New Sweet-Tasting Oleanane-Type Triterpenoid Saponins from "Tugancao" (Derris eriocarpa How)

With the aim to investigate the sweet-tasting compounds in Derris eriocarpa How (a substitute for licorice in "Zhuang" and "Dai" ethnopharmacy in Guangxi and Yunnan provinces of China) as well as to ascertain why the stem of D. eriocarpa can be used to substitute for licorice in the sweetness taste aspect, taste sensory-guided fractionation was conducted to isolate sweet constituents from the extract of D. eriocarpa. Four sweet-tasting triterpenoid saponins were obtained, including millettiasaponin A (1) and three new saponins named derrisaponins A-C (2-4). The sweetness potency was evaluated by a human sensory panel test. The sweetness intensities of compounds 1-4 were determined to be approximately 150, 80, 2, and 0.5 times relative to sucrose at the concentration of 1%, respectively, of which compounds 1 and 2, with a free carboxyl group at the C-30 position, showed more potent sweetness intensity. In addition, compounds 1 and 2 showed no acute toxic activity at doses of 250 and 400 mg/kg of body weight, respectively, assessed through caudal vein injection to ICR mice. The contents of the sweetest compounds in stems were analyzed quantitatively as 352.80 mg/kg for compound 1 and 1887.60 mg/kg for compound 2 performed by ultra-performance liquid chromatography-tandem mass spectrometry.