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Objective: To investigate the mechanism of Qingkailing Injection in the treatment of coronavirus disease 2019 (COVID-19). Methods: The active components and target proteins of Gardeniae Fructus, Isatidis Radix, Lonicerae Japonicae Flos, and other materials in Qingkailing Injection were obtained by means of literature search and TCMSP. Uniprot database was used to search the target genes corresponding to the active ingredients, and Cytoscape 3.7.2 was used to construct the drug-compound-target network. The enrichment analysis of KEGG pathway was carried out with the help of DAVID database to predict its mechanism. Core active components and potential targets of anti-COVID-19 drugs were verified by molecular docking. Results: The drug-compound- target network consisted of five drugs, 62 compounds and 70 targets. The KEGG pathway enrichment analysis included 41 signaling pathways (P < 0.05), which were mainly involved in cell apoptosis, Fc epsilon RI signaling pathway, TNF signaling pathway, etc. Molecular docking results showed that acacetin and syrigin had strong affinity with potential targets of anti-COVID-19 drugs. Conclusion: In this study, the effect of Qingkailing Injection has the characteristics of multiple components, multiple targets and multiple pathways. The active component, acacetin, can regulate the apoptosis pathway and TNF pathway by acting on CASP3, CASP8, FASLG, and other targets, so as to realize the potential therapeutic effect on COVID-19.
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Objective: To study the chemical constituents from Sinopodophyllum hexandrum and their antitumor activities. Methods: The constituents were separated by chromatography of silica gel, ODS, Sephadex LH20 and pre-TLC. Their structures were elucidated by spectroscopic means. The in vitro cytotoxic activities of the isolated compounds were studied by MTT method. Results: Nine compounds were isolated and identified as 8,2'-diprenylquercetin 3-methyl ether-4'-O-β-D-glucoside (1), 8,2'-diprenyl quercetin-3- methylether (2), 5,7,4'-trihydroxy-3'-(3-methylbut-2-enyl)-3-methoxy flavone (3), 8-prenylkaempferol (4), sophoflavescenol (5), podoverine A (6), sinoflavonoid K (7), diosmetin (8) and acacetin (9). Conclusion: Compound 1 is a new compound named sinoflavonoid glycosides A, and compounds 5-9 are isolated from S. hexandrum for the first time. Compounds 1-5 show cytotoxicities against HeLa cells with IC50 of 42.6, 46.9, 26.9, 16.1 and 31.2 μmol/L, respectively.
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Objective: To study the chemical constituents from Stelleropsis tianschanica. Methods: The constituents were isolated from S. tianschanica and purified by column chromatography, and the structures were identified by spectral analysis and chemical methods. Results: A total of 12 compounds were isolated from S. tianschanica, including seven flavonoids compounds, two lignans compounds, and the other three compounds, and the structures were identified as wikstrol A (1), wikstrol B (2), viburnolide A (3), genkwanol B (4), genkwanol C (5), stelleranol (6), dipropyl phthalate (7), diisobutyl phthalate (8), 1,3,5-triol-2-methoxybenzene (9), coniferin (10), syringin (11), and acacetin (12). Conclusion: Compounds 1-2, 5-6, 9-12 are isolated from the genus Stelleropsis for the first time.
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The purpose of this research is to investigate the effects of acacetin on serum lipid metabolism and atherosclerosis in mice and explore its molecular mechanism. HepG2 cells were treated with different concentrations of acacetin. The expression of LDL receptor (LDLR) and sterol-regulatory element binding protein-2 (SREBP-2) were detected by RT-qPCR and/or Western blot. C57BL/6J mice were given acacetin (50 mg·kg-1) for 5 weeks by gavage. Serum total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), high-density lipoprotein cholesterol (HDL-C) and triglyceride (TG) were analyzed by an automatic biochemical analyzer. The expression of LDLR or SREBP-2 was detected by Western blot. After 12 weeks of intragastric administration of acacetin (30 mg·kg-1) in apolipoprotein E knockout (ApoE KO) mice, the serum lipid levels were determined by an automatic biochemical analyzer. The lipid deposition in aortic plaque (en face) and aortic root plaque were stained with oil red O. The expression of LDLR and SREBP-2 were detected by RT-qPCR and/or Western blot. The intestinal content microflora was analyzed by 16S rDNA sequencing (All animal studies were approved by the Animal Experimentation Ethics Committee of Institute of Medicinal Biotechnology, CAMS & PUMC). In vitro results indicated that acacetin significantly up-regulated LDLR mRNA and protein levels, and stimulated LDLR transcription factor SREBP-2 protein expression. As indicated from in vivo studies, compared with control group, acacetin significantly decreased the serum levels of TC and LDL-C in C57BL/6J mice by 34% and 57% (P<0.01), respectively. Furthermore, mechanic study showed that acacetin significantly increased the protein expression of hepatic LDLR and SREBP-2. Although the results of serum lipid profiles, hepatic LDLR/SREBP-2 expression and area of atherosclerotic lesions in aorta and aortic root in ApoE KO mice showed differences between acacetin and high-fat diet group, the differences did not reach statistical significance. Nevertheless, acacetin exhibited a profound influence on the composition of the intestinal microbiota as indicated by 16s rDNA sequencing analysis. In conclusion, these results demonstrated that acacetin can decrease the serum lipid levels in C57BL/6J mice through up-regulation of hepatic LDLR and SREBP-2, and alter gut microflora in high-fat diet fed Apo KO mice. This study suggests the possibility that acacetin has a potential role in inhibiting the progression of atherosclerosis.
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Objective:To establish an HPLC method for the simultaneous determination of chlorogenic acid , aesculetin, rutin, acacetin-7-O-β-D-glucoside, quercetin and luteolin in the extract of Viola yedoensis Makino.Methods:The HPLC analysis was carried out on a Hypersil ODS C18 column (250 mm ×4.6 mm, 5μm) with 0.1％phosphoric acid (A)-methanol (B) as the mobile phase with gradient elution at the flow rate of 1.0 ml· min-1 .The detection wavelength was 345 nm and the column temperature was 35℃. Results:Good linear relationship was found within the range of 4.3175-172.7000 mg· L-1 for chlorogenic acid, 2.7350-109.4000 mg· L1 for aesculetin, 6.9800-279.2000 mg · L-1 for rutin, 3.7200-148.8000 mg · L-1 for acacetin-7-O-β-D-glucoside, 4.1350-165.4000 mg· L-1 for quercetin, and 3.3950-135.8000 mg · L-1 for luteolin.The average recovery was 99.06％, 98.84％, 98.77％, 99.40％, 98.53％and 98.71％, respectively.The content of chlorogenic acid , aesculetin, rutin, acacetin-7-O-β-D-glucoside, quercetin and luteolin in the extract of Viola yedoensis Makino was 1.6290, 1.1910, 4.5850, 2.2810, 3.1790 and 1.9710 mg· g-1, respectively.Conclusion:The method is accurate and reliable with good reproducibility , which can be used for the quality control of the extract of Viola yedoensis Makino.
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Objective To improve the in vivo analgesic activity of acacetin and find leads for the development of new drugs, novel acacetin derivatives containing alkyl amide groups with different length of carbon chain were designed and synthesized according to the molecular structure of the active hit compound found in our previous work. Methods Using apigenin as the initial chemical ma-terial,the acacetin was synthesized through 3 steps,then the target compounds were prepared by conjugating hydroxy group of acace-tin at position 7 with bromoalkyl amides. The analgesic activity of the target compounds was evaluated by acetic acid writhing model of mice. Results and Conclusion Novel acacetin alkyl amide derivatives showed more potent analgesic activities than that of clinical medicine diclofenac,which could be used as leads for further development of new drugs.
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OBJECTIVE: To study the chemical constituents in the flowers of Chrysanthemum morifolium Ramat. METHODS: The compounds were isolated with Diaion HP-20, Toyopearl HW-40, Sephadex LH-20, silica gel column chromatography and preparative HPLC. The structures of the compounds were identified by physiochemical properties and spectral analysis. RESULTS: Twenty compounds were obtained, and their structures were identified as luteolin (1), apigenin (2), acacetin (3), diosmetin (4), acacetin 7-O-β-D-glucoside (5), acacetin 7-O-β-D-glucoside (6), acacetin7-O-(6″-O-acetyl)-β-D-glucoside (7), eriodictyol (8), naringenin (9), artemetin (10), 5-hydroxy-6, 7, 3', 4'-tetramethoxyflavone (11), 5, 7-dihydroxy-3', 4'-dimethoxyflavone (12), 4'-methoxyctricin (13), 3', 5'-dimethoxy-4', 5, 7-trihydroxyflavone (14), 5, 6-dihydroxy-3, 7, 3', 4'-tetramethoxyflavone (15), luteolin 7-O-β-D-glucuronide methyle ester (16), dihydroquercetin-7-β-D-glucoside (17), quercetin 3-O-β-D-glucoside(18), quercetin 3-O-β-D-glucoside (19), and acacetin 7-O-β-(6″-(E)-crotonylglucopyranoside) (20). CONCLUSION: Compounds 9-20 were isolated for the first time from this plant.
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OBJECTIVE: To study the chemical constituents from the flower buds and inflorescences of Buddleja officinalis. METHODS: Various chromatographic techniques such as silica gel and Sephadex LH-20 chromatography were used in this experiment. RESULTS: Sixteen compounds were isolated from the medicinal plant, and their structures were identified as follows acacetin(1), apigenin(2), luteolin(3), acacetin-7-O-glucoside(4), cosmosiin(5), luteolin-7-O-glucoside(6), acacetin-7-O-glucuronide(7), apigenin-7-O-glucuronide(8), linarin(9), luteolin-7-O-rutinoside(10), neobudofficide(11), acteoside(12), crocin III(13), crocin II(14), crocin I(15), and N1, N5, N10-(E)-tri-p-coumaroylspermidine(16). CONCLUSION: Compounds 4, 7, 8, 14-16 are obtained from the medicinal plant for the first time, and compounds 7, 8, 14-16 are obtained from Loganiaceae for the first time.
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Objective To investigate the chemical constituents of Ajuga ovalifolia var. calantha. Methods The 95% ethanol extract from the whole herb of A. ovalifolia var. calantha was separated and purified by column chromatography over silica gel, Sephadex LH-20, ODS, and RP-HPLC. Their chemical structures were identified on the basis of physicochemical characteristics and spectral analyses. Results Thirteen compounds were isolated and identified as (16S)-12,16-epoxy-11,14-dihydroxy-17 (15→16)-abeo-abieta- 8,11,13-trien-7-one (1), ajuforrestin B (2), ajudecumin A (3), 14,15-dihydroajugapitin (4), cyasterone (5), β-sitosterol (6), acacetin (7), apigenin (8), luteolin (9), scopoletin (10), isoscopoletin (11), 4-hydroxy-3-methoxy-benzaldehyde (12), and acetovanillon (13). Conclusion Compounds 1 and 10-13 are reported from the genus Ajuga Linn., and compounds 2-5 and 7 are isolated from this plant for the first time. Single crystal X-ray diffraction experiment is carried out for compound 1, and the crystal structure data of single crystal X-ray diffraction of compound 1 is obtained for the first time.
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Aim To investigate the effect of acacetin on cell proliferation and the influence of acacetin on estrogen receptor expression in vitro.Methods The proliferation rates and the cell cycle changes of acace-tin-treated T47D cells were measured by sulforhodam-ine B(SRB)assay and flow cytometry,respectively. Moreover,the mRNA expressions of estrogen receptor-alpha(ERα),estrogen receptor-beta(ERβ)and pro-liferating antigen(Ki67)were determined by quantita-tive real time PCR (qPCR).Western blot was em-ployed to detect the ERαand ERβprotein expression. Results Acacetin significantly promoted the prolifera-tion and increased the amount of cells arrested in S and G2 /M phase under the concentration of 0.001 ~1 0μmol·L -1 .Ki67 mRNA level and the ERαprotein level in T47D cells were remarkably upregulated after acacetin treatment.To clarify which estrogen receptors played a role in acacetin induced the proliferation of T47D cells,the combination treatment of acacetin and ERαinhibitor (MPP)/ERβ inhibitor (PHTPP) was employed.We found that MPP could reverse the cell proliferation,the cell arrested in S and G2 /M phase and the increased Ki67 mRNA level induced by acace-tin.PHTPP also alleviated the T47D cell proliferation induced by acacetin,whereas no significant changes were found in cell cycle and Ki67 mRNA level.Con-clusion Acacetin stimulates the cell proliferation of T47D cells in the concentration from 0.001 μmol · L -1 to 1 0 μmol·L -1 ,which is mainly mediated by ERα.
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To study the extraction technology for the active constituents in Dracocephali Moldavici Herba (the aerial parts of Dracocephalum moldevica) and to compare their contents Dracocephali Moldavici Herba from various habitats. The contents of luteolin-7-O-glucuronide (I), apigenin-7-O-glucuronide (II), rosmarinic acid, diosmetin-7-O-glucuronide (III), tilianin, and acacetin-7-O-glucuronide (IV) in Dracocephali Moldavici Herba were measured using HPLC method. Based on single-factor test, and the influence of the extracting menstrua, menstruum dosage, and extracting time were investigated using orthogonal design method. Based on the optimal technology, the contents of I, II, rosmarinic acid, III, tilianin, and IV in Dracocephali Moldavici Herba from various habitats were compared. The optimal conditions for the extracting for one time, each time for 5 h with 50 times of amount of 40% ethanol. D. moldevica produced in Jimusar, Xinjiang had the higher contents of I, II, rosmarinic acid, III, tilianin, and acacetin-7-O-glucuronide. This extraction technology is reasonable, stable, and feasible. The contents of I, II, rosmarinic acid, III, tilianin, and IV in Dracocephali Moldavici Herba from different habitats have some differences. The multi-index contents of I, apigenin-7-O-glucuronide, rosmarinic acid, III, tilianin, and IV could reflect the quality of Dracocephali Moldavici Herba more comprehensively.
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Objective: To study the chemical constituents from the stems of Pleioblastus amarus. Methods: The compounds were isolated and purified by means of chromatographic techniques and their structures were identified on the basis of spectral data. Results: Fifteen known phenolic compounds were isolated in the methanol extract from the dry stems of P. amarus and thire structures were identified as tricin (1), apigenin (2), 5, 7, 2′, 4′, 6′-pentamethoxyflavone (3), 5, 7-dihydroxy-3′, 4′, 5′-trimethoxyflavone (4), acacetin (5), luteolin (6), cirsimaritin (7), p-hydroxybenzaldehyde (8), 2-hydroxybenzoic acid (9), trans-p-hydroxycoumaric acid (10), 2, 4-dihydroxybenzaldehyde (11), gallic acid (12), methyl gallate (13), questin (14), and isorhodoptilometrin (15). Conclusion: Compounds 2-7 and 10-13 are first obtained from this plant; Compounds 14 and 15 are first isolated from the plants of Pleioblastus Nakai.
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OBJECTIVE: To study the chemical constituents of Oxalis pes-caprae L. METHODS: The chemical constituents were isolated and purified with silica column chromatography and gel chromatography, etc. Their structures were identified by physicochemical properties and various spectroscopic methods including NMR spectrum, MS, UV, etc. RESUTLS: Twelve compounds were isolated from the ethyl acetate part, among which 10 compounds were elucidated as daucosterol(1), β-sitosterol(2), vitexin(3), isovitexin(4), acacetin(5), robinin(6), β-tocopherol(7), tartaric acid(8), vanillic acid(9), and luteolin(10). CONCLUSION: All compounds are isolated from Oxalis pes-caprae L. for the first time.
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OBJECTIVE: To study the active substances of Acanthopanax sessiliflorus (Rupr. Et Maxim.) Seem for better using the traditional Chinese medicine.
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Objective: To study the chemical constituents from the whole herb of Lagochilus platyacanthus. Methods: The chemical constituents were isolated and purified by various chromatographic techniques and the structures were identified by spectral analysis. Results: Twenty-one compounds were isolated from the 95% ethanol extract of L. platyacanthus, including 15 flavonoids: apigenin-7, 4'-dimehyl ether (1), acacetin (2), apigenin (3), luteolin-7, 3', 4'-trimethyl ether (4), luteolin-7, 4'-dimethyl ether (5), diosmetin (6), chrysoeriol (7), quercetin-3-O-rutinoside-7-O-glucoside (8), rutin (9), horridin (10), apigenin-6, 8-di-C-β-D-glucopyranoside (11), isorhamnetin-3-O-rutinoside (12), isorhamnetin-3-O-robinobioside (13), isorhamnetin-3-O-β-D-glucoside (14), and isorhamnetin-3-O- rutinoside-4'-O-glucoside (15); three lignans: 1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1, 2, 3-trihydroxypropyl)-2-methoxy]-phenoxy- 1, 3-propandiol (16), (+)-isolarisiresinol 3-α-O-β-D-glucopyranoside (17), and (-)-isolarisiresinol 3-α-O-β-D-glucopyranoside (18); two iridoids: 8-O-acetylharpagide (19) and geniposidic acid (20), and one phenylethanoid glycoside: lavandulifolioside (21). Conclusion: All the compounds are obtained from this plant for the first time. The compounds are isolated from the plants in genus Lagochilus Bunge for the first time except compounds 1, 3, 9, 19, and 20.
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Objective: To search for the bioactive compounds from the vine of Lonicera dasystyla. Methods: The compounds were isolated and purified by column chromatography on silica gel, sephadex LH-20 gel, and ODS, and their structures were elucidated on the basis of spectroscopic analysis, such as MS, NMR, etc. Results: Nine compounds were isolated from the vine of L. dasystyla. Their structures were identified as dihydrosesamin-9-O-β-D-glucopyranoside (1), isoferulic acid (2), p-methoxycoumaric acid (3), kaempferol-7-O-(2″-E-p-coumaroyl)-α-L-arabinofuranoside (4), macranthoidin B (5), loganin (6), kaempferol (7), acacetin (8), and quercetin (9). Conclusion: All of these compounds belong to four types, phenylpropanoids (1-3), flavonoids (4, 7-9), triterpenoid saponin (5), and iridoid (6). Compound 1 is a new one and compounds 5 and 6 as marker compounds exist in most of Lonicera Linn. plants, while known compounds 2-4 and 8 were isolated from Lonicera Linn. plants for the first time. The identification of these chemicals lays the foundation for searching bioactive compounds of this plant, and these compounds have great importance for chemotaxonomy of this plant.
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Object To determine the amount of acacetin-7-O-β-D-glucoside and apigenin-7-O-β-D-glucoside in Chrysanthemum morifolium Ramat. from different localities. Methods By the use of HPLC. Results The contents of acacetin-7-O-β-D-glucoside in Boju1, Chuju2, Gongju3 and Hangju4 were 0.082 6%～0.124 9%, 0.015 7% and 0.033 5% respectively; the contents of apigenin-7-O-β-D-glucoside in Chuju, Boju, Gongju and Hangju were 0.012 6%, 0.027 4%, 0.117 7% and 0.587 7% respectively. Conclusion The contents of the two flavone glycoside in C. morifolium from different localities were markedly different.