Polyhydroxylated eudesmane sesquiterpenoids and sesquiterpenoid glucoside from the flower buds of Tussilago farfara / 中国天然药物

Chemical fractionation of the n-BuOH partition, which was generated from the EtOH extract of the flower buds of Tussilago farfara, afforded a series of polar constituents including four new sesquiterpenoids (1-4), one new sesquiterpenoid glucoside (5) and one known analogue (6) of the eudesmane type, as well as five known quinic acid derivatives (7-11). Structures of the new compounds were unambiguously characterized by detailed spectroscopic analyses, with their absolute configurations being established by X-ray crystallography, electronic circular dichroism (ECD) calculation and induced ECD experiments. The inhibitory effect of all the isolates against LPS-induced NO production in murine RAW264.7 macrophages was evaluated, with isochlorogenic acid A (7) showing significant inhibitory activity.

A new norsesquiterpene glycoside from fruits of Actinidia arguta / 中草药

Objective: To study the chemical constituents in the fruits of Actinidia arguta. Methods: The compounds were isolated by column chromatography on silica gel, ODS, and Sephadex LH-20, preparative TLC, and semi-preparative HPLC. The structures were established by the analyses of the spectroscopic data. Results: Fifteen compounds were obtained from the n-BuOH fraction of the 75% ethanol extract of the fruits of A. arguta and identified as (2R,6R,9R)-trihydroxy-megastigmane-4,7E-dien-3-one-9-O-β-D- glucopyranoside (1), (6S,9R)-roseoside (2), quercetin-3-O-b-D-galactopyranside (3), astragalin (4), vanillic acid-4-O-β-D- glucopyranoside (5), 1-O-feruloyl-β-D-glucopyranoside (6), ferulic acid-4-O-β-D-glucopyranoside (7), rhodioloside (8), 3-hydroxy-1-(4-O-β-D-glucopyranosyl-3- methoxyphenyl) propan-1-one (9), 5-O-caffeoyl quinic acid methyl ester (10), 5-O-caffeoyl quinic acid butyl ester (11), 5-O-feruloyl quinic acid methyl ester (12), 5-O-coumaroyl quinic acid methyl ester (13), caffeic acid (14), and protocatechuic acid (15). Conclusion: Compound 1 is a new norsesquiterpene glycoside with the megastigmane scaffold, named actinargutaside A. Compounds 2, 5, and 7-13 are isolated from the Actinidia genus for the first time and compound 6 is firstly isolated from A. arguta.

Chemical constituents from roots of Arctium lappa / 中草药

Objective: To research the chemical constituents from the roots of Arctium lappa. Methods: The compounds were isolated and purified by column chromatography over normal phase silical gel, reverse phase silical gel, ODS column chromatography and semi-preparative HPLC. Their structures were identified by various spectroscopic analysis, including NMR. Results: Fourteen compounds were isolated from the 55% EtOH extract of the roots of A. lappa. And their structure were identified as 1,5-di-O-caffeoyl-3-O-maloyl quinic acid (1), 3,5-di-O-caffeoyl-1-O-(2-O-caffeoyl-4-maloyl)-quinic acid (2), 3,5-di-O- caffeoyl-1-(2-O-caffeoyl-4-maloyl methyl ester)-quinic acid (3), 3,5-di-O-caffeoyl-1-O-succinyl methyl ester quinic acid (4), 3,4-di-O-caffeoyl-1-O-succinyl methyl ester quinic acid (5), 1,3,5-tri-O-caffeoyl-4-O-succinyl quinic acid (6), 1,5-di-O- caffeoyl-3-O-succinyl quinic acid (7), 1,5-di-O-caffeoyl-4-O-succinyl quinic acid (8), 1,5-di-O-caffeoyl-4-O-succinyl methyl ester quinic acid (9), 1,5-di-O-caffeoyl-3-O-succinyl methyl ester quinic acid (10), 1,3,4-tri-O-caffeoyl quinic acid (11), 1,4,5-tri-O-caffeoyl quinic acid methyl ester (12), 3-O-caffeoyl quinic acid (13), and 4-hydroxy-phenylacetic acid (14). Conclusion: Compounds 3-5, 9, 11, 12 are obtained from Arctium genus for the first time, and compound 14 is isolated from A. lappa for the first time.

Chemical constituents and hypoglycemic activity of Phlomis tuberosa / 中草药

Objective: To study the chemical constituents and hypoglycemic activity of Phlomis tuberosa. Methods: The db/db diabetic mice was used to screen the hypoglycemic active site of P. tuberosa. The chemical constituents were isolated and purified by various separation and analysis techniques. The structures of these compounds were identified by spectroscopic analysis (1H-, 13C-NMR and MS). The hypoglycemic activities of these compounds were verified by the DPP-4 inhibitory activity in vitro. Results: Ethyl acetate extract of P. tuberosa showed significant hypoglycemic effect. Twenty-five compounds were isolated from the active site, containing β-stiosterol (1), stigmasterol (2), daucosterol (3), clerosterol-stigmast-4-ene-3,6-dione (4), 22-dehydro- stigmast-4-ene-3,6-dione (5), ellagic acid (6), ethyl gallate (7), gllagic acid (8), 4-hydroxybenzoic acid (9), 3,4-diohydroxybenzoic acid (10), cinnamic acid (11), p-hydroxy-cinnamic acid (12), caffeic acid (13), 5-hydromethylfuraldehyde (14), quinic acid (15), chlorogenic acid (16), ferulic (17), 2,3-dimethoxy-5-methyl-6-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaen-1- yl)-2,5-cyclohexadiene-1,4-dione (18), 1-O-caffeoyl- quinic acid (19), 3,5-dimethoxy-4-hydroxy-benzene carbonic-1-O-β-D-glucoside (20), 2-O-butyl-α-D-fructofuranoside (21), n-octadecanoic acid (22), stearic acid (23), methyl-5-(hydroxymethyl) furan-2-carboxylate (24) and 4-hydroxy-3-methoxy-benzaldehyde(25). Nine compounds were obtained from the genus Phlomis for the first time, in which ellagic acid (6), quinic acid (15), and 1-O- caffeoylquinic acid (19) showed strong DPP-4 inhibitory activity with IC50 of 72.3, 89.2, and 103.4 μmol/L, respectively. The IC50 of the positive drug diprotin A was 50 μmol/L. Conclusion: Compounds (3-7 and 18-21) are obtained from the genus Phlomis for the first time. Compound 6, 15, and 19 show DPP-4 inhibitory activities.

Caffeoyl quinic acids in Chrysanthemum morifolium improve LPS-induced HUVEC vascular endothelial cell injury by regulating ERK/MAPK signaling pathway / 药学学报

To explore the effect of total extract of Chrysanthemum morifolium on lipopolysaccharide (LPS)-induced acute lung injury in mice, we studied the effects of three caffeoyl quinic acids isolated from Chrysanthemum morifolium on vascular endothelial cell injury and their mechanisms of action. All animal experiments were carried out strictly in accordance with the National Animal Welfare Ethics and Protection Regulations. A mouse model of acute lung injury was established by intranasal instillation of LPS. After 6 days of oral administration of chrysanthemum extract, the lung wet weight/dry weight ratio, tumour necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1β (IL-1β) were measured in mouse bronchoalveolar lavage fluid. Human umbilical vein endothelial cells (HUVEC) were serum starved for 12 h and treated with 2.5 μg·mL-1 LPS for 24 h to establish the in vitro model of vascular endothelial cell injury. After 24 h of treatment of caffeoyl quinic acids from Chrysanthemum morifolium, the levels of TNF-α, IL-6, IL-1β, vascular cell adhesion molecule-1 (VCAM-1) and endothelin-1 (ET-1) were measured by ELISA in the cell culture supernatant, the malondialdehyde (MDA) level was detected by TBA method, the superoxide dismutase (SOD) level was determined by hydroxylamine method, and the nitric oxide (NO) level was assayed by a one-step method. The levels of p-MEK1/2, MEK1/2, p-ERK1/2, ERK1/2, p-JNK, JNK, p-P38 and P38 of mitogen-activated protein kinase (MAPK) signaling pathway were detected by Western blot. The total extract of Chrysanthemum morifolium can significantly reduce the wet weight/dry weight ratio of lung in mice and the levels of TNF-α, IL-6 and IL-1β in alveolar lavage fluid. The caffeoyl quinic acids from Chrysanthemum morifolium significantly increased the levels of SOD and NO, decreased the levels of TNF-α, IL-6, IL-1β, VCAM-1, ET-1 and MDA, and significantly reduced the levels of p-MEK1/2, p-ERK1/2. In conclusion, total extracts of Chrysanthemum morifolium exhibit certain protective effect on mice with acute lung injury, and three caffeoyl quinic acids from Chrysanthemum morifolium may improve LPS-induced vascular endothelial cell injury by inhibiting inflammatory cytokines and oxidative stress, and regulating inter-cellular adhesion molecule and vasomotor factors through ERK/MAPK signaling pathway.

Anti-nociceptive and Anti-inflammatory Properties of Ilex latifolia and its Active Component, 3,5-Di-caffeoyl Quinic Acid Methyl Ester

The present study was conducted to investigate anti-nociceptive and anti-inflammatory effects of the leaves of Ilex latifolia Thunb (I. latifolia) in in vivo and in vitro. Writhing responses induced by acetic acid and formalin- and thermal stimuli (tail flick and hot plate tests)-induced pain responses for nociception were evaluated in mice. I. latifolia (50 – 200 mg/kg, p.o.) and ibuprofen (100 mg/kg, p.o.), a positive non-steroidal anti-inflammatory drug (NSAID), inhibited the acetic acid-induced writhing response and the second phase response (peripheral inflammatory response) in the formalin test, but did not protect against thermal nociception and the first phase response (central response) in the formalin test. These results show that I. latifolia has a significant anti-nociceptive effect that appears to be peripheral, but not central. Additionally, I. latifolia (50 and 100 µg/mL) and 3,5-di-caffeoyl quinic acid methyl ester (5 µM) isolated from I. latifolia as an active compound significantly inhibited LPS-induced NO production and mRNA expression of the pro-inflammatory mediators, iNOS and COX-2, and the pro-inflammatory cytokines, IL-6 and IL-1β, in RAW 264.7 macrophages. These results suggest that I. latifolia can produce antinociceptive effects peripherally, but not centrally, via anti-inflammatory activity and supports a possible use of I. latifolia to treat pain and inflammation.

Chemical constituents from stems of Acanthopanax henryi / 中草药

Objective To study the chemical constituents from stems of Acanthopanax henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model. Methods The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography, as well as Prep-TLC and recrystallization methods. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results Eighteen compounds were obtained from A. henryi and their chemical structures were identified as p-hydroxybenzoic acid (1), trans-p-hydroxycinnamic acid (2), (E)-caffeic acid methyl ester (3), caffeic acid (4), trans-coniferyl aldehyde (5), syringaldehyde (6), vanillin (7), 6-methoxy-7-hydroxycoumarin (8), trans-sinapaldehyde (9), undecane-1,11-dioic acid monomethyl ester (10), (-)-sesamin (11), 3-O-caffeoyl-quinic acid (12), 5-O-caffeoyl-quinic acid (13), 1,3-di-O-caffeoyl-quinic acid (14), 1,4-di-O-caffeoyl-quinic acid (15), 1,5-di-O-caffeoyl-quinic acid (16), stigmasterol (17), and β-sitosterol (18), respectively. Conclusion To the best of our knowledge, compound 10 was isolated from Araliaceae for the first time. Except compounds 12, 14, 17, and 18, all of other compounds were obtained from this species for the first time.

Anti-oxidant chemical constituents from Patrinia villosa / 中草药

Objective: To study the antioxidant chemical constituents and antioxidant activity of Patrinia villosa. Methods: The 70% ethanol-water extract of the herb was separated by silica gel column chromatography, ODS column chromatography and sephadex column chromatography. Then, the compound were further purified and extracted by semi-preparative HPLC. Their structures were elucidated by physiochemical property and spectral analysis. DPPH and ABTS methods were used to determine the antioxidant bioactivities of the isolated compounds. Results: A total of ten compounds were isolated and synthesized, including chlorogenic acid butyl ester (1), 3,4-di-O-caffeoyl quinic acid methyl ester (2), luteolin-7-O-rutinoside (3), 1β-O-β-D-glucopyranosy- 15-O-(p-hydroxylphenylacetate)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (4), 3,4-di-O-caffeoyl quinic acid ethyl ester (5), 4,5-di-O-caffeoyl quinic acid methyl ester (6), 4,5-di-O-caffeoyl quinic acid n-butyl ester (7), luteolin-7-O-β-D-glucuronide methyl ester (8), luteolin-7-O-β-D-glucuronide ethyl ester (9), and apigenin-7-O-β-D-glucuronide methyl ester (10). The DPPH radical scavenging IC50 of compounds 3, 8, and 9 were (23.95 ± 0.71), (73.09 ± 0.33), and (25.06 ± 0.65) μmol/L, respectively. The ABTS radical scavenging IC50 was (7.13 ± 0.07), (11.48 ± 0.21), (5.15 ± 0.08) mol/L, respectively. Conclusion: Eight compounds except compounds 3 and 8 are obtained from this species for the first time. Compounds 3, 8, and 9 had significant antioxidant activity.

Study on chemical constituents of Artemisia integrifolia (II) / 中草药

Objective: To study the chemical constituents of Artemisia integrifolia. Methods: Solvent extraction, silica gel column chromatography, and HPLC were used for isolation and purification. The structure was identified by NMR spectrum analysis. Anti-oxidant activity tests were performed using DPPH. Results: A total of 21 monomeric compounds were isolated from A. integrifolia and identified as 2R-(2Z-pentenoic acid methyl ester)-3S-(methyl acetate) cyclopentanone (1), methyl-4S-6α-hydroxy-3- oxoeudesma-1,11 (13)-dien-12-oate (2), methyl caffeate (3), dextrin inositol (4), monobutyl fumarate (5), caffeic acid (6), monobutyl malonate (7), 6,8-dimethoxycoumarin-7-O-β-D-glucoside (8), 3,5-O-di-caffeoyl quinic acid butyl ester (9), 3,4-O-dicaffeoyl quinic acid butyl ester (10), 4,5-O-dicaffeoyl quinic acid butyl ester (11), 3,5-O-dicaffeoyl quinic acid methyl ester (12), 4,5-O- dicaffeoylquinic acid (13), 1,5-O-dicaffeoylquinic acid (14) 3,5-O-dicaffeoylquinic acid (15), o-hydroxycinnamic acid glucoside (16), 1,3-O-dicaffeoyl quinic acid (17), chlorogenic acid (18), 3,4-O-dicaffeoylquinic acid (19), methyl 3,4-O-dicaffeoylquinate (20), and o-hydroxycinnamate methyl glucoside (21). Conclusion: Compound 1 is a new natural product. Compounds 2, 5, 7-11, 14, 16, and 21 are isolated from Artemisia for the first time, and the rest are isolated from A. integrifolia for the first time. Both caffeoyl quinic acid compounds had strong anti-oxidant capacity, and the activity is basically equivalent to Vc.

Anti-neuroinflammatory effects of ethanolic extract of black chokeberry (Aronia melanocapa L.) in lipopolysaccharide-stimulated BV2 cells and ICR mice

BACKGROUND/OBJECTIVES: One of the mechanisms considered to be prevalent in the development of Alzheimer's disease (AD) is hyper-stimulation of microglia. Black chokeberry (Aronia melanocapa L.) is widely used to treat diabetes and atherosclerosis, and is known to exert anti-oxidant and anti-inflammatory effects; however, its neuroprotective effects have not been elucidated thus far. MATERIALS/METHODS: We undertook to assess the anti-inflammatory effect of the ethanolic extract of black chokeberry friut (BCE) in BV2 cells, and evaluate its neuroprotective effect in the lipopolysaccharide (LPS)-induced mouse model of AD. RESULTS: Following stimulation of BV2 cells by LPS, exposure to BCE significantly reduced the generation of nitric oxide as well as mRNA levels of numerous inflammatory factors such as inducible nitric oxide synthase (iNOS), cyclooxygenase 2 (COX-2), interleukin 1 beta (IL-1β), and tumor necrosis factor alpha (TNF-α). In addition, AD was induced in a mouse model by intraperitoneal injection of LPS (250 µg/kg), subsequent to which we investigated the neuroprotective effects of BCE (50 mg/kg) on brain damage. We observed that BCE significantly reduced tissue damage in the hippocampus by downregulating iNOS, COX-2, and TNF-α levels. We further identified the quinic acids in BCE using liquid chromatography-mass spectrometry (LCMS). Furthermore, we confirmed the neuroprotective effect of BCE and quinic acid on amyloid beta-induced cell death in rat hippocampal primary neurons. CONCLUSIONS: Our findings suggest that black chokeberry has protective effects against the development of AD.

Inhibitory effect of the Pseudobrickellia brasiliensis (Spreng) R.M. King & H. Rob. aqueous extract on human lymphocyte proliferation and IFN-γ and TNF-α production in vitro

Pseudobrickellia brasiliensis (Asteraceae) is a plant commonly known as arnica-do-campo and belongs to the native flora of the Brazilian Cerrado. The alcoholic extract of the plant has been used as an anti-inflammatory agent in folk medicine, but the biological mechanism of action has not been elucidated. The present study evaluated the composition of P. brasiliensis aqueous extract and its effects on pro-inflammatory cytokine production and lymphocyte proliferation. The extracts were prepared by sequential maceration of P. brasiliensis leaves in ethanol, ethyl acetate, and water. Extract cytotoxicity was evaluated by trypan blue exclusion assay, and apoptosis and necrosis were measured by staining with annexin V-FITC and propidium iodide. The ethanolic (ETA) and acetate (ACE) extracts showed cytotoxic effects. The aqueous extract (AQU) was not cytotoxic. Peripheral blood mononuclear cells stimulated with phorbol myristate acetate and ionomycin and treated with AQU (100 μg/mL) showed reduced interferon (IFN)-γ and tumor necrosis factor (TNF)-α expression. AQU also inhibited lymphocyte proliferative response after nonspecific stimulation with phytohemagglutinin. The aqueous extract was analyzed by liquid chromatography coupled with photodiode array detection and mass spectrometry. Quinic acid and its derivatives 5-caffeoylquinic acid and 3,5-dicaffeoylquinic acid, as well as the flavonoids luteolin and luteolin dihexoside, were detected. All these compounds are known to exhibit anti-inflammatory activity. Taken together, these findings demonstrate that P. brasiliensis aqueous extract can inhibit the pro-inflammatory cytokine production and proliferative response of lymphocytes. These effects may be related to the presence of chemical substances with anti-inflammatory actions previously reported in scientific literature.

Analysis on chemical composition of Farfarae Flos by UPLC-Q-TOF-MS / 中草药

Objective: The chemical constituents in the methanol extract from Farfarae Flos were rapidly identified using UPLC-Q-TOF-MS in positive and negative ion modes. Methods: The analysis was performed on an Agilent Poroshell 120 EC-C18 chromatographic column (100 mm × 2.1 mm, 2.7 μm). The mobile phase consisted of acetonitrile and 0.1% aq formic acid. In positive ion mode, gradient elution: 0-1 min, 5%-17% B; 1-3 min, 17%-19% B; 3-14 min, 19%-44% B; 14-16 min, 44%-66% B; 16-26 min, 66%-87% B; 26-28 min, 87%-95% B; 28-33 min, 95% B. In negative ion mode, gradient elution: 0-2 min, 5%-14% B; 2-10 min, 14%-32% B; 10-15 min, 32% B. The flow rate was 0.4 mL/min, and the injection volume was 5 μL. The information of the compounds was analyzed by positive and negative ion modes mass spectrum information, elements composition, reference substance retention time or mass spectrum parameters of compounds in literature. Results: Thirty-four compounds in Farfarae Flos extracts were identified, combined with provided accurate molecular weight compounds by UPLC-Q-TOF-MS, including 12 kinds of terpenoids, eight kinds of flavonoids, seven kinds of phenolic acids, two kinds of pyran compounds, one kind of phenolic ketones, one kind of fat ketones, and three kinds of alkaloids. Conclusion: The method provides the theory basis for quality control and the clinical reasonable application and provides the reference for clarifying its efficacy material base.

Study on chemical constituents from inflorescence of Echinops latifolius / 中草药

Objective To study the chemical constituents of the inflorescence of Echinops latifolius as a Mongolia herbal medicine. Methods The compounds were and purified by column chromatography on silica gel, ODS, and Sephadex LH-20. Their structures were elucidated on the basis of spectroscopic methods, including MS and NMR. Results Fourteen compounds were isolatied from the inflorescence of E. latifolius Tausch, and identified as ψ-taraxasteryl acetate (1), apigenin (2), daucosterol (3), 13-propyl-pentacosane (4), apigenin 7-O-(4″-O-p-coumaroyl)-β-glucoside (5), apigenin-7-O-glucoside (6), caffeic acid (7), 1,5-O-dicaffeoylquinic acid (8), 3,5-O-dicaffeoyl quinic acid (9), methyl 3,4-O-dicaffeoyl quinic acid (10), methyl 3,5-O-dicaffeoyl quinic acid (11), apigenin 7-O-β-D-(4″-p-coumaroyl) glucoside (12), 3,4-O-dicaffeoyl quinic acid (13), and methyl-1-O-methyl 3,5-O-dicaffeoyl quinic acid (14). Conclusion Compounds 1, 4, 5, and 12 are isolated from this plant for the first time. Compound 7-11, 13, and 14 are isolated from the genus Echinops for the first time.

Simultaneous Determination of Flavonoids and Phenolic Acids in Herba Gnaphalium Affinis by HPLC / 中国药师

Objective:To develop an HPLC method for the simultaneous determination of flavonoids and phenolic acids in Herba Gnaphalium Affinis. Methods:The analysis was carried out on a Diamonsil C18 column (200 mm × 4. 6 mm, 5μm) with gradient elu-tion using methanol-0. 4% phosphoric acid as the mobile phase. The flow rate was 1. 0 ml·min-1 and the detection wavelength was 327 nm for flavonoids and 360nm for phenolic acids,the column temperature was 30℃, and the sample size was 10 μl. Results:The calibration curves were linear over the range of 0. 041-0. 821 μg for chlorogenic acidrutin, 0. 127-2. 549 μg for 3, 5-O-dicaffeoyl quin-ic acid, 0. 020-0. 411 μg for quercetin and 0. 040-0. 806μg for luteolin. The average recovery was 98. 31% ( RSD = 1. 19%), 97. 51%(RSD=1. 52%), 98. 29%(RSD=1. 22%) and 98. 73%(RSD=1. 47%), respectively. Conclusion:The described meth-od is simple and reproducible, which can be used for the quality control of Herba Gnaphalium Affinis.

1,5-O-Dicaffeoyl-quinic Acid as a Novel Potential NMDA Receptor Inhibitor from Traditional Chinese Medicine Database by Virtual Screening / 中草药·英文版

Objective Neurodegenerative diseases, such as ischemia, traumatic injury, Alzheimer's disease, and Parkinson's disease are characterized by neuronal loss and dysfunction. It is known that glutamate-induced toxicity plays an important role in neurodegenerative diseases. Glutamate toxicity seems to be mediated by excessive influx of Ca2+ into neuronal cells through activation of N-methyl-D-aspartate (NMDA) receptor. To search for potential NMDA receptor inhibitors in traditional Chinese medicine. Methods A series of computer methods including drug-likeness evaluation, ADMET tests as well as molecular docking have been used. Results 1,5-O-dicaffeoyl-quinic acid was identified as NMDA receptor inhibitor by virtual screening. Its neuroprotective activity was further confirmed by in vitro test. 1,5-O-dicaffeoyl-quinic acid showed strong neuroprotection against NMDA-induced cell injury. Conclusion 1,5-O-Dicaffeoylquinic acid may be regarded as a potential NMDA receptor inhibitor for the prevention and treatment of neurodegenerative disorders.

Chemical constituents in stems of Ilex cornuta / 中草药

Objective: To investigate the chemical constituents in the stems of Ilex cornuta and the ability of scavenging free radicals of compounds 1-9. Methods: The compounds were isolated and purified by silica gel, medium pressure column chromatography, and semi-preparative liquid chromatography, and their structures were elucidated by chemical properties and spectroscopic analyses. The antifreeradical efficiency of compounds 1-9 was evaluated by DPPH radical scavenging assay. Results: Fifteen compounds were isolated and their structures were identified as isochlorogenic acid B (1), 3,4,5-tricaffeoylquinic acid (2), 4,5-di-O-caffeoyl quinic acid methyl ester (3), 3,4-di-O-caffeoyl quinicacid methyl ester (4), 3,5-di-O-caffeoyl quinicacid methyl ester (5), 3,4,5-tri-O-caffeoyl quinic acid methyl ester (6), 3,5-dimethoxy-4-hydroxybenzaldehyde (7), ethyl gallate (8), dihydrosyringenin (9), 2,6-dimethoxy-1,4-benzoquinone (10), arctigenin (11), 1-O-(vanillic acid)-6-O-(3″, 5″-dimethoxy-galloyl)-β-D-glycoside (12), (+)-1-hydroxypinoresinol-1-O-β-D-glucopyranoside (13), (+)-(7S,8S)-syringylglycerol 8-O-β-D-glucopyranoside (14), and schaftoside (15). Compounds 1-7 had good antifreeradical efficiency. Conclusion: Compounds 6,8-10,14, and 15 are obtained from the plants of Ilex L. the first time, and compounds 2,7,11, and 12 are obtained from this plant for the first time. Compounds 1-6 have good antifreeradical efficiency.

Phenolic constituents from Erycibe schmidtii / 中草药

Objective: To investigate the chemical constituents of Erycibe schmidtii. Methods: The compounds were separated and purified by silica gel and Sephadex LH-20 column chromatography, and semipreparative HPLC. Their structures were determined by nuclear magnetic resonance (NMR) spectroscopy analysis method. The anti-inflammatory activity of some compounds was tested by relative NO productivity. Results: Twelve compounds were isolated and identified as caffeic acid (1), N-trans-p-hydroxyphenethyl ferolamine (2), chlorogenic acid (3), chlorogenic acid methyl ester (4), 4-O-caffeoylquinic acid (5), 4-O-caffeoylquinic acid methyl ester (6), 4,5-di-O-caffeoylquinic acid (7), 4,5-di-O-caffeoylquinic acid methyl ester (8), 3,5-di-O-caffeoylquinic acid (9), 3,5-di-O-caffeoylquinic acid methyl ester (10), 3,4-di-O-caffeoylquinic acid (11), and 3,4-di-O-caffeoylquinic acid methyl ester (12). Compounds 1 and 2 showed some inhibitory activity for RAW cells 264.7 releasing NO. Conclusion: Compounds 5-7, 9, 11, and 12 are obtained from the plants of Erycibe Roxb. for the first time, while compounds 1, 2, and 4-12 are separated from this plant for the first time. Compounds 1 and 2 exhibit certain anti-inflammatory activity.

Simultaneous determination of 10 constituents in Boyun Tuiyi Pill by HPLC / 中草药

Objective: To develop an HPLC-DAD method for the simultaneous determination of liquiritin, ammonium glycyrrhizinate, vitexicarpin, pulegone, ferulic acid, chlorogenic acid, 3,5-dicaffeoyl quinic acid, berberine hydrochloride, kaempferol, and buddleoside in Boyun Tuiyi Pill (BTP). Methods: Shim-pack VP-ODS C18 column (250 mm × 4.6 mm, 5 μm) was adopted. The mobile phase was composed of methanol-acetonitrile (50:50, A) and 0.05% phosphoric acid (B) with gradient elution. Gradient elution: 0-5.0 min, 50% A; 5.0-30.0 min, 50%-80% A; 30.0-32.0 min, 80%-50% A; and 32.0-40.0 min, 50% A; Injection volume was 10 μL. The flow rate was 1.0 mL/min and the column temperature was 40℃. Results: liquiritin, ammonium glycyrrhizinate, vitexicarpin, pulegone, ferulic acid, chlorogenic acid, 3,5-dicaffeoyl quinic acid, berberine hydrochloride, kaempferol, and buddleoside were separated well. The linear calibration curves were obtained in 2-20 μg/mL for liquiritin, r = 0.999 2; 20-200 μg/mL for ammonium glycyrrhizinate, r = 0.999 5; 3-30 μg/mL for vitexicarpin, r = 0.999 4; 2-20 μg/mL for pulegone, r = 0.999 7; 1.2-12.0 μg/mL for ferulic acid, r = 0.999 5; 3.5-35.0 μg/mL for chlorogenic acid, r = 0.999 2; 8-80 μg/mL for 3,5-dicaffeoyl quinic acid, r = 0.999 3; 9-90 μg/mL for berberine hydrochloride, r = 0.999 3; 2-20 μg/mL for kaempferol, r = 0.999 6; and 3-30 μg/mL for buddleoside, r = 0.999 5. The average recoveries of the 10 constituents were 99.1%, 101.1%, 100.2%, 99.4%, 101.9%, 98.5%, 100.5%, 101.7%, 100.8%, and 99.7% with RSD of 0.62%, 0.79%, 0.77%, 0.83%, 0.47%, 0.38%, 0.97%, 1.05%, 0.86%, and 1.11%. The contents of six batches of the liquiritin, ammonium glycyrrhizinate, vitexicarpin, pulegone, ferulic acid, chlorogenic acid, 3,5-dicaffeoyl quinic acid, berberine hydrochloride, kaempferol, and buddleoside were 0.505-0.685, 1.793-2.012, 0.227-0.268, 0.183-0.206, 1.258-1.324, 0.348-0.381, 0.648-0.720, 1.544-1.722, 1.543-1.627, and 3.434-3.883 mg/pill, respectively. Conclusion: The method is rapid and has high sensitivity, high accuracy, and good specificity. It can be applied to the quality control of BTP.

Chemical Constituents from the Aerial Parts of Bupleurum falcatum L. and Biological Evidences

In this study, phytochemical investigation on the aerial parts of Bupleurum falcatum resulted in the isolation of fourteen compounds including three quinic acid derivatives (1 - 3), five flavonoids (4 - 8), three monoterpene glycosides (9 - 11), and three saikosaponins (12 - 14). Compound 1 was first isolated from nature and unambiguously determined to be 3-O-feruloyl 5-O-caffeoylquinic acid on the basis of the extensive spectroscopic evidence. Biological testing revealed that saikosaponin A (12) and saikosaponin D (13) showed moderate antiproliferative effects on HL-60 and HepG2 cancer cell lines.

Studies on chemical constituents in n-butanol extracts from epicarp of green fruit of Juglans mandshurica / 中草药

Objective: To study the chemical constituents in n-butanol extracts from the epicarp of green fruits of Juglans mandshurica. Methods: The compounds were isolated and purified by silica gel, ODS, Sephadex LH-20 columns, high preparative performance liquid chromatography, etc. And their structures were identified by spectral analysis. Results: Fourteen compounds were obtained and identified as 5-O-cafffeoyl quinic acid butyl ester (1), 3,5-di-O-caffeoylquinic acid butyl ester (2), vanillic acid-4-O-β-D-(6'-O-galloyl) glucopyranoside (3), 4-hydroxy-2,6-dimethoxyphenol-1-O-β-D-glucopyranoside (4), 4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucopyranoside (5), 1,4,8- trihydroxynaphthalene-1-O-β-D-glucopyranoside (6), 1,4,5-trihydroxynaphthalene-1,4-di-O-β-D-glucopyranoside (7), kaempferol-3-O-β- D-glucopyranoside (8), quercetin-3-O-β-D-glucopyranoside (9), quercitrin (10), myricitrin (11), afzelin (12), hyperin (13), and daucosterol (14). Conclusion: Compounds 1-4 are isolated from the plants of Juglans L. for the first time, Compounds 5, 8-12 are isolated from the epicarps of J. mandshurica for the first time.