used to provide reference for the comprehensive evaluation of TAI quality. The determination results of 10 batches of TAI showed the content of each batch had no significant difference. The results may provide a basis for the quality control of TAI.

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. © 2017, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

Objective: To study the antiviral constituents from the active fraction of Re-Du-Ning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the mice model loaded with restraint stress infected with influenza virus. The chemical constituents were isolated by chromatography on silica gel, ODS, Sephadex LH-20 & Toyopearl HW-40 columns, and reverse phase MPLC & HPLC repeatedly. Their structures were identified by spectral data and physicochemical property. Results: The 95% ethanol eluate of RDN Injection on the macroporous adsorption resin column was proved to be the antivirus active fraction of RDN Injection. Fourteen compounds were isolated and identified as (2E,6S)-8-[α-L-arabinopyranosyl-(1″-6')-β-D-glucopyranosyloxy]- 2,6-dimethylct-2-eno-1,2″-lactone (1), lyoniresinol (2), 5'-methoxyisolariciresinol (3), ent-isolariciresinol (4), (7R,8R)-4,7,9,9'- tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (5), (7S,8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan (6), ceplignan (7), 5'-methoxyceplignan (8), (-)-dihydrodehydrodiconiferyl alcohol (9), (7S,8R)-3,3',5-trimethoxy-4',7-epoxy-8,5'-neolignan-4,9,9'-triol (10), (2-cis, 4-trans)-abscisic acid (11), (2-trans, 4-trans)-abscisic acid (12), (1S,3R,4R,5S,7R,9R)-decane-6-carboxylic acid (13), and (1S,3R,4S,5S,7R,9R)-decane-6-carboxylic acid (14); Among them, compound 1 exhibited the antivirus activity against Dengue virus. Conclusion: Compound 8 is a new compound and the other isolated compounds are reported from RDN Injection for the first time, and compound 1 shows the anti-virus activity against Dengue virus. © 2016, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

Objective: To investigate the chemical constituents from Re-Du-Ning Injection (RDN). Methods: The chemical constituents were isolated by chromatography on silica gel, ODS, Sephadex LH-20, and Toyopearl HW-40 columns and reverse phase MPLC and HPLC repeatedly. Their structures were identified by spectral data and physicochemical property. Results: Sixteen compounds were isolated and identified as 5-O-caffeoylquinic acid (1), 5-O-caffeoylquinic acid methyl ester (2), 4-O-caffeoylquinic acid (3), 5-O-caffeoylquinic acid methyl ester (4), 4,5-di-O-caffeoylquinic acid (5), 4,5-di-O-caffeoylquinic acid methyl ester (6), 3,5- di-O-caffeoylquinic acid (7), 3,5-di-O-caffeoylquinic acid methyl ester (8), 3,4-di-O-caffeoylquinic acid (9), 3,4-di-O-caffeoylquinic acid methyl ester (10), secologanic acid (11), vogeloside (12), 7-epi-vogeloside (13), E-aldosecologanin (14), Z-aldosecologanin (15), and 5H,8H-pyrano[4,3-d] thiazolo[3,2-a] pyridine-3-carboxylic acid (16). Compounds 1-10 showed high efficiency and low toxicity with antivirus activity against RSV. Conclusion: All the isolated compounds are reported from RDN Injection for the first time, and caffeoylquinic acids may be one of antivirus pharmacodynamic material bases of RDN. ©, 2015, Editorial Office of Chinese Traditional and Herbal Drugs. All right reserved.

Objective: To study the antiviral constituents from the active fraction of Re-Du-Ning (RDN) Injection. Methods: In this study, the active fraction of RDN Injection was screened by the mice model loaded with restraint stress infected with influenza virus. The investigation on this fraction led to the isolation and identification of compounds through various chromatographic techniques and spectroscopic methods. In addition, the in vitro activity on influenza virus A (A/PR/8/34 H1N1) of the flavonoids was evaluated in vitro by the method for the detection of anti-influenza virus neuraminidase activity. Results: Through the macroporous adsorption resin, 95% ethanol eluate of RDN Injection was proved to be the antivirus active fraction of RDN Injection. Twenty compounds were obtained and characterized as syringic acid (1), ferulic acid (2), benzoic acid (3), caffeic acid (4), p-hydroxy benzaldehyde (5), vanillin (6), 4-hydroxy-3-methoxy styrene acrylic acid (7), trans-p-hydroxy cinnamic acid (8), trans-o-hydroxy cinnamic acid (9), trans-cinnamic acid (10), 7-hydroxy-6-methoxy coumarin (11), 7-hydroxy-6, 8-dimethoxy coumarin (12), coumarin (13), 3-hydroxy-1, 2-bis (4-hydroxy-3-methoxyphenyl)-1-propanone (14), isorhamnetin (15), quercetin (16), luteolin (17), rutin (18), hyperoside (19), and luteolin-7-O-β-D-glucoside (20). Among them, luteolin exhibited the antivirus activity against Flu A virus. Conclusion: All the isolated compounds are reported from RDN Injection for the first time, and luteolin exhibits the most potential activity against H1N1.