Phytochemical Analysis and Biological Evaluation of Carob Leaf (Ceratonia siliqua L.) Crude Extracts Using NMR and Mass Spectroscopic Techniques
Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spect...
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| Published in | Molecules (Basel, Switzerland) Vol. 29; no. 22; p. 5273 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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01.11.2024
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| ISSN | 1420-3049 1420-3049 |
| DOI | 10.3390/molecules29225273 |
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| Abstract | Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL−1) and a-glucosidase enzyme (IC50 = 67.5 ± 2.4 μg mL−1) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4-O-glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. |
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| AbstractList | Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL[sup.−1]) and a-glucosidase enzyme (IC[sub.50] = 67.5 ± 2.4 μg mL[sup.−1]) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4-O-glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL-1) and a-glucosidase enzyme (IC50 = 67.5 ± 2.4 μg mL-1) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4-O-glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications.Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL-1) and a-glucosidase enzyme (IC50 = 67.5 ± 2.4 μg mL-1) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4-O-glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL−1) and a-glucosidase enzyme (IC50 = 67.5 ± 2.4 μg mL−1) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4-O-glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on (MIC = 50 μg mL ) and a-glucosidase enzyme (IC = 67.5 ± 2.4 μg mL ) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4- -glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. Carob leaves have gained attention for their bioactive properties and traditional medicinal uses, including as treatment for diabetes, digestive disorders, and microbial infections. The aim of this study was to explore the phytochemical composition of carob leaf acetone extracts using advanced spectroscopic techniques. The combined use of heteronuclear nuclear magnetic resonance (NMR) experiments with 1D selective nuclear Overhauser effect spectroscopy (NOESY) offers detailed structural insights and enables the direct identification and quantification of key bioactive constituents in carob leaf extract. In particular, the NMR and mass spectrometry techniques revealed the presence of myricitrin as a predominant flavonoid, as well as a variety of glycosylated derivatives of myricetin and quercetin, in acetone extract. Furthermore, siliquapyranone and related gallotannins are essential constituents of the extract. The potent inhibitory effects of the carob leaf extract on Staphylococcus aureus (MIC = 50 μg mL −1 ) and a-glucosidase enzyme (IC 50 = 67.5 ± 2.4 μg mL −1 ) were also evaluated. Finally, the antibacterial potency of carob leaf constituents were calculated in silico; digalloyl-parasorboside and gallic acid 4- O -glucoside exert a stronger bactericidal activity than the well-known myricitrin and related flavonoids. In summary, our findings provide valuable insights into the bioactive composition and health-promoting properties of carob leaves and highlight their potential for pharmaceutical and nutraceutical applications. |
| Audience | Academic |
| Author | Grdadolnik, Simona Golič Tzakos, Andreas G. Nikoloudakis, Nikolaos Christou, Atalanti Goulas, Vlasios Parisis, Nikolaos Goričan, Tjaša Gerothanassis, Ioannis P. Venianakis, Themistoklis Botsaris, George |
| AuthorAffiliation | 1 Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece; vethemis@gmail.com (T.V.); nparisis@uoi.gr (N.P.); atzakos@uoi.gr (A.G.T.); igeroth@uoi.gr (I.P.G.) 2 Department of Agricultural Sciences, Biotechnology and Food Science, Cyprus University of Technology, 3603 Lemesos, Cyprus; atalanti.christou@cut.ac.cy (A.C.); n.nikoloudakis@cut.ac.cy (N.N.); george.botsaris@cut.ac.cy (G.B.) 3 Laboratory for Molecular Structural Dynamics, National Institute of Chemistry, Theory Department, Hajdrihova 19, SI-1000 Ljubljana, Slovenia; tjasa.gorican@ki.si (T.G.); simona.grdadolnik@ki.si (S.G.G.) |
| AuthorAffiliation_xml | – name: 1 Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece; vethemis@gmail.com (T.V.); nparisis@uoi.gr (N.P.); atzakos@uoi.gr (A.G.T.); igeroth@uoi.gr (I.P.G.) – name: 2 Department of Agricultural Sciences, Biotechnology and Food Science, Cyprus University of Technology, 3603 Lemesos, Cyprus; atalanti.christou@cut.ac.cy (A.C.); n.nikoloudakis@cut.ac.cy (N.N.); george.botsaris@cut.ac.cy (G.B.) – name: 3 Laboratory for Molecular Structural Dynamics, National Institute of Chemistry, Theory Department, Hajdrihova 19, SI-1000 Ljubljana, Slovenia; tjasa.gorican@ki.si (T.G.); simona.grdadolnik@ki.si (S.G.G.) |
| Author_xml | – sequence: 1 givenname: Themistoklis surname: Venianakis fullname: Venianakis, Themistoklis – sequence: 2 givenname: Nikolaos orcidid: 0000-0003-1473-7970 surname: Parisis fullname: Parisis, Nikolaos – sequence: 3 givenname: Atalanti orcidid: 0000-0003-2130-6538 surname: Christou fullname: Christou, Atalanti – sequence: 4 givenname: Vlasios orcidid: 0000-0001-7527-1559 surname: Goulas fullname: Goulas, Vlasios – sequence: 5 givenname: Nikolaos orcidid: 0000-0002-3935-8443 surname: Nikoloudakis fullname: Nikoloudakis, Nikolaos – sequence: 6 givenname: George orcidid: 0000-0003-3197-6535 surname: Botsaris fullname: Botsaris, George – sequence: 7 givenname: Tjaša orcidid: 0009-0000-7736-7941 surname: Goričan fullname: Goričan, Tjaša – sequence: 8 givenname: Simona Golič orcidid: 0000-0002-0873-9593 surname: Grdadolnik fullname: Grdadolnik, Simona Golič – sequence: 9 givenname: Andreas G. orcidid: 0000-0001-6391-0288 surname: Tzakos fullname: Tzakos, Andreas G. – sequence: 10 givenname: Ioannis P. orcidid: 0000-0002-3745-9902 surname: Gerothanassis fullname: Gerothanassis, Ioannis P. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39598662$$D View this record in MEDLINE/PubMed |
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| Keywords | galloyl derivatives myricetin carob leaf mass spectrometry antimicrobial activity NMR spectroscopy flavonoids carbohydrate digestive enzyme inhibition |
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| Title | Phytochemical Analysis and Biological Evaluation of Carob Leaf (Ceratonia siliqua L.) Crude Extracts Using NMR and Mass Spectroscopic Techniques |
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