Fusicoccins P and Q, and 3-epifusicoccins H and Q, new polar fusicoccins from isolate Niigata 2-A of a peach Fusicoccum canker fungus.
Our search for new polar fusicoccins biosynthetically related to fusicoccin A from the culture filtrate of isolate Niigata 2-A of a peach Fusicoccum canker fungus resulted in the isolation of new fusicoccins named fusicoccins P and Q, and 3-epifusicoccins H and Q, together with 3'-deacetylfusicoccin A and 16-O-demethyl-3-epifusicoccin J. The structures of fusicoccins P and Q, and of 3-epifusicoccin Q were determined to be those of deisopentenylfusicoccin J, 12alpha-hydroxyfusicoccin H and 12alpha-hydroxy-3-epifusicoccin H, respectively, by NMR spectrometry and chemical derivation from known fusicoccins. 3-Epifusicoccin H was identified by comparing its 400 MHz NMR spectra with those of fusicoccin H. The lettuce seed germination-stimulating activity of these new fusicoccins was examined in the presence of ABA: fusicoccin P was highly active, while 3-epifusicoccins H and Q were slightly active, and fusicoccins H and Q were almost inactive. Possible biosynthetic pathways incorporating these new fusicoccins and 3-epifusicoccins from geranylgeranyl diphosphate to 3'-deacetlyfusicoccin A and 16-O-demethyl-3-epifusicoccin J are discussed.
Sassa
Takeshi
T
Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Wakaba-cho, Tsuruoka 997-8555, Japan. tsassa@tds1.tr.yamagata-u.ac.jp
Tajima
Naoto
N
Sato
Mitsuyoshi
M
Takahashi
Ai
A
Kato
Nobuo
N
D000040:Abscisic Acid / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003624:Darkness; D005670:Fusarium / Q000737:chemistry*; D018525:Germination / Q000187:drug effects; D006027:Glycosides / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D019906:Nuclear Magnetic Resonance, Biomolecular; D027861:Prunus / Q000382:microbiology; D012639:Seeds / Q000187:drug effects / Q000254:growth & development
D006027:Glycosides; C007808:fusicoccin; D000040:Abscisic Acid