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OBJECTIVE: To isolate and purify the reference compounds and improve the quality standard of Korean medicinal Herba Artemisiae sacrorum. METHODS: The chemical constituents were isolated from the aerial parts of Korean medicinal herb Artemisia sacrorum by silica gel, ODS column chromatography and preparative HPLC, and the structures were identified by NMR and MS. RESULTS: Fourteen known compounds were isolated and identified as follows:1α-acetoxyeudesm-4-en-6β,11βH-12,6-olide(1),(11S)-3-oxoeudesma-1,4(15)-dieno-12,6α-lactone(2), 1-epi-dehydroisoerivanin(3), 11-epi-taurin(4), chrysanthemolide(5), 1α-acetyl-gallicadiol(6), erivanin(7), 1α, 4α-dihydroxyeudesm-2-en-5α, 6β, 11βH-12, 6-olide(8), vulgarin(9),(+)-dehydrovomifoliol(10), isoevodionol(11),(+)-epi-pinoresinol(12), lariciresinol-4'-O-β-D-glucopyranoside(13), and lariciresinol-4-O-β-D-glucopyranoside(14). CONCLUSION: All compounds are obtained from this plant for the first time. These compounds can be used as reference substances for the quality control of this ethnic medicine.
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Objective: To investigate the lignans of the roots of Diphylleia sinensis. Methods: The chemical components were isolated and purified by chromatographic techniques (silica gel, sephadex LH-20 and semi preparative-HPLC) and the chemical structures were determined by spectral data analysis (1D/2D NMR, MS, and IR). Results: Seven lignans were obtained and identified as diphyllin A (1), (1S,2R,5S,6R)-2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo [3.3.0] octane (2), (7S,8R,7’S,8’R)-3,4,3’,4’-tetramethoxy-9,7-dihydroxy-8.8’,7.O.9’-lignan (3), (-)-lariciresinol (4), vladinol D (5), podophyllotoxone (6), and justicidin A (7). Conclusion: Diphyllin A (1) is a new compound and 2-4 are obtained from D. sinensis for the first time.
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Objective To study the chemical constituents of the stems and leaves of Mappianthus iodoides. Methods The chemical constituents of M. iodoides were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies, and preparative HPLC. Their structures were identified by physicochemical properties, spectroscopic analysis, as well as comparisons with the data reported in literature. Results Sixteen compounds were isolated from the 90% ethanol extract of the stems and leaves of M. iodoides, which were identified as 9-hydroxy-4,6-megastigmadien-3-one (1), 9-hydroxy-4,7-megastigmadien-3-one (2), blumenol A (3), 9,10-dihydroxy-4,7-megastigmadien-3-one (4), 5,12-epoxy-9-hydroxy-7-megastigmen-3-one (5), 5,12-epoxy-6,9-hydroxy-7- megastigmen-3-one (6), loliolide (7), lariciresinol (8), isolariciresinol (9), 5′-methoxylariciresinol (10), olivil (11), dehydrodiconiferyl alcohol (12), chushizisin I (13), 3,3-didemethoxyverrucosin (14), 4-epi-larreatricin (15), and glycerol monolinoleate (16). Conclusion All compounds are isolated from the genus Mappianthus for the first time.
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Objective To investigate the chemical constituents of the whole plants of Viola yedoensis. Methods The chemical constituents were isolated and purified by column chromatography over silica gel and Sephadex LH-20, as well as on the semi-preparative HPLC. The structures of the isolates were identified by the NMR spectroscopic method. Results Twenty-three compounds were isolated and their structures were identified as pubinernoid A (1), (2R,6R,9R)-2,9-dihydroxy-4-megastigmen-3-one (2), 3S,5R-dihydroxy-6R,7-megastigmadien-9-one (3), dehydrovomifoliol (4), blumenol A (5), blumenol B (6), oleanolic acid (7), 2α,3α-dihydroxyurs-12-ene-28-oic acid (8), 1α,2α,3β-trihydroxyolean-12-ene-28-oic acid (9), 2α,19α-dihydroxyursolic acid (10), 3α-hydroxyfriedel-2-one (11), 7-oxopetrosterol (12), 7-oxositosterol (13), syringaresinol (14), lariciresinol (15), daphneticin (16), umbelliferone (17), trans-p-hydroxycinnamic acid methyl ester (18), p-hydroxyphenylpropionic acid (19), p-hydrobenzaldehyde (20), p-methoxybenzaldehyde (21), p-methoxybenzoic acid (22), and 5-hydroxymethyl-2-furfural (23). Conclusion Compounds 1-16 and 18-23 are isolated from the genus Viol for the first time, and compound 17 is isolated from the plant for the first time.
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Objective: To further study the chemical constituents of Stelleropsis tianschanica. Methods: The constituents were isolated and purified by silica gel chromatography repeatedly, and the structures were identified by spectra analysis and chemical methods. Results: Twelve compounds including five lignans and three diphenylpentane derivatives were obtained, and named as kusunokinin (1), pluviatolide (2), dibutyl phthalate (3), dipropyl phtalate (4), p-dihydroxybenzene (5), daphneolon (6), 2(S)- hydroxy-1-(4-hydroxy phenyl)-5-phenyl-1-pentanone (7), (2R,3R)-1,5-diphenylpentane-2,3-diol (8). lariciresinol (9), isolariciresinol (10), matairesinol (11), and 4α,5βH-guai-9,7(11)-dien-12,8-olide-12,8α-diol (12). Conclusion: Compounds 1-12 are all obtained from the plant of S. tianschanica and the genus Stelleropsis Pobed. for the first time.
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Objective Identifying laccases, as one of the key synthetases in the lariciresinol biosynthetic pathway, by analyzing the transcriptome sequencing results in Isatis indigotica would provide a dependable foundation for later functional study of Isatis indigotica′s laccases. Methods Bioinformatical softwares and kinds of analytical methods online were used to find out the characteristics of the laccases from I. indigotica, including physical and chemical properties, homology, and the properties after induction of MeJA. Results The transcriptional results showed that Iilac3 and Iilac5 from I. indigotica were corresponded ith the accumulation of the effective metabolites, making them the potential functional genes participated in lariciresinol synthesis. Conclusion Through the detailed bioinformatical analysis of Iilacs,which laid a solid foundation for the further study of the physiological and biochemical mechanisms and structural characteristics of the functional proteins.
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Objective: To study the secondary metabolites of Genkwa Flos (the buds of Daphne genkwa). Methods: The compounds were separated and purified by silica gel chromatography and thin layer chromatography, and their structures were determined by analyses of the physicochemical properties and spectral data. Results: Three lignans were obtained and identified as lariciresinol- 9-O-pentatriacontanoate (1), pinoresinol (2), 4-hydroxysesamin (3) from the ethanol extract of D. genkwa. Conclusion: Compound 1 is a new tetrahydrofuranoid lignan, and known compound 3 is obtained for the first time from this plant.
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Objective: To study the chemical constituents of ethyl acetate fraction from Patrinia scabra. Methods: Chemical constituents were isolated and purified by macroporous resin, silica gel, and Sephadex LH-20 column chromatography. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. Results: Twelve compounds were isolated and purified. Their structures were identified as 5-O-feruloylquinic acid (1), 7α-morroniside (2), 7β-morroniside (3), villosol (4), protocatechuic acid (5), β-daucosterol (6), isopatriscabroside I (7), patriscabroside I (8), patrinioside (9), pinoresinol-4,4'-di-O-β-D-glucopyranoside (10), lariciresinol-4'-O-β-D-glucopyranoside (11), and villosolside (12). Conclusion: Compounds 2-6 are isolated from this plant for the first time and the compound 1 is isolated from the plants of Patrinia Juss. (Valerianaceae) for the first time.
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Objective: To study the chemical constituents from the stem bark of S. perkinsiae. Methods: The chemical constituents were separated and purified by chromatographic methods after solvent extraction and were identified by spectroscopic analyses. Results: Ten lignans were isolated from the stem bark of S. perkinsiae and identified as following: obassioside B (1), lariciresinol 4-O-β-D-glucoside (2), (-)-secoisolariciresinol 4-O-β-D-glucopyranoside (3), lariciresinol 4′-O-β-D-glucoside (4), lanicepside A (5), isolariciresinol 4-O-β-D-glucopyranoside (6), (+)-lariciresinol 9-O-β-D-glucopyranoside (7), isotachioside (8), 2R*, 3S*-dihydro-dehydrodiconiferyl alcohol 4′-O-β-D-glucopyranoside (9), and pinoresinol (10). Conclusion: Eight compounds (2-9) are isolated from the plants of Styrax Linn. for the first time.
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Objective: To study the chemical constituents from Glechoma longituba and their anti-oxidant activity in vitro. Methods: The chemical constituents were isolated and purified by solvent extraction, repeated silica gel column chromatography, and reverse phase preparative HPLC. Their structures were identified on the basis of ESI-MS and NMR spectra. The anti-oxidant activities of these compounds were screened by DPPH free radical scavenging assay in vitro. Results: Ten compounds were isolated and elucidated as cosmosiin (1), dihydrocaffeic acid (2), caffeic acid (3), isololiolide (4), vomifoliol (5), glecholone (6), apigenin (7), aurantiamide (8), (+)-lariciresinol (9), and (-)-syringaresinol (10). Conclusion: Compounds 2, 4, and 8-10 are isolated from the plants in Glechoma L. for the first time; Compounds 9 and 10 are lignans firstly obtained from this plant. DPPH free radical scavenging assays show that compounds 2, 3, 9, and 10 exhibit potential anti-oxidant activity.
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Objective: To study the chemical constituents from the barks of Cinnamomum cassia. Methods: Silica gel, ODS, Sephadex LH-20 column chromatography, and semi-preparative HPLC were used to isolate the compounds. The structures of the compounds were identified on the basis of their physicochemical properties, spectroscopic data, and with the literature. Results: Fifteen compounds were isolated from the barks of C. cassia growing in China, including cinnzeylanine (1), anhydrocinnzeylanine (2), anhydrocinnzeylanol (3), cinnzeylanol (4), (-)-lariciresinol (5), evofolin B (6), 5'-medioresinol (7), (+)-syringaresinol (8), 2-hydroxyl cinnamie acid (9), 1, 10-seco-4ζ-hydroxy-muurol-ene-1, 10-diketone (10), (-)-epicatechin (11), kaempferol (12), proanthocyanidin A2 (13), stigmasterol (14), and stearic acid (15). Conclusion: Compounds 5-7 and 10 are lignans isolated from the plant for the first time, and compounds 1-4 are ryanodanediterpenes isolated from the barks of C. cassia growing in China for the first time.
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Objective: To investigate the chemical constituents from the aerial parts of Achillea alpina. Methods: The compounds were isolated and purified by various chromatographic techniques and their structures were characterized on the basis of physicochemical properties and their spectral analyses. Results: Eleven compounds were isolated. Their structures were identified as epifriedelanol (1), spinasterol (2), β-sitosterol (3), 5, 6-epoxy-24(R)-methylcholesta-7, 22-dien-3β-ol (4), β-daucosterol (5), schensianol A (6), negunfurol (7), (3S, 5S, 8R)-3, 5-dihydroxymegastigma-6, 7-dien-9-one (8), saropeptate (9), (+)-syringaresinol (10), and (±)-lariciresinol (11). Conclusion: All the compounds are isolated from the aerial parts of A. alpina for the first time, and compounds 1, 2, 4, 6-11 are reported to obtain from the plants in Achillea L. for the first time.
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Objective: To study the chemical constituents in the antiviral fraction of Isatidis Radix and the activity of the monomer components. Methods: The water extract of Isatidis Radix was adsorbed by macroporous resin, and the antiviral fraction was eluted with 10% and 50% ethanol, repeatedly separated and purificated by silica gel column chromatography, reverse phase silica gel column chromatography, and Sephadex LH-20. The chemical structures were identificated using physicochemical constants and spectral data. Results: Ten compounds were isolated from the active fraction of water extract, and they were respectively identified as syringin (1), 4-(1, 2, 3-trihydroxypropyl)-2, 6-dimethoxyphenyl-1-O-β-D-glucopyranoside (2), isolariciresino (3), isolariciresinol 4-O-β-D-glucopyranoside (4), lariciresinol-4-O-β-D-glucopyranoside (5), lariciresinol-4, 4'-bis-O-β-D-glucopyranoside (6), 2-hydroxy-1, 4-benzenedi carboxylic acid (7), D-mannitol (8), indole-3-acetonitrile6-O-β-D-glucopyranoside (9), and 3-[2'-(5'-hydroxymethyl) furyl]-1(2H)-isoquinoline-7-O-β-D-glucopyranoside (10). Conclusion: Compounds 2, 4, 7, 8, and 10 are isolated from Isatidis Radix for the first time. Compound 10 has the significant effect of anti-HSV-2 virus. Therapeutic index (TI) is 6.07. Compounds 1, 5, and 6 also show some inhibition to HSV virus.
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Objective: To study the chemical constituents from the rhizome of Drynaria fortunei. Methods: Silica gel, ODS, Sephadex LH-20 column chromatography, and semi-preparative HPLC were used to isolate pure compounds. The compounds were identified on the basis of their physicochemical properties and spectroscopic data. Results: Fourteen compounds were isolated from the rhizome of D. fortunei, including three lignans (1-3) and eight flavonoids (4-11). By spectroscopic techniques, such as 1H-NMR, 13C-NMR, and ESI-MS, these compounds were identified as (7′R,8′S)-dihydrodehydrodiconiferyl alcohol 4′-O-β-D-glucopyranoside (1), lariciresinol 4′-O-β-D-glucopyranoside (2), (-)-secoisolariciresinol 4-O-β-D-glucopyranoside (3), eriodictyol (4), eriodictyol 7-O-β-D-glucopyranoside (5), neoeriocitrin (6), naringin (7), luteolin (8), luteolin 7-O-β-D-glucopyranoside (9), luteolin 8-C-β-D- glucopyranoside (10), 2′,4′-dihydroxydihydrochalcone (11), maltol 3-O-β-D-glucopyranoside (12), β-sitosterol (13), and daucosterol (14). Conclusion: Compounds 1-3, and 11 are isolated from the plants in Polypodiaceae family for the first time, and compounds 5 and 8-10 are isolated from the plants of Drynaria (Bory) J. Sm. for the first time. Compound 1 is present as rotamers at room temperature.