title: Synthesis of new sugar derivatives from Stachys sieboldi Miq and antibacterial evaluation against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus.
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.
authors.affiliation: Department of Molecular Health Sciences, Graduate School of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan.
authors.forename: Taku
authors.initials: T
authors.lastname: Chiba
authors.forename: Takemasa
authors.initials: T
authors.lastname: Takii
authors.forename: Kenji
authors.initials: K
authors.lastname: Nishimura
authors.forename: Yoshifumi
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Hiroko
authors.initials: H
authors.lastname: Morikawa
authors.forename: Chiyoji
authors.initials: C
authors.lastname: Abe
authors.forename: Kikuo
authors.initials: K
authors.lastname: Onozaki
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D008969:Molecular Sequence Data; D009162:Mycobacterium avium / Q000378:metabolism*; D009169:Mycobacterium tuberculosis / Q000378:metabolism*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D031366:Stachys; D013211:Staphylococcus aureus / Q000378:metabolism*
chemical_list: D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D010936:Plant Extracts