Synthesis of new sugar derivatives from Stachys sieboldi Miq and antibacterial evaluation against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus

A series of sugar derivatives (7–14) were synthesized from stachyose, a sugar compound of Stachys sieboldi Miq, and evaluated for antibacterial activity against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus, and their structure–activity relationships were studied. The results showed that the compound OCT359 (allyl O-(2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl)-(1 → 6)-O-(2,3,4-tri-O-acetyl-α-d-galactopyranosyl)-(1 → 6)-O-2,3,4-tri-O-acetyl-β-d-glucopyranoside) (12) exhibited in vitro antibacterial activity. The allyl group at C-1 and the acetoxy groups of the manninotrioside were requisite for the antibacterial activity.

Graphical abstractThe antibacterial properties of sugar derivatives synthesized from stachyose obtained from the root of Stachys sieboldi Miq 12 (MIC = 3–25 μg/ml) is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide