Cyclopeptides have been investigated phytochemically less often because until now there has not been a special chemical method to detect them. Since we found cyclopeptides in Pseudostellaria heterophylla (Caryophyllac...Cyclopeptides have been investigated phytochemically less often because until now there has not been a special chemical method to detect them. Since we found cyclopeptides in Pseudostellaria heterophylla (Caryophyllaceae) in 1991, we have gradually established a special chemical detection method for detecting cyclopeptides in plants, which induces a new thin layer chromatography (TLC) protosite reaction with ninhydrin reagent. With this method, our group isolated and determined 73 cyclopeptides from 17 plants which belong to 5 families and 14 genuses, they are from dicyclopeptides to undecacyclopeptides, including 68 new ones, and were determined based on spectral, chemical and enzymic methods, especially 2D NMR and FAB-MS. Meantime, with this method cyclopeptides can be distinguished from peptidic amides based on their behaviour in TLC.展开更多
In the previous papers, we reported the isolation and structural elucidation of three new cyclopeptides, namely stellarin A, B and C, from the fresh roots of stellaria yunnanensis Franch. In a continued study on this... In the previous papers, we reported the isolation and structural elucidation of three new cyclopeptides, namely stellarin A, B and C, from the fresh roots of stellaria yunnanensis Franch. In a continued study on this plant, other two new cyclopeptides named stellarin D(1) and E(2) were obtained and their structures were established to be cyclo (Gly-Tyr-Leu-Phe-Pro-Ile-Pro)(1), cyclo(Gly-Ile-Pro-Tyr-Ile-Ala-Ala)(2), respectively.展开更多
In the previous papers, we reported the structural elucidation of stellarins A-E, five new cyclopeptides from the fresh roots of Stellaria yunnanensis Franch. Further chemical study on this plant led to the isolation ...In the previous papers, we reported the structural elucidation of stellarins A-E, five new cyclopeptides from the fresh roots of Stellaria yunnanensis Franch. Further chemical study on this plant led to the isolation of two other new cyclopeptide named stellarins F(1) and G(2). By a combination of 2D-NMR, enzymatic degradation and FABMS, their structures were established to by cyclo(Gly-Ala-Gly-Ser-Pro-Trp-Phe-Pro) and cyclo(Gly-Ala-Tyr-Leu-Ala), respectively.展开更多
Two cyclopeptides,heterophyllin A and B,have been isolated from the roots of Pseudostellaria heterophylla.Their structures were elucidated by chemical, spectroscopic,and enzymatic methods.
The crude enzyme (PH-1) isolated from Pseudostellaria heterophylla by ourgroup has catalyzed enzymatic cyclization of linear peptideNH_2-Gly^1-Gly^2-Leu-Pro-Pro-Pro-lle-Phe-COOH (4) into cyclopeptide heterophyllin B (...The crude enzyme (PH-1) isolated from Pseudostellaria heterophylla by ourgroup has catalyzed enzymatic cyclization of linear peptideNH_2-Gly^1-Gly^2-Leu-Pro-Pro-Pro-lle-Phe-COOH (4) into cyclopeptide heterophyllin B (HB) from plantfor the first time. To ensure this reaction, some analytical methods including TLC, HPLC, MS, NMR,and ^(13)C labeling were used to prove that the reaction of substrate 4 sharing residue ofNH-Phe-Gly-CO was successful.展开更多
Two cyclopeptides, celogentin L(1) and its epimer lyciumin A(2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1 D-, 2...Two cyclopeptides, celogentin L(1) and its epimer lyciumin A(2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1 D-, 2 D-NMR, and HR-ESI/MS. The absolute configurations of amino acid components were assigned via chiral-phase HPLC analyses after acid hydrolysis. Furthermore, the configuration of C-N linkage at the glycine Cα was elucidated by extensive analyses of 2 D-NMR and comparison of the experimental and calculated electronic circular dichroism(ECD) spectra. Cytotoxicity of the two compounds against human alveolar epithelial A549, hepatocellular carcinoma Hep G2, and cervical cancer Hela cell lines was assayed. Although both of them were inactive in these cells, the present findings add new facets for the chemistry of Celosia argentea.展开更多
文摘Cyclopeptides have been investigated phytochemically less often because until now there has not been a special chemical method to detect them. Since we found cyclopeptides in Pseudostellaria heterophylla (Caryophyllaceae) in 1991, we have gradually established a special chemical detection method for detecting cyclopeptides in plants, which induces a new thin layer chromatography (TLC) protosite reaction with ninhydrin reagent. With this method, our group isolated and determined 73 cyclopeptides from 17 plants which belong to 5 families and 14 genuses, they are from dicyclopeptides to undecacyclopeptides, including 68 new ones, and were determined based on spectral, chemical and enzymic methods, especially 2D NMR and FAB-MS. Meantime, with this method cyclopeptides can be distinguished from peptidic amides based on their behaviour in TLC.
基金Project supported by grants from Laboratory of Phytochemistry Kunming Institute of Botany, Chinese Academy of Sciences and State Key Laboratory of Bio-organic & Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Science
文摘 In the previous papers, we reported the isolation and structural elucidation of three new cyclopeptides, namely stellarin A, B and C, from the fresh roots of stellaria yunnanensis Franch. In a continued study on this plant, other two new cyclopeptides named stellarin D(1) and E(2) were obtained and their structures were established to be cyclo (Gly-Tyr-Leu-Phe-Pro-Ile-Pro)(1), cyclo(Gly-Ile-Pro-Tyr-Ile-Ala-Ala)(2), respectively.
基金Project supproted by grants from Laboratory of Phytochemistry,Kunming Institute of Botany,Chinese Academy of Sciences and State Key Laboratory of Bio-Organic Chemistry & Natural Products,Chinese Academy of Sciences.
文摘In the previous papers, we reported the structural elucidation of stellarins A-E, five new cyclopeptides from the fresh roots of Stellaria yunnanensis Franch. Further chemical study on this plant led to the isolation of two other new cyclopeptide named stellarins F(1) and G(2). By a combination of 2D-NMR, enzymatic degradation and FABMS, their structures were established to by cyclo(Gly-Ala-Gly-Ser-Pro-Trp-Phe-Pro) and cyclo(Gly-Ala-Tyr-Leu-Ala), respectively.
文摘Two cyclopeptides,heterophyllin A and B,have been isolated from the roots of Pseudostellaria heterophylla.Their structures were elucidated by chemical, spectroscopic,and enzymatic methods.
文摘The crude enzyme (PH-1) isolated from Pseudostellaria heterophylla by ourgroup has catalyzed enzymatic cyclization of linear peptideNH_2-Gly^1-Gly^2-Leu-Pro-Pro-Pro-lle-Phe-COOH (4) into cyclopeptide heterophyllin B (HB) from plantfor the first time. To ensure this reaction, some analytical methods including TLC, HPLC, MS, NMR,and ^(13)C labeling were used to prove that the reaction of substrate 4 sharing residue ofNH-Phe-Gly-CO was successful.
基金financially supported by the National Natural Science Foundation of China(Nos.81322051 and 31400300)the Natural Science Foundation of Jiangsu Province(No.BK20151442)the Project Funded by the Priority Academic Program Development(PAPD) of Jiangsu Higher Education Institutions
文摘Two cyclopeptides, celogentin L(1) and its epimer lyciumin A(2) were firstly isolated from Celosia argentea L.. The planar structures of the two compounds were fully determined by spectroscopic data, including 1 D-, 2 D-NMR, and HR-ESI/MS. The absolute configurations of amino acid components were assigned via chiral-phase HPLC analyses after acid hydrolysis. Furthermore, the configuration of C-N linkage at the glycine Cα was elucidated by extensive analyses of 2 D-NMR and comparison of the experimental and calculated electronic circular dichroism(ECD) spectra. Cytotoxicity of the two compounds against human alveolar epithelial A549, hepatocellular carcinoma Hep G2, and cervical cancer Hela cell lines was assayed. Although both of them were inactive in these cells, the present findings add new facets for the chemistry of Celosia argentea.
