<i>In vitro</i> study on α-amylase and α-glucosidase inhibitory activities of a new stigmastane-type steroid saponin from the leaves of <i>Vernonia amygdalina</i>

Anh, Hoang Le Tuan; Vinh, Le Ba; Lien, Le Thi Hong; Cường, Phạm Việt; Arai, Masayoshi; Ha, Tran Phuong; Lin, Hoang Ngoc; Dat, Ton That Huu; Cuong, Le Canh Viet; Kim, Young Ho

doi:10.1080/14786419.2019.1607853

Cited by 21 publications

(11 citation statements)

References 15 publications

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“…Its IR spectrum showed characteristic absorption bands corresponding to hydroxyl (3356 cm −1 ), carbonyl (1705 cm −1 ), and aliphatic chains (2935 and 2871 cm −1 ). Its NMR data were similar to those of 1 except for the presence of a glucosyl group ( δ C 102.3, 78.1, 77.9, 75.2, 71.0, and 62.8), which accounted for the additional one degree of unsaturation and was identified as β-D-glucopyranoside via comparison of its NMR data with reported values [ 8 , 25 ]. The position of the sugar was defined based on the HMBC interaction from the anomeric proton H-1’ ( δ H 4.40) to δ C 69.3 (C-3), which was further confirmed by the glycosidation shifts in the resonances of C-2, C-3, and C-4 ( δ C 35.3, 78.6, and 47.0, respectively) as compared to their respective values for compounds 1 and 2 ( Table 1 ).…”

Section: Resultsmentioning

confidence: 54%

“…Ever since, extensive investigations have reported on the occurrences of sesquiterpenoid lactones and stigmastane-type steroids as chemical markers of the genus [ 3 , 4 , 5 , 6 ]. Unlike sesquiterpene lactones, which are distributed throughout the genus, stigmastanes instead occur in few species, including V. guineensis and V. amygdalina [ 4 , 5 , 6 , 7 , 8 ]. Sesquiterpene lactones are able to alkylate cysteine-containing enzymes and proteins, inducing apoptosis in malignant cells [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

et al. 2023

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Four polyoxygenated stigmastanes (1–4) alongside known analogues (7–8) and flavonoids (5–6) were isolated from a dichloromethane/methanol (1:1, v/v) extract of the whole plant of Vernonia kotschyana Sch. Bip. ex Walp. (Asteraceae). Their structures were determined by means of spectroscopic and spectrometric analysis. The relative stereochemistry of the new compounds was established and confirmed via biosynthesis evidence and cyclization of 1 under acidic conditions. A plausible biosynthetic pathway to the new compounds and the chemophenetic significance of the isolated constituents were also discussed. The crude extract, fractions, and compounds (1–3) were assessed for their antibacterial activity against five highly prevalent bacterial strains. The fractions and compounds showed low to moderate activity with minimal inhibitory concentrations (MICs) > 125 µg/mL.

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Section: Resultsmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

et al. 2023

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“…A previous in vitro study indicated the leaves’ hypoglycemic effect. The MeOH extract of the G. amygdalinum leaf was reported to have significantly inhibited alpha-glucosidase [ 17 ]. Despite numerous reports on the secondary metabolite profile of the leaf, no alpha-glucosidase inhibition activity is yet observed in G. amygdalinum flower extracts and fractions.…”

Section: Discussionmentioning

confidence: 99%

In Vitro Alpha-Glucosidase Inhibitory Activity and the Isolation of Luteolin from the Flower of Gymnanthemum amygdalinum (Delile) Sch. Bip ex Walp.

2022

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Diabetes mellitus is a major health issue that has posed a significant challenge over the years. Gymnanthemum amygdalinum is a well-known plant that can be potentially used to treat this disease. Therefore, this study aimed to evaluate the inhibitory effect of its root, stem bark, leaves, and flower extracts on alpha-glucosidase using an in vitro inhibition assay to isolate the bioactive compounds and determine their levels in the samples. The air-dried plant parts were extracted by maceration using methanol. The results showed that the flower extract had the greatest inhibitory effect (IC50 47.29 ± 1.12 µg/mL), followed by the leaves, roots, and stem bark. The methanolic flower extract was further fractionated with different solvents, and the ethyl acetate fraction showed the strongest activity (IC50 19.24 ± 0.12 µg/mL). Meanwhile, acarbose was used as a positive control (IC50 73.36 ± 3.05 µg/mL). Characterization based on UV, 1H-, and 13C-NMR established that the ethyl acetate fraction yielded two flavonoid compounds, namely, luteolin and 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-4H-chromen-4-on, which had IC50 values of 6.53 ± 0.16 µg/mL and 39.95 ± 1.59 µg/mL, respectively. The luteolin levels in the crude drug, methanolic extract, and ethyl acetate fraction were 3.4 ± 0.2 mg (0.3%), 32.4 ± 0.8 mg (3.2%), and 68.9 ± 3.4 mg (6.9%) per 1 g samples, respectively. These results indicated that the G. amygdalinum flower extract exerted potent inhibitory alpha-glucosidase activity.

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“…Diosgenin, steroidal saponin was found to increase insulin‐dependent glucose metabolism by cells through an ERα‐mediated PI3K/Akt activation pathway (Fang et al, 2016). Steroidal saponins: vernoniacums B, vernonioside B1, vernonioside B2, and vernoamyoside E from Vernonia amygdalina were reported to show hyperglycemic activity by inhibiting α‐amylase and α‐glucosidase (Anh et al, 2019). Moreover, the root extract of Atractylodes japonica was found to enhance adipogenic differentiation of 3 T3‐L1 preadipocytes and promoted glucose transport to the cells by up‐regulating the glucose transport 4, PI3K, and insulin receptor substrates‐1 (IRS‐1), thus improving insulin resistance (Han, Jung, & Park, 2012).…”

Section: Mechanism Of Action and Bioactivity Of Plant‐based Steroidsmentioning

confidence: 99%

Pharmacologic activities of phytosteroids in inflammatory diseases: Mechanism of action and therapeutic potentials

Marahatha

Gyawali

Sharma

et al. 2021

Phytotherapy Research

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Natural products and their derivatives are known to be useful for treating numerous diseases since ancient times. Because of their high therapeutic potentials, the use of different medicinal plants is possible to treat varied inflammation‐mediated chronic diseases. Among natural products, phytosteroids have emerged as promising compounds mostly because they have diverse pharmacological activities. Currently, available medications exert numerous systemic toxicities, including hypertension, immune suppression, osteoporosis, and metabolic abnormalities. Thus, further research on phytosteroids to subside these complications is of significant importance. In this study, the information on phytosteroids, their types, and actions against inflammation, and allergic complications was collected by a systematic survey of literature on several scientific search engines. The literature review suggested that phytosteroids exhibit antiinflammatory action via different modes through transrepression or selective COX‐2 enzymes. Also, in silico ADMET analysis was carried out on available phytosteroids to uncover their pharmacokinetic properties. Our analysis has shown that eight compounds: withaferin A, stigmasterol, β‐sitosterol, guggulsterone, diosgenin, sarsasapogenin, physalin A, and dioscin, −isolated from medicinal plants show similar pharmacokinetic properties as compared to dexamethasone, commercially available glucocorticoid. These phytosteroids could be useful for the treatment of inflammatory diseases, such as rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, asthma, and cardiovascular diseases. Thus, systematic research is required to explore potent phytosteroids with lesser side effects, which might substitute the current medications.

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In vitro study on α-amylase and α-glucosidase inhibitory activities of a new stigmastane-type steroid saponin from the leaves of Vernonia amygdalina

Cited by 21 publications

References 15 publications

Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

In Vitro Alpha-Glucosidase Inhibitory Activity and the Isolation of Luteolin from the Flower of Gymnanthemum amygdalinum (Delile) Sch. Bip ex Walp.

Pharmacologic activities of phytosteroids in inflammatory diseases: Mechanism of action and therapeutic potentials

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