Genome-based discovery of two previously
unreported fungal bifunctional
terpene synthases (BFTSs) from phytopathogenic fungi are reported:
FoFS catalyzing the formation of fusoxypenes A–C (1–3) and (−)-astellatene (4) and AtAS capable of synthesizing preaspterpenacid I (6). Interestingly, FoFS and AtAS catalyzed the formation of enantiomeric
sesterterpenes with a 5–6–7–3–5 ring system.
C22-oxidative modification of preaspterpenacid I by AtP450 was characterized
as well. Plausible cyclization pathways of the fusoxypenes were illustrated
by DFT calculations.
Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A (1a/1b), (±)-1-epi-epicospirocin A (2a/2b), two (+)-enantiomers of aspermicrones, ent-aspermicrone B (3b) and ent-aspermicrone C (4b), together with two hemiacetal epimeric mixtures, epicospirocin B/1-epi-epicospirocin...
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