An unusual C-18 norditerpenoid, aspergiloid I (1), was isolated from the culture broth of Aspergillus sp. YXf3, an endophytic fungus derived from Ginkgo biloba. Its structure was unambiguously established by analysis of HRMS-ESI and spectroscopic data, and the absolute configuration was determined by low-temperature (100 K) single crystal X-ray diffraction with Cu K alpha radiation. This compound is structurally characterized by a new carbon skeleton with an unprecedented 6/5/6 tricyclic ring system bearing an alpha,beta-unsaturated spirolactone moiety in ring B, and represents a new subclass of norditerpenoid, the skeleton of which is named aspergilane. The hypothetical biosynthetic pathway for 1 was also proposed. The cytotoxic, antimicrobial, anti-oxidant and enzyme inhibitory activities of 1 were evaluated.
1.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Lab Biol & Genet Resources Trop Crops, Minist Agr, Haikou 571101, Peoples R China 2.Hainan Acad Ocean & Fisheries Sci, Haikou 570203, Hainan, Peoples R China 3.Nanjing Univ, Inst Funct Biomol, State Key Lab Pharmaceut Biotechnol, Nanjing 210093, Jiangsu, Peoples R China 4.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650204, Peoples R China
Guo,Zhi Kai;Wang,Rong;Huang,Wei;Li,Xiao Nian;Jiang,Rong;Tan,Ren Xiang;Ge,Hui Ming.Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp YXf3,BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,2014,114(8):1701-1709