Pregnane glycosides from <i>Gymnema inodorum</i> and their α-glucosidase inhibitory activity

Trang, Đỗ Thị; Yến, Dương Thị Hải; Hoài, Nguyễn Thị; Tài, Bùi Hữu; Đoán, Vũ Văn; Yến, Phạm Hải; Quang, Trần Hồng; Nhiệm, Nguyễn Xuân; Minh, Châu Văn; Kiệm, Phan Văn

doi:10.1080/14786419.2019.1663517

Cited by 21 publications

(12 citation statements)

References 10 publications

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“…In 20-hydroxy-C/D-cis-pregnane-type steroids, steric hindrance between H-16, H-20, H-18 and H-21 of the cyclopentane ring can lead to chemical shifts and is indicative of the absolute configuration of the C-20 [27]. The NOE's between H-9 (δ H 1.87~1.90) and H-12 (δ H 4.74~4.77), between H-18 (δ H 1.60) and H-20 (δ H 4.84), and our experimental data were similar to the closest structures published in the literature, which led to the deduction of the 20S configuration [28][29][30]. Thus, compound 1 was determined as 12-O-cinnamoyl-20-O-benzoyl-heptahydroxy-(20S)-pregn-6-enyl-3-O-β cymaropyranoside-(1→4)-β-cymaropyranoside.…”

Section: Resultssupporting

confidence: 88%

Identification of C21 Steroidal Glycosides from Gymnema sylvestre (Retz.) and Evaluation of Their Glucose Uptake Activities

Liu

Zhou²,

Zhang³

et al. 2021

Molecules

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Gymnema sylvestre (Retz.) Schult is a multi-purpose traditional medicine that has long been used for the treatment of various diseases. To discover the potential bioactive composition of G. sylvestre, a chemical investigation was thus performed. In this research, four new C21 steroidal glycosides sylvepregosides A-D (1–4) were isolated along with four known compounds, gymnepregoside H (5), deacetylkidjoladinin (6), gymnepregoside G (7) and gymnepregoside I (8), from the ethyl acetate fraction of G. sylvestre. The structures of the new compounds were established by extensive 1D and 2D nuclear magnetic resonance (NMR) spectra with mass spectroscopy data. Compounds 1–6 promoted glucose uptake by the range of 1.10- to 2.37-fold, respectively. Compound 1 showed the most potent glucose uptake, with 1.37-fold enhancement. Further study showed that compounds 1 and 5 could promote GLUT-4 fusion with the plasma membrane in L6 cells. The result attained in this study indicated that the separation and characterization of these compounds play an important role in the research and development of new anti-diabetic drugs and pharmaceutical industry.

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Section: Resultssupporting

confidence: 88%

Identification of C21 Steroidal Glycosides from Gymnema sylvestre (Retz.) and Evaluation of Their Glucose Uptake Activities

Liu

Zhou²,

Zhang³

et al. 2021

Molecules

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“…All the NMR assignments of 1 were done by HSQC, HMBC, and COSY spectra (Tables 1 and 2). Furthermore, the configuration of 1 were proven by the similar biogenetic pregnane from Gymnema genus, 21,22 and further confirmed by the ROESY spectrum (Figure 2). The observed ROESY correlations between Hα−9 (δ H 2.21) and Hα−1 (δ H 1.57), between Hα−1 and H-3 (δ H 4.07) suggested S8).…”

Section: Resultsmentioning

confidence: 55%

Gymsyloside F and Gymsyloside G, Two New Pregnane Glycosides From the Leaves of Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities

Yến

Thanh

et al. 2021

Natural Product Communications

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Two new pregnane glycosides were isolated from the leaves of Gymnema sylvestre (Retz.) R.Br. ex Sm. Their chemical structures were determined as (20 S)−12 β-tigloyloxy-5 α-hydroperoxy-3 β,8 β,14 β,17 β,20-pentahydroxypregn-6-ene 3- O-β-D-glucopyranosyl-(1→4)‐6-deoxy-3- O-methyl- β-D-allopyranosyl-(1→4)- β-D-oleandropyranosyl-(1→4)- β-D-cymaropyranosyl-(1→4)- β-D-cymaropyranoside (1) and (20 S)−12 β-benzoyloxy-5 α-hydroperoxy-3 β,8 β,14 β,17 β,20-pentahydroxypregn-6-ene 3- O-β-D-glucopyranosyl-(1→4)‐6-deoxy-3- O-methyl- β-D-allopyranosyl-(1→4)- β-D-oleandropyranosyl-(1→4)- β-D-cymaropyranosyl-(1→4)- β-D-cymaropyranoside (2) on the basis of the extensive spectroscopic methods, including 1D, 2D NMR, HRESIMS, and in comparison with the reported data. At the concentration of 200 µM, compounds 1 and 2 showed moderate anti α-glucosidase and α-amylase activities with inhibitory percentage of 31.1 ± 1.2 and 42.3 ± 1.7% (for α-glucosidase), and 27.8 ± 1.3 and 34.5 ± 1.5% (for α-amylase), respectively.

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“…The bioactive components from this plant include pregnane glycosides [5], triterpene saponins [6,7], and flavonoids [8]. Our previous study reported pregnane glycosides from Gymnema inodorum and their α-glucosidase inhibitory activity [9]. As a part of our ongoing investigation on anti-diabetic compounds from Vietnamese plants [10], a methanol extract of the leaves of G. sylvestre was found to inhibit α-glucosidase and α-amylase activities.…”

Section: Isolation Of Compoundsmentioning

confidence: 94%

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

et al. 2020

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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.

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Pregnane glycosides from Gymnema inodorum and their α-glucosidase inhibitory activity

Cited by 21 publications

References 10 publications

Identification of C21 Steroidal Glycosides from Gymnema sylvestre (Retz.) and Evaluation of Their Glucose Uptake Activities

Identification of C21 Steroidal Glycosides from Gymnema sylvestre (Retz.) and Evaluation of Their Glucose Uptake Activities

Gymsyloside F and Gymsyloside G, Two New Pregnane Glycosides From the Leaves of Gymnema sylvestre and Their α-Glucosidase and α-Amylase Inhibitory Activities

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

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