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Five new polyketide-terpene hybrid metabolites ( 1 – 5 ) with highly functionalized groups, together with six known derivatives ( 6 – 11 ), were isolated from the endolichenic fungus  Pestalotiopsis  sp. Their structures were elucidated by extensive NMR experiments including  1 H,  13 C, HMQC, COSY, and HMBC. The relative configurations of the new compounds were determined by analysis of coupling constants and ROESY correlations. The absolute configurations especially the secondary alcohol at C-15 in  1  and secondary alcohol at C-14 in  5  were established via the CD experiments of the in situ formed [Rh 2 (OCOCF 3 ) 4 ] complex with the acetonide derivatives. These compounds were tested for their inhibition activity against six plant pathogens. Compounds  1  and  5  exhibited pronounced efficiency against  Fusarium oxysporum , and compounds  5  and  6  potently inhibited  Fusarium gramineum  with MIC value of 8  µ g/mL, which revealed the plausible ecological role of endolichenic fungus in providing chemical protection for its host lichen in the fungus-plant relationship. The biosynthetic pathway of compounds  1 – 11  was postulated for the first time, which paved the way for its further biosynthesis research.

Polyketide-Terpene Hybrid Metabolites from an Endolichenic Fungus Pestalotiopsis sp.