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Five compounds were isolated from the ethyl acetate fraction of Semen Persicae by using various chromatographic methods, including ODS, Sephadex LH-20, HPLC and semipreparative HPLC. Their structures were identified by 1D-NMR, 2D-NMR, HR-ESI-MS, UV, IR, circular dichroism (CD) and ECD calculation techniques: (2R,3R)-5,7,4′-trihydroxy-3′-methoxy-3-formylflavan-3-ol-5-O-β-D-glucopyranoside (1), (7R,8S)-dihydrodehydrodiconiferyl 6″-benzoyl alcohol-9-O-β-D-glucopyranoside (2), (7R,8S)-dihydrodehydrodiconiferyl alcohol-9-β-O-D-glucopyranosid (3), 2-methoxy-4-(2-propenyl)-phenyl-O-β-D-glucopyranoside (4), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol (5). Compound 1 and 2 are new compounds, and compounds 3-5 were obtained from Prunus davidiana (Carr.) Franch. for the first time.
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Two undescribed terpene glycosides and two compounds were isolated from the n-butanol fraction of Alpiniae Oxyphyllae Fructus by using various chromatographic methods, including MCI Gel, Sephadex LH-20, ODS, silica gel and semi-preparative HPLC. The structures of the isolated compounds were identified by spectroscopy methods (1D, 2D NMR, UV, IR, MS, etc.), and the absolute configuration of the compound 1 was determined by ECD calculation and acid hydrolysis. Compounds 1 and 2 are new compound, and compounds 3 and 4 were isolated from Alpiniae Oxyphyllae Fructus for the first time.
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One undescribed diterpenoid acid and six compounds were isolated from the 95% ethanol fraction of Pinus kesiya var. langbianensis (A.Chev.) Gaussen ex Bui resin by using various chromatographic methods, including MCI Gel, Sephadex LH-20, ODS, silica gel and semi-preparative HPLC. The planar structures were identified by spectroscopy methods (1D, 2D NMR, UV, IR, MS, etc.), and the absolute configuration of the new compound was determined by ECD calculation. Compound 1 is a new compound, and compounds 2, 5-7 were isolated from Pinus kesiya var. langbianensis (A.Chev.) Gaussen ex Bui for the first time.
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Three diarylheptanoids were isolated from the n-butanol fraction of Zingiber officinale peel by MCI Gel CHP-20, Sephadex LH-20, ODS and semipreparative high performance liquid chromatography. Their structures were identified by MS and NMR spectroscopy techniques: (2S,2'S,3R,3'R,4R,4'R,6R,6'R)-6,6'-bis((S)-1-hydroxy-2-(4-hydroxyphenyl)ethyl)-2,2'-bis(4-hydroxy-3-methoxyphenyl)octahydro-2H,2'H-[3,3'-bipyran]-4,4'-diol (1), (E)-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hept-4-en-3-one (2), and alpinin B (3). Compound 1 is a new compound, and compounds 2-3 were obtained from Zingiber officinale peel for the first time.
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OBJECTIVE@#To detect the level of vascular endothelial growth factor (VEGF) in bone marrow of patients with non-M3 acute leukemia (AL), and estimate its relationship with prognosis.@*METHODS@#From January 2016 to December 2019, 114 patients with AL in department of Hematology, Wuwei People's Hospital were selected as study group, and 25 healthy volunteers were enrolled as control group. The concentration of VEGF in bone marrow was detected by ELISA. The patients were divided into high and low concentration group according to the level of VEGF. The overall survival (OS) and event-free survival (EFS) were compared among different groups.@*RESULTS@#The level of VEGF in patients with AL was significantly higher than that in the control group. The median OS and EFS in the low concentration group was 34.5 and 32 months, respectively, while, in the high concentration group was 30 and 26 months, respectively. The differences between the two groups were statistically significant (P=0.010). There were significant differences in OS rate (P=0.035) and EFS rate (P=0.026) between low and high concentration group. Multivariate analysis showed that high VEGF concentration was an independent risk factor affecting OS (HR=2.619, 95%CI 1.070-6.406, P=0.035) and EFS (HR=2.221, 95%CI 1.074-4.552, P=0.031) in AL patients.@*CONCLUSION@#VEGF highly expresses in the bone marrow of patients with AL at initial diagnosis and relapse, and shows adverse effects on the prognosis.
Subject(s)
Humans , Bone Marrow , Disease-Free Survival , Leukemia, Myeloid, Acute , Prognosis , Vascular Endothelial Growth Factor AABSTRACT
OBJECTIVE@#To explore the regulation effect of myeloid leukemia No.1 Chinese herb medicine prescription combined with chemotherapy on Th17 cells in bone marrow fluid of AML patients, so as to provide guidance for improving AML treatment effect and patients' long-term survival.@*METHODS@#Seventy patients with AML who were hospitalized in Department of Hematology, Wuwei People's Hospital from April 2017 to August 2019 were selected and enrolled in AML group, 25 healthy volunteers were selected and enrolled in control group; then according to therapeutic regimen, AML patients were divided into 2 groups: combined therapy group (myeloid leukemia NO.1 Chinese herb medicine prescription combined with chemotherapy) and non-combined therapy group (chemotherapy alone). Flow cytometry was used to detect the ratio of CD3@*RESULTS@#The ratio of CD3@*CONCLUSION@#Th17 cells expression in bone marrow of newly diagnoses and relapsed AML patients significantly increase, and decrease significantly after treatment. Myeloid leukemia No.1 Chinese herb prescription combined with chemotherapy can significantly increase the CR rate and reduce the RL rate for AML.
Subject(s)
Humans , Bone Marrow , China , Leukemia, Myeloid, Acute/drug therapy , Medicine , Prescriptions , Th17 Cells , Vascular Endothelial Growth Factor AABSTRACT
Five monoterpenoid compounds(1-5) were isolated and purified from the acetone fraction of the aqueous extract of Zingiberis Rhizoma Recens by MCI, Sephadex LH-20, silica gel, semi-preparative HPLC, and TLC. Their structures were identified with multiple spectroscopical methods including 1 D-NMR, 2 D-NMR, and MS. The five compounds were identified as(2E,6Z)-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate(1),(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-die-noic acid(2),(E)-1,8-dihydroxy-3,7-dimethyl-2-octenoic acid(3), linalyl-β-D-glucopyranoside(4), and β-D-glucopyranoside-(2E)-3,7-dimethyl-2,6-octadien-1-yl(5), respectively.Compound 1 was a new monoterpene ester, and compounds 4-5 were isolated from this plant for the first time.
Subject(s)
Chromatography, High Pressure Liquid , Esters , Monoterpenes , RhizomeABSTRACT
The chemical constituents of Zingiber officinale peel were isolated and purified by various chromatographic separation techniques such as Diaion HP-20, MCI Gel CHP-20, Sephadex LH-20, ODS, silica gel and semi-preparative HPLC. Seven terpenoids were identified by physicochemical properties and spectral data: (4R,6S)-1-(hydroxymethyl)-5,5-dimethylbicyclo[3.1.1]hept-2-en-4-ol (1), 4-(hydroxymethyl)-1-isopropylcyclohex-2-ene-3,4-diol (2), 3,5,6-trihydroxy-7-megastigmen-9-one (3), 3-(3-hydroxybutyl)-2,4,4-trimethyl-2,5-cyclohexadien-1-one (4), angelicoidenol (5), grasshopper ketone (6), and dihydrophaseic acid (7), in which compounds 1, 2 are new compounds, named: (4R,6S)-1-(hydroxymethyl)-5,5-dimethylbicyclo[3.1.1]hept-2-en-4-ol and 4-(hydroxymethyl)-1-isopropylcyclohex-2-ene-3,4-diol, and compounds 3-7 were obtained from this plant for the first time.
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We separated and purified five chemical constituents of dried ginger by Diaion HP-20, Sephadex LH-20, silica gel and semi-preparative high performance liquid chromatography. Five gingerols were identified by physicochemical properties and MS and NMR spectroscopy techniques: 4-(2-butyl-6-methyl-4H-pyran-4-yl)-2-methoxyphenol (1), 4-(2-hexyl-6-methyl-4H-pyran-4-yl)-2-methoxyphenol (2), 1-(4-hydroxy-3-methoxyphenyl)tridecane-3,5-diol (3), [10]-gingerdiol (4) and 1-[1-(4-hydroxy-3-methoxy phenyl)-3-oxodecan-5-yl]pyrrolidin-2-one (5a, 5b). Compounds 1-3, 5a, 5b are new compounds.
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Two new diarylheptane derivatives were isolated from Rhizoma Zingiberis by Diaion HP-20, MCI Gel CHP-20, ODS, silica gel column and reverse phase semi-prepared high performance liquid chromatography. Their structures were elucidated by spectrum technology (MS, UV, IR, NMR), which were identified as 3-keto-5R-ethoxy-1-(3-methoxy-4-hydroxyphenyl)-7-(3,4-dihydroxyphenyl)heptane (1) and 3-keto-5R-ethoxy-1-(3-methoxy-4-hydroxyphenyl)-7-(3-methoxy-4,5-dihydroxyphenyl)heptane (2). Compounds 1 and 2 are new compounds.
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AIM To study chemical constitutes from Achyranthis bidentata Bl.and their effects on cells proliferation.METHODS The aqueous extract from dregs of a decoction of A.bidentata was isolated and purified by Diaion HP-20,Sephadex LH-20,ODS,silica and HPLC colum,then the structures of obtained compounds were identified by physicochemical properties and spectral data.The effects on proliferation of endothelial cells were evaluated by MTT.RESULTS Ten compounds were isolated and identified as cynarasaponin A (1),ginsenoside R0 (2),chikusetsusaponin Ⅳ a (3),chikusetsusaponin Ⅳ a methyl ester (4),chikusetsusaponin Ⅳ a ethylester (5),chikusetsusaponin Ⅳ a butyl ester (6),chikusetsusaponin-1 (7),zingibroside R1 (8),3-O-β-D-glucuronic acid glycosides-oleanolic acid (9),3-O-β-D-glucuronic acid glycosides ethylester-oleanolic acid (10).Compounds 1,6,7,8 exhibited obviously inhibiting effects on HUVEC proliferation.CONCLUSION Compounds 1 and 10 are isolated from A.bidentata for the first time;compounds 1,6,7,8 have strong inhibiting effects on cells proliferation.
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OBJECTIVE: To study the chemical constituents in the roots of Anemone altaica. METHODS: The isolation and purification of the compounds were performed by chromatography on Diaion HP-20, Sephadex LH-20, and silica gel, combined with preparation liquid chromatography. Their structures were determined by comparison of their physicochemical characteristics and spectral data with literatures. RESULTS: Eleven compounds were obtained, and their structures were identified as methyl feruloyl-tartarate A (I), methyl feruloyl-tartarate B (II), ethyl feruloyl-tartarate B (III), mono-methyl feruloyl-lactate (IV), dimethyl feruloyl-lactate (V), vanillic acid-4-O-β-D-glucopyranoside (VI), p-hydroxybenzoic acid glucoside (VII), methyl chlorogenate (VIII), 3-O-fernloylquini acid (IX), 5-O-feruloyl-3-O-(β-D-glucopyranosyl)-2-deoxy-D-ribono-γ-lactone (X), and carboxymethyl isoferulate (XI). CONCLUSION: Compounds I-V are new compounds, and are speculated to be a man-made products. Compounds VI-XI are isolated from the plants of anemone genus for the first time.
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To explore the antibacterial activity and mechanism of total alkaloids and berberine from Coptidis Rhizoma on Aeromonas hydrophila, and determine the effect of total alkaloids and berberine from Coptidis Rhizoma on minimum inhibitory concentrations, permeability and fluidity of cell membrane, conformation of membrane proteins and virulence factors of A. hydrophila. The results showed that both total alkaloids and berberine from Coptidis Rhizoma had antibacterial activities on A. hydrophila, with minimum inhibitory concentrations of 62.5 and 125 mg · L(-1), respectively. Total alkaloids and berberine from Coptidis Rhizoma could increase the fluidity of membrane, change the conformation of membrane porteins and increase the permeability of bacteria membrane by 24.52% and 19.66%, respectively. Besides, total alkaloids and berberine from Coptidis Rhizoma significantly decreased the hemolysis of exotoxin and the mRNA expressions of aerA and hlyA (P < 0.05, P < 0.01), the secretion of endotoxin and the mRNA expression of LpxC (P < 0.05, P < 0.01). The results suggested that the antibacterial activity of total alkaloids and berberine from Coptidis Rhizoma on A. hydrophila may be related to the bacteria membrane injury. They inhibited the bacterial growth by increasing membrane lipid fluidity and changing conformation of membrane proteins, and reduced the secretion of virulence factors of A. hydrophila to weaken the pathogenicity.
Subject(s)
Aeromonas hydrophila , Genetics , Metabolism , Alkaloids , Pharmacology , Anti-Bacterial Agents , Pharmacology , Bacterial Proteins , Genetics , Metabolism , Bacterial Toxins , Berberine , Pharmacology , Cell Membrane , Genetics , Metabolism , Coptis , Chemistry , Drugs, Chinese Herbal , Pharmacology , Membrane Fluidity , Rhizome , ChemistryABSTRACT
AIM@#To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring.@*METHODS@#Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods.@*RESULTS@#Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4- O-β-D-glucopyranoside (2), (+)-medioresinol-4-O-β-D-glucopyranoside (3), pinoresinol-4, 4'-di-O-β-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8).@*CONCLUSION@#Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.
Subject(s)
Benzofurans , Chemistry , Furans , Chemistry , Glucosides , Chemistry , Lignans , Chemistry , Molecular Structure , Plant Extracts , Chemistry , Plant Stems , Chemistry , Quercetin , Chemistry , Selaginellaceae , ChemistryABSTRACT
Objective: To study the chemical constituents in the rhizoma of Anemone altaica. Methods: The isolation and purification of the compounds were performed by Diaion HP-20 macroporous resin, Sephadex LH-20, and silica gel column chromatography, and their structures were determined by comparing their physicochemical characters and spectral data with literatures. Results: Fourteen compounds were obtained, and their structures were identified, including six phenolic compounds: ferulic acid (1), mono-feruloyl-tartaric acid (2), chlorogenic acid (3), glucosyringic acid (4), feruloyl-6'-O-α-D-glucopyranoside (5), and feruloyl-6'-O-β-D-glucopyranoside (6); two lignans: (+)-isolariciresino-1-9-O-β-D-glucopyranoside (7) and (+)-pinoresinol-4-O-β-D-glucopyranoside (8); one courmarin: esculetin (9); and five nitrogen-containing compounds: 2, 3, 4, 9-tetrahydro-1H-pyridine pyrido [3, 4-b] indole-3-carboxylic acid (10), phenylalanine (11), adenine (12), thymidine (13), and adenosine (14). Conclusion: Compounds 2-13 are isolated from the plants of the genus Anemone L. for the first time.
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To study the effects of alkaloids from Coptidis Rhizoma on low-density lipoprotein receptor (LDLR) mRNA expression and antihyperlipedemic levels. The LDLR mRNA expression were detected by real time fluorescence quantitative PCR, and the levels of total cholesterol (TC), triglyceride (TG), low density lipoprotein (LDL-c) and high-density lipoprotein cholesterol (HDL-c) in serum were measured at the first and last examination. The results show that, after the drug treatment, compared with the model group, each drug group showed a lipid-lowering effect. Especially, coptisine, palmatine, jatrorrhinze were significantly reduced TC, TG, LDL-c (P < 0.05, P < 0.01), and increased HDL-c (P < 0.01). In addition, they also increased mRNA expression of the LDLR in liver and HepG2 cells. The results showed that alkaloids from Coptidis Rhizoma can regulate lipid metabolism disorder, and coptisine have the best lipid-lowering effect.
Subject(s)
Animals , Cricetinae , Humans , Alkaloids , Cholesterol , Metabolism , Drugs, Chinese Herbal , Hyperlipidemias , Drug Therapy , Genetics , Metabolism , Hypoglycemic Agents , Lipid Metabolism , Lipids , Blood , Lipoproteins, LDL , Metabolism , Mesocricetus , Receptors, Lipoprotein , Genetics , Metabolism , Triglycerides , MetabolismABSTRACT
To separate and identify the chemical constituents from the leaves of Broussonetia papyrifera (Linn.) Vent, various columns including Diaion HP-20, Toyopearl HW-40C, Sephadex LH-20, silica gel were employed for the isolation and purification of compounds from the leaves of B. papyrifera. The structures of the compounds were elucidated by their physiochemical characteristics and spectral data. Nineteen compounds were isolated from the leaves of B. papyrifera and their structures were identified as apigenin (1), apigenin-7-O-beta-D-glucopyranoside (2), chrysoerid-7-O-beta-D-glucopyranoside (3), apigenin-7-O-beta-D-glucopyranuronide (4), vitexin-7-O-beta-D-glucopyranoside (5), luteolin (6), 5,7,4'-trihydroxyl-6-C-[a-L-rhamnopyranosyl (1-->2)]-beta-D-glucopyranosyl flavone (7), 5,7,4'-trihydroxyl-8-C-[a-L-rhamnopyranosyl (1-->2)]-beta-D-glucopyranosyl flavone (8), saponaretin (9), vitexin (10), benzyl benzoate-2, 6-di-O-beta-D-glucopyranoside (11), (2R, 3R, 5R, 6S, 9R)-3-hydroxy-5,6-epoxy-beta-ionol-2-O-beta-D-glucopyranoside (12), (2R, 3R, 5R, 6S, 9R)-3-hydroxyl-5,6-epoxy-acetyl-beta-ionol-2-O-beta-D-glucopyranoside (13), ficustriol (14), (6S, 9S)-roseoside (15), 3beta-hydroxy-5alpha,6alpha-epoxy-beta-ionone-2alpha-O-beta-D-glucopyranoside (16), icariside B1 (17), sammangaoside A (18), 3-hydroxy-5alpha,6alpha-epoxy-beta-ionone (19). Compounds 11, 12 and 13 are new compounds, the others are isolated from this genus Broussonetia for the first time.
Subject(s)
Apigenin , Chemistry , Broussonetia , Chemistry , Glucosides , Chemistry , Luteolin , Chemistry , Molecular Structure , Plant Leaves , Chemistry , Plants, Medicinal , ChemistryABSTRACT
Pueraria lobata (Willd.) Ohwi. was extracted for two times with 70% ethanol and the 70% ethanol-extracts was condensed. Various column chromatography with AB-8 macroreticular resin, Toyopearl HW-40, pharmadex LH-20, and silica gel were employed for the isolation and purification of the 70% ethanol-extracts from Pueraria lobata (Willd.) Ohwi. Five compounds were isolated and their structures were identified by physiochemical properties and spectral analysis (UV, IR, MS, 1H NMR, 13C NMR, HMQC, HMBC, etc.): (4R)-3-[ 2-hydroxy-4-methoxyphenyl]-4-(4-beta-D-glucopyranosyloxybenzyl) but-2-en-4-olide (1), 4', 8-dimethoxyl-7-O-beta-D-glucopyranosyl isoflavone (2), eicosanoic acid (3), hexadecanoic acid (4), tetracosanoid acid-2,3-dihydroxypropyl ester (5). Compound 1 was a new compound, and compounds 2, 3, 4 were isolated from this plant for the first time.
Subject(s)
Eicosanoic Acids , Chemistry , Glucosides , Chemistry , Molecular Structure , Palmitic Acid , Chemistry , Plant Roots , Chemistry , Plants, Medicinal , Chemistry , Pueraria , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents of the water-extracts of the pine needles of Pinus massoniana Lamb..</p><p><b>METHODS</b>Pine needles were collected in Xixia country and extracted with boiling water for two times and the water-extracts were concentrated. The crude extract of pine needles was fractionated into four fractions by Et2O, EtOAc and n-BuOH. Various column chromatography with D-101 macroreticular resin, Toyopearl HW-40 and silica gel were employed for the isolation and purification of compounds from the n-BuOH fraction of pine needles. The structures of the compounds were identified by physiochemical properties and spectral analysis (UV, IR, MS, 1HNMR, 13CNMR, DEPT, HMQC, HMBC, etc.).</p><p><b>RESULTS</b>Four compounds were isolated from the n-BuOH fraction of water-extracts, and their structures were identified as 3-methoxyl-9'-O-alpha-L-rhamnopyranosyl-4':7,5':8-diepoxyneoligan-4,9-diol (massonianoside E, I), 4,4',8,8',9-pentahydroxyl-3,3'-dimethoxyl-7,9'-monoepoxylignan (II), umbelliferon (III), 4-(4'-hydroxyl-3'-methoxylbenzyl)-2-butanone (IV).</p><p><b>CONCLUSION</b>Compound I is a new compound, and compounds II, III and IV were isolated from this plant for the first time.</p>
Subject(s)
Lignans , Chemistry , Molecular Conformation , Molecular Structure , Pinus , Chemistry , Plant Leaves , Chemistry , Plants, Medicinal , Chemistry , Umbelliferones , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents from the water-extracts of pine needles of Pinus massoniana Lamb.</p><p><b>METHODS</b>Chromatographic techniques were used to separate and purify compounds. Their physico-chemical properties and spectral data (UV, IR, MS, 1H-1H, 13C-1H NMR, DEPT, HMBC etc.) were used to elucidate the structures.</p><p><b>RESULTS</b>Three lignans were isolated from the n-BuOH fraction of water-extracts. Their structures were identified as (7S,8R)-3',4,9'-tridihydroxy-4-methoxy- 9-O-shikimoyl-7,8-dihydrobenzofuran-1'-propylneolignan (massonianoid A, I), (7S,8R)-4,9-dihydroxy-3,3'-dimethoxy-7,8- dihydrobenzofuran-1'-propylneolignan (II) and 4,4',8-trihydroxy-4,4'-dimethoxy-9-lignanolide (III).</p><p><b>CONCLUSION</b>Compound I is a new compound. While II and III were isolated from this plant for the first time.</p>