title: Tafuketide, a phylogeny-guided discovery of a new polyketide from Talaromyces funiculosus Salicorn 58.
abstract: A phylogeny-guided approach was applied to screen endophytic fungi containing type I polyketide synthase (PKS I) biosynthetic gene sequences and aimed to correlate genotype to chemotype for the discovery of novel bioactive polyketides. Salicorn 58, which was identified as Talaromyces funiculosus based on its internal transcribed spacer (ITS) and ribosomal large-subunit (LSU) DNA sequences, showed significant target bands. A chemical investigation of the culture of Salicorn 58 was allowed for the isolation of a new polyketide, Talafun (1), and a new natural product, N-(2'-hydroxy-3'-octadecenoyl)-9-methyl-4,8-sphingadienin (2), together with six known compounds, including chrodrimanin A (3), chrodrimanin B (4), N-(4-hydroxy-2-methoxyphenyl) acetamide (5), butyl β-glucose (6), 3β,15β-dihydroxyl-(22E, 24R)-ergosta-5,8(14),22-trien-7-dione (7), and (3β,5a,8a,22E)-5,8-epidioxyergosta-6,22-dien-3-ol (8). Their chemical structures were elucidated by extensive spectroscopic analysis and electro circular dichroism (ECD) spectrum calculations. Antioxidant experiments revealed that compound 5 showed strong ABTS(+) radical scavenging activity with an IC50 value of 11.43 ± 1.61 μM and potent ferric reducing activity (FRAP assay) with FRAP value of 187.52 ± 2.97. Antimicrobial assays revealed that compounds 1 and 4 showed high levels of selectivity toward Escherichia coli with MIC values of 18 ± 0.40 and 43 ± 0.52 μM, respectively. Compounds 2 and 3 exhibited broad-spectrum antimicrobial activity against Staphylococcus aureus, Mycobacterium smegmatis, Micrococcus tetragenus, Mycobacterium phlei, and E. coli, respectively. The results from the current research highlight the advantage of phylogeny-guided pipeline for the screening of new polyketides from endophytic fungi containing PKS I genes.
authors.affiliation: Key Laboratory of Food Processing and Quality Control, College of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China.|Shenzhen Key Laboratory of Fermentation, Purification and Analysis, Shenzhen Polytechnic, Shenzhen, Guangdong, 518055, People's Republic of China.
authors.forename: Jia
authors.initials: J
authors.lastname: Guo
authors.affiliation: Key Laboratory of Food Processing and Quality Control, College of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China.
authors.forename: Huomiao
authors.initials: H
authors.lastname: Ran
authors.affiliation: School of Food Science, Henan Institute of Science and Technology, Xinxiang, 453003, People's Republic of China.
authors.forename: Jie
authors.initials: J
authors.lastname: Zeng
authors.affiliation: Shenzhen Key Laboratory of Fermentation, Purification and Analysis, Shenzhen Polytechnic, Shenzhen, Guangdong, 518055, People's Republic of China.
authors.forename: Dong
authors.initials: D
authors.lastname: Liu
authors.affiliation: Key Laboratory of Food Processing and Quality Control, College of Food Science and Technology, Nanjing Agricultural University, Nanjing, 210095, People's Republic of China. xzhfood@njau.edu.cn.
authors.forename: Zhihong
authors.initials: Z
authors.lastname: Xin
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055808:Drug Discovery / Q000379:methods; D060026:Endophytes / Q000201:enzymology / Q000235:genetics*; D004926:Escherichia coli / Q000187:drug effects; D005838:Genotype; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D020102:Mycobacterium smegmatis / Q000187:drug effects; D010802:Phylogeny; D048630:Polyketide Synthases / Q000235:genetics* / Q000302:isolation & purification*; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013057:Spectrum Analysis; D013211:Staphylococcus aureus / Q000187:drug effects; D032901:Talaromyces / Q000737:chemistry* / Q000201:enzymology / Q000235:genetics / Q000254:growth & development
chemical_list: D000900:Anti-Bacterial Agents; D061065:Polyketides; D048630:Polyketide Synthases; C087193:polyketide beta-ketoacylsynthase
keywords: A phylogeny-guided approach; Antimicrobial activity; Antioxidant activity; PKS I gene