Co-reporter:Yong-Jun Jiang, Li-She Gan, Wan-Jing Ding, Zhe Chen, Zhong-Jun Ma
Tetrahedron Letters 2017 Volume 58, Issue 38(Issue 38) pp:
Publication Date(Web):20 September 2017
DOI:10.1016/j.tetlet.2017.08.035
•Two new gephyromycins (1–2) were identified from Streptomyces sp. SS13I.•The structure of 1 was elucidated by X-ray diffraction data.•The absolute configurations of compounds 1–2 were evidenced by ECD calculations.•Compound 2 exhibited significant cytotoxicity against PC3 cell lines.Two new gephyromycins (1–2), belonging to angucyclinones, were identified from Streptomyces sp. SS13I. Their structures were elucidated by analysis of HRESIMS, 1D and 2D NMR spectroscopic data, and the structure of 1 was further elucidated by X-ray diffraction data. The absolute configurations of compounds 1–2 were evidenced by ECD calculations. To our best knowledge, Compounds 1–2 were the second reported gephyromycin-type angucyclinones. Compound 2 exhibited significant cytotoxicity against PC3 cell lines with IC50 values of 1.38 ± 0.47 μM.Download high-res image (57KB)Download full-size image
Co-reporter:Liyan Yu, Haibing He, Zhifei Hu, Zhongjun Ma
Journal of Proteomics 2016 Volume 142() pp:82-90
Publication Date(Web):16 June 2016
DOI:10.1016/j.jprot.2016.05.011
•A robust system for N-glycoproteome quantification was established.•774 N-glycosylation sites in 406 proteins were identified in F. graminearum.•N-glycoproteins were highly enriched in cell wall and membrane regions.•The protein and glycosylation synthesis was heavily suppressed by fungicide.•The protease and glycosyl-transferase activity were decreased upon fungicide.Glycoproteomics is greatly developed in recent years and big data of N-glycoproteome in mammalian tissues and cells were already established. However, the glycoproteomic studies on plant, fungus and bacteria are far left behind. In this study, we comprehensively mapped and quantified the N-glycosylation of Fusarium graminearum by combining stable isotope dimethyl labeling, hydrophilic interaction chromatography (HILIC) and high-resolution mass spectrometry. The N-glycosylation changes in Fusarium graminearum after fungicide treatment were extensively studied. Altogether we identified 927 N-glycopeptides, corresponding to 406 proteins and 774 sites and the glycosylation level was found to be largely down-regulated upon fungicide treatment. With the help of advanced bioinformatics, it was found that the N-glycoproteome changes were highly enriched in cell wall, membrane and extracellular regions. Moreover, the fungal metabolism, protein and glycosylation synthesis, and protease and glycosyl-transferase activity were all closely related with the down-regulated proteins, indicates that fungicide may affect fungal development in these aspects. These results will be useful for future studies on fungal biology. The established system for N-glycoproteome quantification has comparative or better performance compared with previous strategies and will be helpful in N-glycoproteomics of fungus and other species.SignificanceWe developed a robust HILIC-based system for N-glycoproteome quantification in fungus and established the largest quantitative N-glycosylation dataset in fungus, showing the high performance of the new system. The identified N-glycoproteins were proved to be high confident due to the high percentage of proteins in extracellular region and plasma. The quantification results were also accuracy and reproducible in two replicates. By the help of advanced bioinformatic tools, the obtained data was systematically analyzed. It was found that the N-glycosylation level was largely changed in cell wall, membrane and extracellular regions. Moreover, the cell metabolism, protein synthesis, and protease activity were also greatly deceased after fungicide treatment.
Co-reporter:Wanjing Ding, Zhijuan Hu, Zhewen Zhang, Qiaoqiao Ma, Huifang Tang, and Zhongjun Ma
Journal of Agricultural and Food Chemistry 2015 Volume 63(Issue 43) pp:9504-9512
Publication Date(Web):September 29, 2015
DOI:10.1021/acs.jafc.5b03045
The present data showed that a natural compound isolated from the plant Physalis pubescens L. (Solanaceae), physapubescin B, exhibited antitumor activity against prostate cancer in vitro and in vivo. Treating prostate cancer cells with physapubescin B resulted in the accumulation of cells in the G2/M phase, which was associated with reduced Cdc25C levels and increased levels of CyclinB1, P21 as well as p-Cdk1 (Tyr15). Additionally, reactive oxygen species (ROS) generation was increased in physapubescin B-treated PC-3 cells. Furthermore, the physapubescin B-induced decrease of Cdc25C protein expression together with the G2/M phase cell cycle arrest were significantly abrogated by antioxidant NAC and GSH. Our data also demonstrated that physapubescin B exhibited strong in vivo antitumor efficacy in human prostate cancer PC3 xenograft. In conclusion, our results provide clear evidence that physapubescin B exhibits antitumor activity both in vitro and in vivo and deserves further development as an anticancer agent.
Co-reporter:Liyan Yu;Zhifei Hu;Zhijuan Hu
Current Microbiology 2015 Volume 71( Issue 6) pp:706-712
Publication Date(Web):2015 December
DOI:10.1007/s00284-015-0908-5
Competitive coexistence of different microorganism species is a fundamental ecological process in the evolution and maintenance of biodiversity. This work studied the interactions happened in the competitive coexistence process of actinomycete Streptomyces sp. and Escherichia coli from morphological and secondary metabolites perspective. We found three important interactions occurred in their successful coexistence process: medium pH was elevated, indole alkaloids with dual inhibiting effects were produced, and culture environment was spatially structured. For the weed-like superior competitor E. coli, its massive growth was suppressed by the elevated pH and the newly produced novel bisindole alkaloid hepchrome. For the inferior Streptomyces sp., its mycelium floated to the medium surface for further colonization, and the growth in liquid medium was inhibited by its self-produced alkaloids such as halichrome A, 1,1,1-Tris (3-indolyl) methane, vibrindole A, and hepchrome. The coexistence of E. coli and Streptomyces sp. was thereby achieved through reduction of spatial and energy resource overlapping and suppression of competition.
Co-reporter:Liping Luo, Liming Shen, Fang Sun, Zhongjun Ma
Food Chemistry 2013 Volume 138(Issue 1) pp:315-320
Publication Date(Web):1 May 2013
DOI:10.1016/j.foodchem.2012.10.043
Affinity chromatography, applied to discover the enzyme inhibitors, needs special column with target protein and its carrier. Selection of stationary phase and mobile phase needs careful considerations due to the characteristics of proteins. In this study, a method immunoprecipitation (IP) coupled with HPLC-DAD–MS was developed to discover the aromatase ligands from Glycyrrhiza uralensis. An SB-C18 column was employed to separate target compounds without special consideration in mobile phase. Twenty-one compounds, including isolated compounds 4, 7, 8, 10, 11, 13, 15, 18–20, 23 and non-isolated compounds A-J, were found to have good affinity to aromatase by LC–MS. Seven of them (7, 15, 18, 19, 23, D, E) were detected to bind with aromatase in MCF-7 cells by IP coupled with HPLC–MS/MS. Bioassays disclosed aromatase inhibitory activities of the isolated compounds mentioned above, verifying the efficiency of IP coupled with HPLC–MS/MS as a method to screen aromatase ligands.Highlights► IP coupled with LC–MS was applied to find aromatase ligands from Glycyrrhiza uralensis. ► Twenty-one compounds were found to have good affinity to aromatase. ► Seven compounds were found binding to aromatase in MCF-7 cells. ► Compounds bound to aromatase showed good aromatase inhibitory activity.
Co-reporter:Liping Luo, Ruihan Wang, Xiaojun Wang, Zhongjun Ma, Ning Li
Food Chemistry 2012 Volume 131(Issue 3) pp:992-998
Publication Date(Web):1 April 2012
DOI:10.1016/j.foodchem.2011.09.099
A LC–MS method, which GSH was used as substrate, was employed to reveal the compounds with NQO1 induction activity from Angelica keiskei. Some compounds, proposed as isobavachalcone, xanthoangelol and 4-hydroxyderricin, have NQO1 induction activity. To make the actual structures and bioactivities of these compounds clear, 23 compounds, including above mentioned compounds and two new compounds 4-hydroxy-3,5,5-trimethyl-4-(1,2,3-trihydroxybutyl)cyclohex-2-enone (18) and (Z)-2-(3-hydroxypent-1-ynyl)-3-(non-1-enyl)oxiran-2-ol (23), were isolated from the 95% ethanol extract of A. keiskei. The bioassay results suggested the compounds had notable NQO1 induction activity. The radical scavenging and α-glucosidase inhibition activities of the isolated compounds were also tested. Compounds (E)-1-(2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1), (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (2), 1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethanone (17), 4-hydroxy-3,5,5-trimethyl-4-(1,2,3-trihydroxybutyl)cyclohex-2-enone (18) could scavenge DPPH radical by more than 20%. Compounds (E)-1-(2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1), (E)-1-(3-((E)-3,7-dimethylocta-2,6-dienyl)-2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (2), (E)-1-(2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (3), 7-hydroxy-6-(3-methylbut-2-enyl)-2H-chromen-2-one (5), 10-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[6,5-H]chromen-9-yl)-3-methylbut-2-enoate (9), 2-(4-hydroxyphenyl)-7-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one (16), (10S,15R,Z)-10,15-dihydroxyheptadeca-8,16-dien-11,13-diynyl acetate (20), (3R,8S,Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol (21) exhibited excellent α-glucosidase inhibition activity.Highlights► A LC–MS method was applied to reveal compounds with QR induction activity. ► Twenty three compounds, including two new ones were isolated from Angelica keiskei. ► Isolated compounds showed QR induction and α-glucosidase inhibiting activities. ► Isolated compounds could scavenge DPPH.
Co-reporter:Liping Luo, Liming Shen, Fang Sun, Yujie Dai, Heng Zheng, Zhongjun Ma, Ying Xu and Zengjun Guo
Analytical Methods 2012 vol. 4(Issue 1) pp:230-235
Publication Date(Web):09 Dec 2011
DOI:10.1039/C1AY05659J
Aromatase (CYP19), which can catalyze the conversion of androgens to estrogens, has been one of the main inducers of hormone-related cancers. As a result, it is very important and necessary to find an aromatase inhibitor quickly and effectively. In this article, we screened for compounds that can bind to aromatase in the extract of Broussonetia papyrifera. The screening method HPLC/ESI-MS was employed in this presentation. Structures of twelve compounds were studied on the basis of LC-MS data. Six compounds were characterized as aromatase ligands through HPLC. Three of the ligands were identified as the glucosides of scopoletin, kaempferol and apigenin, whilst the others were vitexin, luteolin-7-O-β-D-glucopyranosid and dihydrochalcone. The bioassay indicated these compounds had aromatase inhibitory activity. We concluded that HPLC/ESI-MS was an effective means to reveal aromatase ligands. Moreover, five of the ligands found in this study were flavonoids. The C2, C3 double bond and the 7-OH were essential for the binding activity, which may be the binding sites for flavonoids.
Co-reporter:Fang Sun, Liming Shen, Zhongjun Ma
Food Chemistry 2011 Volume 126(Issue 3) pp:1337-1343
Publication Date(Web):1 June 2011
DOI:10.1016/j.foodchem.2010.11.096
Aromatase, a cytochrome P450 (CYP19) enzyme that catalyses the conversion of androgens to oestrogens, is an important target for breast cancer therapy. Flavonoid has been proved to be potential therapeutic agent for breast cancer by inhibiting the activity of aromatase and is one of the main active constituents of mulberry leaves. In this study, twelve flavonoids, 3,5,7,3′,4′-pentahydroxyflavone-3-glucosyl-glucoside/3,5,7,3′,4′-pentahydroxyflavone-3,7-diglucoside, mulberroside F, 3,5,7,3′,4′-pentahydroxyflavone-3-(6″-malonyl)-glucoside, 3,5,7,4′-tetrahydroxyflavone-3-(6″-malonyl)-glucoside, 3,5,7,4′-tetrahydroxyflavone-3-O-(6″-acetyl)-glucoside, 3,5,7,3′,4′-pentahydroxyflavone-3-rutinoside, 3,5,7,3′,4′-pentahydroxyflavone-3-glucoside/3,5,7,2′,4′-pentahydroxyflavone-3-glucoside, kuwanon G, 5,7,3′,4′-tetrahydroxyflavone-7-rutinoside/3,5,7,4′-tetrahydroxyflavone-3-rutinoside, 3,5,7,4′-tetrahydroxyflavone-3-glucoside, 3,5,7,3′,4′-pentahydroxyflavone-3-O-(6″-acetyl)-glucoside and chalcomoracin/mongolicin F, and three fatty acids, 9,12,15-octadecatrienoic acid, compounds 12 and 13, were tentatively identified by HPLC-DAD-ESI-MS/MS method. Seven of the compounds, 3,5,7,3′,4′-pentahydroxyflavone-3-rutinoside, 3,5,7,3′,4′-pentahydroxyflavone-3-glucoside/3,5,7,2′,4′-pentahydroxyflavone-3-glucoside, 3,5,7,4′-tetrahydroxyflavone-3-glucoside, chalcomoracin/mongolicin F and 9,12,15-octadecatrienoic acid, were revealed unequal binding capability for aromatase by HPLC-DAD-ESI-MS/MS.Research highlights► We discovered firstly inhibitors of aromatase from mulberry (Mori albaL.) leaf. ► We used a method by HPLC-MS instead of bio-experiment to discover the inhibitors. ► We have verified our theory by a bio-assay model system. ► The most quality of our method is fast and efficient.
Co-reporter:Lijun Wang, Guodong Lou, Zhongjun Ma, Xueming Liu
Food Chemistry 2011 Volume 126(Issue 3) pp:1081-1087
Publication Date(Web):1 June 2011
DOI:10.1016/j.foodchem.2010.11.133
Litchi (Litchi chinensis Sonn.) is widely accepted as a delicious fruit in China and its seeds have been commonly used in traditional Chinese medicine to relieve neuralgic pain. In the present study, chemical investigation of the 95% ethanol extract of Litchi chinensis seeds led to the isolation of four new compounds, 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β-8-catechin) (5), 2β,3β-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4α-8-epicatechin) (7), litchiol A (9) and litchiol B (12), together with 11 known ones, 2,5-dihydroxy-hexanoic acid (1), soscopoletin (2), coumaric acid (3), protocatechuic acid (4), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β−8)-epicatechin (6), pterodontriol d-6-O-β-d-glucopyranoside (8), Narirutin (10), naringin (11), dihydrocharcone-4′-O-β-d-glucopyranoside (13), pinocembrin-7-rutinoside (14), pinocembrin-7-neohesperidoside (15). Their structures were mainly elucidated on the basis of NMR, MS, IR, CD and UV spectral evidences. Antioxidant activities of 14 compounds were determined by DPPH radical-scavenging assay and Trolox equivalent antioxidant capacity assay, and the results showed that four compounds, protocatechuic acid (4), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β-8-catechin (5), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β−8)-epicatechin (6), 2β,3β-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4α-8)-epicatechin (7), exhibited moderate antioxidant activities.Research highlights► Fifty compounds have been isolated from the seeds of litchi. ► Four compounds (5, 7, 9, 12) have not been reported previously. ► Four compounds (4–7) showed moderate antioxidant activities.
Co-reporter:Xiaoyu Zhang;Zhihang Song;Jinzhong Xu
Chemical Biology & Drug Design 2011 Volume 78( Issue 4) pp:558-566
Publication Date(Web):
DOI:10.1111/j.1747-0285.2011.01171.x
NAD(P)H: quinone oxidoreductase1 (NQO1) is an important detoxification enzyme that can protect mammalian cells against toxic quinones and reduce the risk of tumorigenesis. In this study, it was found that salvianolic acid B (SaB), lithospermic acid (LA), and rosmarinic acid (RA), three main hydrophilic constituents in Danshen, conjugated with glutathione (GSH) easily in vitro but exhibited no NQO1-inducing activities in Hepa 1c1c7 cells, which might attribute to their poor absorptions. After a simple methylation strategy that aimed at improving the liposolubility, both the NQO1-inducing activities and the absorptions in cells of the phenolic acids improved obviously, without losing the GSH-conjugating abilities. The concentration to double the specific activity of NQ01 values of methylated products of lithospermic acid and rosmarinic acid were 17.86 ± 2.34 μg/mL and 11.97 ± 0.60 μg/mL, respectively. The findings indicated that methylation is an effective strategy to improve the NQO1-inducing activities of phenolic acids in Danshen.
Co-reporter:Jinzhong Xu, Juan Lu, Fang Sun, Huanzhang Zhu, Lijun Wang, Xiaoyu Zhang, Zhongjun Ma
Phytochemistry 2011 Volume 72(11–12) pp:1482-1487
Publication Date(Web):August 2011
DOI:10.1016/j.phytochem.2011.03.018
An abietane diterpenoid, triptobenzene Y and six sesquiterpene polyol esters, wilforsinines C–H, together with 14 known compounds, have been isolated from the roots of Tripterygiumwilfordii. The structures of the compounds were elucidated on the basis of spectroscopic analyses. The quinone reductase (QR) induction assay indicated that two compounds showed moderate QR-inducing activities at concentrations of 25 μM and 50 μM, respectively.Graphical abstractAn abietane diterpenoid, triptobenzene Y (1) and six sesquiterpene polyol esters, wilforsinines C–H, together with 14 known compounds all based on the dihydroagarofuran skeleton (2), have been isolated from roots of Tripterygiumwilfordii. Quinone reductase (QR) induction properties were also tested, these having moderate activities.Highlights► Seven previously-unreported and 14 known compounds have been isolated from Tripterygiumwilfordii. ► The seven new compounds including an abietane diterpene and six sesquiterpene polyol esters. ► Sesquiterpene polyol esters showed moderate quinone reductase activities.
Co-reporter:Xiaoyu Zhang and Zhongjun Ma
Analytical Methods 2010 vol. 2(Issue 10) pp:1472-1478
Publication Date(Web):27 Aug 2010
DOI:10.1039/C0AY00305K
In the present study, a simple fluorescein isothiocyanate (FITC)-based screening method was established for the rapid discovery of electrophilic compounds from natural products. The test sample is firstly allowed to alkylate a certain proportion of glutathione (GSH) under basic conditions (pH 8.0), then FITC is added to conjugate with the remaining GSH from the first step. By analyzing the fluorescence intensity of the reaction solution under acidic conditions (pH 3.0), it could be determined whether the test sample contained electrophilic compounds. A botanical sample, the ethyl acetate extract of Radix Salvia miltiorrhiza, was tested using this screening assay and we successfully discovered four electrophilic compounds from it, which were miltirone and its three derivatives (1-oxomiltirone, 4-methylenemiltirone, and 1,2-didehydromiltirone). The findings indicate that the screening method is effective and suitable for high-throughput screening (HTS) assays in the future.
Co-reporter:Lin Cheng;Li-Ming Shen;Min Zhang;Ning Li;Xian Li;Zhong-Jun Ma;Hai-Bin Qu
Helvetica Chimica Acta 2010 Volume 93( Issue 11) pp:2263-2275
Publication Date(Web):
DOI:10.1002/hlca.201000131
Abstract
Eleven new triterpenes, cavalerols A–K (1–11, resp.), ten of which were derivatives of hopane and one was derivative of dammarane, were isolated from the twigs of Eurycorymbus cavaleriei. Their structures were elucidated by spectroscopic methods including 2D-NMR analysis. Cavalerol D (4) and cavalerol F (6), cavalerol B (2), and cavalerol G (7) were two pairs of isomers, and silver ion was introduced for their differentiation by multi-stage tandem mass spectrometry. And nine compounds, except 5 and 10, were tested for quinone reductase (QR) induction activities in vitro, and results showed that compounds 2, 4, and 7 exhibited moderate induction activities with CD values of 8.62, 9.13, and 2.56 μg/ml, respectively, and compounds 6 and 8 showed cytotoxicity against hepa 1c1c7 cell line with IC50 values of no more than 1 μg/ml.
Co-reporter:Lin Cheng, Xiaoyu Zhang, Min Zhang, Peng Zhang, Zhihang Song, Zhongjun Ma, Yiyu Cheng, Haibin Qu
Journal of Chromatography A 2009 Volume 1216(Issue 24) pp:4859-4867
Publication Date(Web):12 June 2009
DOI:10.1016/j.chroma.2009.04.031
In the present study, we examined the potential chemopreventive activity of dichloromethane extract of Eurycorymbus cavaleriei by investigating the change of constitutions after incubation with glutathione (GSH). The major constitutions in the dichloromethane extract of E. cavaleriei were cumarin compounds and their cleavage pattern was examined by LC–MS-MS and the characteristic product ions at m/z 206 and 207 were helpful to determine the substitutions of coumarinolignoid compounds. The mechanism of conjugations of 5′-demethylaquillochin and its isomer with GSH was discussed and validated through analysis of the conjugations of reference compound 6-hydroxy-7-methoxycoumarin with GSH by LC–MS-MS and NMR spectrum. The relative ability to induce the detoxification enzyme, NAD(P)H:quinone oxidoreductase 1 (NQO1) of nine coumarin compounds was tested which also showed 5′-demethylaquillochin exhibited the most potential chemopreventive ability. These observations suggest that 5′-demethylaquillochin and its isomer from the dichloromethane extract of E. cavaleriei have potential as chemopreventive agents through induction of detoxification enzymes.
Co-reporter:Zhongjun Ma, Xiaoyu Zhang
Phytochemistry Letters 2009 Volume 2(Issue 4) pp:152-158
Publication Date(Web):19 November 2009
DOI:10.1016/j.phytol.2009.05.003
From the twigs of Eurycorymbus cavaleriei, seven new benzeneacetic acid derivatives cavaol A–G (1–7) were isolated. The structures were elucidated on the basis of the results of spectroscopic (NMR, IR, UV and MS) analysis. In the present study, the quinone reductase (QR) induction activities of compounds 1–7 were assayed. Compounds 3 and 4 showed moderate QR induction with concentrations to double the enzyme activity (CD) of 9.9 ± 0.3 and 7.9 ± 0.5 μg/mL, respectively. LC-MS-MS analysis revealed that the quinone reductase induction activity of compounds 3 and 4 was not due to alkylating the sulfhydryl groups of Keap1. There must be some other pathways for compounds 3 and 4 to induce quinone reductase.From the twigs of Eurycorymbus cavaleriei, seven new benzeneacetic acid derivatives were isolated. The structures were elucidated on the basis of the results of spectroscopic analysis, mainly NMR and MS. The quinone reductase induction activities of the compounds were also evaluated.
Co-reporter:Peng Zhang, Wei Huang, Zhihang Song, Min Zhang, Lin Cheng, Yiyu Cheng, Haibin Qu, Zhongjun Ma
Phytochemistry Letters 2008 Volume 1(Issue 2) pp:103-106
Publication Date(Web):21 August 2008
DOI:10.1016/j.phytol.2008.05.001
Two new diterpenes, including one with an unprecedented 6/6/8 carbon ring skeleton (curcuminol D, 1) and another with 19 carbons (curcuminol E, 2), were isolated from the radix of Curcuma wenyujin. The structures of 1 and 2 were elucidated on the basis of spectroscopic analysis, mainly NMR and MS. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against the human cancer cell lines HL-60 and K562. Compound 1 exhibited medium cytotoxicity with IC50 values of 11.2 and 3.2 μg/mL, respectively, and compound 2 showed better activity against the above cancer cell lines with IC50 values of 4.2 and 2.7 μg/mL, respectively.Two new unusual diterpenes, curcuminols D and E (1 and 2) were isolated from the Radix of Curcuma wenyujin. Compounds 1 and 2 presented medium cytotoxic activity against the HL-60 and K562 cancer cell lines.
Co-reporter:Wei Huang;Peng Zhang;Ye-Cheng Jin;Qiang Shi;Yi-Yu Cheng;Hai-Bin Qu ;Zhong-Jun Ma
Helvetica Chimica Acta 2008 Volume 91( Issue 5) pp:944-950
Publication Date(Web):
DOI:10.1002/hlca.200890100
Abstract
Bioassay-guided fractionation of ethanolic extract from the root tuber of Curcuma wenyujin afforded three new diterpenes, curcumrinols A–C (1–3), where 2 is the (14S)-epimer of 1. The structures of 1–3 were established on the basis of spectroscopic analysis, mainly NMR and MS. 1–3 were tested in vitro for their cytotoxic activity against the HL-60 and K562 cancer cells. Among the compounds tested, 1 exhibited medium cytotoxicity against K-562 and HL60 human cancer cells with IC50 values of 11.2 and 3.2 μg/ml, respectively. However, 2 showed only weak activity against the above cancers cells, which suggested that C(14) may be an important position for cytotoxic activity.
Co-reporter:Lin Cheng;Zhi-Hang Song;Peng Zhang;Min Zhang;Hai-Bin Qu ;Zhong-Jun Ma
Helvetica Chimica Acta 2008 Volume 91( Issue 9) pp:1659-1661
Publication Date(Web):
DOI:10.1002/hlca.200890181
Abstract
A novel symmetric dimeric compound, cavalerol (1), was isolated from the 95% EtOH extract of the twigs of Eurycorymbus cavaleriei. Compound 1 contains an unprecedented dimeric skeleton with two identical chiral meroterpene moieties.
Co-reporter:Long Ji, Yonglei Yuan, Zhongjun Ma, Zhe Chen, Lishe Gan, Xiaoqiong Ma, Dongsheng Huang
Steroids (September 2013) Volume 78(Issue 9) pp:860-865
Publication Date(Web):1 September 2013
DOI:10.1016/j.steroids.2013.05.008
•Two compounds conjugating with GSH well were identified from the DEPP by UPLC–ESI-MS.•Three new withanolides were isolated and their structures were characterized.•Compounds 1 and 2 had potent QR-induce activity.In the present study, it was demonstrated that the dichloromethane extract of Physalis pubescens L. (DEPP) had weak potential quinone reductase (QR) inducing activity, but an UPLC–ESI-MS method with glutathione (GSH) as the substrate revealed that the DEPP had electrophiles (with an α,β-unsaturated ketone moiety). These electrophiles could induce quinone reductase (QR) activity, which might be attributed to the modification of the highly reactive cysteine residues in Keap1. Herein, four withanolides, including three new compounds physapubescin B (2), physapubescin C (3), physapubescin D (4), together with one known steroidal compound physapubescin (1) were isolated. Structures of these compounds were determined by spectroscopic analysis and that of physapubescin C (3) was confirmed by a combination of molecular modeling and quantum chemical DFT-GIAO calculations. Evaluation of the QR inducing activities of all withanolides indicated potent activities of compounds 1 and 2, which had a common α,β-unsaturated ketone moiety.Download full-size image
Co-reporter:Zhongjun Ma, Xiaoyu Zhang, Lin Cheng, Peng Zhang
Fitoterapia (September 2009) Volume 80(Issue 6) pp:320-326
Publication Date(Web):1 September 2009
DOI:10.1016/j.fitote.2009.04.003
Four compounds, including one new lignan cavaol H (1), one new coumarinolignoid 5′-hydroxycleomiscosin B (4) and two known lignans (2–3) were isolated from the 95% ethanol extract of the twigs of Eurycorymbus cavaleriei. Their structures were established on the basis of various spectroscopic analyses including 1D-(1H, 13C, and DEPT) and 2D-NMR (COSY, HMQC, and HMBC). The absolute stereochemistry of the two known lignans was firstly reported in this article by 1H NMR studies on Mosher's ester derivatives. In the present study, quinone reductase induction activities of compounds 1–4 were assayed, compound 4 showed moderate quinone reductase induction with concentration to double the enzyme activity (CD) of 10.5 ± 0.8 μg/mL. Then we established LC-MS-MS analysis of glutathione (GSH) incubation with compound 4 to explain whether compound 4 induced quinone reductase through alkylating of the sulfhydryl groups of Keap1. Reconstructed selected ion chromatogram (SIC) of m/z 706 after compound 4 incubation with GSH was different from that with Tris–HCl buffer solution, which meant the quinone reductase induction activity of compound 4 attributed to alkylating the sulfhydryl groups of Keap1.Graphical abstractFour compounds, including one new lignan cavaol H (1), one new coumarinolignoid 5′-hydroxycleomiscosin B (4) and two known lignans (2–3) were isolated from the 95% ethanol extract of the twigs of Eurycorymbus cavaleriei. The structures were elucidated on the basis of the results of spectroscopic analysis, mainly NMR and MS. And quinone reductase activities were assayed.Download full-size image
Co-reporter:Hui Ding, Zhijuan Hu, Liyan Yu, Zhongjun Ma, Xiaoqiong Ma, Zhe Chen, Dan Wang, Xiaofeng Zhao
Steroids (August 2014) Volume 86() pp:32-38
Publication Date(Web):1 August 2014
DOI:10.1016/j.steroids.2014.04.015
•Eleven compounds from PA conjugated well with GSH.•Three new withanolides along with four known ones were isolated.•QR induction activity was measured for these compounds.•Two compounds showed potent QR induction activities.•Three compounds showed moderate QR induction activities.In the present study, the EtOAc extract of the persistent calyx of Physalis angulata L. var. villosa Bonati (PA) was tested for its potential quinone reductase (QR) inducing activity with glutathione (GSH) as the substrate using an UPLC–ESI-MS method. The result revealed that the PA had electrophiles that could induce quinone reductase (QR) activity, which might be attributed to the modification of the highly reactive cysteine residues in Keap1. Herein, three new withanolides, compounds 3, 6 and 7, together with four known withanolides, compounds 1, 2, 4 and 5 were isolated from PA extract. Their structures were determined by spectroscopic techniques, including 1H-, 13C NMR (DEPT), and 2D-NMR (HMBC, HMQC, 1H, 1H-COSY, NOESY) experiments, as well as by HR-MS. All the seven compounds were tested for their QR induction activities towards mouse hepa 1c1c7 cells.Graphical abstractDownload full-size image
Co-reporter:Long Ji, Yonglei Yuan, Liping Luo, Zhe Chen, Xiaoqiong Ma, Zhongjun Ma, Lin Cheng
Steroids (April 2012) Volume 77(Issue 5) pp:441-447
Publication Date(Web):1 April 2012
DOI:10.1016/j.steroids.2011.11.016
Michael reaction acceptors (MRAs) are a class of active molecules that are directly or indirectly involved in various cellular processes, including the regulation of many signaling pathways. In this study, the inducible nitric oxide synthase (iNOS) assay was used to demonstrate that the dichloromethane extract of Physalis alkekengi var. franchetii (DCEP) possesses anti-inflammatory activity that might be attributed to the modification of key cysteine residues in IKKβ by the MRAs in DCEP. To isolate these MRAs, glutathione (GSH) was employed, and a simple ultra-performance liquid chromatography/tandem mass spectrometry (UPLC-MS/MS) screening method was developed to investigate the GSH conjugates with potential MRAs. Five physalins, including one new compound isophysalin A (2), together with four known steroidal compounds, physalin A (1), physalin O (3), physalin L (4) and physalin G (5), were isolated to evaluate the GSH conjugating abilities, and it was indicated that compounds 1, 2 and 3, which had a common α,β-unsaturated ketone moiety, exhibited conjugating abilities with GSH and also showed significant nitric oxide (NO) production inhibiting activities. The anti-inflammatory activities of compounds 1, 2 and 3 might be attributed to their targeting multiple cysteine residues on IKKβ; therefore, the alkylation of IKKβ by compound 1 was further studied by micrOTOF-MS. The result showed that six cysteine residues (C59, C179, C299, C370, C412, and C618) were alkylated, which indicated that IKKβ is a potential target for the anti-inflammatory activity of physalin A.Download full-size image
Co-reporter:Wenrong Jin, Qiang Shi, Chengtao Hong, Yiyu Cheng, Zhongjun Ma, Haibin Qu
Phytomedicine (3 September 2008) Volume 15(Issue 9) pp:768-774
Publication Date(Web):3 September 2008
DOI:10.1016/j.phymed.2007.10.007
The dichloromethane fraction of the crude ethanol extract of Echinops grijissi Hance roots exhibited different cytotoxicity against a panel of four human tumor cell lines, HepG2, K562, HL60 and MCF-7. By a bioassay-guided fractionation, eight thiophenes were isolated from the dichloromethane fraction, one of them was isolated from the plant for the first time. And they were assayed for their toxicity against the cell lines in order to compare their relative anti-tumor activity and find candidates of potential anti-tumor drugs. The dichloromethane fraction and isolated thiophenes showed different activity against the cell lines, and the anti-tumor activity of the dichloromethane fraction was also studied in vivo in S180 implanted ICR mice, however, it exhibited no anti-tumor activity at dosage of 20 or 40 mg/kg/d. There were also deaths recorded and the animals showed signs of toxicity when the dosage is 200 mg/kg/d.
Co-reporter:Xiaoyu Zhang, Xiaofeng Zhao, Zhongjun Ma
Toxicology Letters (10 November 2010) Volume 199(Issue 1) pp:93-101
Publication Date(Web):10 November 2010
DOI:10.1016/j.toxlet.2010.08.011
Keap1–Nrf2 pathway has emerged as a regulator for the endogenous antioxidant response, which is critical in defending cells against carcinogenesis. Herein, we demonstrated that depleting the cellular level of glutathione (GSH) by a novel electrophilic agent 2-(pro-1-ynyl)-5-(5,6-dihydroxypenta-1,3-diynyl) thiophene (PYDDT) could activate Keap1–Nrf2 pathway. In above process, it was found that Keap1 was modified by S-glutathionylation, an important post-translational modification of protein cysteines with critical roles in oxidative stress and signal transduction. We concluded from our findings that conjugation with intracellular GSH by PYDDT might lead to Keap1 S-glutathionylation and was a key event involved in its Nrf2 inducing activity.
Co-reporter:
Analytical Methods (2009-Present) 2012 - vol. 4(Issue 1) pp:
Publication Date(Web):
DOI:10.1039/C1AY05659J
Aromatase (CYP19), which can catalyze the conversion of androgens to estrogens, has been one of the main inducers of hormone-related cancers. As a result, it is very important and necessary to find an aromatase inhibitor quickly and effectively. In this article, we screened for compounds that can bind to aromatase in the extract of Broussonetia papyrifera. The screening method HPLC/ESI-MS was employed in this presentation. Structures of twelve compounds were studied on the basis of LC-MS data. Six compounds were characterized as aromatase ligands through HPLC. Three of the ligands were identified as the glucosides of scopoletin, kaempferol and apigenin, whilst the others were vitexin, luteolin-7-O-β-D-glucopyranosid and dihydrochalcone. The bioassay indicated these compounds had aromatase inhibitory activity. We concluded that HPLC/ESI-MS was an effective means to reveal aromatase ligands. Moreover, five of the ligands found in this study were flavonoids. The C2, C3 double bond and the 7-OH were essential for the binding activity, which may be the binding sites for flavonoids.
Co-reporter:Xiaoyu Zhang and Zhongjun Ma
Analytical Methods (2009-Present) 2010 - vol. 2(Issue 10) pp:NaN1478-1478
Publication Date(Web):2010/08/27
DOI:10.1039/C0AY00305K
In the present study, a simple fluorescein isothiocyanate (FITC)-based screening method was established for the rapid discovery of electrophilic compounds from natural products. The test sample is firstly allowed to alkylate a certain proportion of glutathione (GSH) under basic conditions (pH 8.0), then FITC is added to conjugate with the remaining GSH from the first step. By analyzing the fluorescence intensity of the reaction solution under acidic conditions (pH 3.0), it could be determined whether the test sample contained electrophilic compounds. A botanical sample, the ethyl acetate extract of Radix Salvia miltiorrhiza, was tested using this screening assay and we successfully discovered four electrophilic compounds from it, which were miltirone and its three derivatives (1-oxomiltirone, 4-methylenemiltirone, and 1,2-didehydromiltirone). The findings indicate that the screening method is effective and suitable for high-throughput screening (HTS) assays in the future.
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