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Isolation, structural characterization and in silico drug-like properties prediction of a natural compound from the ethanolic extract of Cayratia trifolia (L.).

Perumal PC, Sowmya S, Pratibha P, Vidya B, Anusooriya P, Starlin T, Ravi S, Gopalakrishnan VK - Pharmacognosy Res (2015 Jan-Mar)

Bottom Line: Natural products have continually played an important role in drug discovery because it serves as active principles in drugs as well as templates for synthesis of new drugs.In silico ADME properties, prediction of the compound was under acceptable range.Based on the results, it can be concluded that, the isolated natural compound of linoleic acid that has been exhibited good medicinal properties.

View Article: PubMed Central - PubMed

Affiliation: Department of Biochemistry, Karpagam University, Eachanari, Coimbatore, Tamil Nadu, India.

ABSTRACT

Background: Natural products have continually played an important role in drug discovery because it serves as active principles in drugs as well as templates for synthesis of new drugs. Cayratia trifolia (L.) is a medicinal plant, which has been reported to have antiviral, antibacterial, antiprotozoal, hypoglycemic, anticancer and diuretic activities.

Objective: Therefore, the objective of this study is to isolate and identify the natural compound from the ethanolic extract of Cayratia trifolia (L.) and to predict the Absorption, Distribution, Metabolism and Excretion (ADME) properties of isolated natural compound.

Materials and methods: Column chromatography and thin layer chromatography were used to isolate the natural compound and Fourier-transform infrared (FTIR) spectroscopy was used to predict the functional groups present in the isolated natural compound. The structural characterization studies were functionally carried out using (1)H, (13)C, two-dimensional nuclear magnetic resonance (NMR) and mass spectrometry methods.

Results: FTIR showed that, the groups of OH, C-H, C = C may be present in the isolated natural compound. (1)H, (13)C, two-dimensional NMR and mass spectrometry data suggests that the isolated natural compound probably like linoleic acid. In silico ADME properties, prediction of the compound was under acceptable range.

Conclusion: Based on the results, it can be concluded that, the isolated natural compound of linoleic acid that has been exhibited good medicinal properties.

No MeSH data available.


13C NMR spectrum analysis of the isolated natural compound
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Figure 5: 13C NMR spectrum analysis of the isolated natural compound

Mentions: The absorptions of the NMR spectrometry have made a tremendous impact in many areas of chemistry, biology and medicine. In the 1H NMR [Figure 3] spectrum the triplet at δ 0.81 is due to a terminal methyl group, the strong singlet at δ 1.28 is due to long chain methylene groups. The strong signals at δ 1.59, 1.79 and 1.98 are due to methylene protons attached to unsaturated systems and the signal at δ 2.30 are due to two bis allylic protons. The signals at δ 4.56 (1H), 5.12 (2H) and at 5.36 (1H) suggest that the compound contains two double bonds. In the 1H–1H COSY NMR [Figure 4] spectrums cross peaks are observed between double bonded protons and the allylic methylene protons. The protons of one double bond are not coupled with the protons of the other double bond. The coupling between the methyl group at δ 0.81 and methylene protons at δ 1.59, 1.79 and 1.98 were observed. In the 13C NMR [Figure 5] spectrum the signal at δ 15.9 is due to the methyl group, a single at δ 39.4 is due to the α-carbon atom to the carbonyl group, the bunch of signals between 17.6 and 34.4 are due to long chain methylene carbons. The signals at 124.6, 129.3, 134.8 and 135.6 are due to four unsaturated carbon atoms. In the HSQC [Figure 6] spectrum the unsaturated protons and the unsaturated carbons are correlated. Being a long chain fatty acid, mostly it will be a mixture with its homologues fatty acids. The weak signal at δ 173.0 is due to a quaternary carbon (carbonyl carbon). Mass spectrometry analysis revealed [Figure 7] that, molecular weight of the isolated compound was 280.44 (g/mol). All the data suggests that, the compound may be an unsaturated long chain fatty acid probably like linoleic acid [Figure 8 and Table 3]. ADME properties of the isolated natural compound of linoleic acid shown in Table 4 and it was under acceptable range.


Isolation, structural characterization and in silico drug-like properties prediction of a natural compound from the ethanolic extract of Cayratia trifolia (L.).

Perumal PC, Sowmya S, Pratibha P, Vidya B, Anusooriya P, Starlin T, Ravi S, Gopalakrishnan VK - Pharmacognosy Res (2015 Jan-Mar)

13C NMR spectrum analysis of the isolated natural compound
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4285641&req=5

Figure 5: 13C NMR spectrum analysis of the isolated natural compound
Mentions: The absorptions of the NMR spectrometry have made a tremendous impact in many areas of chemistry, biology and medicine. In the 1H NMR [Figure 3] spectrum the triplet at δ 0.81 is due to a terminal methyl group, the strong singlet at δ 1.28 is due to long chain methylene groups. The strong signals at δ 1.59, 1.79 and 1.98 are due to methylene protons attached to unsaturated systems and the signal at δ 2.30 are due to two bis allylic protons. The signals at δ 4.56 (1H), 5.12 (2H) and at 5.36 (1H) suggest that the compound contains two double bonds. In the 1H–1H COSY NMR [Figure 4] spectrums cross peaks are observed between double bonded protons and the allylic methylene protons. The protons of one double bond are not coupled with the protons of the other double bond. The coupling between the methyl group at δ 0.81 and methylene protons at δ 1.59, 1.79 and 1.98 were observed. In the 13C NMR [Figure 5] spectrum the signal at δ 15.9 is due to the methyl group, a single at δ 39.4 is due to the α-carbon atom to the carbonyl group, the bunch of signals between 17.6 and 34.4 are due to long chain methylene carbons. The signals at 124.6, 129.3, 134.8 and 135.6 are due to four unsaturated carbon atoms. In the HSQC [Figure 6] spectrum the unsaturated protons and the unsaturated carbons are correlated. Being a long chain fatty acid, mostly it will be a mixture with its homologues fatty acids. The weak signal at δ 173.0 is due to a quaternary carbon (carbonyl carbon). Mass spectrometry analysis revealed [Figure 7] that, molecular weight of the isolated compound was 280.44 (g/mol). All the data suggests that, the compound may be an unsaturated long chain fatty acid probably like linoleic acid [Figure 8 and Table 3]. ADME properties of the isolated natural compound of linoleic acid shown in Table 4 and it was under acceptable range.

Bottom Line: Natural products have continually played an important role in drug discovery because it serves as active principles in drugs as well as templates for synthesis of new drugs.In silico ADME properties, prediction of the compound was under acceptable range.Based on the results, it can be concluded that, the isolated natural compound of linoleic acid that has been exhibited good medicinal properties.

View Article: PubMed Central - PubMed

Affiliation: Department of Biochemistry, Karpagam University, Eachanari, Coimbatore, Tamil Nadu, India.

ABSTRACT

Background: Natural products have continually played an important role in drug discovery because it serves as active principles in drugs as well as templates for synthesis of new drugs. Cayratia trifolia (L.) is a medicinal plant, which has been reported to have antiviral, antibacterial, antiprotozoal, hypoglycemic, anticancer and diuretic activities.

Objective: Therefore, the objective of this study is to isolate and identify the natural compound from the ethanolic extract of Cayratia trifolia (L.) and to predict the Absorption, Distribution, Metabolism and Excretion (ADME) properties of isolated natural compound.

Materials and methods: Column chromatography and thin layer chromatography were used to isolate the natural compound and Fourier-transform infrared (FTIR) spectroscopy was used to predict the functional groups present in the isolated natural compound. The structural characterization studies were functionally carried out using (1)H, (13)C, two-dimensional nuclear magnetic resonance (NMR) and mass spectrometry methods.

Results: FTIR showed that, the groups of OH, C-H, C = C may be present in the isolated natural compound. (1)H, (13)C, two-dimensional NMR and mass spectrometry data suggests that the isolated natural compound probably like linoleic acid. In silico ADME properties, prediction of the compound was under acceptable range.

Conclusion: Based on the results, it can be concluded that, the isolated natural compound of linoleic acid that has been exhibited good medicinal properties.

No MeSH data available.