Talaromycolides A–C, Novel Phenyl-Substituted Phthalides Isolated from the Green Chinese Onion-Derived Fungus Talaromyces pinophilus AF-02

Abstract

The green Chinese onion (Allium fistulosum L.), which is widely cultivated and has been naturalized in many places, is an important spice and vegetable in East and Southeast Asia. It is used to treat the common cold in China. In the ongoing search for antibacterial activity in fungi derived from natural, pungently scented vegetables, the secondary metabolites of Talaromyces pinophilus AF-02, which was isolated from the stem of the green Chinese onion, were investigated. The genus Talaromyces (Trichocomaceae) is an important fungal genus because of its ubiquity and the role of many of its species in food and agriculture production. Three new phthalide derivatives, talaromycolides A-C, 1-3; a new long-chain dicarboxylic acid, 11; and 12 known compounds were isolated from methanolic extracts of this fungus. Their structures were determined via extensive NMR, HR-ESI-MS, and CD spectroscopic analyses. Compounds 1-3 are rare phthalide derivatives with a novel linkage position between the phenyl and phthalide moieties. The biological properties of 1-16 were evaluated using six different bacteria, and 1-3, 5, and 11 exhibited significant antibacterial activity in response to some of the tested strains.

Genome sequencing and analysis of Talaromyces pinophilus provide insights into biotechnological applications

“…We used data from the PE library with an average insert size of 500 bp from T. pinophilus 1–95 to map the entire genome sequence of T. cellulolyticus Y-94 7 . The PE reads covered 35 scaffolds with 32.06 Mb of sequence from the T. cellulolyticus Y-94 genome, resulting in 88% average coverage and 83-times average depth (see Supplementary Table S4).…”

“…These results suggested that T. pinophilus 1–95 has potential for producing bioactive secondary metabolites. Although thus far, several bioactive secondary metabolites have been extracted and characterized from T. pinophilus 6, 7 , according to the genomic data, additional secondary metabolites could be generated using this species.…”

“…Therefore, T. pinophilus is considered a potential alternative to Trichoderma reesei for cellulase production and efficient biomass hydrolysis. T. pinophilus produces a variety of medically useful metabolites such as 3- O -methylfunicone, which is used to inhibit mesothelioma cell motility 6 , and talaromycolides 1–3, 5 and 11, which inhibit the growth of the human pathogen methicillin-resistant Staphylococcus aureus 7 .…”

Endophytic fungi harbored in the root of Sophora tonkinensis Gapnep: Diversity and biocontrol potential against phytopathogens

“…The species F. solani , F. oxysporum, C. perangustum , Cladosporium sp., T. pinophilus , P. coffeae , and M. verrucaria were dominant in this work, possibly due to the high spore production of these fungi and their cosmopolitan nature, which statistically increases their chance to become established as endophytes, as indicated in previous studies (Mishra et al., ; Raviraja, ; Schulthess & Faeth, ). In addition, based on the “balanced antagonisms” hypothesis (Schulz, Haas, Junker, Andree, & Schobert, ; Schulz, Rommert, Dammann, Aust, & Strack, ), they as dominant species might not only secrete toxic metabolites to inhibit microbial competitors (Breinholt et al., ; Lee & Lee, ; Zhai et al., ) but also possess the ability to resist the attack of the host alkaloids with antitumor and antifungal activities (Liu et al., ; Yang, Zhao, & Ju, ).…”

The Bioactive Secondary Metabolites from Talaromyces species

“…Three known diketopiperazines, cyclo( l -proline- l -leucine) ( 13 ), cyclo( l -proline- l -phenylalanine) ( 14 ), and cyclo( l -tyrosine- l -phenylalanine) ( 15 ), were isolated from the methanolic extracts of the green Chinese onion-derived fungus T. pinophilus AF-02 [ 7 ]. …”