Yongzheng Hui

Synthesis of three diosgenyl saponins: dioscin, polyphyllin D, and balanitin 7

Dioscin, polyphyllin D, and balanitin 7, which belong to a group of structurally similar diosgenyl saponins with promising bioactivities, were synthesized by stepwise glycosylation.

An improved synthesis of the saponin, polyphyllin D

Polyphyllin D, namely diosgenyl alpha-L-rhamnopyranosyl-(1 --> 2)- [(alpha-L-arabinofuranosyl)-(1 --> 4)]-[beta-D-glucopyranoside, was synthesized from diosgenyl-beta-D-glucopyranoside in four steps and in 30% overall yield, taking advantage of regioselective pivaloylation and alpha-L-rhamnopyranosylation reactions.

Synthesis of glycosides bearing the disaccharide of OSW-1 or its 1-->4-linked analogue and their antitumor activities.

Twelve glycosides bearing the disaccharide of OSW-1, namely 2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl-(1-->3)-2-O-acetyl-alpha-L-arabinopyranosides, or its 1-->4-linked analogue, were synthesized, and their antitumor activities were determined.

Synthesis of diosgenyl α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucopyranoside (gracillin) and related saponins

Abstract Diosgenyl α - l -rhamnopyranosyl-(1→2)-[ β - d -glucopyranosyl-(1→3)]- β - d -glucopyranoside (gracillin), a monodesmosidic saponin isolated from paris , dioscorea , and costacea species with promising cardiovascular and antitumor activities, was synthesized by stepwise glycosylation.

Synthesis of OSW-1 analogues and a dimer and their antitumor activities

Five analogues, including a 16-epi-isomer (6), and a 3-terephthalic acid linked dimer (8) of OSW-1 were synthesized. Their inhibitory activities on P388 and A-549 cells were detected.

A facile synthetic approach to a group of structurally typical diosgenyl saponins

Abstract A facile approach was developed for synthesizing an important group of plant diosgenyl saponins, three members (dioscin, polyphyllin D, and balanitin 7) with promising bioactivities were prepared.

Synthesis of steroidal glycosides bearing the disaccharide moiety of OSW-1 and their antitumor activities.

Nine glycosides bearing the disaccharide of OSW-1, namely 2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl-(1-->3)-2-O-acetyl-alpha-L-arabinopyranosides, were synthesized, and their antitumor activities were tested.

First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)

Abstract The first total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside ( 1 ), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope muscari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidts “inverse procedure” is demonstrated.

The first synthetic route to furostan saponins

Abstract 26- O -β- d -Glucopyranosyl-22-methoxy-25( R )-furost-5-en-3β-ol 3- O -β- d -glucopyranoside is synthesized from diosgenin in 11 steps and 26% overall yield. The present synthetic route represents the first one to furostan saponins.

Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation

Abstract A group of natural diosgenyl saponins was synthesized in a highly efficient manner employing the ‘one-pot sequential glycosylation’ protocol with the combined use of glycosyl trichloroacetimidates and thioglycosides.