Isoflavans

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Luca Rastrelli - One of the best experts on this subject based on the ideXlab platform.

  • cuban and brazilian red propolis botanical origin and comparative analysis by high performance liquid chromatography photodiode array detection electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2011
    Co-Authors: Anna Lisa Piccinelli, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Osmany Cuestarubio, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also ident...

  • Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography-Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry
    'American Chemical Society (ACS)', 2011
    Co-Authors: Anna Lisa Piccinelli, Osmany Cuesta-rubio, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also identified as two C30 Isoflavans, the new retusapurpurin B (19) and retusapurpurin A (20). PPBs and pigments were isolated and unambiguously characterized by 1D and 2D NMR analysis. These results show that red propolis samples from different tropical zones have a similar chemical composition. DEE is the main red propolis source, but the presence of PPBs in BRP suggests the contribution of different botanical sources for Brazilian samples. This chemical information is important for quality control of red propolis and its commercial products and for biological study

  • Chemical constituents of red Mexican propolis
    'American Chemical Society (ACS)', 2010
    Co-Authors: Cinzia Lotti, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Anna Lisa Piccinelli, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Mexican propolis sample has led to the isolation of three new compounds, 1-(30,40-dihydroxy-20-methoxyphenyl)-3-(phenyl)propane (1), (Z)-1-(20-methoxy-40,50-dihydroxyphenyl)-2-(3-phenyl)propene (2) and 3-hydroxy-5,6-dimethoxyflavan (3), together with seven known flavanones, Isoflavans, and pterocarpans. Structural determination, was accomplished by spectroscopic analysis, particularly 2D NMR and ESI-MS/MS techniques. The present study appears to be the first report on the occurrence of isoflavonoids in Mexican propolis. In addition, the presence of compounds with a 1,3-diarylpropane and 1,3-diarylpropene carbon skeleton were found for the first time in propolis. Isolated compounds 1-10 indicated the possible relation between red Mexican propolis and the genus Dalbergia

  • Isoflavonoids isolated from cuban propolis
    Journal of Agricultural and Food Chemistry, 2005
    Co-Authors: Anna Lisa Piccinelli, Ferrara Simone, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Cuban propolis sample has led to the isolation of 11 isoflavonoids (2 isoflavones, 3 Isoflavans, and 6 pterocarpans), together with gallic acid, isoliquiritigenin, and (-)-liquiritigenin. Structural determination, including the absolute stereochemistry, was accomplished by spectroscopic analysis, particularly CD and 2D NMR techniques. The fragmentation behavior of pterocarpans was studied by electrospray ionization (ESI) tandem mass spectrometry (MS/MS) using an ion-trap analyzer, and a generalized fragmentation pathway, useful in the identification and structural characterization of pterocarpans, is proposed. Isoflavonoids are reported for the first time from propolis samples.

Anna Lisa Piccinelli - One of the best experts on this subject based on the ideXlab platform.

  • cuban and brazilian red propolis botanical origin and comparative analysis by high performance liquid chromatography photodiode array detection electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2011
    Co-Authors: Anna Lisa Piccinelli, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Osmany Cuestarubio, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also ident...

  • Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography-Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry
    'American Chemical Society (ACS)', 2011
    Co-Authors: Anna Lisa Piccinelli, Osmany Cuesta-rubio, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also identified as two C30 Isoflavans, the new retusapurpurin B (19) and retusapurpurin A (20). PPBs and pigments were isolated and unambiguously characterized by 1D and 2D NMR analysis. These results show that red propolis samples from different tropical zones have a similar chemical composition. DEE is the main red propolis source, but the presence of PPBs in BRP suggests the contribution of different botanical sources for Brazilian samples. This chemical information is important for quality control of red propolis and its commercial products and for biological study

  • Chemical constituents of red Mexican propolis
    'American Chemical Society (ACS)', 2010
    Co-Authors: Cinzia Lotti, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Anna Lisa Piccinelli, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Mexican propolis sample has led to the isolation of three new compounds, 1-(30,40-dihydroxy-20-methoxyphenyl)-3-(phenyl)propane (1), (Z)-1-(20-methoxy-40,50-dihydroxyphenyl)-2-(3-phenyl)propene (2) and 3-hydroxy-5,6-dimethoxyflavan (3), together with seven known flavanones, Isoflavans, and pterocarpans. Structural determination, was accomplished by spectroscopic analysis, particularly 2D NMR and ESI-MS/MS techniques. The present study appears to be the first report on the occurrence of isoflavonoids in Mexican propolis. In addition, the presence of compounds with a 1,3-diarylpropane and 1,3-diarylpropene carbon skeleton were found for the first time in propolis. Isolated compounds 1-10 indicated the possible relation between red Mexican propolis and the genus Dalbergia

  • Isoflavonoids isolated from cuban propolis
    Journal of Agricultural and Food Chemistry, 2005
    Co-Authors: Anna Lisa Piccinelli, Ferrara Simone, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Cuban propolis sample has led to the isolation of 11 isoflavonoids (2 isoflavones, 3 Isoflavans, and 6 pterocarpans), together with gallic acid, isoliquiritigenin, and (-)-liquiritigenin. Structural determination, including the absolute stereochemistry, was accomplished by spectroscopic analysis, particularly CD and 2D NMR techniques. The fragmentation behavior of pterocarpans was studied by electrospray ionization (ESI) tandem mass spectrometry (MS/MS) using an ion-trap analyzer, and a generalized fragmentation pathway, useful in the identification and structural characterization of pterocarpans, is proposed. Isoflavonoids are reported for the first time from propolis samples.

Mercedes Campo Fernández - One of the best experts on this subject based on the ideXlab platform.

  • cuban and brazilian red propolis botanical origin and comparative analysis by high performance liquid chromatography photodiode array detection electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2011
    Co-Authors: Anna Lisa Piccinelli, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Osmany Cuestarubio, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also ident...

  • Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography-Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry
    'American Chemical Society (ACS)', 2011
    Co-Authors: Anna Lisa Piccinelli, Osmany Cuesta-rubio, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also identified as two C30 Isoflavans, the new retusapurpurin B (19) and retusapurpurin A (20). PPBs and pigments were isolated and unambiguously characterized by 1D and 2D NMR analysis. These results show that red propolis samples from different tropical zones have a similar chemical composition. DEE is the main red propolis source, but the presence of PPBs in BRP suggests the contribution of different botanical sources for Brazilian samples. This chemical information is important for quality control of red propolis and its commercial products and for biological study

  • Chemical constituents of red Mexican propolis
    'American Chemical Society (ACS)', 2010
    Co-Authors: Cinzia Lotti, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Anna Lisa Piccinelli, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Mexican propolis sample has led to the isolation of three new compounds, 1-(30,40-dihydroxy-20-methoxyphenyl)-3-(phenyl)propane (1), (Z)-1-(20-methoxy-40,50-dihydroxyphenyl)-2-(3-phenyl)propene (2) and 3-hydroxy-5,6-dimethoxyflavan (3), together with seven known flavanones, Isoflavans, and pterocarpans. Structural determination, was accomplished by spectroscopic analysis, particularly 2D NMR and ESI-MS/MS techniques. The present study appears to be the first report on the occurrence of isoflavonoids in Mexican propolis. In addition, the presence of compounds with a 1,3-diarylpropane and 1,3-diarylpropene carbon skeleton were found for the first time in propolis. Isolated compounds 1-10 indicated the possible relation between red Mexican propolis and the genus Dalbergia

  • Isoflavonoids isolated from cuban propolis
    Journal of Agricultural and Food Chemistry, 2005
    Co-Authors: Anna Lisa Piccinelli, Ferrara Simone, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Cuban propolis sample has led to the isolation of 11 isoflavonoids (2 isoflavones, 3 Isoflavans, and 6 pterocarpans), together with gallic acid, isoliquiritigenin, and (-)-liquiritigenin. Structural determination, including the absolute stereochemistry, was accomplished by spectroscopic analysis, particularly CD and 2D NMR techniques. The fragmentation behavior of pterocarpans was studied by electrospray ionization (ESI) tandem mass spectrometry (MS/MS) using an ion-trap analyzer, and a generalized fragmentation pathway, useful in the identification and structural characterization of pterocarpans, is proposed. Isoflavonoids are reported for the first time from propolis samples.

Cinzia Lotti - One of the best experts on this subject based on the ideXlab platform.

  • cuban and brazilian red propolis botanical origin and comparative analysis by high performance liquid chromatography photodiode array detection electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2011
    Co-Authors: Anna Lisa Piccinelli, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Osmany Cuestarubio, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also ident...

  • Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography-Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry
    'American Chemical Society (ACS)', 2011
    Co-Authors: Anna Lisa Piccinelli, Osmany Cuesta-rubio, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also identified as two C30 Isoflavans, the new retusapurpurin B (19) and retusapurpurin A (20). PPBs and pigments were isolated and unambiguously characterized by 1D and 2D NMR analysis. These results show that red propolis samples from different tropical zones have a similar chemical composition. DEE is the main red propolis source, but the presence of PPBs in BRP suggests the contribution of different botanical sources for Brazilian samples. This chemical information is important for quality control of red propolis and its commercial products and for biological study

  • Chemical constituents of red Mexican propolis
    'American Chemical Society (ACS)', 2010
    Co-Authors: Cinzia Lotti, Osmany Cuesta-rubio, Ingrid Márquez Hernández, Mercedes Campo Fernández, Anna Lisa Piccinelli, Luca Rastrelli
    Abstract:

    Chemical investigation of a red-type Mexican propolis sample has led to the isolation of three new compounds, 1-(30,40-dihydroxy-20-methoxyphenyl)-3-(phenyl)propane (1), (Z)-1-(20-methoxy-40,50-dihydroxyphenyl)-2-(3-phenyl)propene (2) and 3-hydroxy-5,6-dimethoxyflavan (3), together with seven known flavanones, Isoflavans, and pterocarpans. Structural determination, was accomplished by spectroscopic analysis, particularly 2D NMR and ESI-MS/MS techniques. The present study appears to be the first report on the occurrence of isoflavonoids in Mexican propolis. In addition, the presence of compounds with a 1,3-diarylpropane and 1,3-diarylpropene carbon skeleton were found for the first time in propolis. Isolated compounds 1-10 indicated the possible relation between red Mexican propolis and the genus Dalbergia

Luca Campone - One of the best experts on this subject based on the ideXlab platform.

  • cuban and brazilian red propolis botanical origin and comparative analysis by high performance liquid chromatography photodiode array detection electrospray ionization tandem mass spectrometry
    Journal of Agricultural and Food Chemistry, 2011
    Co-Authors: Anna Lisa Piccinelli, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Osmany Cuestarubio, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also ident...

  • Cuban and Brazilian Red Propolis: Botanical Origin and Comparative Analysis by High-Performance Liquid Chromatography-Photodiode Array Detection/Electrospray Ionization Tandem Mass Spectrometry
    'American Chemical Society (ACS)', 2011
    Co-Authors: Anna Lisa Piccinelli, Osmany Cuesta-rubio, Mercedes Campo Fernández, Cinzia Lotti, Luca Campone, Luca Rastrelli
    Abstract:

    Chemical composition of propolis depends on the specificity of the local flora at the site of collection and thus on the geographic and climatic characteristics of this place. This paper describes a comparative analysis of Cuban red propolis (CRP), Brazilian red propolis (BRP), and Dalbergia ecastophyllum exudates (DEE) by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry. The aim of this study was to investigate the overall chemical profile and the botanical origin of red propolis and to suggest similarities and differences between samples collected in different tropical regions. Isoliquiritigenin (1), liquiritigenin and naringenin (2 and 17), isoflavones (3–4 and 16), Isoflavans (5–7 and 18), and pterocarpans (8–13) were detected in CRP, BRP, and DEE, whereas polyisoprenylated benzophenones (PPBs) guttiferone E/xanthochymol (14a,b) and oblongifolin A (15) were detected only in BRP. Pigments responsible for the red color of DEE and red propolis were also identified as two C30 Isoflavans, the new retusapurpurin B (19) and retusapurpurin A (20). PPBs and pigments were isolated and unambiguously characterized by 1D and 2D NMR analysis. These results show that red propolis samples from different tropical zones have a similar chemical composition. DEE is the main red propolis source, but the presence of PPBs in BRP suggests the contribution of different botanical sources for Brazilian samples. This chemical information is important for quality control of red propolis and its commercial products and for biological study