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《Biomedical chromatography : BMC》2017,31(11)
A simple and specific high‐performance liquid chromatographic method has been developed and validated to simultaneously determine seven secoiridoid glucosides for the first time. Three of them were separated from the ethanolic extract of the roots of Ilex pubescens for the first time, namely nuezhenide A, ligusides B and oleonuezhenide. In quantitative analysis, all of the calibration curves showed good linear regression (r > 0.999) within the tested ranges, and the mean recoveries of three different concentrations ranged from 97.6 to 101.2%. The limit of detection and limit of quantification were <4.18 and 11.63 ng mL−1, respectively. The relative standard deviation for repeatability and the precision of seven analytes were <3.4 and 1.9%, respectively. The established method was successfully applied to simultaneous determination of seven secoiridoid glucosides in 11 batches of samples collected from different habitats in China. 相似文献
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T. Iossifova B. Mikhova I. Kostova 《Monatshefte für Chemie / Chemical Monthly》1995,126(11):1257-1264
Summary The isolation and structure elucidation of the secoiridoid hydroxyornoside is described. The behaviour of secoiridoid dilactones on acid methanolysis is discussed.
Ein Secoiridoiddilacton aus der Rinde vonFraxinus ornus
Zusammenfassung Die Isolierung und Strukturaufklärung des Secoiridoids Hydroxyornosid wird beschrieben. Das Verhalten von Secoiridoiddilactonen bezüglich saurer Methanolyse wird diskutiert.相似文献
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Kyo Bin Kang Dong Young Lee Mi Song Kim Tae Bum Kim Tae-Jin Yang 《Natural product research》2018,32(7):788-794
A new secoiridoid-derived guanidine alkaloid, argininosecologanin (1), along with 12 known iridoids and secoiridoids (2–13), was isolated from the roots of Lonicera insularis. The structures of the isolated compounds were established by the spectroscopic analysis and comparison of their spectral data with previously reported data. Compound 1 was assigned as the first secoiridoid-derived guanidine alkaloid isolated as a natural product. A plausible biogenetic pathway for 1 is suggested based on its structural similarity to (E)-aldosecologanin (4). 相似文献
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Hao-Chiun Chang Shih-Wei Wang Chin-Yen Chen Tsong-Long Hwang Ming-Jen Cheng Ping-Jyun Sung Kuang-Wen Liao Jih-Jung Chen 《Molecules (Basel, Switzerland)》2020,25(24)
Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4′′-O-methylligstroside (1), (8E)-4′′-O-methyldemethylligstroside (2), and 3′′,4′′-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4–26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4′′-O-methylligstroside (1), (8E)-4′′-O-methyldemethylligstroside (2), 3′′,4′′-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50 ≤ 7.65 μg/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leuckyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 9, 11, 14, 21, and 22 inhibited fMLP/CB-induced elastase release with IC50 ≤ 3.23 μg/mL. In addition, compounds 2, 9, 11, 14, and 21 showed potent inhibition with IC50 values ≤ 27.11 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines, tumor necrosis factor-alpha (TNF-α) and interleukin 6 (IL-6), were also inhibited by compounds 1, 9, and 14. Compounds 1, 9, and 14 displayed an anti-inflammatory effect against NO, TNF-α, and IL-6 through the inhibition of activation of MAPKs and IκBα in LPS-activated macrophages. In addition, compounds 1, 9, and 14 stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that compounds 1, 9, and 14 could be considered as potential compounds for further development of NO production-targeted anti-inflammatory agents. 相似文献
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Wei Li Wei Zhou Sohyun Kim Jung-Eun Koo Yuna Kim Young-Sang Koh 《Natural product research》2015,29(20):1920-1927
Three new (1–3) and 17 known (4–20) iridoid and secoiridoid glycosides were isolated from a methanol extract of the rhizomes and roots of Gentiana scabra. Their chemical structures were elucidated from 1D and 2D NMR, IR absorption, and HR-ESI-MS spectra, as well as comparisons of these data with reported values. The effects of the isolated compounds on lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells were investigated. Compounds 6, 10 and 20 exhibited significant inhibitory effects on LPS-induced IL-12 p40 and IL-6 production with IC50 values of 1.62–14.29 μM. Compound 10 also showed a strong inhibitory effect on the LPS-stimulated production of TNF-α with an IC50 value of 10.45 μM. 相似文献
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Characterization of antioxidant phenolics in Syringa vulgaris L. flowers and fruits by HPLC‐DAD‐ESI‐MS
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Gergő Tóth Csenge Barabás Anita Tóth Ágnes Kéry Szabolcs Béni Imre Boldizsár Erzsébet Varga Béla Noszál 《Biomedical chromatography : BMC》2016,30(6):923-932
In this study the polyphenolic composition of lilac flowers and fruits was determined for the first time. For the identification of compounds, accurate molecular masses and formulas, acquired by LC and ESI‐TOF‐MS and fragmentation pattern given by LC‐ESI/MS/MS analyses, were used. Our chromatographic system in conjunction with tandem MS was found to be valuable in the rapid separation and determination of the multiple constituents in methanolic extracts of lilac flowers and fruits. Altogether 34 phenolics, comprising 18 secoiridoids, seven phenylpropanoids, four flavonoids and five low‐molecular‐weight phenols, were identified. As marker compounds two secoiridoids (oleuropein and nuzhenide), two phenylpropanoids (acteoside and echinacoside) and rutin were quantified by validated methods. As a result of quantitative analysis, it was confirmed that flowers contain significant amounts of phenylpropanoids (acteoside, 2.48%; echinacoside, 0.75%) and oleuropein (0.95%), while in fruits secoiridoid oleuropein (1.09%) and nuzhenide (0.42%) are the major secondary metabolites. The radical scavenging activities of the extracts and the constituents were investigated by DPPH (2,2‐diphenyl‐1‐picrylhydrazyl) and ABTS [2,2′‐azino‐bis‐(3‐ethylbenzothiazoline‐6‐sulfonic acid)] assays. Both extracts show remarkable antioxidant activities. Our results clearly show that lilac flowers and fruits are inexpensive, readily available natural sources of phenolic compounds with pharmacological and cosmetic applications. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
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Ji-Yeon Park Ah-Reum Han Yun-Seo Kil Unwoo Kang Se-Hee Kim 《Natural product research》2016,30(13):1504-1510
A new secoiridoid glycoside, 7β-O-dimethyl butanedioate morroniside (1) was isolated from the fruits of Cornus officinalis (Cornaceae) along with the known compound, caffeoyltartaric acid dimethyl ester (2) which was isolated from the family Cornaceae for the first time. Their structures were elucidated by physical and spectroscopic data analysis, including 1D and 2D NMR, ESI-MS and CD experiments. 相似文献
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Pantelis Charisiadis Constantinos G. Tsiafoulis Andreas G. Tzakos Ioannis P. Gerothanassis 《Magnetic resonance in chemistry : MRC》2014,52(12):764-768
The direct in situ NMR observation and quantification, based on the aldehyde –CH chemical shift region, of the inter‐conversion of secoiridoid derivatives due to temperature and solvent effects is demonstrated in complex extracts of natural products without prior isolation of the individual components. The equilibrium between the aldehyde hydrate form and the dialdehyde form of the oleuropein aglycon of an olive leaf aqueous extract in D2O was shown to be temperature dependent. The resulting thermodynamic values of the Van't Hoff plot with ΔHo = ?26.34 ± 1.00 kJ mol?1 and TΔS° (298 K) = ?24.70 ± 1.00 kJ mol?1 demonstrate a significant entropy term which nearly compensates the effect of enthalpy at room temperature. The equilibrium between the two diastereomeric hemiacetal forms and the dialdehyde form of the oleuropein 6‐O‐β‐d ‐glucopyranoside aglycon of an olive leaf aqueous extract in CD3OD was also shown to be strongly temperature dependent again because of the significant entropy term (TΔS° (298 K) = ?26.50 ± 1.39 kJ mol?1) compared with that of the enthalpy term (ΔHo = ?36.64 ± 1.46 kJ mol?1). This is the first demonstration of the significant role of the entropy parameter in determining the equilibrium of chemical transformations in complex mixtures of natural products due to solvent and temperature effects. Copyright © 2014 John Wiley & Sons, Ltd. 相似文献
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Chunshi Jin Mei Jin Ren Li Shengbao Diao Jinfeng Sun Ying Jie Ma 《Natural product research》2020,34(4):518-524
AbstractA new secoiridoid, (1R,5S,8S,9R)-1-methyl-kingiside aglucone (1), along with nine known compounds (2–10), were isolated from the ethanol extract of the stem bark of Syringa reticulata (Bl.) Hara. The structure of compound 1 was elucidated using HR-ESI-MS, 1D and 2D NMR spectroscopy. Compounds 1–10 were evaluated for their inhibitory activity against NO, TNF-α and IL-6 production. Compounds 1, 3, 5 and 7–10 significantly inhibited the levels of NO, TNF-α and IL-6 in LPS-induced RAW264.7 cells from concentrations of 3 to 30?μM. 相似文献
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Michel Boni Bitchi Faustin Aka Kabran Philomène Akoua Yao-Kouassi Abdulmagid Alabdul Magid Dominique Harakat Laurence Voutquenne-Nazabadioko 《Natural product research》2020,34(15):2157-2166
AbstractFour new saponins, camelliagenin A and B derivatives, and one new secoiridoid glucoside were isolated from the stem bark of Aptandra zenkeri Engl. (Aptandraceae) together with two known secoiridoid glucosides. Their structures were determined based on a combination of 1D- and 2D-NMR experiments techniques and HR-ESI-MS analysis. This is the first report on saponins in genus Aptandra. 相似文献
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