Phytotoxic sesterterpene, 11-epiterpestacin, from Bipolaris sorokiniana NSDR-011.
The structure of siccanol, a phytotoxic sesterterpene of fungal origin, was analyzed after chemical conversion by NMR spectroscopy. Siccanol was found to be an epimer of terpestacin that has been isolated from Arthrinium sp., and was thus renamed 11-epiterpestacin. Its stereochemistry was also identical with that of fusaproliferin, a structurally related mycotoxin from Fusarium proliferatum. Therefore, this sesterterpene may also be referred to as 24-deacetyl fusaproliferin. The phytotoxicity of 11-epiterpestacin was almost equal to that of terpestacin, but significantly higher than that of fusaproliferin.
Nihashi
Yoichiro
Y
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan.
Lim
Chi-Hwan
CH
Tanaka
Chihiro
C
Miyagawa
Hisashi
H
Ueno
Tamio
T
D001203:Ascomycota / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D010935:Plant Diseases / Q000382:microbiology; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D012434:Secale / Q000187:drug effects / Q000254:growth & development
D001643:Bridged Bicyclo Compounds; C080890:terpestacin