Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces pinophilus.

Maria Salvatore,Marina Dellagreca,Anna Andolfi,Daniele Naviglio,Francesco Salvatore,Rosario Nicoletti,Francesco Vinale

doi:10.3390/molecules23040950

Abstract

Talarodiolide, a new 12-membered macrodiolide, was isolated and characterized from the culture filtrate of strain LT6 of Talaromyces pinophilus. The structure of (Z)-4,10-dimethyl-1,7-dioxa-cyclododeca-3,9-diene-2,8-dione was assigned essentially based on NMR and MS data. Furthermore, several known compounds were isolated and identified in the crude extract of the culture filtrate and mycelium of this strain. EI mass spectrum at 70 eV of all isolated metabolites was acquired and compiled in a custom GC/MS library to be employed to detect metabolites in the crude extracts.

Highlights

IntroductionWith a widespread occurrence in very diverse environmental contexts, from the soil to the sea [1,2,3], the species Talaromyces pinophilus (=Penicillium pinophilum) (Eurotiales: Trichocomaceae) has received increasing attention in mycological research for its ability to act as a fungal antagonist and plant-growth promoter [1,4,5], and for possible biotechnological applications based on the production of enzymes [6,7] and bioactive metabolites [8,9,10].Two strains (LT4 and LT6), possibly deriving from the same wild clone since they were both recovered from the rhizosphere of a tobacco plant cropped near Lecce (Apulia, Southern Italy), have been studied in our laboratories after they were shown to produce a novel fungitoxic and cytostatic compound named 3-O-methylfunicone (OMF) [1,11]
The present paper reports findings from the first GC/MS-based investigation on secondary metabolites culture andextracts mycelial first GC/MS-based investigation on secondary metabolites in culture in filtrate andfiltrate mycelial of extracts of T. pinophilus
The present paper describes the isolation and structural characterization of the first 12-membered macrodiolide, named talarodiolide, from the culture filtrate of strain LT6 of T. pinophilus

Summary

Introduction

With a widespread occurrence in very diverse environmental contexts, from the soil to the sea [1,2,3], the species Talaromyces pinophilus (=Penicillium pinophilum) (Eurotiales: Trichocomaceae) has received increasing attention in mycological research for its ability to act as a fungal antagonist and plant-growth promoter [1,4,5], and for possible biotechnological applications based on the production of enzymes [6,7] and bioactive metabolites [8,9,10].Two strains (LT4 and LT6), possibly deriving from the same wild clone since they were both recovered from the rhizosphere of a tobacco plant cropped near Lecce (Apulia, Southern Italy), have been studied in our laboratories after they were shown to produce a novel fungitoxic and cytostatic compound named 3-O-methylfunicone (OMF) [1,11]. OMF is part of a homogeneous family comprising about 20 structurally related secondary metabolites which have been mainly characterized from cultures of Talaromyces strains [12] It has notable antitumor properties based on several biomolecular mechanisms of action resulting from a series of preclinical assays [13,14,15,16,17]. It represents the main extrolite produced by our strains, other funicone variants have been occasionally extracted [18,19], indicating that some factors act during the culturing cycle which may lead to the accumulation of intermediate or side products. Within our recent activity aiming at the standardization of OMF production, additional compounds were detected from cultures of strain LT6

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Conclusion