Gracillin

Gracillin is a kind of steroidal saponin isolated from the root bark of wild yam Dioscorea nipponica with antitumor agent.Gracillin could induce cell cycle arrest, oxidative stress, and apoptosis in HL60 cells.[1]

Gracillin is a triterpenoid.

0.5 g (0.57 mmol) of fine diosgenin, 0.77 g (1.70 mmol) of DMT-Cl was dissolved in 10 mL of pyridine, reacted at room temperature overnight, and TCL showed the end of the reaction. The reaction solution was concentrated under reduced pressure, and water was added to precipitate a white solid which was filtered through a silica gel column, trichloromethane / methanol 30: 1 and the eluent was concentrated to give 0.12 g of a white solid.0.5 g (0.57 mmol) of finely diosgenin was dissolved in 15 mL of pyridine, 0.1g DMAP and 1.94 g (10.18 mmol) of p-toluenesulfonyl chloride were added successively under ice-cooling to control the drip rate. At room temperature for 6 h, TCL showed the end of the reaction. The reaction solution was concentrated under reduced pressure, and water was added to precipitate a white solid which was filtered through a silica gel column, trichloromethane / methanol 40: 1 and the eluent was concentrated to give a final white 0.1g solid.0.5 g (0.57 mmol) of fine diosgenin, 0.93 g (7.63 mmol) of benzoic acid was dissolved in 20 mL of dichloromethane under ice-cooling conditions, 0.18 g of DMAP was added in turn and 2. 1 g (10.18 mmol) of DCC was added in batches to control the drip rate. The reaction was at room temperature overnight, TCL showed the end of the reaction. The reaction solution was concentrated under reduced pressure, dissolved in ethyl acetate, and the insoluble matter was filtered off, and the filtrate was saturated sodium bicarbonate aqueous solution washed twice, saturated sodium chloride aqueous solution washed once, with base layer plus anhydrous sodium sulfate, concentrated under reduced pressure, was filtered through a silica gel column, ethyl acetate: petroleum ether 1:10 wash, the eluent was concentrated, and finally the white solid was 0.6g.0.5 g (0.57 mmol) of fine diosgenin was dissolved in 10 mL of N, N-dimethylformamide and 0.48 g (20.35 mmol) of sodium hydride was added slowlyunder ice-cooling, after 1 hour. Under ice bath condtions, 0.18g tetrabutylammonium bromide and 1.74 g (10.18 mmol) of benzyl bromide was added dropwise to control the drip rate. the reaction was at room temperature overnight, TCL showed the end of the reaction. To the reaction solution was added water and extracted twice with ethyl acetate, dried over anhydrous sodium sulfate, concentrated under reduced pressure, was filtered through a silica gel column, ethyl acetate: petroleum ether 2:1, the eluent was concentrated and finally gave 0.6 g of a pale yellow oil.General procedure: Each compound (1 mg) was treated with 2 M HCl (10 ml) under conditions of reflux at 80 C this being maintained for 4 h. Each reaction mixture was concentrated to dryness, partitioned between CHCl3 and H2O and then the H2O layer was concentrated to dryness to yield a mixture of sugars. Each mixture was dissolved in anhydrous pyridine (1 ml) and reacted with l-cysteine methyl ester hydrochloride (1 mg) in an oven at 60 C for 2 h. After the reaction mixture was evaporated under a stream of N2, trimethylsilyl imidazole (0.2 ml) was added, and the mixture warmed to 60 C for another 1 h. After drying the solution, the products were partitioned between cyclohexane and H2O. The same reactions were applied to standard sugars. Then the cyclohexane layers were analyzed by gas chromatography on a column, AT-SE-30 (0.5 mum × 0.32 mm × 30 m); column temperature, 250 C; detector temperature, 250 C; injection temperature, 230 C; carrier gas, N2. The derivatives of d-glucose, l-glucose, l-rhamnose, d-apiose, l-arabinose and d-xylose gave peaks at tR 25.67, 26.81, 16.33, 12.69, 13.09 and 12.94 min, respectively.

Molecular Weight:885.0
XLogP3:1.4
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:17
Rotatable Bond Count:8
Exact Mass:884.47695082
Monoisotopic Mass:884.47695082
Topological Polar Surface Area:256
Heavy Atom Count:62
Complexity:1620
Defined Atom Stereocenter Count:26
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes