Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

Thirty-three metabolites including five phenalenone derivatives ( 1 – 5 ), seven cytochalasins ( 6 – 12 ), thirteen butenolides ( 13 – 25 ), and eight phenyl derivatives ( 26 – 33 ) were isolated from Aspergillus sp. CPCC 400735 cultured on rice. The structures of all compounds were elucidated by NMR, MS, and CD experiments, of which 1 – 5 (asperphenalenones A–E), 6 (aspochalasin R), and 13 (aspulvinone R) were identified as new compounds. Specifically, asperphenalenones A–E ( 1 – 5 ) represent an unusual structure composed of a linear diterpene derivative linked to a phenalenone derivative via a C–C bond. Compounds 1, 4, 10, and 26 exhibited anti-HIV activity with IC 50 values of 4.5, 2.4, 9.2, and 6.6 μM, respectively (lamivudine 0.1 μM; efavirenz, 0.4 × 10 –3 μM).