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Ultra high performance liquid chromatography tandem linear ion trap orbitrap mass spectrometry (UHPLC-LTQ-orbitrap-MS) was applied to analyze and identify flavonoids and phenylethanoid glycosides in the Tibetan herb Lagotis brevituba Maxim. A method of data-dependent scan coupling with dynamic exclusion was developed for analyzing flavonoids and phenylethanoid glycosides under positive and negative ion mode of electrospray ionization (ESI). The compounds of Lagotis brevituba Maxim. were systematically identified through exact molecular mass, fragmentation patterns, retention time and reported references. A total of 167 compounds were detected, of which 84 were flavonoids and 83 were phenylethanoid glycosides, which greatly enriched the number and types of flavonoids and phenylethanol glycosides in Lagotis genus medicinal plants. Baohuoside Ⅰ, 4 disaccharide O-glycoside flavonoids (composed of deoxyhexose and glucuronic acid), 9 C-glycoside flavonoids, 15 tetrasaccharide phenylethanoid glycosides and 5 phenylethanoid glycosides with substituents on the β-position of the phenylethyl group were identified in Lagotis genus medicinal plants for the first time. This study provides scientific support for elucidating the material basis and improving the quality control of Lagotis brevituba Maxim.
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The 95% ethanol extract of Baphicacanthis Cusiae Rhizoma et Radix was purified by multi-chromatographic methods including microporous resin, silica gel, Sephadex LH-20, and C_(18) reversed-phase column chromatography. Fourteen compounds were isolated and structurally identified, including five phenylethanoid glycosides, five phenylpropanoids, one lupinane triterpene, two alkaloids, and one flavonoid, listed as follows: 2-(4-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-5-methoxyphenyl)-3-oxo-1-propanol B(1), threo-2,3-bis-(4-hydroxy-3-methoxybenzene)-3-methoxypropanol(2), 2-(3-hydroxy-4-methoxyphenyl)-ethanol-1-O-[3,4-O-di-acetyl-(1→3)-O-α-L-rhamnopyranosyl]-β-D-glucopyranoside(3), verbascoside(4), 2″,3″-di-O-acetyl martynoside(5),(+)-pinore-sinol(6), diospyrosin(7), daidzein(8), wiedemannioside B(9), buddlenol A(10), 2″-O-acetyl martyonside(11), lupeol(12), indirubin(13), and tryptanthrin(14). Compound 3 was a new phenylethanoid glycoside, and the other 10 compounds were isolated for the first time from Baphicacanthis Cusiae Rhizoma et Radix except compounds 12, 13, and 14.
Subject(s)
Cardiac Glycosides , Flavonoids , Glycosides , Molecular Structure , Phenylethyl Alcohol , RhizomeABSTRACT
OBJECTIVE: To study the chemical constituents in the roots of Scrophularia ningpoensis Hemsl. METHODSE: Compounds were isolated by chromatographic techniques and their structures were elucidated by spectral methods. The anti-inflammatory activities of all isolated compounds were evaluated by lipopolysaccharides (LPS)-stimulated BV2 cells model. RESULTS: Eighteen compounds were isolated and identified as 2'''-acetyl angroside C (1), saccatoside (2), 6-O-α-L-(2″-O-feruloyl)rhamnopyranosylcatalpol (3), scrophularioside (4), harprocumbide A (5), 6″-O-β-D-glucopyranosylharpagoside (6), harpagoside (7), 8-O-(p-coumaroyl)-harpagide (8), 8-O-feruloylharpagide (9), 6-O-α-D-galactopyranosylharpagoside (10), 6'-O-cinnamoylharpagide (11), angoroside B (12), angoroside C (13), scrophuloside B1 (14), 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-α-L-arabinopyranosyl-(1→6)-O-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (15), darendoside B (16), 6-O-caffeoyl-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside (17), and sibirioside A (18). CONCLUSION: Compound 1 is new compound, and compounds 2-4, 12, 14, and 17 are isolated from this plant for the first time. Compounds 1, 12, and 13 show significant inhibition against nitric oxide production in LPS-stimulated BV2 cells model.
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OBJECTIVE: To study the chemical constituents from the rhizome of Phlomis umbrosa. METHODS: Chemical constituents were isolated by repeated column chromatographies(Toyopearl HW-40C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis. RESULTS: Seventeen compounds were isolated from the 95% ethanol aqueous extract of P. umbrosa and the structures were identified as lamalbid (1), phloyoside (2), phloyoside Ⅱ(3), 6-O-acetylshanzhiside methyl ester(4), shanzhiside methyl ester (5), 8-acetylshanzhiside methyl ester(6), sesamoside(7), 5,9-epi-7,8-didehydropenstemoside(8), verbascoside(9), isoverbascoside(10), forsythoside B(11), alyssonoside(12), echinacoside(13), (17S)-2α,3α,18β,23,24-pentahydroxy-19(18→17)-abeo-28-norolean-12-en-21-one(14),(17S)-19(18→17)-abeo-12-en-28-norolean-2α,3α,18β,19,23,24-hexaol (15), friedelin(16), and daidzein(17). CONCLUSION: All compounds are isolated from this plant for the first time, compounds 1, 8, 16-17 are isolated from genus Phlomis for the first time.
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Gardenia jasminoides is a traditional Chinese herbal medicine, which is also the first batch of being used for both medicine and food issued by Ministry of Health of China. In recent years, G. jasminoides has been applied widely in medicine and health food, so the quality evaluation of G. jasminoides has become a key problem urgently needed to be solved in this industry. Based on the review of its chemical composition and pharmacological effects, combined with the definition of Q-marker, this study processed predictive analysis on Q-marker of G. jasminoides from several aspects at chemical composition, new clinical use, measurable composition, traditional medicine properties and efficacy, plasma composition, and storage time, which provides the basis for quality evaluation of G. jasminoides.
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Semen Plantaginis is a traditional Chinese herbal medicine, which widely distributed in various parts of China and the medicine source is rich. In recent years, domestic and overseas scholars have taken up in-depth research on the various aspects of Semen Plantaginis, and its effective ingredients and application development research has attracted much attention, and has broad application prospect. Based on the review of its chemical composition and pharmacological effects, according to the definition of Q-marker, the quality control component of Semen Plantaginis were predicted from the aspects of the correlation between chemical composition and traditional medicinal properties, traditional efficacy, and new clinical use, plasma composition, measurable composition, active ingredients in different compatibility, storage time and so on, which provides a scientific basis for quality evaluation of Semen Plantaginis.
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In order to clarify the chemical constituents of Cistanche deserticola cultured in Tarim desert, a systematically phytochemical investigation was carried out. The chemical constituents were isolated by column chromatography, such as silica gel, Sephadex LH-20, MCI gel, ODS and semi-preparative HPLC, and their structures were determined on the basis of MS, NMR spectroscopic analysis, and comparison with literature data. Four compounds were isolated from the 85% ethanol extract of the stems of C. cultured in Tarim desert. Their structures were identified as cis-tubuloside (1), cis-cistanoside (2), cis-cistanoside J (3), and cis-isocistanoside C(4). Compounds 1-4 were four new cis-phenylethanoid glycosides. Herein, we firstly report the ¹H, ¹³C-NMR data of the new compounds(1-4) for the first time. This study will provide the scientific evidence for comprehensively analyzing the chemical constituents of C. deserticola cultured in Tarim desert.
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(CD) is one of the two authoritative source plants of Cistanches Herba, a well-known medicinal plant. Herein,H NMR spectroscopy was employed to characterize the chemical profile and to distinguish the different parts, as well as to propose a new processing workflow for CD. Signal assignment was achieved by multiple one and two dimensional NMR spectroscopic techniques in combination with available databases and authentic compounds. The upper parts of the plant were distinguished from the lower parts by combiningH NMR spectroscopic dataset with multivariate statistical analysis. A new processing method that hyphenated steaming with freeze-drying, was demonstrated to be superior to either steaming coupled with oven-drying or direct freeze-dryingholisticH NMR-based metabolomic characterization. Phenylethanoid glycosides, mainly echinacoside and acteoside, were screened out and confirmed as the chemical markers responsible for exhibiting the superiority of the new processing workflow, whereas serial primary metabolites, especially carbohydrates and tricarboxylic acid cycle metabolites, were found as the primary molecules governing the discrimination between the upper and lower parts of the plant. Collectively,H NMR spectroscopy was demonstrated as a versatile analytical tool to characterize the chemical profile and to guide the in-depth exploitation of CD by providing comprehensive qualitative and quantitative information.
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Objective: To investigate the chemical constituents of Rehmannia chingii. Methods: The compounds were isolated from an aqueous extract from the whole plants of R. chingii by a combination of various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic analysis including MS and NMR data. Results: Seventeen compounds were isolated and identified as 8-methyloctahydrocyclopenta[c] pyran-1,3,6,8-tetraol (1), 3,4-dihydroxy-phenethyl alcohol (2), 3-methoxyl-4-hydroxyphenyl alcohol (3), phenylethyl-8-O-β-D-glucopyranoside (4), 3,4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranoside (5), 2-phenylethyl-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (6), deacyl-martynoside (7), acteoside (8), isoacteoside (9), martynoside (10), isomartynoside (11), jionoside C (12), jionoside A1 (13), jionoside B1 (14), 3,4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-galacopyranosyl-(1→6)-4-O-caffeoyl-β-D-glucopyranoside (15), cistanoside F (16), and isocistanoside F (17). Conclusion: Among the isolated seventeen compounds, compound 1 is a new compound named rehmachinin, and compounds 16-17 are isolated from the plants of Rehmannia Libosch. ex Fisch. et Mey. for the first time. In the preliminary assays, compounds 9, 12, and 14-16 exhibit the obvious inhibition against aldose reductase.
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OBJECTIVE:To investigate the improving effect of phenylethanoid glycosides (PhGCs) from Tibetan medicine Phlomis younghusbandii on rats with acute high-altitude cerebral edema. METHODS:60 Wistar rats were randomly divided into a normoxia control group (isometric sterile water for injection),a hypoxia model group (isometric sterile water for injection),a dexamethasone group(4 mg/kg),and three groups of PhGCs at high(400 mg/kg),middle(200 mg/kg)and low(50 mg/kg)dos-es,with 10 rats in each group. The rats were given drugs,ig,6 d before the establishment of models. On the 4th day of administra-tion,ig,the rats in all groups except the normoxia blank group were placed in a simulated 8 000 m altitude plateau environment for 72 h hypoxic exposure to establish the rat models of high-altitude cerebral edema. Following HE stain,the pathological changes in rats’brain tissues were observed under the light microscope. Dry-wet proportion method was used to determine the water con-tents in rats’brain. The content of MDA and the activities of SOD and GSH in rats’brain tissues were detected. Enzyme-linked im-munosorbent assay was adopted to determine the contents of IL-1β and TNF-α in rats’serum and brain tissues. RESULTS:Com-pared to the rats in the normoxia control group,those in the hypoxia model group showed obvious brain edema,and thickened lacu-nas around cells and vessels and inflammatory cell infiltration, higher water contents and MDA and weaker activities of SOD and GSH in brain,and higher contents of IL-1β and TNF-α in serum and brain tissues. There were statistically significances (P<0.01 or P<0.05). Compared to the rats in the hypoxia model group,those in the groups of PhGCs at high,middleand low dosages demonstrated less inflammatory cell infiltration and lower water contents in brain tissues,in which the groups of PhGCs at high and middle dosages demonstrated lower content of MDA and stronger activities of SOD and GSH in brain tissues, and lower contents of IL-1β and TNF-α in serum and brain tissues. There were statistically significances (P<0.01 or P<0.05). CONCLUSIONS:PhGCs can obviously alleviate the acute cerebral injury in rats which is caused by acute hypoxia and has im-provement effect to some degree on the rats with acute high-altitude cerebral edema.
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Objective: To study the chemical constituents from the roots of Incarvillea compacta (Tibetan medicine). Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatography, and preparative HPLC. Their structures were elucidated on the basis of their physicochemical properties and spectral data. Results: Four phenylethanoid glycosides were obtained from the ethanol extract in the roots of I. compacta and identified as Z-3‴-O-methylisocrenatoside (1), 3‴-O-methylcrenatoside (2), crenatoside (3), and isomartynoside (4), respectively. Conclusion: Compound 1 is a new phenylethanoid glycoside and compounds 2-4 are isolated from the plants of Incarvillea A. Juss. for the first time.
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OBJECTIVE: To study the chemical constituents in the leaves of Rehmannia glutinosa Libosch. METHODS: The compounds were isolated and purified by Diaion HP-20, Toyopearl HW40, Sephadex LH-20, MCI Gel CHP-20, and silica gel column chromatography, and the structures were elucidated on the basis of spectral data and physiochemical properties. RESULTS: Twenty-seven compounds were obtained from the 50% acetone extract, and their structures were identified as p-hydroxybenzoic acid(1), gentisic acid(2), 6, 7-dihydroxycoumarin(3), p-hydroxyphenylethyl alcohol(4), 3, 4-dihydroxyphe-nylethyl alcohol(5), protocatechuic acid(6), 1, 2, 4-trihydroxybenzene(7), diosmetin(8), luteolin-7-O-β-D-glucuronide(9), apigenin(10), 2β, 3β, 19α-trihydroxyolean-12-ene-13, 28-dioic acid(11), 2α, 3β-dihydroxyolean-12-ene-28-oic acid(12), glutinolic acid(13), β1-hydroxyacteoside(14), echinacoside(15), jionoside B,(16), acteoside(17), isoacteoside(18), ajugol(19), catalpol(20), 8-epiloganic acid(21), luteolin(22), oleanolic acid(23), ursolic acid(24), oleanonic acid(25), β-sitosterol(26) and daucosterol(27). CONCLUSION: Compounds 1-14 and 23-25 are isolated from this plant for the first time.
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Objective: To optimize the extraction and purification technology of phenylethanoid glycoside from Cistanche tubulosa. Methods: Orthogonal design L9(34) was employed to optimize the extraction conditions by taking the extraction yield of echinacoside and acteoside as indexes. The absorption-desorption characteristics of seven macroporous resins were evaluated, then the best purification conditions were optimized. Results: The optimal extraction conditions were as follows: The air-dried stems of C. tubulosa were powdered and extracted twice with 12-fold 50% ethanol for 1 h each time, temperature was 70℃; The supernatant was concentrated to 5-fold weight of the stems of C. tubulosa. The concentrated liquid was subjected to macroporous resin (HPD750) column and then eluted with deionezed water (3 BV) and 30% ethanol (4 BV), respectively. The 30% ethanol fraction was evaporated under vacuum to give the phenylethanoid glycoside-rich C. tubulosa stem extract. The purity of phenylethanoid glycoside was above 75%. Conclusion: The optimized extraction and purification process is stable, efficient, and suitable for industrial production.
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Object To study the difference of phenylethanoid glycoside between the cultured cells of Cistanche salsa (C. A. Mey.) Benth. et Hook. f. and Herba Cistanche. Methods Making comparison by means of FTIR and HPLC technique. Results Using the FTIR technique, the infrared spectrum of cutured cell of C. salsa was similar to that of native Herba Cistanche at a certain extent. The HPLC analysis indicated that the main chemical constituents in cultured cells of C. salsa were similar to that of native Herba Cistanche while considerable difference of constituents was found between them. Conclusion On the whole, there are much more constituents in the cultured cells of C. salsa comparing with the native Herba Cistanche. The content of echinacoside and acteoside in the cultured cells is much higher than that in the native Herba Cistanche.