Sorbicillactone A: a Structurally Unprecedented Bioactive Novel-Type Alkaloid from a Sponge-Derived Fungus

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Abstract
This chapter deals with the discovery of sorbicillactone A, as an illustrative example of the fruitful cooperation within BIOTECmarin — its isolation and chemical characterization, and its biological activities. Sorbicillactone A was isolated from a strain of Penicillium chrysogenum cultured from a sample of the Mediterranean sponge Ircinia fasciculata; it possesses a unique bicyclic lactone structure, seemingly derived from sorbicillin. Among the numerous known sorbicillin-derived structures, it is the first found to contain nitrogen and thus the first representative of a novel type of ‘sorbicillin alkaloids’, apparently originating from a likewise remarkable biosynthesis. Furthermore, the compound exhibits promising activities in several mammalian and viral test systems, in particular a highly selective cytostatic activity against murine leukemic lymphoblasts (L5178y) and the ability to protect human T cells against the cytopathic effects of HIV-1. These properties qualify sorbicillactone A or one of its derivatives for animal and (hopefully) also future therapeutic human trials.