Bioorganic & Medicinal Chemistry Letters 2007-05-01

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

Taku Chiba, Takemasa Takii, Kenji Nishimura, Yoshifumi Yamamoto, Hiroko Morikawa, Chiyoji Abe, Kikuo Onozaki

Index: Bioorg. Med. Chem. Lett. 17 , 2487-91, (2007)

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Abstract

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-alpha-D-galactopyranosyl)-(1-->6)-O-(2,3,4-tri-O-acetyl-alpha-D-galactopyranosyl)-(1-->6)-O-2,3,4-tri-O-acetyl-beta-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.