qingyao shou - Academia.edu (original) (raw)
Papers by qingyao shou
Se pu = Chinese journal of chromatography / Zhongguo hua xue hui, 2010
A method of reversed-phase high performance liquid chromatography (RP-HPLC) using diode array det... more A method of reversed-phase high performance liquid chromatography (RP-HPLC) using diode array detection (DAD) was developed for the quantitative determination of 3'-geranyl-5,7,4'-trihydroxyisoflavone (compound 1) and 8,9-dihydroxy-1-methoxy-[6',6'-dimethylpyrano(2',3': 2,3)]pterocarpene (compound 2) in Campylotropis hirtella. The separation and quantification were achieved using an Agilent Zorbax SB-C18 column (250 mm x 4.6 mm, 5 microm), and mobile phases of acetonitrile and 0. 1% formic acid with gradient elution at a flow rate of 1.0 mL/min and 30 degrees C. The calibration curves for compounds 1 and 2 were linear in the ranges of 4.4-13.2 microg and 0.428-1.284 microg, respectively. The recoveries were 99.65% and 99.11% with the relative standard deviations of 1.83% and 2.59% (n=5), respectively. This RP-HPLC-DAD method is rather simple, accurate and convenient. It can be used for the quantitative determination of the active flavonoids in Campylotropis h...
Se pu = Chinese journal of chromatography / Zhongguo hua xue hui, 2008
A method of reversed-phase high performance liquid chromatography (HPLC) coupled with evaporative... more A method of reversed-phase high performance liquid chromatography (HPLC) coupled with evaporative light scattering detection (ELSD) was developed for the determination of jervine and veratramine in veratrum plants. The extraction method of total active alkaloids from the raw material was also established. The separation and quantification were achieved using a Kromasil C8column (250 mm x 4.6 mm, 5 microm), and a mobile phase of acetonitrile and 0.1% trifluoroacetic acid with the following gradient elution: 20% acetonitrile at the first 5 mm, 20%-40% acetonitrile at the 5-30 mm, 40%-20% acetonitrile at the 30-40 mm, 20% acetonitrile at the 40-45 mm with a flow rate of 0.8 mL/min; column temperature of 35 t and monitored by an ELSD detector with the drift tube of 98 t and the nitrogen flow rate of 2.2 L/min. The calibration curves for jervine and veratramine were linear over the ranges of 42.05-980 mg/L and 43.52-1020 mg/L, respectively. The recoveries were 99.2% and 101.4% with relat...
Tetrahedron Letters, 2009
ABSTRACT Two novel diterpenoids were isolated from the bulbs of Fritillaria anhuiensis S. C. Chen... more ABSTRACT Two novel diterpenoids were isolated from the bulbs of Fritillaria anhuiensis S. C. Chen and S. E. Yin. Compound 1 was the first diterpenoid containing a sulfonyl group isolated from nature. Compound 2 was a novel kaurane-type diterpenoid. Their structures were determined by extensive spectroscopic analysis (IR, MS, NMR, and X-ray diffraction). Compound 1 significantly attenuated nitric oxide (NO) production of a macrophage cell line of Raw 264.7 cells stimulated with IFN-γ.
Planta Medica, 2010
From the dried roots of Campylotropis hirtella (Franch.) Schindl., five novel isoflavonoids, 3( S... more From the dried roots of Campylotropis hirtella (Franch.) Schindl., five novel isoflavonoids, 3( S)-7,2',4'-trihydroxy-5,5'-dimethoxy-6-(3-methylbut-2-enyl)-isoflavan ( 1), 3( S)-2',4'-dihydroxy-5,5'-dimethoxy-(6'',6''-dimethylpyrano)-(2'',3'':7,6)-isoflavan ( 2), 3( R)-5,4'-dihydroxy-2'-methoxy-3'-(3-methylbut-2-enyl)-(6'',6''-dimethylpyrano)-(7,6 : 2'',3'')-isoflavanone ( 3), 3( R)-5,4'-dihydroxy-2'-methoxy-(6'',6''-dimethylpyrano)-(7,6: 2'',3'')-isoflavanone ( 4), and 3( R)-5,4'-dihydroxy-7,2'-dimethoxy-6-geranylisoflavanone ( 5) were isolated. The structures of the compounds were elucidated on the basis of spectroscopic analysis. All isolates exhibited good immunosuppressive activities on mitogen-induced splenocyte proliferation, and their cytotoxicity on splenic lymphocytes was also tested.
Journal of Agricultural and Food Chemistry, 2009
In an effort to identify new immunosuppressive agents from natural sources, 12 new geranylated fl... more In an effort to identify new immunosuppressive agents from natural sources, 12 new geranylated flavonoids, 5,7,4 0-trihydroxy-3 0-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]isoflavone (1), a racemate of 5,7,2 0 ,4 0-tetrahydroxy-3 0-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]isoflavanone (2), 2 00 (S)-5,7-dihydroxy-[2 00-methyl-2 00-(4-methyl-3-pentenyl)pyrano]-5 00 ,6 00 :3 0 ,4 0-isoflavone (3), (2 00 S,3 00 R,4 00 S)-5,7,3 00 ,4 00-tetrahydroxy[2 00-methyl-2 00-(4-methyl-3-pentenyl)pyrano]-5 00 ,6 00 :3 0 ,4 0-isoflavone (4), a racemate of 3 0-geranyl-5,7,2 0 ,4 0-tetrahydroxyisoflavanone (5), a racemate of 3 0-geranyl-4 0-methoxy-5,7,2 0-trihydroxyisoflavanone (6), 3 0-geranyl-5,7,4 0 ,5 0-tetrahydroxyisoflavone (8), 3 0-geranyl-5,7,2 0 ,5 0-tetrahydroxyisoflavone (9), 3 0-geranyl-4 0-methoxy-5,7,2 0-trihydroxyisoflavone (10), 2(R),3(R)-3 0-geranyl-2,3-trans-5,7,4 0-trihydroxyflavonol (12), (2R,3R)-6-methyl-3 0-geranyl-2,3-trans-5,7,4 0-trihydroxyflavonol (13), and 5,7-dihydroxy-4 0-O-geranylisoflavone (14), were isolated from the roots of Campylotropis hirtella (Franch.) Schindl. together with three previously described flavonoids. Their structures were elucidated by spectroscopic measurements, including two-dimensional nuclear magnetic resonance (NMR) techniques. The immunosuppressive effects of these compounds were assessed using mitogen-induced splenocyte proliferation, and the cytotoxicity of the compounds was also examined. The IC 50 values of the compounds were found to be in the range of 1.49-61.23 μM for T lymphocyte suppression and 1.16-73.07 μM for B lymphocyte suppression. An analysis of their structure-activity relationships revealed that an isoflavonoid carbon skeleton with a C10 substituent at the C3 0 position was necessary for the activity. As many of the compounds exhibited good immunosuppressive activities, they may be promising as novel immunosuppressive agents.
Bioorganic & Medicinal Chemistry Letters, 2009
A pair of isomeric isoflavonoid derivatives, Hirtellanines A (1) and B (2), has been isolated fro... more A pair of isomeric isoflavonoid derivatives, Hirtellanines A (1) and B (2), has been isolated from the roots of Campylotropis hirtella (Franch.) Schindl. and their structures were elucidated on the basis of spectroscopic methods, with special emphasis on 1D and 2D NMR techniques. The in vitro assay showed that
RSC Advances, 2014
Four unusual phloroglucinol-sesquiterpene adducts, rhodomyrtals A–D (1–4), representing two unpre... more Four unusual phloroglucinol-sesquiterpene adducts, rhodomyrtals A–D (1–4), representing two unprecendented carbon frameworks of phloroglucinol coupled eudesmane with the linkage at C-12′, were isolated from Rhodomyrtus psidioides.
Genetics, Jul 11, 2017
It is crucial for animal survival to detect dangers such as predators. A good indicator of danger... more It is crucial for animal survival to detect dangers such as predators. A good indicator of dangers is injury of conspecifics. Here we show that fluids released from injured conspecifics invoke acute avoidance in both free-living and parasitic nematodes. Caenorhabditis elegans avoids extracts from closely related nematode species but not fruit fly larvae. The worm extracts have no impact on animal lifespan, suggesting that the worm extract may function as an alarm instead of inflict physical harm. Avoidance of the worm extract requires the function of a cGMP signaling pathway that includes the cGMP-gated channel TAX-2/TAX-4 in the amphid sensory neurons ASI and ASK. Genetic evidence indicates that the avoidance behavior is modulated by the neurotransmitters GABA and serotonin, two common targets of anxiolytic drugs. Together, these data support a model that nematodes use a nematode-specific alarm pheromone to detect conspecific injury.
The Biochemical journal, Jun 1, 2016
L-Rhamnose is a common component of cell-wall polysaccharides, glycoproteins and some natural pro... more L-Rhamnose is a common component of cell-wall polysaccharides, glycoproteins and some natural products in bacteria and plants, but is rare in fungi and animals. In the present study, we identify and characterize a biosynthetic pathway for dTDP-rhamnose in Caenorhabditis elegans that is highly conserved across nematode species. We show that RML-1 activates glucose 1-phosphate (Glc-1-P) in the presence of either dTTP or UTP to yield dTDP-glucose or UDP-glucose, respectively. RML-2 is a dTDP-glucose 4,6-dehydratase, converting dTDP-glucose into dTDP-4-keto-6-deoxyglucose. Using mass spectrometry and NMR spectroscopy, we demonstrate that coincubation of dTDP-4-keto-6-deoxyglucose with RML-3 (3,5-epimerase) and RML-4 (4-keto-reductase) produces dTDP-rhamnose. RML-4 could only be expressed and purified in an active form through co-expression with a co-regulated protein, RML-5, which forms a complex with RML-4. Analysis of the sugar nucleotide pool in C. elegans established the presence of...
Nature chemical biology, Oct 8, 2016
Polyketides and nonribosomal peptides are two important types of natural products that are produc... more Polyketides and nonribosomal peptides are two important types of natural products that are produced by many species of bacteria and fungi but are exceedingly rare in metazoans. Here, we elucidate the structure of a hybrid polyketide-nonribosomal peptide from Caenorhabditis elegans that is produced in the canal-associated neurons (CANs) and promotes survival during starvation-induced larval arrest. Our results uncover a novel mechanism by which animals respond to nutrient fluctuations to extend survival.
Natural Product Communications, 2019
Seven new oleanane-type triterpenoid saponins (glabasaponin A-G) were isolated from the roots of ... more Seven new oleanane-type triterpenoid saponins (glabasaponin A-G) were isolated from the roots of Glycyrrhiza glabra together with a known compound macedonoside A. The structures of compounds 1-7 were determined on the basis of 1D and 2D NMR as well as the MS data analyses. The sugar moieties of compound 5 were confirmed by gas chromatography after hydrolysis.
Tetrahedron Letters, 2013
Pilidiostigmin, a novel dimeric acylphloroglucinol derivative, was isolated from the leaves of th... more Pilidiostigmin, a novel dimeric acylphloroglucinol derivative, was isolated from the leaves of the Australian plant species Pilidiostigma glabrum (Myrtaceae). Pilidiostigmin exists in the plant in the form of a sodium salt, which is rare in natural products. The elucidation of the structure and relative configuration was achieved by spectroscopic measurements with special emphasis on 1D and 2D NMR techniques. Pilidiostigmin was found to display biological activity; it significantly and dose-dependently inhibited the synthesis of nitric oxide in LPS-stimulated RAW 264.7 macrophages at low micromolar concentrations.
Se pu = Chinese journal of chromatography / Zhongguo hua xue hui, 2010
A method of reversed-phase high performance liquid chromatography (RP-HPLC) using diode array det... more A method of reversed-phase high performance liquid chromatography (RP-HPLC) using diode array detection (DAD) was developed for the quantitative determination of 3'-geranyl-5,7,4'-trihydroxyisoflavone (compound 1) and 8,9-dihydroxy-1-methoxy-[6',6'-dimethylpyrano(2',3': 2,3)]pterocarpene (compound 2) in Campylotropis hirtella. The separation and quantification were achieved using an Agilent Zorbax SB-C18 column (250 mm x 4.6 mm, 5 microm), and mobile phases of acetonitrile and 0. 1% formic acid with gradient elution at a flow rate of 1.0 mL/min and 30 degrees C. The calibration curves for compounds 1 and 2 were linear in the ranges of 4.4-13.2 microg and 0.428-1.284 microg, respectively. The recoveries were 99.65% and 99.11% with the relative standard deviations of 1.83% and 2.59% (n=5), respectively. This RP-HPLC-DAD method is rather simple, accurate and convenient. It can be used for the quantitative determination of the active flavonoids in Campylotropis h...
Se pu = Chinese journal of chromatography / Zhongguo hua xue hui, 2008
A method of reversed-phase high performance liquid chromatography (HPLC) coupled with evaporative... more A method of reversed-phase high performance liquid chromatography (HPLC) coupled with evaporative light scattering detection (ELSD) was developed for the determination of jervine and veratramine in veratrum plants. The extraction method of total active alkaloids from the raw material was also established. The separation and quantification were achieved using a Kromasil C8column (250 mm x 4.6 mm, 5 microm), and a mobile phase of acetonitrile and 0.1% trifluoroacetic acid with the following gradient elution: 20% acetonitrile at the first 5 mm, 20%-40% acetonitrile at the 5-30 mm, 40%-20% acetonitrile at the 30-40 mm, 20% acetonitrile at the 40-45 mm with a flow rate of 0.8 mL/min; column temperature of 35 t and monitored by an ELSD detector with the drift tube of 98 t and the nitrogen flow rate of 2.2 L/min. The calibration curves for jervine and veratramine were linear over the ranges of 42.05-980 mg/L and 43.52-1020 mg/L, respectively. The recoveries were 99.2% and 101.4% with relat...
Tetrahedron Letters, 2009
ABSTRACT Two novel diterpenoids were isolated from the bulbs of Fritillaria anhuiensis S. C. Chen... more ABSTRACT Two novel diterpenoids were isolated from the bulbs of Fritillaria anhuiensis S. C. Chen and S. E. Yin. Compound 1 was the first diterpenoid containing a sulfonyl group isolated from nature. Compound 2 was a novel kaurane-type diterpenoid. Their structures were determined by extensive spectroscopic analysis (IR, MS, NMR, and X-ray diffraction). Compound 1 significantly attenuated nitric oxide (NO) production of a macrophage cell line of Raw 264.7 cells stimulated with IFN-γ.
Planta Medica, 2010
From the dried roots of Campylotropis hirtella (Franch.) Schindl., five novel isoflavonoids, 3( S... more From the dried roots of Campylotropis hirtella (Franch.) Schindl., five novel isoflavonoids, 3( S)-7,2',4'-trihydroxy-5,5'-dimethoxy-6-(3-methylbut-2-enyl)-isoflavan ( 1), 3( S)-2',4'-dihydroxy-5,5'-dimethoxy-(6'',6''-dimethylpyrano)-(2'',3'':7,6)-isoflavan ( 2), 3( R)-5,4'-dihydroxy-2'-methoxy-3'-(3-methylbut-2-enyl)-(6'',6''-dimethylpyrano)-(7,6 : 2'',3'')-isoflavanone ( 3), 3( R)-5,4'-dihydroxy-2'-methoxy-(6'',6''-dimethylpyrano)-(7,6: 2'',3'')-isoflavanone ( 4), and 3( R)-5,4'-dihydroxy-7,2'-dimethoxy-6-geranylisoflavanone ( 5) were isolated. The structures of the compounds were elucidated on the basis of spectroscopic analysis. All isolates exhibited good immunosuppressive activities on mitogen-induced splenocyte proliferation, and their cytotoxicity on splenic lymphocytes was also tested.
Journal of Agricultural and Food Chemistry, 2009
In an effort to identify new immunosuppressive agents from natural sources, 12 new geranylated fl... more In an effort to identify new immunosuppressive agents from natural sources, 12 new geranylated flavonoids, 5,7,4 0-trihydroxy-3 0-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]isoflavone (1), a racemate of 5,7,2 0 ,4 0-tetrahydroxy-3 0-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]isoflavanone (2), 2 00 (S)-5,7-dihydroxy-[2 00-methyl-2 00-(4-methyl-3-pentenyl)pyrano]-5 00 ,6 00 :3 0 ,4 0-isoflavone (3), (2 00 S,3 00 R,4 00 S)-5,7,3 00 ,4 00-tetrahydroxy[2 00-methyl-2 00-(4-methyl-3-pentenyl)pyrano]-5 00 ,6 00 :3 0 ,4 0-isoflavone (4), a racemate of 3 0-geranyl-5,7,2 0 ,4 0-tetrahydroxyisoflavanone (5), a racemate of 3 0-geranyl-4 0-methoxy-5,7,2 0-trihydroxyisoflavanone (6), 3 0-geranyl-5,7,4 0 ,5 0-tetrahydroxyisoflavone (8), 3 0-geranyl-5,7,2 0 ,5 0-tetrahydroxyisoflavone (9), 3 0-geranyl-4 0-methoxy-5,7,2 0-trihydroxyisoflavone (10), 2(R),3(R)-3 0-geranyl-2,3-trans-5,7,4 0-trihydroxyflavonol (12), (2R,3R)-6-methyl-3 0-geranyl-2,3-trans-5,7,4 0-trihydroxyflavonol (13), and 5,7-dihydroxy-4 0-O-geranylisoflavone (14), were isolated from the roots of Campylotropis hirtella (Franch.) Schindl. together with three previously described flavonoids. Their structures were elucidated by spectroscopic measurements, including two-dimensional nuclear magnetic resonance (NMR) techniques. The immunosuppressive effects of these compounds were assessed using mitogen-induced splenocyte proliferation, and the cytotoxicity of the compounds was also examined. The IC 50 values of the compounds were found to be in the range of 1.49-61.23 μM for T lymphocyte suppression and 1.16-73.07 μM for B lymphocyte suppression. An analysis of their structure-activity relationships revealed that an isoflavonoid carbon skeleton with a C10 substituent at the C3 0 position was necessary for the activity. As many of the compounds exhibited good immunosuppressive activities, they may be promising as novel immunosuppressive agents.
Bioorganic & Medicinal Chemistry Letters, 2009
A pair of isomeric isoflavonoid derivatives, Hirtellanines A (1) and B (2), has been isolated fro... more A pair of isomeric isoflavonoid derivatives, Hirtellanines A (1) and B (2), has been isolated from the roots of Campylotropis hirtella (Franch.) Schindl. and their structures were elucidated on the basis of spectroscopic methods, with special emphasis on 1D and 2D NMR techniques. The in vitro assay showed that
RSC Advances, 2014
Four unusual phloroglucinol-sesquiterpene adducts, rhodomyrtals A–D (1–4), representing two unpre... more Four unusual phloroglucinol-sesquiterpene adducts, rhodomyrtals A–D (1–4), representing two unprecendented carbon frameworks of phloroglucinol coupled eudesmane with the linkage at C-12′, were isolated from Rhodomyrtus psidioides.
Genetics, Jul 11, 2017
It is crucial for animal survival to detect dangers such as predators. A good indicator of danger... more It is crucial for animal survival to detect dangers such as predators. A good indicator of dangers is injury of conspecifics. Here we show that fluids released from injured conspecifics invoke acute avoidance in both free-living and parasitic nematodes. Caenorhabditis elegans avoids extracts from closely related nematode species but not fruit fly larvae. The worm extracts have no impact on animal lifespan, suggesting that the worm extract may function as an alarm instead of inflict physical harm. Avoidance of the worm extract requires the function of a cGMP signaling pathway that includes the cGMP-gated channel TAX-2/TAX-4 in the amphid sensory neurons ASI and ASK. Genetic evidence indicates that the avoidance behavior is modulated by the neurotransmitters GABA and serotonin, two common targets of anxiolytic drugs. Together, these data support a model that nematodes use a nematode-specific alarm pheromone to detect conspecific injury.
The Biochemical journal, Jun 1, 2016
L-Rhamnose is a common component of cell-wall polysaccharides, glycoproteins and some natural pro... more L-Rhamnose is a common component of cell-wall polysaccharides, glycoproteins and some natural products in bacteria and plants, but is rare in fungi and animals. In the present study, we identify and characterize a biosynthetic pathway for dTDP-rhamnose in Caenorhabditis elegans that is highly conserved across nematode species. We show that RML-1 activates glucose 1-phosphate (Glc-1-P) in the presence of either dTTP or UTP to yield dTDP-glucose or UDP-glucose, respectively. RML-2 is a dTDP-glucose 4,6-dehydratase, converting dTDP-glucose into dTDP-4-keto-6-deoxyglucose. Using mass spectrometry and NMR spectroscopy, we demonstrate that coincubation of dTDP-4-keto-6-deoxyglucose with RML-3 (3,5-epimerase) and RML-4 (4-keto-reductase) produces dTDP-rhamnose. RML-4 could only be expressed and purified in an active form through co-expression with a co-regulated protein, RML-5, which forms a complex with RML-4. Analysis of the sugar nucleotide pool in C. elegans established the presence of...
Nature chemical biology, Oct 8, 2016
Polyketides and nonribosomal peptides are two important types of natural products that are produc... more Polyketides and nonribosomal peptides are two important types of natural products that are produced by many species of bacteria and fungi but are exceedingly rare in metazoans. Here, we elucidate the structure of a hybrid polyketide-nonribosomal peptide from Caenorhabditis elegans that is produced in the canal-associated neurons (CANs) and promotes survival during starvation-induced larval arrest. Our results uncover a novel mechanism by which animals respond to nutrient fluctuations to extend survival.
Natural Product Communications, 2019
Seven new oleanane-type triterpenoid saponins (glabasaponin A-G) were isolated from the roots of ... more Seven new oleanane-type triterpenoid saponins (glabasaponin A-G) were isolated from the roots of Glycyrrhiza glabra together with a known compound macedonoside A. The structures of compounds 1-7 were determined on the basis of 1D and 2D NMR as well as the MS data analyses. The sugar moieties of compound 5 were confirmed by gas chromatography after hydrolysis.
Tetrahedron Letters, 2013
Pilidiostigmin, a novel dimeric acylphloroglucinol derivative, was isolated from the leaves of th... more Pilidiostigmin, a novel dimeric acylphloroglucinol derivative, was isolated from the leaves of the Australian plant species Pilidiostigma glabrum (Myrtaceae). Pilidiostigmin exists in the plant in the form of a sodium salt, which is rare in natural products. The elucidation of the structure and relative configuration was achieved by spectroscopic measurements with special emphasis on 1D and 2D NMR techniques. Pilidiostigmin was found to display biological activity; it significantly and dose-dependently inhibited the synthesis of nitric oxide in LPS-stimulated RAW 264.7 macrophages at low micromolar concentrations.