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Molecular docking studies of (4Z, 12Z)-cyclopentadeca-4, 12-dienone from Grewia hirsuta with some targets related to type 2 diabetes.

Natarajan A, Sugumar S, Bitragunta S, Balasubramanyan N - BMC Complement Altern Med (2015)

Bottom Line: This leads to increasing demand for natural products with antidiabetic activity with fewer side effects.Evaluation of hypoglycemic activity through an extensive in silico docking approach with molecular targets such as aldose reductase, glucokinase, pyruvate dehydrogenase kinase isoform 2, peroxisome proliferator-activated receptor-gamma, glycogen synthase kinase-3, 11β-Hydroxysteroid dehydrogenase, and glutamine: fructose-6-phosphate amidotransferase were performed.Thus enabling a possibility of this plant extract as a new alternative to existing diabetic approaches.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, SRM University, Kattankulathur, 603203, India. abirami.n@ktr.srmuniv.ac.in.

ABSTRACT

Background: Management of diabetes without any side effects is still a challenge to the medical system. This leads to increasing demand for natural products with antidiabetic activity with fewer side effects. Grewia hirsuta (Tiliaceae) is a traditional herbal medicinal plant and is reported to possess a variety of pharmacological actions. In the present research, a compound (4Z, 12Z)-cyclopentadeca-4, 12-dienone isolated from Grewia hirsuta was taken as ligand for molecular docking studies. Evaluation of hypoglycemic activity through an extensive in silico docking approach with molecular targets such as aldose reductase, glucokinase, pyruvate dehydrogenase kinase isoform 2, peroxisome proliferator-activated receptor-gamma, glycogen synthase kinase-3, 11β-Hydroxysteroid dehydrogenase, and glutamine: fructose-6-phosphate amidotransferase were performed.

Methods: Isolation of the (4Z, 12Z)-cyclopentadeca-4,12-dienone from the methanol extract of the leaves of Grewia hirsuta was performed by the column chromatography to yield different fractions. These fractions were then subjected to purification and the structure was elucidated and confirmed by spectroscopic methods including UV, FTIR, (1)H, (13)C NMR and the accurate mass determination was carried out using the Q-TOF mass spectrometer. In-vivo experimentation was performed with evaluation of α-glucosidase, α-amylase and MTT assay that had been reported by the author in the earlier paper. Molecular docking study was performed with GLIDE docking software.

Results: The docking studies of the ligand (4Z, 12Z)-cyclopentadeca-4, 12-dienone with seven different target proteins showed that this is a good inhibitor, which docks well with various targets related to diabetes mellitus. Hence (4Z, 12Z)-cyclopentadeca-4,12-dienone can be considered for developing into a potent anti-diabetic drug.

Conclusion: The results of the current study have revealed that the leaves of the selected plant Grewia hirsuta contains a potential inhibitor for diabetes (4Z, 12Z)-cyclopentadeca-4,12-dienone. Thus enabling a possibility of this plant extract as a new alternative to existing diabetic approaches.

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Molecular structure of (4Z, 12Z)- Cyclopentadeca-4, 12-dienone.
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Fig3: Molecular structure of (4Z, 12Z)- Cyclopentadeca-4, 12-dienone.

Mentions: Under the influence of UV, four distinct compounds with Rf values 0.876, 0.765, 0.634 and 0.500 were recognized. When treated with iodine compounds with Rf values 0.765, 0.634 and 0.500 were seen. (4Z, 12Z)-cyclopentadeca-4, 12-dienone was an orange yellowish oily colored compound (yield: 650 mg) with the Rf value of 0.876 (9:1, chloroform: methanol) on TLC was observed with m.pt 68-69°C (Figure 1). Among the compounds, (4Z, 12Z)-cyclopentadeca-4, 12-dienone (Rf =0.876) gave good result of 52.3% α-amylase inhibitory activity and the other compounds gave only poor results on inhibitory effect [12]. The Q-TOF spectrum of (4Z, 12Z)-cyclopentadeca-4, 12-dienone showed a molecular ion peak at m/z 220 (100%,) (Figure 2) indicating the molecular weight with molecular formula is C15H24O (Figure 3). UV (methanol): λmax = 221 nm (double bonds presence), at 528 nm (coloured compound) (Figure 4). FTIR studies: υmax at 1711 cm−1 (presence of carbonyl group), 1641 cm−1 (–C = C), 2924–2853 cm −1 (–CH 2) [12]. The 1H NMR (CDCl3, 300 MHz) δ: 5.02-5.13 (m, olefinic protons), 0.86-2.10 (m, CH2 protons) The 13CNMR (CDCl3, 300 MHz) δ: 22.70- 39.77 ppm [presence of carbons in the aliphatic regions (-CH2)],173.77 (carbonyl carbon), 124.45 and 134.90 (olefinic carbons) [12]. The elemental analysis report revealed the presence of C (84.76%), H (8.98%) and O (6.26%) in the compound and absence of N.Figure 1


Molecular docking studies of (4Z, 12Z)-cyclopentadeca-4, 12-dienone from Grewia hirsuta with some targets related to type 2 diabetes.

Natarajan A, Sugumar S, Bitragunta S, Balasubramanyan N - BMC Complement Altern Med (2015)

Molecular structure of (4Z, 12Z)- Cyclopentadeca-4, 12-dienone.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4378231&req=5

Fig3: Molecular structure of (4Z, 12Z)- Cyclopentadeca-4, 12-dienone.
Mentions: Under the influence of UV, four distinct compounds with Rf values 0.876, 0.765, 0.634 and 0.500 were recognized. When treated with iodine compounds with Rf values 0.765, 0.634 and 0.500 were seen. (4Z, 12Z)-cyclopentadeca-4, 12-dienone was an orange yellowish oily colored compound (yield: 650 mg) with the Rf value of 0.876 (9:1, chloroform: methanol) on TLC was observed with m.pt 68-69°C (Figure 1). Among the compounds, (4Z, 12Z)-cyclopentadeca-4, 12-dienone (Rf =0.876) gave good result of 52.3% α-amylase inhibitory activity and the other compounds gave only poor results on inhibitory effect [12]. The Q-TOF spectrum of (4Z, 12Z)-cyclopentadeca-4, 12-dienone showed a molecular ion peak at m/z 220 (100%,) (Figure 2) indicating the molecular weight with molecular formula is C15H24O (Figure 3). UV (methanol): λmax = 221 nm (double bonds presence), at 528 nm (coloured compound) (Figure 4). FTIR studies: υmax at 1711 cm−1 (presence of carbonyl group), 1641 cm−1 (–C = C), 2924–2853 cm −1 (–CH 2) [12]. The 1H NMR (CDCl3, 300 MHz) δ: 5.02-5.13 (m, olefinic protons), 0.86-2.10 (m, CH2 protons) The 13CNMR (CDCl3, 300 MHz) δ: 22.70- 39.77 ppm [presence of carbons in the aliphatic regions (-CH2)],173.77 (carbonyl carbon), 124.45 and 134.90 (olefinic carbons) [12]. The elemental analysis report revealed the presence of C (84.76%), H (8.98%) and O (6.26%) in the compound and absence of N.Figure 1

Bottom Line: This leads to increasing demand for natural products with antidiabetic activity with fewer side effects.Evaluation of hypoglycemic activity through an extensive in silico docking approach with molecular targets such as aldose reductase, glucokinase, pyruvate dehydrogenase kinase isoform 2, peroxisome proliferator-activated receptor-gamma, glycogen synthase kinase-3, 11β-Hydroxysteroid dehydrogenase, and glutamine: fructose-6-phosphate amidotransferase were performed.Thus enabling a possibility of this plant extract as a new alternative to existing diabetic approaches.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, SRM University, Kattankulathur, 603203, India. abirami.n@ktr.srmuniv.ac.in.

ABSTRACT

Background: Management of diabetes without any side effects is still a challenge to the medical system. This leads to increasing demand for natural products with antidiabetic activity with fewer side effects. Grewia hirsuta (Tiliaceae) is a traditional herbal medicinal plant and is reported to possess a variety of pharmacological actions. In the present research, a compound (4Z, 12Z)-cyclopentadeca-4, 12-dienone isolated from Grewia hirsuta was taken as ligand for molecular docking studies. Evaluation of hypoglycemic activity through an extensive in silico docking approach with molecular targets such as aldose reductase, glucokinase, pyruvate dehydrogenase kinase isoform 2, peroxisome proliferator-activated receptor-gamma, glycogen synthase kinase-3, 11β-Hydroxysteroid dehydrogenase, and glutamine: fructose-6-phosphate amidotransferase were performed.

Methods: Isolation of the (4Z, 12Z)-cyclopentadeca-4,12-dienone from the methanol extract of the leaves of Grewia hirsuta was performed by the column chromatography to yield different fractions. These fractions were then subjected to purification and the structure was elucidated and confirmed by spectroscopic methods including UV, FTIR, (1)H, (13)C NMR and the accurate mass determination was carried out using the Q-TOF mass spectrometer. In-vivo experimentation was performed with evaluation of α-glucosidase, α-amylase and MTT assay that had been reported by the author in the earlier paper. Molecular docking study was performed with GLIDE docking software.

Results: The docking studies of the ligand (4Z, 12Z)-cyclopentadeca-4, 12-dienone with seven different target proteins showed that this is a good inhibitor, which docks well with various targets related to diabetes mellitus. Hence (4Z, 12Z)-cyclopentadeca-4,12-dienone can be considered for developing into a potent anti-diabetic drug.

Conclusion: The results of the current study have revealed that the leaves of the selected plant Grewia hirsuta contains a potential inhibitor for diabetes (4Z, 12Z)-cyclopentadeca-4,12-dienone. Thus enabling a possibility of this plant extract as a new alternative to existing diabetic approaches.

Show MeSH
Related in: MedlinePlus