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.
Murakami
Takanori
T
Faculty of Agriculture and Bioscience, Hirosaki University, 3-Bunkyo-cho, Hirosaki, 036-8561, Japan.
Takahashi
Yukiko
Y
Fukushi
Eri
E
Kawabata
Jun
J
Hashimoto
Masaru
M
Okuno
Toshikatsu
T
Harada
Yukio
Y
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