Gui-Xin Chou

Shanghai University of Traditional Chinese Medicine, Shanghai, Shanghai Shi, China

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Publications (59)79.56 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Eleven new sesquiterpenoids, wenyujinins A-K (1-11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calculated ECD spectra. The absolute configuration of 5 was determined from the ECD data of the [Rh2(OCOCF3)4] complex, whereas those of 7 and 12 were determined from the ECD spectra of the compounds alone. Compounds 7 and 7a strongly inhibited the induction of NO production by LPS, with IC50 values of 7.6 and 8.5 μM, respectively. Compounds 6 and 10 moderately inhibited NO production with IC50 values of 47.7 and 48.6 μM, respectively.
    Journal of Natural Products 10/2014; · 3.29 Impact Factor
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    ABSTRACT: Six new diterpenoids, 4-epi-7α-O-acetylscoparic acid A (1), 7α-hydroxyscopadiol (2), 7α-O-acetyl-8,17β-epoxyscoparic acid A (3), neo-dulcinol (4), dulcinodal-13-one (5), and 4-epi-7α-hydroxydulcinodal-13-one (6), and a new flavonoid, dillenetin 3-O-(6″-O-p-coumaroyl)-β-d-glucopyranoside (10), along with 12 known compounds, were isolated from the aerial parts of Scoparia dulcis. The 7S absolute configuration of the new diterpenoids 1-4 and 6 was deduced by comparing their NOESY spectra with that of a known compound, (7S)-4-epi-7-hydroxyscoparic acid A (7), which was determined by the modified Mosher's method. The flavonoids scutellarein (11), hispidulin (12), apigenin (15), and luteolin (16) and the terpenoids 4-epi-scopadulcic acid B (9) and betulinic acid (19) showed more potent α-glucosidase inhibitory effects (with IC50 values in the range 13.7-132.5 μM) than the positive control, acarbose. In addition, compounds 1, 11, 12, 15, 16, and acerosin (17) exhibited peroxisome proliferator-activated receptor gamma (PPAR-γ) agonistic activity, with EC50 values ranging from 0.9 to 24.9 μM.
    Journal of natural products. 06/2014;
  • Zan-Shan Xu, Gui-Xin Chou, Zheng-Tao Wang
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    ABSTRACT: A new triglycoside flavone, luteolin-4'-O-α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranoside (1) was isolated from the leaves of Ficus ischnopoda, together with five known flavonoids (2-6) and seven known lignans (7-13). Their structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Compounds 1-13 were reported in this plant for the first time. Compounds 1 and 3-6 exhibited significant anti-HSV-1 activity in vitro.
    Natural product research 04/2014; · 1.01 Impact Factor
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    ABSTRACT: Four diterpenoids (1–4) and two phenylethanoid glycosides were isolated from Clerodendrum bungei roots. Some of the isolated compounds showed angiotensin converting enzyme or α-glucosidase inhibitory effects.
    Phytochemistry 01/2014; · 3.35 Impact Factor
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    ABSTRACT: Four new compounds, impecylone (1), deacetylimpecyloside (2), seguinoside K 4-methylether (3) and impecylenolide (4), were isolated from Imperata cylindrica along with two known compounds, impecyloside (5) and seguinoside K (6). Their structures were elucidated mainly by spectroscopic analyses including 1D- and 2D-NMR techniques, and the absolute configuration of 1 was confirmed by X-ray diffraction analysis. In calcium assay, the result indicated that compounds 1, 2, 4 and 5 cannot obviously inhibit the calcium peak value compared with the negative control, and suggested that the four compounds could not have anti-inflammatory activity.
    Journal of Natural Medicines 07/2013; · 1.52 Impact Factor
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    ABSTRACT: Aim:To explore the effects of norisoboldine (NOR), a major isoquinoline alkaloid in Radix Linderae, on joint destruction in rats with adjuvant-induced arthritis (AIA) and its underlying mechanisms.Methods:AIA was induced in adult male SD rats by intradermal injection of Mycobacterium butyricum in Freund's complete adjuvant at the base of the right hind paw and tail. From d 14 after immunization, the rats were orally given NOR (7.5, 15, or 30 mg/kg) or dexamethasone (0.5 mg/kg) daily for 10 consecutive days. Joint destruction was evaluated with radiological scanning and H&E staining. Fibroblast-like synoviocytes (FLS) were prepared from fresh synovial tissues in the AIA rats. The expression of related proteins and mRNAs were detected by ELISA, Western blotting and RT-PCR.Results:In AIA rats, NOR (15 and 30 mg/kg) significantly decreased the swelling of paws and arthritis index scores, and elevated the mean body weight. NOR (30 mg/kg) prevented both the infiltration of inflammatory cells and destruction of bone and cartilage in joints. However, NOR (15 mg/kg) only suppressed the destruction of bone and cartilage, but did not obviously ameliorate synovial inflammation. NOR (15 and 30 mg/kg) significantly decreased the serum levels of receptor activator of nuclear factor κB ligand (RANKL), IL-6, PGE(2), and MMP-13, but not the osteoprotegerin and MMP-1 levels. The mRNA levels of RANKL, IL-6, COX-2, and MMP-13 in synovium were also suppressed. Dexamethasone produced similar effects in AIA rats as NOR did, but without elevating the mean body weight. In the cultured FLS, treatment with NOR (10 and 30 mmol/L) significantly decreased the secretion of RANKL, IL-6, PGE(2), and MMP-13 proteins. Furthermore, the treatment selectively prevented the activation of MAPKs, AKT and transcription factor AP-1 component c-Jun, but not the recruitment of TRAF6 or the activation of JAK2/STAT3. Treatment of the cultured FLS with the specific inhibitors of p38, ERK, AKT, and AP-1 significantly decreased the secretion of RANKL, IL-6, PGE(2), and MMP-13 proteins.Conclusion:NOR can alleviate joint destruction in AIA rats by reducing RANKL, IL-6, PGE(2), and MMP-13 expression via the p38/ERK/AKT/AP-1 pathway.
    Acta Pharmacologica Sinica 02/2013; · 2.35 Impact Factor
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    ABSTRACT: Norisoboldine (NOR) is the main alkaloid constituent in the dry root of Lindera aggregata (Sims) Kosterm. (L. strychnifolia Vill.). As reported previously, orally administered NOR displayed a robust inhibition of joint bone destruction present in both mouse collagen-induced arthritis and rat adjuvant-induced arthritis with lower efficacious doses than that required for ameliorating systemic inflammation. This attracted us to assess the effects of NOR on differentiation and function of osteoclasts, primary effector cells for inflammatory bone destruction, to get insight into its anti-rheumatoid arthritis mechanisms. Both RAW264.7 cells and mouse bone marrow-derived macrophages (BMMs) were stimulated with RANKL (100 ng/mL) to establish osteoclast differentiation models. ELISA, RT-PCR, gelatin zymography, western blotting, immunoprecipitation and EMSA were used to reveal related signalling pathways. NOR (10 and 30 µM), without significant cytotoxicity, showed significant reduction of the number of osteoclasts and the resorption pit areas, and it targeted osteoclast differentiation at the early stage. In conjunction with the anti-resorption effect of NOR, mRNA levels of cathepsin K and MMP-9 were decreased, and the activity of MMP-9 was attenuated. Furthermore, our mechanistic studies indicated that NOR obviously suppressed the ubiquitination of TRAF6, the accumulation of TRAF6-TAK1 complexes and the activation of ERK and p38 MAPK, and reduced the nuclear translocation of NF-κB-p65 and DNA-binding activity of NF-κB. However, NOR had little effect on expressions of TRAF6 or the phosphorylation and degradation of IκBα. Moreover, NOR markedly inhibited expressions of transcription factor NFATc1, but not c-Fos. Intriguingly, the subsequent nuclear translocations of c-Fos and NFATc1 were substantially down-regulated. Hence, we demonstrated for the first time that preventing the differentiation and function of osteoclasts at the early stage was an important anti-bone destruction mechanism of NOR, which might be attributed to inhibition of ubiquitination of TRAF6, the accumulation of TRAF6-TAK1 complexes and the activation of MAPKs/NF-κB/c-Fos/NFATc1 pathways.
    PLoS ONE 01/2013; 8(3):e59171. · 3.53 Impact Factor
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    ABSTRACT: AimTo study the chemical constituents of the rhizomes of Imperata cylindrica.Methods The compounds were isolated by silica gel and Sephadex LH-20 column chromatography. Their structures were elucidated mainly by spectroscopic analyses including IR, HR-ESI-MS, 1D- and 2D-NMR.ResultsTwo new chromones, 8-hydroxy-2-(2-phenylethyl)chromone (1) and 2-(2-phenylethyl) chromone-8-O-β-D-glucopyranoside (2), and a new flavone glycoside, 4′-methoxyflavone-6-O-β-D-glucopyranoside (5), along with five known compounds, flidersiachromone (3), 5-hydroxy-2-(2-phenylethyl) chromone (4), flavone (6), 4′-hydroxy-5-methoxyflavone (7) and 5-hydroxyflavone (8) were isolated from Imperata cylindrica.Conclusion Compounds 1, 2 and 5 were new compounds.
    Chinese Journal of Natural Medicines 01/2013; 11(1):77–80.
  • Ji-Cheng Shu, Jian-Qun Liu, Gui-Xin Chou
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    ABSTRACT: To investigate the chemical constituents of Verbena officinalis L., five triterpenoid constituents were isolated and elucidated as 3α,19,23-trihydroxyurs-12-en-28-oic acid, namely, 4-epi-barbinervic acid (1), 2α,3β-dihydroxyurs-12-en-28-oic acid (2), 3α,24-dihydroxyurs-12-en- 28-oic acid (3), 3α,24-dihydroxy-olean-12-en-28-oic acid (4), ursolic acid (5), using spectroscopic methods and comparing with published data. Compounds 2 and 4 were obtained from V. officinalis for the first time, and compound 1 is a new triterpenoid compound, which exhibits significantly higher antitumor activity against human hepatoma cell line Bel 7402 in vitro than the blank control.
    Natural product research 10/2012; · 1.01 Impact Factor
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    ABSTRACT: Qian-wang-hong-bai-san (QW), a Chinese herbal formula, is traditionally used as a skin whitening agent in China. Aim of study: In our previous screening assays, QW was identified as an effective tyrosinase inhibitor. In this study, we aim to investigate the underlying mechanism of the anti-melanogenic effect of QW in B16 cells. Cytotoxicity of QW in B16 cell line was examined by MTT assay. Cellular tyrosinase activity was determined based on the melanin content measured at 475 nm with a microplate spectrophotometer. Protein expression was analyzed by Western blotting and quantified by Quantity One. QW dose-dependently inhibited tyrosinase activity and decreased melanin content at 48 h without significant cytotoxicity in B16 cells. Western blot analysis showed that QW treatment down-regulated the expression levels of phospho-p38, phospho-CREB, MITF, tyrosinase, TRP-1 and TRP-2 in a dose-dependent manner. At the same time, QW treatment for 48 h inhibited IBMX-induced elevation of cellular melanin content and tyrosinase activity. However, the attenuation of IBMX-mediated up-regulations of phospho-CREB and phospho-PKA was readily observed with 60 min of QW treatment. The anti-melanogenic activity of QW in B16 melanoma cells can be attributed, at least in part, to the inhibition of the p38 MAPK and PKA signaling pathways. These findings shed new light on the molecular mechanisms of the skin-whitening property of QW.
    Journal of Ethnopharmacology 06/2012; 141(2):622-628. · 2.94 Impact Factor
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    ABSTRACT: The rare noriridoids, Andrographidoids A-E (1-5), along with a known iridoid curvifloruside F (6), were isolated from roots of Andrographis paniculata. All noriridoids were aglycones and 1-4 had (semi-) acetal structures located at C-3 but not at C-1. Their structures were established by a series of 1D and 2D NMR analyses. The antibacterial activity of these iridoids was also assessed using the microtitre plate broth dilution method.
    Phytochemistry 02/2012; 77:275-9. · 3.35 Impact Factor
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    ABSTRACT: Norisoboldine is an alkaloid and has been identified as the major active component in Linderae Radix. A novel method for quantitative analysis of norisoboldine in Linderae Radix using ultra performance liquid chromatography (UPLC) with UV detection was developed for quality control. A similar and conventional HPLC protocol was simultaneously developed for comparison purposes. Chromatographic separation of norisoboldine was performed on an Acquity UPLC BEH C18 column (50 mm × 2.1 mm ID, 1.7 µm) for UPLC and on a Waters X-Bridge C18 column (250 mm × 4.6 mm ID, 5.0 µm) for HPLC. In the UPLC method, the average recovery was 97.3% (n = 9, RSD 1.1%); the limit of detection (LOD) and limit of quantification (LOQ) were 0.151 and 0.302 ng, respectively. In the HPLC method, the average recovery was 98.9% (n = 9, RSD 1.7%); the LOD and LOQ were 1.51 and 3.02 ng, respectively. The UPLC method provided a shorter analysis time, a better sensitivity in detection and quantitation, and less solvent was used in comparing to the HPLC method. The amount of norisoboldine detected in each Linderae Radix sample from different sources were in good agreement in both HPLC and UPLC methods.
    Journal of Liquid Chromatography & Related Technologies - J LIQ CHROMATOGR RELAT TECHNO. 01/2012; 35(6):788-797.
  • Ji-Cheng Shu, Gui-Xin Chou, Zheng-Tao Wang
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    ABSTRACT: To investigate the chemical constituents of Psidium guajava L, the EtOH/H(2)O extract of the fresh leaves was subjected to various chromatography. One diphenylmethane, one benzophenone, and eight flavonoids were isolated and elucidated as 2,6-dihydroxy-3-formaldehyde-5-methyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-diphenylmethane (1), 2,6-dihydroxy-3,5-dimethyl-4-O-(6″-O-galloyl-β-D-glucopyranosyl)-benzophenone (2), kaempferol (3), quercetin (4), quercitrin (5), isoquercitrin (6), guaijaverin (7), avicularin (8), hyperoside (9), reynoutrin (10) by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS spectrometry as well as by comparison with published data. Compounds 5 and 10 are obtained from P. guajava for the first time, and compound 1 is a new diphenylmethane compound.
    Natural product research 11/2011; 26(21):1971-5. · 1.01 Impact Factor
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    ABSTRACT: One new bibenzyl, 7, and one new diarylheptanone, diobulbinone A (18), together with sixteen known compounds, 1-6 and 8-17, have been isolated form the rhizomes of Dioscorea bulbifera. Their structures were elucidated by NMR and MS analyses. Compound 7 showed high antioxidant capacity in FRAP assay and DPPH radical-scavenging activity.
    Chemistry & Biodiversity 11/2011; 8(11):2110-6. · 1.81 Impact Factor
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    ABSTRACT: Atractylenolide II (AT-II) is a sesquiterpene compound isolated from the dried rhizome of Atractylodes macrocephala (Baizhu in Chinese), which is traditionally prescribed for melanoma treatment by Chinese medicine practitioners. Our previous study showed that AT-II can inhibit B16 cells proliferation. Here we investigate the mechanistic basis for the anti-proliferative activity of AT-II in B16 melanoma cells. Cell viability was examined by MTT assay. Cell cycle distribution and apoptosis were determined by flow cytometry. Protein expression was determined by Western blotting. AT-II treatment for 48 h dose-dependently inhibited cell proliferation with an IC(50) of 82.3 μM, and induced G1 phase cell cycle arrest. Moreover, treatment with 75 μM AT-II induced apoptosis. These observations were associated with the decrease of the expression of Cdk2, phosphorylated-Akt, phosphorylated-ERK and Bcl-2, the increase of the expression of phosphorylated-p38, phosphorylated-p53, p21, p27, and activation of caspases-8, -9 and -3. In addition, a chemical inhibitor of p53, PFTα, significantly decreased AT-II-mediated growth inhibition and apoptosis. We demonstrated that the G1-arresting and apoptotic effects of AT-II in B16 cells involve p38 activation as well as ERK and Akt inactivation, and the cytotoxic/apoptotic effects of AT-II are potentially p53 dependent. These findings provided chemical and pharmacological basis for the traditional application of Baizhu in melanoma treatment.
    Journal of ethnopharmacology 06/2011; 136(1):279-82. · 2.32 Impact Factor
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    ABSTRACT: Microbial transformation of cardamonin by Mucor spinosus (CGMCC 3.3450) in preparative scale resulted in the isolation of two new products. Their structures were elucidated unambiguously by ESI-MS, 1H NMR, 13C NMR and 2D NMR spectra analyses as 4-O-beta-D-glucopyranosyl-6-hydroxy-2-methoxychalcone (1, 4-GluC) and 6-O-beta-D-glucopyranosyl-4-hydroxy-2-methoxychalcone (2, 6-GluC), respectively. The time-course of biotransformation by M. spinosus showed that both 4-GluC and 6-GluC appeared on the 2nd day. The optimal biotransformation temperature was 28 degrees C, the optimal biotransformation time was 72 h and the optimal concentration for cardamonin was 40 mg x mL(-1). This is the first time for successful microbial glycosylation of cardamonin in present research.
    Yao xue xue bao = Acta pharmaceutica Sinica 06/2011; 46(6):733-7.
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    ABSTRACT: We investigated the involvement of MAPK pathways in the melanogenic effect of apigenin in B16 cells. Apigenin treatment for 48 h dose (5-20 μm)-dependently up-regulated protein expression levels of microphthalmia-associated transcription factor (MITF) and melanogenic enzymes including tyrosinase, tyrosinase-related protein-1 (TRP-1) and TRP-2 and enhanced the phosphorylation of p38 MAPK, without affecting the phosphorylation of JNK or ERK MAPK. Treatment with 10 μm apigenin time (6-48 h)-dependently elevated the protein expressions of p-p38, MITF and melanogenic enzymes. Moreover, PD169316, a selective inhibitor of p38 kinase, suppressed the stimulatory effects of apigenin on tyrosinase activity and melanin synthesis, which were accompanied by decreased MITF protein expression. In conclusion, apigenin increased melanogenesis in B16 cells, at least in part, by activating the p38 MAPK pathway. The novel findings of this study shed light on the molecular mechanisms underlying the melanogenic activity of apigenin and suggest that apigenin/its derivatives may be potentially used for treating hypopigmentation disorders.
    Experimental Dermatology 05/2011; 20(9):755-7. · 3.58 Impact Factor
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    ABSTRACT: Six iridoids, geleganoids, designated A-F, and five iridoid glycosides, geleganosides A and B together with three previously reported compounds, were isolated from leaves of Gelsemium elegans. Their structures were elucidated by spectroscopic and chemical analyses. The relative configuration of geleganoid A was confirmed by X-ray crystallographic diffraction analysis, and the absolute configuration of geleganoid B was determined by a modified Mosher's method. Selected compounds were evaluated for PC12 cell neurite outgrowth activity, but they were inactive.
    Phytochemistry 04/2011; · 3.35 Impact Factor
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    ABSTRACT: Norisoboldine (NIB) is one of the main bioactive isoquinoline alkaloids in Linderae Radix. A rapid, selective and sensitive method using UPLC-ESI/MS was first developed for simultaneous determination of NIB and norisoboldine-9-O-α-glucuronide (NIB-Glu), its major metabolite in rat plasma. A one-step protein precipitation with methanol was employed as sample preparation technique. Chromatographic separation was carried out on an Acquity UPLC BEH C(18) column (50 × 2.1 mm, i.d. 1.7 µm) with a gradient mobile phase consisting of acetonitrile and water containing 0.1% formic acid. Detection and quantification were performed using a quadrupole mass spectrometer by selective ion reaction-monitoring mode. Good linearity was achieved using weighted (1/x(2) ) least squares linear regression over the concentration ranges 0.01-2 µg/mL for NIB and 0.025-25 µg/mL for NIB-Glu. The lower limit of quantification of NIB and NIB-Glu was 0.01 and 0.025 µg/mL, respectively. The intra- and inter-day precisions (relative standard deviations) of the assay at all three quality control levels were 4.6-14.1% for NIB, and 5.0-12.2% for NIB-Glu. The accuracies (relative error) were -13.5-8.1% for NIB and -12.8-7.6% for NIB-Glu, respectively. This developed method was successfully applied to an in vivo pharmacokinetic study in rats after a single intravenous dose of 10 mg/kg NIB.
    Biomedical Chromatography 03/2011; 25(3):367-72. · 1.95 Impact Factor
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    ABSTRACT: The aims of this study were to isolate sesquiterpene compounds from the largehead atractylodes rhizome (LAR) and to investigate their effects on B16 cancer cells. A total of 8 sesquiterpenes from LAR were identified, of which eudesm-4 (15), 7-diene-9α, 11-diol (7) was isolated for the first time. All 8 compounds inhibited growth of B16 cells, and atractylenolide I (AT-I), atractylenolide II (AT-II), and atractylenolactam (ATR) were the most potent, with IC(50) values of 76.46, 84.02, and 54.88 μΜ, respectively. Monomer lactone or lactam structures in the 8 compounds appeared to be critical for their antiproliferative activities. In addition, AT-I, AT-II, and ATR could induce cell differentiation and inhibit cell migration. Western blot analysis indicated that 2 of the compounds, AT-I and AT-II, could inactivate ERK, where all 3 inhibited AKT activation, suggesting that Ras/ERK and PI3K/AKT signaling pathways are involved in the action mechanisms of the LAR sesquiterpene compounds.
    Integrative Cancer Therapies 03/2011; 10(1):92-100. · 2.35 Impact Factor

Publication Stats

178 Citations
79.56 Total Impact Points

Institutions

  • 2003–2014
    • Shanghai University of Traditional Chinese Medicine
      • • Institute of Chinese Materia Medica
      • • Key Laboratory of Standardization of Chinese Medicines of Ministry of Education
      Shanghai, Shanghai Shi, China
  • 2010–2011
    • Hong Kong Baptist University
      • Centre for Cancer and Inflammation Research (CCIR)
      Kowloon, Hong Kong
  • 2004–2011
    • China Pharmaceutical University
      • Department of Pharmacognosy
      Nan-ching-hsü, Jiangxi Sheng, China
    • Gansu College of Traditional Chinese Medicine
      Kan-shui, Chongqing Shi, China
  • 2003–2007
    • Shanghai University
      Shanghai, Shanghai Shi, China