Biosynthesis of sespendole.
Sespendole is the first reported fungal metabolite having an indolosesquiterpene core structure. The biosynthesis of sespendole was studied here by feeding experiments with [13C]acetate, [15N]anthranilic acid and [13C]tryptophan. The data suggested that a farnesyl residue derived from the mevalonate pathway and an anthranilate-derived indole-3-glycerol phosphate residue are condensed, and then cyclization occurs along with rearrangement to form the indolosesquiterpene core.
Uchida
Ryuji
R
School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Tomoda
Hiroshi
H
Omura
Satoshi
S
D000085:Acetates / Q000378:metabolism; D004224:Diterpenes / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D014364:Tryptophan / Q000378:metabolism; D062367:ortho-Aminobenzoates / Q000378:metabolism
D000085:Acetates; D004224:Diterpenes; D007211:Indoles; D062367:ortho-Aminobenzoates; C510263:sespendole; C031385:anthranilic acid; D014364:Tryptophan