Biosynthesis of lambertellols based on the high specific incorporation of the 13C-labeled acetates and their biological properties.
Biosyntheses of lambertellols A (1) and B (2) as well as lambertellin (3) were investigated by isotope labeling experiments. Nearly 40% of specific incorporation of [1,2-(13)C(2)]acetate was achieved, and all the carbons in 1 and 2 were labeled. This high incorporation of the labeled acetate was realized by providing INADEQUATE spectra by employing only 0.4 and 0.7 mg of 1 and 2, respectively. Our studies revealed that 1-3 are biogenetically synthesized via loss of two carbons from octameric acetate. A biological assay against Monilinia fructicola revealed those remarkably inhibited hyphal germinations. However, neither of them killed the spores immediately, even in high concentration. These conditions induced the formation of microconidia.
Faculty of Agriculture and Bioscience, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan.
Takanori
T
Murakami
Yukiko
Y
Takahashi
Eri
E
Fukushi
Jun
J
Kawabata
Masaru
M
Hashimoto
Toshikatsu
T
Okuno
Yukio
Y
Harada
D000085:Acetates / Q000737:chemistry / Q000378:metabolism*; D000935:Antifungal Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D001203:Ascomycota / Q000187:drug effects / Q000378:metabolism; D002247:Carbon Isotopes; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D013141:Spiro Compounds / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology
D000085:Acetates; D000935:Antifungal Agents; D002247:Carbon Isotopes; D009281:Naphthalenes; D013141:Spiro Compounds; C492699:lambertellol A; C492700:lambertellol B