Aldose reductase and protein tyrosine phosphatase 1B inhibitory active compounds fromSyzygium cuminiseeds

Abstract

Context: Syzygium cumini (L.) Skeels (Myrtaceae), commonly known as jamun, is an Indian plant, traditionally well known for its medicinal properties including antidiabetic activity. Objective: To isolate the antidiabetic compounds from Syzygium cumini seeds and evaluate their activity using aldose reductase (AR) and protein-tyrosine phosphatase 1B (PTP1B) inhibition assays. Materials and methods:The dried seeds were extracted with methanol and partitioned with ethyl acetate, butanol, and water. The extracts were screened for antidiabetic activity at a concentration of 100 mg/mL using in vitro AR and PTP 1B inhibition assays. Results and discussion: The highly enriched fractions obtained from broad ethyl acetate fraction yielded maslinic acid (1), 5-(hydroxymethyl) furfural (2), gallic acid (3), valoneic acid dilactone (4), rubuphenol (5), and ellagic acid (6). Structures were elucidated by 1 H-NMR and 13 C-NMR. The initial ethyl acetate fraction showed AR inhibitory activity with the IC 50 value of 2.50 mg/mL and PTP1B enzyme inhibition with the IC 50 value of 26.36 mg/mL. Compounds 3, 4, 5, and 6 were found to inhibit AR with IC 50 values of 0.77, 0.075, 0.165, and 0.12 mg/mL while the compounds 4, 5, and 6 inhibited PTP1B with IC 50 values of 9.37, 28.14, and 25.96 mg/mL, respectively. Conclusion:The results of this study demonstrate that the isolated constituents show promising in vitro antidiabetic activity and, therefore, can be candidates for in vivo biological screening using relevant models to ascertain their antidiabetic activity.

Flower Infusions From Cornus mas and Cornus kousa Inhibit Aldose Reductase Enzyme, Without Any Effects on Lipotoxicity

“…Their activity nearly meets the IC 50 values of the pure plant metabolites, for example, chlorogenic, gallic acids, and quercetin used as references for plant aldose reductase inhibitors. [28][29][30][31] In our case, the above-mentioned acids and quercetin derivatives represent approximately 70% of the content.…”

Unlocking the Therapeutic Potential of Syzygium cumini Seeds Extract

“…The fruit pulp is sweet and seeds are acrid, sour and tonic. They have biological activities such as hypoglycemic, hypolipidemic, cardio protective, hepatoprotective, antibacterial, antiinflammatory and anti-allergic effects have been reported previously with consumption of S. cumini (11,12). It is rich in polyphenols and contains compounds such as flavonoids, anthocyanin, 404 tannins, terpenes and aliphatic acids (13,14).…”

Cataract Preventive Role of Isolated Phytoconstituents: Findings from a Decade of Research

“…During a search for possible cataractogenesis activities for isolated ellagic acid, three plants from Korea were found with most potent inhibitions. Ellagic acid isolated from Phellinus linteus , Geranium thunbergii (Thunberg’s geranium), and Syzygium cumini (L.) Skeels (jambolan, Java plum, black plum) inhibits RLAR activity with IC 50 value ranging from 0.12 µM to 6.9 µM [ 67 , 85 , 86 , 87 ]. The compound was also effective in the inhibition of AGE formation (IC 50 = 26.0 µM).…”

“…The repeated column chromatography and preparative HPLC of seed methanolic extract of Syzygium cumini (L.) Skeels lead to the isolation of six phytoconstituents with valoneic acid dilactone showed the highest activity against RLAR inhibitory activity at IC 50 value of 0.075 µM [ 87 ]. Valoneic acid dilactone were the first constituents from this plant reported to possess RLAR inhibitory activity.…”