title: Asymmetric total synthesis of 6-Tuliposide B and its biological activities against tulip pathogenic fungi.
abstract: The structure-activity relationship was investigated to evaluate the antifungal activities of tuliposides and tulipalins against tulip pathogenic fungi. 6-Tuliposide B was effectively synthesized via the asymmetric Baylis-Hillman reaction. Tuliposides and tulipalins showed antifungal activities against most of the strains tested at high concentrations (2.5 mM), while Botrytis tulipae was resistant to tuliposides. Tulipalin formation was involved in the antifungal activity, tulipalin A showed higher inhibitory activity than 6-tuliposide B and tulipalin B. Both the tuliposides and tulipalins showed pigment-inducing activity against Gibberella zeae and inhibitory activity against Fusarium oxysporum f. sp tulipae. These activities were induced at a much lower concentration (0.05 mM) than the antifungal MIC values.
authors.affiliation: Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Japan.
authors.forename: Kengo
authors.initials: K
authors.lastname: Shigetomi
authors.forename: Shoko
authors.initials: S
authors.lastname: Omoto
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Kato
authors.forename: Makoto
authors.initials: M
authors.lastname: Ubukata
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005670:Fusarium / Q000187:drug effects* / Q000472:pathogenicity*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006885:Hydroxybutyrates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D031447:Tulipa / Q000382:microbiology*
chemical_list: C551332:6-tuliposide B; D000935:Antifungal Agents; D005960:Glucosides; D006885:Hydroxybutyrates