THE METABOLITES OF TRICHODERMA-LONGIBRACHIATUM .1. ISOLATION OF THE METABOLITES AND THE STRUCTURE OF TRICHODIMEROL

Trichoderma longibrachiatum Rifai aggr. is a fungus reported to be antagonistic to the fungus Mycena citricolor, the causative agent of the American leaf spot disease of coffee. We have investigated the metabolites produced when T. longibrachiatum is grown in liquid culture and have isolated the known compounds sorbicillin (2), bisvertinol (3), and bisvertinolone (4) as well as several new compounds including trichodimerol (1), an interesting new natural product possessing a proper axis of symmetry. The structure of trichodimerol (1) was determined by a combination of spectroscopic techniques, including H-1 and C-13 nuclear magnetic resonance, infrared, ultraviolet, circular dichroism, optical rotatory dispersion, and mass spectrometry, and by transformation to octahydrotrichodimerol (6) and symmetrical and unsymmetrical derivatives thereof. The relative stereochemistry of bisvertinol (3) and bisvertinolone (4) has been revised. The metabolites described are not biologically active against Mycena citricolor.