Yong Jiang

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Organization: Peking University

Department: School of Pharmaceutical Sciences

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TOPICS

Inorganic Chemistry

Porphyrin

Chemicals
References

New terpenoids and thiophene derivatives from the aerial parts of Artemisia sieversiana

Co-reporter:Xu-Dong Zhou, Chen Zhang, Shan He, Bin Zheng, Ke-Wu Zeng, Ming-Bo Zhao, Yong Jiang, Peng-Fei Tu

Bioorganic & Medicinal Chemistry Letters 2017 Volume 27, Issue 24(Issue 24) pp:

Publication Date(Web):15 December 2017

DOI:10.1016/j.bmcl.2017.10.077

One new highly oxygenated nortriterpene, named sieverlactone (1), one new sesquiterpene, 1β,10β-epoxy-8α-acetoxyachillin (2), one new natural product, 5-propinyl-thiophene-2-carboxylic acid (3), and one new thiophene, 3-hydroxy-5-propinyl-2-acetyl-thiophene (4), together with 10 other known compounds (5−14), were isolated from the dried aerial parts of Artemisia sieversiana. Their structures were elucidated by a combination of extensive spectroscopic analysis, including 1D, 2D NMR spectroscopic and mass spectrometric data. Meanwhile, the stereochemistry of 1 and 2 was confirmed by single-crystal X-ray diffraction technique using Cu radiation. All the isolates were evaluated for their anti-neuroinflammatory effects on the lipopolysaccharide-induced nitric oxide production in BV-2 murine microglial cells. Compounds 2, 5, and 6 exhibited the significant activities with IC50 values of 6.5 ± 0.5, 11.9 ± 0.7, and 10.1 ± 0.3 μM, respectively, comparable to the positive control, quercetin, with an IC50 value of 16.3 ± 0.4 μM.Download high-res image (149KB)Download full-size image

Application of 1H NMR-based metabolomics for discrimination of different parts and development of a new processing workflow for Cistanche deserticola

Co-reporter:Pingping Zou, Yuelin Song, Wei Lei, Jun Li, Pengfei Tu, Yong Jiang

Acta Pharmaceutica Sinica B 2017 Volume 7, Issue 6(Issue 6) pp:

Publication Date(Web):1 November 2017

DOI:10.1016/j.apsb.2017.07.003

Cistanche deserticola (CD) is one of the two authoritative source plants of Cistanches Herba, a well-known medicinal plant. Herein, 1H 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 combining 1H 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-drying via holistic 1H 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, 1H 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.With the application of 1H-NMR-based metabolomics, a new processing method was proposed for the medicinal slices of Cistanche deserticola and the different parts of C. deserticola were also differentiated, indicating that 1H-NMR-based metabolomics is a versatile analytical platform.Download high-res image (202KB)Download full-size image

Four new phenolic glycosides from Baoyuan decoction

Co-reporter:Xiaoli Ma, Xiaoyu Guo, Mingbo Zhao, Pengfei Tu, Yong Jiang

Acta Pharmaceutica Sinica B 2017 Volume 7, Issue 2(Issue 2) pp:

Publication Date(Web):1 March 2017

DOI:10.1016/j.apsb.2016.08.004

Four new phenolic glycosides, including two flavonoid glycosides (1 and 2) and two lignan glycosides (3 and 4), were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods. Furthermore, the sources of the four new compounds were determined by the UPLC-Qtrap-MS method, which proved that 1 and 2 are originated from Glycyrrhiza uralensis, and 3 and 4 are from Cinnamomum cassia.Four new phenolic glycosides, including two flavonoid glycosides (1 and 2) and two lignan glycosides (3 and 4), were isolated from the traditional Chinese medicine formula, Baoyuan decoction. Their absolute configurations were determined by experimental electronic circular dichroism data and chemical methods, and their sources were analyzed by the UPLC–Qtrap-MS method.Download high-res image (234KB)Download full-size image

Nitric Oxide Inhibitory Dimeric Sesquiterpenoids from Artemisia rupestris

Co-reporter:Chen Zhang; Shu Wang; Ke-Wu Zeng; Jun Li; Daneel Ferreira; Jordan K. Zjawiony; Bing-Yu Liu; Xiao-Yu Guo; Hong-Wei Jin; Yong Jiang;Peng-Fei Tu

Journal of Natural Products 2016 Volume 79(Issue 1) pp:213-223

Publication Date(Web):December 22, 2015

DOI:10.1021/acs.jnatprod.5b00894

Twelve new dimeric sesquiterpenoids (1–12) were isolated from the dried whole plants of Artemisia rupestris. Their structures were determined using MS and NMR data, and the absolute configurations were elucidated on the basis of experimental and calculated ECD spectra. Compounds 1–9 are presumably formed via biocatalyzed [2+2] or [4+2] cycloaddition reactions. Stereoselectivity of the [4+2] Diels–Alder reaction dictated the formation of endo-products. The dimeric sesquiterpenoids exhibited moderate inhibition on NO production stimulated by lipopolysaccharide in BV-2 microglial cells, with IC50 values in the range 17.0–71.8 μM.

An integrated strategy to quantitatively differentiate chemome between Cistanche deserticola and C. tubulosa using high performance liquid chromatography–hybrid triple quadrupole-linear ion trap mass spectrometry

Co-reporter:Yuelin Song, Qingqing Song, Jun Li, Na Zhang, Yunfang Zhao, Xiao Liu, Yong Jiang, Pengfei Tu

Journal of Chromatography A 2016 Volume 1429() pp:238-247

Publication Date(Web):15 January 2016

DOI:10.1016/j.chroma.2015.12.045

•A strategy was proposed for comprehensive targeted and comparative metabolomics.•EMS, Prec, predefined MRM, NL, and triggered EPI were used for component screening.•513 components were detected from CH, and 379 ones were annotated.•sMRM was employed for large-scale relatively quantitative analysis of 513 targets.•Betaine, TCA intermediates, and PhGs were responsible to distinguish CD and CT.It is important to conduct large-scale detection, identification, and quantitation of metabolites in a given sample. Herein, a practical strategy was proposed to quantitatively compare the chemome between Cistanche deserticola (CD) and C. tubulosa (CT), which have been widely believed as the ideal edible and medicinal plants for conquering the deserts. The entire workflow was implemented on high performance liquid chromatography–hybrid triple quadrupole-linear ion trap mass spectrometer and consisted of three primary steps: (1) component detection and identification, various mass spectrometric approaches were applied to globally screen the chemical constituents, and structural elucidation was achieved by comparing with authentic compounds, analyzing MS2 spectra, and referring to the literature along with accessible databases; (2) comprehensive relative quantitation, scheduled multiple reaction monitoring algorithm was introduced for relative quantitation of all detected ingredients; and (3) chemome comparison, the quantitative dataset was subjected for multivariate statistical analysis to carry out comparative study. A total of 513 metabolites were detected and relatively quantitated, and 379 ones were annotated. Betaine, Krebs cycle intermediates, phenylethanoid glycosides, and iridoids were picked out as the chemical markers being responsible for the discrimination of the chemical profiles between CD and CT. Above all, the quantitative chemome of CD and CT were exhaustively characterized and compared, which could advance their values concerning drug development, economics, and desertification control. The proposed strategy is expected as a reliable choice for widely targeted metabolomics of plants.

An integrated platform for directly widely-targeted quantitative analysis of feces part I: Platform configuration and method validation

Co-reporter:Yuelin Song, Qingqing Song, Jun Li, Jiao Zheng, Chun Li, Yuan Zhang, Lingling Zhang, Yong Jiang, Pengfei Tu

Journal of Chromatography A 2016 Volume 1454() pp:58-66

Publication Date(Web):8 July 2016

DOI:10.1016/j.chroma.2016.05.077

•A new online PLE-TFC-LC–MS/MS platform was configured and validated.•An application of simultaneous determination of 24 analytes was performed in feces.•A long PEEK tube was used to generate desired pressure for extraction vessel.•TFC column was online introduced as SPE column to trap low molecular analytes.Direct analysis is of great importance to understand the real chemical profile of a given sample, notably biological materials, because either chemical degradation or diverse errors and uncertainties might be resulted from sophisticated protocols. In comparison with biofluids, it is still challenging for direct analysis of solid biological samples using high performance liquid chromatography coupled with tandem mass spectrometry (LC–MS/MS). Herein, a new analytical platform was configured by online hyphenating pressurized liquid extraction (PLE), turbulent flow chromatography (TFC), and LC–MS/MS. A facile, but robust PLE module was constructed based on the phenomenon that noticeable back-pressure can be generated during rapid fluid passing through a narrow tube. TFC column that is advantageous at extracting low molecular analytes from rushing fluid was employed to link at the outlet of the PLE module to capture constituents-of-interest. An electronic 6-port/2-position valve was introduced between TFC column and LC–MS/MS to fragment each measurement into extraction and elution phases, whereas LC–MS/MS took the charge of analyte separation and monitoring. As a proof of concept, simultaneous determination of 24 endogenous substances including eighteen steroids, five eicosanoids, and one porphyrin in feces was carried out in this paper. Method validation assays demonstrated the analytical platform to be qualified for directly simultaneous measurement of diverse endogenous analytes in fecal matrices. Application of this integrated platform on homolog-focused profiling of feces is discussed in a companion paper.

Source attribution and structure classification-assisted strategy for comprehensively profiling Chinese herbal formula: Ganmaoling granule as a case

Co-reporter:Jinfeng Chen, Ziyi Shi, Yuelin Song, Xiaoyu Guo, Mingbo Zhao, Pengfei Tu, Yong Jiang

Journal of Chromatography A 2016 Volume 1464() pp:102-114

Publication Date(Web):16 September 2016

DOI:10.1016/j.chroma.2016.08.028

•Source attribution and structural classification were integrated to profile CHF.•Automated source attribution was achieved by the “Quantitate” function.•Online parameter optimization for CE was used to achieve the highest sensitivity.•Structural classification was achieved by integrating DFIF and MDF.•A total of 261 ingredients, including 148 trace ones were assigned from GMLG.Chinese herbal formula (CHF) has extremely complex chemical composition. Herein, a source attribution and structure classification-assisted strategy was established based on reductionism for rapidly and comprehensively profiling CHF, and Ganmaoling granule (GMLG) was selected as a representative case to illustrate such a strategy and to confirm its applicability. Firstly, comprehensive data acquisition was achieved using neutral losses along with full scan on a liquid chromatography coupled with hybrid ion trap-time of flight mass spectrometer (LC-IT-TOF-MS). Then, the detected precursor and product ions were paired to construct a list of ion transitions for profiling GMLG and its constituent herbs using the scheduled multiple reaction monitoring (sMRM) mode on a LC coupled with hybrid triple quadrupole-linear ion trap mass spectrometer (LC-Q-Trap-MS). The mass parameters of sMRM were optimized using an online optimization strategy to achieve the highest sensitivity, and the automated source attribution was performed with the assistant of the “Quantitate” function of Analyst software. The target peaks were then structurally classified into seven classes through integrating the mass defect filtering (MDF) and diagnostic fragment ion filtering (DFIF), and identified by combination of the mass fragmentation rules and a ‘structure extension’ approach. Using this strategy, 261 components, including 148 trace ones (with the intensity lower than 100,000 cps), were tentatively characterized. The findings demonstrated that such a comprehensive source attribution and structure classification-assisted strategy is qualified to be an efficient approach for rapidly and globally characterizing the chemical profile of CHF.

Differentiation of two types of pu-erh teas by using an electronic nose and ultrasound-assisted extraction-dispersive liquid–liquid microextraction-gas chromatography-mass spectrometry

Co-reporter:Jing Ye, Wenguang Wang, Chitang Ho, Jun Li, Xiaoyu Guo, Mingbo Zhao, Yong Jiang and Pengfei Tu

Analytical Methods 2016 vol. 8(Issue 3) pp:593-604

Publication Date(Web):25 Nov 2015

DOI:10.1039/C5AY02652K

It is a challenging task to discriminate raw pu-erh tea, notably aged raw tea, from ripened pu-erh tea, both of which are the two primary types of pu-erh teas, only based on the taster's sensory evaluation. In the current study, a workflow was proposed to differentiate those two clusters of pu-erh teas, as well as to point out and verify the markers responsible for the discrimination. Initially, an electronic nose was utilized for the rapid discrimination. Then, an efficient method based on ultrasound-assisted extraction-dispersive liquid–liquid microextraction-gas chromatography-mass spectrometry (UAE-DLLME-GC-MS) coupled with chemometric methods was developed to disclose the metabolic profiles and pinpoint the markers for discrimination. Afterwards seven methoxyphenolic derivatives were simultaneously determined in both pu-erh teas. The role of volatile components in the classification of pu-erh teas was proved using the electronic nose (E-nose). Diverse parameters were optimized for UAE-DLLME-GC-MS, and a total of 84 volatile constituents were detected and identified. The methoxyphenolic derivatives as well as some alcohol derivatives were screened out as the primary markers by principle component analysis, and significant differences were revealed for the contents of methoxyphenolic compounds in these two types of pu-erh teas. Taken together, methoxyphenolic compounds as well as alcohol derivatives were found and verified as the markers for the differentiation between raw and ripened pu-erh teas, and either an E-nose or UAE-DLLME-GC-MS could be applied as a reliable tool to achieve the discrimination.

Murradiate and murradiol, two structurally unique heterodimers of carbazole-monoterpene and carbazole-phenylethanol from Murraya tetramera

Co-reporter:Hai-Ning Lv, Ying Zhou, Ran Wen, Meng-Ling Shi, Ke-Wu Zeng, Fang Xia, Peng-Fei Tu, Yong Jiang

Phytochemistry Letters 2016 Volume 15() pp:113-115

Publication Date(Web):March 2016

DOI:10.1016/j.phytol.2015.12.002

•Two novel heterodimers were isolated from Murraya tetramera.•Murradiate (1) is the first carbazole alkaloid coupled with p-menthane monoterpene.•Murradiol (2) possesses a rare carbazole-phenylethanol dimeric skeleton.•Both compounds exhibited weak inhibition of nitric oxide production in BV-2 microglial cells stimulated with lipopolysaccharide.In the course of our ongoing search for biologically active compounds from Murraya tetramera (Rutaceae), two novel heterodimers of carbazole-monoterpene and carbazole-phenylethanol, murradiate (1) and murradiol (2), were isolated from a natural plant source, and their structures were elucidated by a comprehensive analysis of NMR and MS spectroscopic data. Compounds 1 and 2, at concentrations of 100 μM, inhibited nitric oxide production in BV-2 microglial cells stimulated with lipopolysaccharide, with inhibition rates of 42% and 47%, respectively.

Exotines A and B, Two Heterodimers of Isopentenyl-Substituted Indole and Coumarin Derivatives from Murraya exotica

Co-reporter:Bing-Yu Liu, Chen Zhang, Ke-Wu Zeng, Jun Li, Xiao-Yu Guo, Ming-Bo Zhao, Peng-Fei Tu, and Yong Jiang

Organic Letters 2015 Volume 17(Issue 17) pp:4380-4383

Publication Date(Web):August 27, 2015

DOI:10.1021/acs.orglett.5b02230

Exotines A and B (1 and 2), two heterodimers of isopentenyl-substituted indole and coumarin derivatives linked through a new fused heptacyclic ring system, were isolated from the roots of Murraya exotica. Their structures were established by comprehensive NMR and MS spectroscopic data analysis, and the absolute configurations were determined by single-crystal X-ray crystallographic analysis and ECD calculations. Compounds 1 and 2 showed inhibition of nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells with IC50 values of 9.2 and 39.9 μM, respectively.

Homolog-focused profiling of ginsenosides based on the integration of step-wise formate anion-to-deprotonated ion transition screening and scheduled multiple reaction monitoring

Co-reporter:Yuelin Song, Na Zhang, Shepo Shi, Jun Li, Yunfang Zhao, Qian Zhang, Yong Jiang, Pengfei Tu

Journal of Chromatography A 2015 Volume 1406() pp:136-144

Publication Date(Web):7 August 2015

DOI:10.1016/j.chroma.2015.06.007

•Formate anion > deprotonated ion pairing is specific and sensitive for ginsenoside.•Step-wise MRM was used to detect ginsenosides in ginseng and American ginseng.•Scheduled MRM was utilized to quantitatively analyze all 221 detected ginsenosides.•Comparative metabolomics was performed for ginseng and American ginseng.Homolog-focused profiling is a favored option to bridge targeted metabolomics toward non-targeted metabolomics. In current study, an attempt was made for the large-scale ginsenoside-specific analysis in ginseng (G) and American ginseng (AG). When formic acid (0.1%, v/v) was introduced as the mobile phase additive, formate anion-to-deprotonated ion transitions ([M+HCOO]− > [M−H]−) with an optimal collision energy (−32 eV) could result in satisfactory responses for ginsenosides. Therefore, a step-wise multiple reaction monitoring (MRM)-based method employing [M+HCOO]− > [M−H]− ion pairs was constructed to screen ginsenosides among 501–1250 u (for Q1) with a step-size of 2 u, and MRM also served as a survey experiment to trigger enhanced product ion scans for MS2 spectrum acquisition on a hybrid triple quadrupole-linear ion trap mass spectrometer; then, the identification of those observed ginsenosides was achieved on the basis of the well-defined mass cracking patterns for ginsenosides; afterwards, scheduled MRM was introduced for large-scale relatively quantitative analysis of all detected ginsenosides. Finally, comparative metabolomics were performed to differentiate G, AG, and their processed products. Method validation was carried out using thirteen authentic compounds. A total of 221 ginsenosides, among which 185 ones were annotated, were observed and relatively quantitated. All crude materials were obviously classified into groups I–III. Above all, the MRM-based homolog-focused profiling of ginsenosides could be used as a reliable tool to gain an in-depth view for ginsenoside-enriched herbal products.

Large-scale qualitative and quantitative characterization of components in Shenfu injection by integrating hydrophilic interaction chromatography, reversed phase liquid chromatography, and tandem mass spectrometry

Co-reporter:Yuelin Song, Na Zhang, Shepo Shi, Jun Li, Qian Zhang, Yunfang Zhao, Yong Jiang, Pengfei Tu

Journal of Chromatography A 2015 Volume 1407() pp:106-118

Publication Date(Web):14 August 2015

DOI:10.1016/j.chroma.2015.06.041

•sMIM- and pMRM-IDA-EPI were combined to characterize polar ingredients in SFI.•157 hydrophilic components were detected from SFI, and 154 ones were identified.•Column-switching HILIC-RPLC-MS/MS system was built and validated.•Trap, HILIC, and RP-C18 columns constructed the chromatographic separation system.•40 polar and apolar compounds were quantitatively analyzed in complex matrices.It is of great importance to clarify in depth the chemical composition, including qualitative and quantitative aspects, of traditional Chinese medicine (TCM) injection that contains a great number of hydrophilic and hydrophobic ingredients to guarantee its safe medication in clinic. Column-switching hydrophilic interaction liquid chromatography-reversed phase liquid chromatography coupled with tandem mass spectrometry (HILIC-RPLC-MS/MS) has been revealed to be advantageous at simultaneous measurement of compounds covering a broad polarity range. Previous studies have profiled the hydrophobic components, mainly aconite alkaloids and ginsenosides, in Shenfu Injection (SFI); however, the hydrophilic substances haven’t been taken into account. In the present study, we aim to holistically characterize the hydrophilic constituents and to simultaneously quantitate both hydrophilic and hydrophobic components in SFI. A strategy integrating predefined multiple reaction monitoring, step-wise multiple ion monitoring, and enhanced product ion scans was proposed to universally screen the hydrophilic substances using a hybrid triple quadrupole-linear ion trap mass spectrometer. Structural identification was carried out by comparing with authentic compounds, analyzing MS2 spectra, and referring to accessible databases (e.g., MassBank, METLIN and HMDB). A total of 157 hydrophilic compounds were detected from SFI, and 154 ones were identified as amino acids, nucleosides, organic acid, carbohydrates, etc. A column-switching HILIC-RPLC-MS/MS system was developed and validated for simultaneously quantitative analysis of 40 primary hydrophilic and hydrophobic ingredients in SFI, including eleven amino acids, nine nucleosides, nine aconite alkaloids, and eleven ginsenosides. Taken together, the findings obtained could provide meaningful information for comprehensively understanding the chemical composition and offer a reliable approach for the quality control of SFI.

Anti-inflammatory Coumarin and Benzocoumarin Derivatives from Murraya alata

Co-reporter:Hai-Ning Lv; Shu Wang; Ke-Wu Zeng; Jun Li; Xiao-Yu Guo; Daneel Ferreira; Jordan K. Zjawiony; Peng-Fei Tu

Journal of Natural Products 2015 Volume 78(Issue 2) pp:279-285

Publication Date(Web):January 26, 2015

DOI:10.1021/np500861u

Two new rare 8-methylbenzo[h]coumarins, muralatins A and B (1, 2), nine new C-8-substituted coumarins, muralatins C–K (3–11), and 22 known analogues (12–33) were isolated from the leaves of Murraya alata. The absolute configurations of compounds 5, 11, 23, 24, 27, 30, and 33 were assigned via comparison of their specific rotations, by Mosher’s method, and by single-crystal X-ray diffraction and electronic circular dichroism (ECD) data of the in situ formed transition metal complexes. A putative biosynthesis pathway to 1 and 2 is proposed, and the chemical synthesis of 1 was accomplished through electrocyclization of 5,7-dimethoxy-8-[(Z)-3-methylbut-1,3-dienyl)]coumarin (12). Compounds 1, 2, 8, 12, and 31 showed inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 6.0–14.5 μM.

Anti-Neuroinflammatory Effect of MC13, a Novel Coumarin Compound From Condiment Murraya, Through Inhibiting Lipopolysaccharide-Induced TRAF6-TAK1-NF-B, P38/ERK MAPKS and Jak2-Stat1/Stat3 Pathways

Co-reporter:Ke-Wu Zeng;Qian Yu;Li-Xi Liao;Fang-Jiao Song;Hai-Ning Lv;Peng-Fei Tu

Journal of Cellular Biochemistry 2015 Volume 116( Issue 7) pp:1286-1299

Publication Date(Web):

DOI:10.1002/jcb.25084

ABSTRACT

MC13 is a novel coumarin compound found in Murraya, an economic crop whose leaves are widely used as condiment (curry) in cuisine. The aims of the present study were to investigate the neuroprotective effects of MC13 on microglia-mediated inflammatory injury model as well as potential molecular mechanism. Cell viability and apoptosis assay demonstrated that MC13 was not toxic to neurons and significantly protected neurons from microglia-mediated inflammatory injury upon lipopolysaccharide (LPS) stimulation. Results showed that MC13 markedly inhibited LPS-induced production of various inflammatory mediators, including nitrite oxide (Griess method), TNF-α and IL-6 (ELISA assay) in a concentration-dependent manner. Mechanism study showed that MC13 could suppress the activation of NF-κB, which was the central regulator for inflammatory response, and also decreased the interaction of TGF-β-activated kinase 1 (TAK1)-binding protein (TAB2) with TAK1 and TNF receptor associated factor (TRAF6), leading to the decreased phosphorylation levels of NF-κB upstream regulators such as IκB and IκB kinase (IKK). MC13 also significantly down-regulated the phosphorylation levels of ERK and p38 MAPKs, which played key roles in microglia-mediated inflammatory response. Furthermore, MC13 inhibited Jak2-dependent Stat1/3 signaling pathway activation by blocking Jak2 phosphorylation, Stat1/3 phosphorylation, and nuclear translocation. Taken together, our results demonstrated that MC13 protected neurons from microglia-mediated neuroinflammatory injury by inhibiting TRAF6-TAK1-NF-κB, p38/ERK MAPKs, and Jak2-Stat1/3 pathways. Finally, MC13 might interact with LPS and interfere LPS-binding to cell membrane surface. These findings suggested that coumarin might act as a potential medicinal agent for treating neuroinflammation as well as inflammation-related neurodegenerative diseases. J. Cell. Biochem. 116: 1286–1299, 2015. © 2015 Wiley Periodicals, Inc.

Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana

Co-reporter:Xu-Dong Zhou, Xing-Yun Chai, Ke-Wu Zeng, Ming-Bo Zhao, Yong Jiang, Peng-Fei Tu

Tetrahedron Letters 2015 Volume 56(Issue 9) pp:1141-1143

Publication Date(Web):25 February 2015

DOI:10.1016/j.tetlet.2015.01.081

Artesin A (1), a rare symmetrical dimeric guaianolide, was isolated from the aerial parts of Artemisia sieversiana. Its structure was determined by analysis of the spectroscopic data, including HRESIMS, 1D, and 2D NMR and the absolute configuration was resolved by single crystal X-ray diffraction. Artesin A exhibited a moderate inhibition effect on the LPS-induced nitric oxide production in BV-2 microglial cells with an IC50 value of 38.78 μM.

Characterization of the herb-derived components in rats following oral administration of Carthamus tinctorius extract by extracting diagnostic fragment ions (DFIs) in the MSn chromatograms

Co-reporter:Jin-Feng Chen, Yue-Lin Song, Xiao-Yu Guo, Peng-Fei Tu and Yong Jiang

Analyst 2014 vol. 139(Issue 24) pp:6474-6485

Publication Date(Web):10 Oct 2014

DOI:10.1039/C4AN01707B

In this study, a new strategy named extracting diagnostic fragment ions (DFIs) in the MSn chromatograms [E(DFI)MSnCs] was proposed to rapidly detect and identify the in vivo components derived from the extract of Carthamus tinctorius (ECT), using high performance liquid chromatography coupled with hybrid ion trap-time of flight mass spectrometry. In order to comprehensively summarize the DFIs for the global identification of in vivo constituents of ECT, chemical profiling was carried out, and then the typical metabolic pathways of the primary components were proposed according to their chemical categories, by orally administering representative reference compounds. Based on the proposed metabolic pathways and the fragmentation rules, a list of DFIs was constructed and adopted to differentiate and identify the metabolites from the endogenous substances in the MSn chromatograms of ECT-treated biological samples, in combination with the neutral loss scan mode as a supplement. As a result, a total of 156 compounds were tentatively assigned in vivo, including 63, 73, 50, and 17 components from rat plasma, urine, bile, and feces, respectively, following oral administration of ECT. Deglycosylation, oxidation, methylation, sulfonation, and glucuronidation were observed as the major metabolic pathways for the chemical constituents of ECT, and dehydroxylation was detected at the A-ring of flavones for the first time. The findings suggested that the E(DFI)MSnCs-based strategy which integrated ideas from single compounds to herbal extracts and from extract chemical profiling to in vivo metabolite profiling, could be used as a reliable tool for rapidly discovering and identifying herb-related constituents in vivo.

Sesquiterpenes from Artemisia argyi: Absolute Configurations and Biological Activities

Co-reporter:Shu Wang;Jian Sun;Kewu Zeng;Xiaoguang Chen;Wanqi Zhou;Chen Zhang;Hongwei Jin;Pengfei Tu

European Journal of Organic Chemistry 2014 Volume 2014( Issue 5) pp:973-983

Publication Date(Web):

DOI:10.1002/ejoc.201301445

Abstract

Nine guaiane-type sesquiterpenes and one eudesmane-type one – namely argyinolides A–J (1–10) – as well as nine known analogues were isolated from the leaves of Artemisia argyi Levl. et Vant. Their structures were determined by interpretation of spectroscopic data (MS, 1D and 2D NMR). A combination of X-ray crystal diffraction, specific optical rotations, CD spectroscopy, ECD calculation, and Mosher ester methods was employed to resolve the absolute configurations of the isolated compounds. Biological investigations into their cytotoxicities and anti-inflammatory effects showed that 1, 13, 16, and 18 were remarkably cytotoxic against Bel-742 and/or A549 cells, with IC₅₀ values of 3.3–6.0 μM, whereas 7, 11–13, 16, and 18 exhibited sound inhibitory activity on LPS-stimulated NO production in BV-2 microglial cells, with IC₅₀ values ranging from 3.2 to 8.6 μM. In addition, a brief discussion on the applicability of Geissman's rule for the sesquiterpene lactones, the probable reason for the presence of chlorine-containing sesquiterpenes, and preliminary structure–activity relationships (SARs) are included.

Characterization of in vitro and in vivo metabolites of carnosic acid, a natural antioxidant, by high performance liquid chromatography coupled with tandem mass spectrometry

Co-reporter:Yuelin Song, Haixia Yan, Jinfeng Chen, Yitao Wang, Yong Jiang, Pengfei Tu

Journal of Pharmaceutical and Biomedical Analysis 2014 Volume 89() pp:183-196

Publication Date(Web):15 February 2014

DOI:10.1016/j.jpba.2013.11.001

•Degradation of carnosic acid (CA) was characterized, and three products were generated.•In vitro and in vivo metabolites of CA were characterized using LC-UV-MS/MS.•Glucuronidation and oxidation metabolisms crucially occurred for CA in vitro.•Oxidation, glucuronidation and methylation were the main metabolic types in vivo.•CA exhibited poor metabolic stability in vitro and in vivo.Carnosic acid (CA) is a widely employed antioxidant and the main active component in rosemary and sage, but its metabolism remains largely unknown. The present study investigated the metabolism of CA in vitro and in vivo for the first time, using high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry (HPLC-Q-trap-MS). A couple of scan modes were adopted in mass spectrometer domain, including Q1 full scan, neutral loss scan-information dependent acquisition-enhanced product ion (NL-IDA-EPI) and precursor ion scan-information dependent acquisition-enhanced product ion (PI-IDA-EPI). In particular, a prediction was carried out on the basis of in vitro metabolism results, and gave birth to a multiple ion monitoring-information dependent acquisition-enhanced product ion (MIM-IDA-EPI) mode aiming to detect the trace metabolites in CA-treated biological samples. A total of ten metabolites (M4–13), along with three degradative products (M1–3), were identified for CA from in vitro metabolism models, including liver microsomes of human and rats (HLMs and RLMs), human intestinal microsomes (HIMs) and two species of Cunninghamella elegans. Twelve (U1–12) and six (F1–6) metabolites were detected from CA-treated urine and feces, respectively. In addition, five metabolites (SM2–6) in vivo were purified and definitely identified using NMR spectroscopy. The results of both in vitro and in vivo metabolism studies indicated poor metabolic stability for CA, and the glucuronidation and oxidation metabolisms extensively occurred for CA in vitro, while oxidation, glucuronidation and methylation were the main metabolic pathways observed in vivo.

Rupestonic acids B–G, NO inhibitory sesquiterpenoids from Artemisia rupestris

Co-reporter:Zhang Chen, Shu Wang, Ke-Wu Zeng, Feng-Xia Cui, Hong-Wei Jin, Xiao-Yu Guo, Yong Jiang, Peng-Fei Tu

Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 17) pp:4318-4322

Publication Date(Web):1 September 2014

DOI:10.1016/j.bmcl.2014.07.008

Six new guaiane sesquiterpenoids, rupestonic acids B–G (1–6), have been isolated from the whole plants of Artemisia rupestris together with six known compounds (7–12). The structures of the new isolates (1–6) were elucidated on the basis of extensive 1D and 2D NMR analysis, and the absolute configurations were established by electronic circular dichroism (ECD) in combination with density functional theory calculations. In in vitro bioassays, compounds 2 and 6 exhibited significant inhibitory effects on LPS-stimulated NO production in BV-2 microglial cells with IC50 values of 2.6 and 2.2 μM, respectively.

Constituents of Vigna angularis and their in vitro anti-inflammatory activity

Co-reporter:Yong Jiang, Ke-Wu Zeng, Bruno David, Georges Massiot

Phytochemistry 2014 Volume 107() pp:111-118

Publication Date(Web):November 2014

DOI:10.1016/j.phytochem.2014.08.011

•Nine compounds with three different structural skeletons were isolated from Vigna angularis.•Potentially toxic carboxyatractyligenin-type ent-kaurane diterpenoids from this food plant are reported.•Saponins and diterpenoids showed potent inhibitory activities for nitric oxide production.Nine non-phenolic compounds, including four furanylmethyl glycosides, angularides A–D, one ent-kaurane diterpene glycoside, angularin A, and four triterpenoid saponins, angulasaponins A–D, were isolated from seeds of Vigna angularis, together with eight known compounds. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic analysis as well as chemical methods. Angularin A, angulasaponins A–C, and azukisaponins III and VI showed inhibition of nitric oxide production in LPS-activated RAW264.7 macrophages, with IC50 values ranging from 13 μM to 24 μM.Nine compounds with three different structural skeletons were isolated from seeds of Vigna angularis and in particular, potentially toxic carboxyatractyligenin-type ent-kaurane diterpenoids were reported from this food plant. Some of the isolated saponins and diterpenes inhibited nitric oxide production in LPS-activated RAW264.7 macrophages.

Dimeric guaianolides from Artemisia absinthium

Co-reporter:Ablajan Turak, She-Po Shi, Yong Jiang, Peng-Fei Tu

Phytochemistry 2014 Volume 105() pp:109-114

Publication Date(Web):September 2014

DOI:10.1016/j.phytochem.2014.06.016

•Five unknown and seven known dimeric guaianolides were isolated from the aerial parts of Artemisia absinthium.•The guaianolide structures were elucidated using NMR spectroscopy, HRESIMS, and X-ray crystallography.•Two dimeric guaianolides exhibited significant inhibitory activities on LPS-induced NO production in BV-2 cells.Five dimeric guaianolides, absinthins A–E, and seven known dimeric guaianolides were isolated from Artemisia absinthium. Their structures were elucidated based on 1D- and 2D-NMR experiments, including 1H NMR, 13C NMR, DEPT, 1H–1H COSY, HSQC, HMBC, and NOESY, and through HRESIMS data analysis. The absolute configuration of the known compound, anabsinthin, was determined by X-ray crystallographic analysis. The isolated compounds were tested to assess their inhibitory activities on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 cells; absinthin C and isoanabsinthin exhibited significant inhibitory effects with IC50 values of 1.52 and 1.98 μM, respectively.Five dimeric guaianolides, denoted absinthins A–E, and seven known dimeric guaianolides were isolated from the aerial parts of Artemisia absinthium. Two of these compounds exhibited significant inhibitory activities on LPS-induced NO production in BV-2 cells.

A simple and specific quantitative method for determination of dictamnine in Dictamni Cortex by 1H NMR spectroscopy

Co-reporter:Pingping Zou, Pengfei Tu and Yong Jiang

Analytical Methods 2013 vol. 5(Issue 4) pp:1062-1067

Publication Date(Web):13 Dec 2012

DOI:10.1039/C2AY26226F

Dictamni Cortex (Baixianpi) is a commonly used medicinal herb in traditional Chinese medicines (TCMs), possessing various bioactivities. Quinoline alkaloids are regarded as one of the main active components in this herb. In the present study, a more convenient, specific and accurate analytical method using 1H NMR has been developed for the quantitative determination of dictamnine, one of the main active quinoline alkaloids in Dictamni Cortex. In a less crowded region δ 8.0–8.5, the signal of H-5 of dictamnine was well separated from other signals in chloroform-d1. The quantity of dictamnine was calculated by means of the integral value of H-5 of dictamnine to that of the known amount of internal standard, pyrazine. This assay was precise and reproducible, with RSDs less than 3%. The recovery results of dictamnine were observed between 92.10 and 108.10% and the limit of detection (LOD) and limit of quantitation (LOQ) were 3.3 μg ml−1 and 13.2 μg ml−1, respectively. This newly developed method was proven to be highly accurate, precise and robust, for the determination of dictamnine in Dictamni Cortex. The results obtained from 1H NMR method were also compared with those from conventional HPLC method, and no remarkable difference was found between these two methods.

Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells

Co-reporter:Tian-Xing Shi, Shu Wang, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang

Bioorganic & Medicinal Chemistry Letters 2013 Volume 23(Issue 21) pp:5904-5908

Publication Date(Web):1 November 2013

DOI:10.1016/j.bmcl.2013.08.085

Five new phenolic glycosides, tenuisides A–E (1−5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7–23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher’s method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 μM, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2–38.5 μM. And their primary structure–activity relationships (SARs) of NO inhibitory effects were also briefly discussed.

Arvestolides A–C, new rare sesquiterpenes from the aerial parts of Artemisia vestita

Co-reporter:Shuaihua Tian, Xingyun Chai, Ke Zan, Kewu Zeng, Xiaoyu Guo, Yong Jiang, Pengfei Tu

Tetrahedron Letters 2013 Volume 54(Issue 37) pp:5035-5038

Publication Date(Web):11 September 2013

DOI:10.1016/j.tetlet.2013.07.023

Three new sesquiterpenes, namely arvestolides A–C (1–3), were isolated from the aerial parts of Artemisia vestita. Their planar structures were determined by extensive analysis of spectroscopic data including MS, 1D, and 2D NMR, and their absolute configurations were resolved by single-crystal X-ray diffraction. Compound 1 is a sesquiterpene with a rare 6/8/3 skeleton, while compounds 2 and 3 possess a rare 5/8/3 sesquiterpene skeleton. Compound 2 exhibited a moderate inhibition effect on the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglial cells with an IC50 value of 38.59 μM.

Quality Assessment of Commercial Magnoliae Officinalis Cortex by 1H-NMR-based Metabolomics and HPLC Methods

Co-reporter:Yong Jiang;Julie Vaysse;Véronique Gilard;Stéphane Balayssac;Sébastien Déjean;Myriam Malet-Martino;Bruno David;Christel Fiorini;Yves Barbin

Phytochemical Analysis 2012 Volume 23( Issue 4) pp:387-395

Publication Date(Web):

DOI:10.1002/pca.1369

ABSTRACT

Introduction

The quality control of Magnoliae officinalis Cortex, a commonly used traditional Chinese medicine, is currently based on the assay of the two active compounds, honokiol and magnolol, by TLC or HPLC.

Objective

To compare ¹H-NMR-based metabolomics with the HPLC method for controlling the quality of Magnoliae officinalis Cortex. To identify the metabolites contributing to the differences between the samples and to discriminate different medicinal parts and geographic origins of these samples by ¹H-NMR-based metabolomics.

Methodology

¹H-NMR and several multivariate analysis techniques were applied to analyse the extracts of 18 batches of Magnoliae officinalis Cortex commercial samples, and the contents of honokiol and magnolol in these samples were determined by HPLC. The correlation analysis between the data from ¹H-NMR and HPLC was performed with the mixOmics software based on an unsupervised method.

Results

Honokiol and magnolol were the main compounds responsible for the discrimination of samples from different batches, thus proving that the choice of these two compounds as markers for quality assessment by HPLC is relevant. The two sources of Magnoliae officinalis Cortex recorded in the Chinese Pharmacopoeia, Magnolia officinalis and Magnolia officinalis var. biloba, could be differentiated from ¹H-NMR data, but the pattern recognition analysis by PLS-DA was unsuccessful in discriminating samples from various geographical origins.

Conclusion

The combination of ¹H-NMR that gives a comprehensive profile of the metabolites and HPLC that targets two biomarkers is an efficient means for a better quality control of Magnoliae officinalis Cortex. Copyright © 2011 John Wiley & Sons, Ltd.

Characterization of the metabolism of sibiricaxanthone F and its aglycone in vitro by high performance liquid chromatography coupled with Q-trap mass spectrometry

Co-reporter:Yuelin Song, Xiaojuan Yang, Yong Jiang, Pengfei Tu

Journal of Pharmaceutical and Biomedical Analysis 2012 70() pp: 700-707

Publication Date(Web):

DOI:10.1016/j.jpba.2012.06.038

A rapid and sensitive HPLC–MS/MS analysis and preliminary pharmacokinetic characterization of sibiricaxanthone F in rats

Co-reporter:Xiaojuan Yang, Guanshen Zhou, Pingping Zou, Ying Ning, Ke Zan, Pengfei Tu, Yong Jiang

Journal of Chromatography B 2011 Volume 879(Issue 25) pp:2513-2518

Publication Date(Web):1 September 2011

DOI:10.1016/j.jchromb.2011.07.002

A simple, rapid and sensitive liquid chromatography–tandem mass spectrometry (LC–MS/MS) method was developed and validated for quantifying sibiricaxanthone F (SF) in rat plasma following oral and intravenous dosings. After addition of the internal standard (IS) kaempferol and the antioxidant, 20% ascorbic acid, plasma samples were precipitated with acetonitrile and separated on an Aglient Zorbax XDB-C18 column (50 mm × 4.6 mm I.D., 2.1 μm) with gradient acetonitrile and water (both containing 0.01% formic acid) as the mobile phase. The detection was performed on a Sciex API 4000 LC–MS/MS with electrospray ionization (ESI) inlet in the negative multiple reaction monitoring (MRM) mode. Good linearity was achieved over the concentration range of 0.5–500.0 ng/mL (r > 0.996). Intra- and inter-day precisions were less than 7.60%, and accuracy ranged from 97.18% to 99.84%. The lower limit of quantification for SF was 0.5 ng/mL, and analytes were stable under various conditions (during freeze-thaw, at room temperature and under deep-freeze conditions). This validated method was successfully applied to the preliminary pharmacokinetic study of SF in rats for the first time, and the absolute bioavailability of SF was found to be only 0.22 ± 0.15%.

Recent analytical approaches in quality control of traditional Chinese medicines—A review

Co-reporter:Yong Jiang, Bruno David, Pengfei Tu, Yves Barbin

Analytica Chimica Acta 2010 Volume 657(Issue 1) pp:9-18

Publication Date(Web):4 January 2010

DOI:10.1016/j.aca.2009.10.024

Traditional Chinese medicines (TCMs) are gaining more and more attention all over the world, due to their specific theory and long historical clinical practice. But the uncontrollable quality is a bottleneck for its modernization and globalization. This paper reviewed the recent analytical methods in the quality control of TCMs, including screening strategies of bioactive markers from TCMs through biochromatographic methods, the traditional chromatographic methods, DNA methods, as well as the spectroscopic methods, including FT-IR, NIR and NMR. The comprehensive methods, such as fingerprint and multi-component quantification are emphasized; hyphenated techniques, like HPLC-MS, GC-MS, CE-MS, LC-NMR, chemometric methods, and combination of chemical and biological methods, such as biofingerprint, metabolic fingerprint are now more and more widely used in TCMs. In a few word, the analysis and quality control of TCMs are moving towards an integrative and comprehensive direction, in order to better address the inherent holistic nature of TCMs.

Nitric oxide inhibitory constituents from the barks of Cinnamomum cassia

Co-reporter:Shan He, Ke-Wu Zeng, Yong Jiang, Peng-Fei Tu

Fitoterapia (July 2016) Volume 112() pp:153-160

Publication Date(Web):1 July 2016

DOI:10.1016/j.fitote.2016.05.005

Six new compounds including one γ-butyrolactone, cinncassin A (1), two tetrahydrofuran derivatives, cinncassins B and C (2, 3), two lignans, cinncassins D and E (4, 5), and one phenylpropanol glucoside, cinnacassoside D (6), together with 14 known lignans (7–20) were isolated from the barks of Cinnamomum cassia. The structures of 1–6 were elucidated by extensive 1D and 2D NMR spectroscopic data analysis as well as chemical methods, and the absolute configurations were established by experimental and calculated ECD data. The anti-inflammatory activities of the isolates were evaluated on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Compounds 5, 7, 8, and 15 showed potent inhibition activities with IC50 values of 17.6, 17.7, 18.7, and 17.5 μM, respectively.Download high-res image (71KB)Download full-size image

Integrated work-flow for quantitative metabolome profiling of plants, Peucedani Radix as a case

Co-reporter:Yuelin Song, Qingqing Song, Yao Liu, Jun Li, Jian-Bo Wan, Yitao Wang, Yong Jiang, Pengfei Tu

Analytica Chimica Acta (8 February 2017) Volume 953() pp:

Publication Date(Web):8 February 2017

DOI:10.1016/j.aca.2016.11.066

•Novel three-step workflow was proposed for non-targeted metabolomics.•Optimal collision energy was firstly utilized for the discrimination of isomers.•Linear ranges were extended by suppressing the responses with inferior parameters.•Authentic compound-free method was implemented for parameter optimization.•Universal quantitation was achieved by a set of diluted herbal extract mixture.Universal acquisition of reliable information regarding the qualitative and quantitative properties of complicated matrices is the premise for the success of metabolomics study. Liquid chromatography-mass spectrometry (LC-MS) is now serving as a workhorse for metabolomics; however, LC-MS-based non-targeted metabolomics is suffering from some shortcomings, even some cutting-edge techniques have been introduced. Aiming to tackle, to some extent, the drawbacks of the conventional approaches, such as redundant information, detector saturation, low sensitivity, and inconstant signal number among different runs, herein, a novel and flexible work-flow consisting of three progressive steps was proposed to profile in depth the quantitative metabolome of plants. The roots of Peucedanum praeruptorum Dunn (Peucedani Radix, PR) that are rich in various coumarin isomers, were employed as a case study to verify the applicability. First, offline two dimensional LC-MS was utilized for in-depth detection of metabolites in a pooled PR extract namely universal metabolome standard (UMS). Second, mass fragmentation rules, notably concerning angular-type pyranocoumarins that are the primary chemical homologues in PR, and available databases were integrated for signal assignment and structural annotation. Third, optimum collision energy (OCE) as well as ion transition for multiple monitoring reaction measurement was online optimized with a reference compound-free strategy for each annotated component and large-scale relative quantification of all annotated components was accomplished by plotting calibration curves via serially diluting UMS. It is worthwhile to highlight that the potential of OCE for isomer discrimination was described and the linearity ranges of those primary ingredients were extended by suppressing their responses. The integrated workflow is expected to be qualified as a promising pipeline to clarify the quantitative metabolome of plants because it could not only holistically provide qualitative information, but also straightforwardly generate accurate quantitative dataset.

Nitrogen Oxide Inhibitory Trimeric and Dimeric Carbazole Alkaloids from Murraya tetramera

Co-reporter:Hai-Ning Lv; Ran Wen; Ying Zhou; Ke-Wu Zeng; Jun Li; Xiao-Yu Guo; Peng-Fei Tu

Journal of Natural Products () pp:

Publication Date(Web):September 1, 2015

DOI:10.1021/acs.jnatprod.5b00527

Two new structurally unique trimeric carbazole alkaloids, murratrines A and B (1, 2), and 11 new carbazole dimers, murradines A–K (3–13), and four known analogues (14–17) were isolated from the leaves and stems of Murraya tetramera. The structures and relative configurations of 1–13 were elucidated on the basis of comprehensive 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism (ECD) data analysis. Murratrines A and B (1, 2) both contain an unprecedented carbazole trimeric skeleton, and murradines A and D (3, 6) are the first natural C-1–C-3′-methyl-linked and C-6–C-3′-methyl-linked dimeric carbazole alkaloids, respectively. Compounds 4, 10, 14, 15, and 17 exhibited inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range of 11.2–19.3 μM.

A simple and specific quantitative method for determination of dictamnine in Dictamni Cortex by 1H NMR spectroscopy

Co-reporter:

Analytical Methods (2009-Present) 2013 - vol. 5(Issue 4) pp:

Publication Date(Web):

DOI:10.1039/C2AY26226F

CAS:1391438-73-5

CAS:1365479-35-1

2,5,2',5'-tetrahydroxy-3'-methoxybibenzyl

CAS:1351956-48-3

2,5,2',5'-tetrahydroxy-3'-methoxybibenzyl

(2beta,2'alpha,3beta,3'alpha)-2,2',3,3'-tetrahydro-2'-(4-hydroxy-3-methoxyphenyl)-3,3'-bis(hydroxymethyl)-7,7'-dimethoxy-5-[(1E)-3-oxoprop-1-en-1-yl] [2,5'-bibenzofuran]

CAS:1314868-59-1

(2beta,2'alpha,3beta,3'alpha)-2,2',3,3'-tetrahydro-2'-(4-hydroxy-3-methoxyphenyl)-3,3'-bis(hydroxymethyl)-7,7'-dimethoxy-5-[(1E)-3-oxoprop-1-en-1-yl] [2,5'-bibenzofuran]