Pregnane-type steroidal glycosides from Gymnema griffithii Craib.

Srisurichan, Suphongphan; Puthong, Songchan; Pornpakakul, Surachai

doi:10.1016/j.phytochem.2014.06.014

Cited by 10 publications

(10 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Replacing the hydroxyl group at C-11 and C-12 of P1 with the tigloyl substituent may have been responsible for the reduced activity. Similar reports to ours have demonstrated in vitro α-glucosidase inhibitory activity of eight pregnane-type steroidal glycosides (gymnema griffithosides A-H) isolated from the methanolic extract of the pericarp of Gymnema griffithii fruits [43].…”

Section: Discussionsupporting

confidence: 90%

Marsectohexol and other pregnane phytochemicals derived from Gongronema latifolium as α-amylase and α-glucosidase inhibitors: in vitro and molecular docking studies

et al. 2020

View full text Add to dashboard Cite

This study employed in vitro and in silico techniques to screen isolated pregnane phytochemicals (P1-P4), as well as their source pregnane-rich chromatographic fractions, which were derived from Gongronema latifolium Benth (GLB), for their inhibitory potentials against α-amylase, α-glucosidase, and sucrase enzyme activities. The results show that, most pregnane-rich chromatographic fractions and isolated compounds exhibited good inhibitory activities against α-amylase, and α-glucosidase enzymes. Among the isolated compounds, marsectohexol (P2) is the most favourable structure that showed inhibition against α-amylase (IC 50 = 3.712 µg/mL) when compared with the reference inhibitor, acarbose ((IC 50 = 15.418 µg/mL). Based on negative and low value of ∆G (Gibb's free energy), docking scores revealed that, marsectohexol has the highest binding affinity (− 8.8 kcal/mol) to human pancreatic α-amylase (HPA) as compared to the standard acarbose (− 8.1 kcal/mol). Marsectohexol and the other phytocompounds were also found to dock into the active site of HPA; interacting with key catalytic amino acid residues (ASP197, GLU233 and ASP300), which are known to involve in the nucleophilic, and the acid/base catalysis of the enzyme. Although, the pregnane phytocompounds have considerable high affinity binding to the human lysosomal α-glucosidase, they interacted with pockets other than the active site. In conclusion, at least, marsectohexol and three other constituent pregnane phytochemicals of GLB are potential inhibitors of the carbohydrate-hydrolyzing enzymes. These compounds may account for the anti-hyperglyceamic and antidiabetic potentials of this food herb.

show abstract

Section: Discussionsupporting

confidence: 90%

Marsectohexol and other pregnane phytochemicals derived from Gongronema latifolium as α-amylase and α-glucosidase inhibitors: in vitro and molecular docking studies

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Thus, for oleanane saponins, the main components could be hightly species-specific of G. sylvestre [7,18]. In addition, new pregnane glycosides were also found in G. alternifolium [19], G. sylvestre [5], and G. griffithii [15]. Five new pregnane glycosides in this report will contribute specific compounds in Gymnema genus.…”

Section: Compound Identificationmentioning

confidence: 56%

“…Recent reports have shown insulin secretion stimulation of G. sylvestre extract [4], antihyperglycemic effects of gmynemic acids [20], α-glucosidase and α-amylase inhibitory activities of pregnane glycosides from G. latifolium [11]. Previous studies have indicated that pregnane glycosides from G. griffithii showed moderate α-glucosidase inhibitory activity [15]. Russelioside B, a pregnane glycoside, possessed antidiabetic and antihyperlipidemic effect in streptozotocin induced diabetic rats [21].…”

Section: α-Glucosidase and α-Amylase Inhibitory Activitiesmentioning

confidence: 98%

“…In addition, the position of this moiety at C-12 was confirmed by HMBC correlation from H-12 (δH 4.68) to Tig C-1 (δC 169.1). Acid hydrolysis of 1 gave three monosaccharides, which were identified as D-cymarose [14], D-oleandrose [14], and D-thevetose [15], by comparing their specific rotation with those reported [16]. The large coupling constants between H-1 and H-2 of monosaccharide moieties and also HMBC correlations between Thv H-1 (δH 4.…”

Section: Compound Identificationmentioning

confidence: 99%

“…Moreover, the sugar linkages, 13 C NMR data of 5 were similar to 2, except for an additional sugar unit at Thv C-4 (Table 2). The sugar moieties were determined as D-cymarose [14], D-oleandrose [14], D-thevetose [15], and D-glucose [17] by acid hydrolysis. The HMBC correlations between Glc H-1 (δ H 4.41) and Thv C-4 (δ C 82.9), Thv H-1 (δ H 4.43) and Ole C-4 (δ C 84.1), Ole H-1 (δ H 4.57) and Cym C-4 (δ C 83.8), and between Cym H-1 (δ H 4.84) and aglycone C-3 (δ C 79.3) confirmed the sequence of sugar linkages, previously reproted from G. sylvestre [5].…”

Section: Compound Identificationmentioning

confidence: 99%

See 2 more Smart Citations

Five New Pregnane Glycosides from Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities

et al. 2020

View full text Add to dashboard Cite

Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A–E (1–5) and four known oleanane saponins, 3β-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (6), gymnemoside-W1 (7), 3β-O-β-D-xylopyranosyl-(1→6)-β-D- glucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (8), and alternoside XIX (9). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds 2–4 showed significant α-amylase inhibitory activity, with IC50 values ranging from 113.0 to 176.2 µM.

show abstract

Pregnane glycosides from Adonis amurensis and their bioactivity

Yan

Zhou

et al. 2022

Phytochemistry

View full text Add to dashboard Cite

Pregnane-type steroidal glycosides from Gymnema griffithii Craib.

Cited by 10 publications

References 36 publications

Marsectohexol and other pregnane phytochemicals derived from Gongronema latifolium as α-amylase and α-glucosidase inhibitors: in vitro and molecular docking studies

Marsectohexol and other pregnane phytochemicals derived from Gongronema latifolium as α-amylase and α-glucosidase inhibitors: in vitro and molecular docking studies

Five New Pregnane Glycosides from Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities

Pregnane glycosides from Adonis amurensis and their bioactivity

Contact Info

Product

Resources

About