Objective To investigate the C₂₁ steroids from Gymnema latifolium and their glucose uptake-promoting activity. Methods The compounds were isolated and purified by various chromatographic techniques including silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC, and their structures were elucidated on the basis of spectroscopic data. The glucose uptake-promoting activity of the isolates was evaluated using a HepG2 cellular glucose uptake model. Results A total of 18 C₂₁ steroids were isolated and identified as gymlatifoside E (1), 20-O-benzoyl-12-O-cinnamoyl-3β,5α,8β,12β,14β,17β,20-heptahydroxy-(20S)-pregn-6-ene (2), gymnepregoside H (3), prosapogenin (4), sylvepregoside E (5), gymnepregoside G (6), penupogenin (7), gymnepregoside I (8), cissasteroid A (9), cynsaccatol L (10), gymnemarsgenin (11), gnetumoside A (12), cynanchin F (13), gagamine (14), 12-O-benzoylsarcostin (15), cissasteroid B (16), 12,20-O-dibenzoylsarcostin (17), hemoside A (18). Among them, compound 1 is a new C₂₁ steroid, and compounds 2—18 were isolated from G. latifolium for the first time. At non-cytotoxic concentrations, treatment with compounds 1—18 resulted in glucose uptake levels ranging from 0.70- to 1.73-fold of the control group in HepG2 cells, among which compounds 4, 8–10, 12–14, 16, and 17 significantly promoted glucose uptake, reaching 1.38- to 1.73-fold of the control group. Conclusion G. latifolium is rich in C₂₁ steroids, and some of these compounds exhibit promising potential anti-diabetic activity, warranting further investigation.

Gymnema latifolium Wall. ex Wight  /  C₂₁ steroidal glycosides  /  gymlatifoside E  /  anti-diabetic activity  /  glucose uptake