Jiangyun Liu

Name:

Organization: Soochow University

Department: College of Pharmaceutical Sciences

Title:

Chemicals
References

Chemical characterization, anti-benign prostatic hyperplasia effect and subchronic toxicity study of total flavonoid extract of Pteris multifida

Co-reporter:Guang-Cheng Dai, Bin Hu, Wen-Fang Zhang, Fang Peng, Rong Wang, Zhi-Yuan Liu, Bo-Xin Xue, Jiang-Yun Liu, Yu-Xi Shan

Food and Chemical Toxicology 2017 Volume 108, Part B(Volume 108, Part B) pp:

Publication Date(Web):1 October 2017

DOI:10.1016/j.fct.2016.11.010

•The decoction of Pteris multifida was applied as anti-BPH agents in TCM.•Flavonoid profile of PME was characterized using HPLC-DAD-MS analysis.•PME exhibited anti-BPH potential on testosterone-induced BPH model in vivo.•PME inhibited VEGF expression and activated TGF-β1 expression levels.•The no-observed-adverse-effect level for PME was 200 mg/kg BW/day in SD rats.The decoction of Pteris multifida had been applied to attenuate symptoms of benign prostatic hyperplasia in Chinese folk medicine. In this study, the total flavonoid extract of Pteris multifida was processed at first. High performance liquor chromatography and tandem mass spectrometer assay revealed 10 flavonoids as key constituents of this extract. After 60-day administration, the total flavonoid extract (180 mg/kg, i. g.) decreased the prostate index in mice of benign prostatic hyperplasia apparently. Immunohistochemical assay revealed inhibition of vascular endothelial growth factor expression, together with activation of transforming growth factor-beta 1 expression in the prostatic samples after administration of the extract. A 90-day subchronic toxicity test was further undertaken in male Sprague-Dawley rats, and the no-observed-adverse-effect level for the extract was 200 mg/kg body weight/day. These results revealed that the total flavonoid extract of Pteris multifida exhibited positive effect with safety, which might be applied in treatment of benign prostatic hyperplasia.

Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers

Co-reporter:Mian Dou, Xi-Hui He, Yan Sun, Fang Peng, Jiang-Yun Liu, Li-Li Hao, Shi-Lin Yang

Chinese Chemical Letters 2015 Volume 26(Issue 2) pp:255-258

Publication Date(Web):February 2015

DOI:10.1016/j.cclet.2014.11.021

Acid hydrolysis mechanisms of orientin-2″-O-galactopyranoside (OGA), orientin and other flavone C-glycosides in the trollflowers (Trollius chinensis Bunge) were studied in this report for the first time. Hydrolysis parameters including temperature, acidity, solvent and reaction time were comprehensively investigated. OGA could be hydrolyzed to orientin, followed by an isomerization to isoorientin via a reversible Wessely–Moser rearrangement reaction under stronger acidic conditions. A first-order kinetic model fitted the hydrolysis process of OGA well. Under the optimal hydrolysis conditions of 80 °C, 1.0 mol/L H+ and 7 h reaction time, about 77% OGA was transformed to orientin with no detectable isoorientin. These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides, as well as the preparation of these valuable components under controlled acid hydrolysis conditions.Under controlled acidic conditions, orientin-2″-O-galactopyranoside (1) could be hydrolyzed to orientin (2); orientin (2), and vitexin (3) could be hydrolyzed to corresponding isoorientin (4) or isovetexin (5) via a reversible Wessely–Moser rearrangement reaction. A first-order kinetic model fitted the hydrolysis process of 1.

Synthesis and structure–activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages

Co-reporter:Hao Chen, Bing-Yang Chen, Chun-Ting Liu, Zeng Zhao, Wen-Hao Shao, Hu Yuan, Kai-Jian Bi, Jiang-Yun Liu, Qing-Yan Sun, Wei-Dong Zhang

European Journal of Medicinal Chemistry 2014 Volume 83() pp:307-316

Publication Date(Web):18 August 2014

DOI:10.1016/j.ejmech.2014.06.043

•Derivatives of guaiane-type sesquiterpene lactone 5 were synthesized.•Compounds 6g, 7h, 7k, 7i and 8g exhibited significant inhibitory effects on NO production.•The structure–activity relationships of compounds have been discussed.A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) release were evaluated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds 6g, 7h, 7i, 7k and 8g, exhibited significant inhibitory effects on NO production, with IC50 values of 14.8, 22.3, 18.3, 17.4 and 7.0 μM, respectively. Their cytotoxicities were also estimated using an MTT assay. The structure–activity relationships of these compounds were also discussed.

Preparative separation of crocins and geniposide simultaneously from gardenia fruits using macroporous resin and reversed-phase chromatography

Co-reporter:Jianyong Feng;Xihui He;Sheng Zhou;Fang Peng;Lili Hao;Heran Li;Guizhen Ao;Shilin Yang

Journal of Separation Science 2014 Volume 37( Issue 3) pp:314-322

Publication Date(Web):

DOI:10.1002/jssc.201300601

Gardenia fruits contain valuable natural food colorants including crocins (gardenia yellow) and geniposide. In this study, a process for the enrichment of crocins and geniposide simultaneously from gardenia fruits was developed using macroporous resin and RP chromatography. The performance of eight different types of macroporous resins was evaluated. Static absorption/desorption experiments revealed that LX60 possessed optimal separating capacity. Further dynamic absorption/desorption experiments on LX60 columns were conducted to obtain the optimal parameters. After one run treatment with LX60, the content of crocin-1 in gardenia yellow reached 29.6%, while geniposide in another fraction reached 83.4%. An extract of crocins was obtained from gardenia yellow in a second-stage separation using RP medium-pressure LC, with its color value to be 756 and the content of crocin-1 reaching 60.8%. The separation process was highly efficient, low cost, and compact, which may be informative for purifications of other natural products from complex plant extracts.

Characterization of tautomeric limonoids from the fruits of Melia toosendan

Co-reporter:Sheng Su, Liqin Shen, Yan Zhang, Jiangyun Liu, Jinna Cai, Lili Hao, Yuling Feng, Shilin Yang

Phytochemistry Letters 2013 Volume 6(Issue 3) pp:418-424

Publication Date(Web):August 2013

DOI:10.1016/j.phytol.2013.05.006

•Four nimbolinin-type limonoids were isolated from the fruits of Melia toosendan.•NMR data of tautomers of one new compound were assigned.•Tautomeric behaviors of four compounds were investigated.•Equilibrium equation of nimbolinin was proposed accordingly.Four nimbolinin-type limonoids, 12α/β-1-O-tigloyl-1-O-deacetyl-nimbolinin B (1), 1-deacetylnimbolinin B (2), nimbolinin B (3) and nimbolinin A (4), were isolated from the fruits of Melia toosendan. 1 was a new compound and existed as a mixture of a pair of tautomers, 12α- (1a) and 12β- (1b). The structures of both tautomers were fully determined by extensive spectroscopic methods including UV, IR, NMR and ESI-MS. Tautomeric behaviors and their relative molar ratios in compounds 1–4 were further investigated using optical rotation, TLC, 1H NMR and HPLC. Equilibrium equation of nimbolinin was proposed accordingly, with 12α- and 12β-isomers interchanging via a 12-hemiacetal intermediate.

Controlled acetylation of water-soluble glucomannan from Bletilla striata

Co-reporter:Jiang-yun Liu, Hu-cheng Wang, Yin Yin, Nan Li, Pei-lie Cai, Shi-lin Yang

Carbohydrate Polymers 2012 Volume 89(Issue 1) pp:158-162

Publication Date(Web):5 June 2012

DOI:10.1016/j.carbpol.2012.02.065

Glucomannans from Bletilla striata (bletillan) were used as excipient for controlled deliveries of drugs, genes and tissue engineering. In the present study, a controlled acetylation method was developed to improve water solubility of bletillan 70 (BT) firstly, by reacting with acetic anhydride (AA) in N,N-dimethylformamide solvent. The preparation parameters, such as reaction temperature, reaction time and molar ratio of BT/AA, were optimized based on degrees of acetyl group in addition. IR and 1H NMR spectra were applied to elucidate the reaction process and substitution pattern, which indicated that the acetylation took place at C-6 and C-2 of the hexose units in a ratio of 2:1, with DS up to 0.83. Relative viscosity analysis revealed that the resulted products had improved water solubilities. This novel method is simple, economic and easily controlled.Highlights► A controlled acetylation method of glucomannan from Bletilla striata was developed. ► Reaction parameters including temperature and material molar ratio were optimized. ► IR and 1H NMR spectra were applied to elucidate the substitution pattern. ► The resulted products could improve their water solubility apparently.

Preparative purification of peoniflorin and albiflorin from peony rhizome using macroporous resin and medium-pressure liquid chromatography

Co-reporter:Rong Wang;Xiaoguo Peng;Liming Wang;Beibei Tan;Yulin Feng;Shilin Yang

Journal of Separation Science 2012 Volume 35( Issue 15) pp:1985-1992

Publication Date(Web):

DOI:10.1002/jssc.201200120

Peoniflorin (PF) and albiflorin (AF) are two principal components of Paeonia species, which exhibit various biological activities such as improvement of blood circulation and immunoregulating function. To further utilization of waste parts of peony plants, an efficient method for preparative purification of these two ingredients from white peony rhizome was developed based on macroporous resin (MAR) and medium-pressure liquid chromatography (MPLC). The separation characteristics of nine typical MARs were investigated by static adsorption/desorption experiments, and LX38 was revealed as optimal one. Further static experiments with LX38 resin indicated that the adsorbents fitted well to the pseudo-second-order kinetics model and both Langmuir and Freundlich isotherm models. Based on the optimal process parameters, a large-scale preparation was successfully applied. After one run treatment with LX38, the contents of PF and AF were increased 15-fold to 24.5 and 16.8% in the refined extract, respectively. Both purified compounds were obtained from refined extract by reversed-phase MPLC at second-stage separation. The process developed is better because of its low cost, high efficiency, and procedural simplicity making it a potential approach for large-scale production of PF and AF for their further applications in functional foods and pharmaceuticals.

Simultaneous Purification of Pulchinenoside B4 and B5 from Pulsatilla chinensis Using Macroporous Resin and Preparative High Performance Liquid Chromatography

Co-reporter:Liming Wang, Qiongming Xu, Sheng Su, Jiangyun Liu, Yulin Feng, Xiaoran Li, Weifeng Zhu, and Shilin Yang

Industrial & Engineering Chemistry Research 2012 Volume 51(Issue 45) pp:14859

Publication Date(Web):October 18, 2012

DOI:10.1021/ie302165v

Pulchinenoside B4 and B5 (PB4, PB5) are two major triterpenoid saponins existing in the roots of Pulsatilla chinensis (Bunge) Regel. In this study, a systematic preparative process was developed for the simultaneous purification of PB4 and PB5 from the herb. The performance and separation characteristics of nine types of macroporous resins were critically evaluated. Static absorption/desorption experiments revealed that LX17 belonging to the polyacrylate class possessed superior separation properties. Further dynamic absorption/desorption experiments on LX17 column were conducted to obtain the optimal parameters. To obtain both compounds with high purity, a second stage procedure was developed using preparative reversed-phase high performance liquid chromatography with a dynamic axial compression column system. The separation process was high-efficiency and low-cost, which indicated potential for industrial applications.

New triterpenoid saponins from Patrinia scabiosaefolia

Co-reporter:Liang Gao, Lin Zhang, Nan Li, Jiang-Yun Liu, Pei-lie Cai, Shi-lin Yang

Carbohydrate Research 2011 Volume 346(Issue 18) pp:2881-2885

Publication Date(Web):27 December 2011

DOI:10.1016/j.carres.2011.10.008

Phytochemical investigation of the methanol extract from the whole plants of Patrinia scabiosaefolia Fisch. resulted in the isolation of four new triterpenoid saponins (1–4) along with six known compounds (5–10). On the basis of spectroscopic and chemical methods, the structures of the new compounds were established as 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-12β,30-dihydroxy-olean-28,13β-olide (1), 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-12β,30-dihydroxy-olean-28,13β-olide (2), 3-O-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl-12β, 30-dihydroxy-olean-28,13β-olide (3), and 3-O-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl-oleanolic acid 28-O-β-d-glucopyranoside (4), respectively. Compounds 1–3 possess a novel 12β,30-dihydroxy-olean-28,13β-lactone aglycone and a 12β-hydroxy substituent that is rarely found in this kind of triterpenoid saponin.Graphical abstractHighlights► Four new triterpenoid saponins (1–4) were isolated from Patrinia scabiosaefolia. ► Compounds 1-3 possess a novel 12β, 30-dihydroxy-olean-28, 13β-lactone aglycone. ► Their structures were established on the basis of spectroscopic and chemical methods.

Synthesis and cytotoxicity of oleanolic acid trisaccharide saponins

Co-reporter:Liming Wang, Zengshang Wang, Sheng Su, Ying Xing, Yali Li, Ming Li, Jiangyun Liu, Shilin Yang

Carbohydrate Research (10 April 2017) Volume 442() pp:

Publication Date(Web):10 April 2017

DOI:10.1016/j.carres.2017.02.010

•An array of oleanolic acid-type saponins were synthesized.•One-by-one glycosylation strategy was applied to synthesize saponins 1–7.•One-pot sequential glycosylation strategy was adopted to synthesize saponins 8–11.•These saponins showed different cytotoxicities against 3 cancer lines.•Terminal monosaccharides and linkage positions affected their cytotoxicities.An array of oleanolic acid-type saponins based on β-hederin has been synthesized in a linear or one-pot manner. The cell viability assays indicate that synthetic saponins show antiproliferation activities in three cancer cell lines with IC50 values of 2.4–15.1 μM and hederacolchiside A1 being the most potent. The results demonstrate that the type of terminal monosaccharides and linkage position have apparent effects on cytotoxicities and selectivities of these saponins against cancer cell lines tested. This study is helpful for future development of more potent anticancer leads.