Multioxidized aromatic polyketides produced by a soil-derived fungus Penicillium canescens

• Published in: Phytochemistry (Oxford) 2022-01, Vol.193, p.113012-113012, Article 113012
• Main Authors: Zang, Yi, Gong, Yihua, Shi, Zhengyi, Qi, Changxing, Chen, Chunmei, Tong, Qingyi, Liu, Junjun, Wang, Jianping, Zhu, Hucheng, Zhang, Yonghui
• Format: Article
• Language: English
• Subjects: Aromatic polyketides; Cytotoxicity; HL-60 Cells; Humans; Molecular Structure; OSMAC; Penicillium; Penicillium canescens; Polyketides - pharmacology; Soil; Trichocomaceae
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2021.113012

Under OSMAC strategy, seven unreported multioxidized aromatic polyketides, penicanesins A‒G, were discovered from a soil-derived fungus Penicillium canescens along with seven known compounds. Their structures were assigned by extensive 1D and 2D NMR spectra in combination with HRESIMS and single crystal X-ray diffraction. Absolute stereochemistry of penicanesins A and D were elucidated by theoretical ECD calculation. (±)-Penicanesins A and B are two pairs of racemic aromatic polyketides with an unusual 6/6/6/6 heterotetracyclic ring core. In bioassay, (−)-penicanesin A shows potential cytotoxicity against human cancer cell lines HL-60 and SW480 with IC50 values at 13.8 ± 0.6 and 12.5 ± 0.9 μM, respectively, whereas the enantiomer (+)-penicanesin A is less active. [Display omitted] •(±)-Penicanesins A and B, with a 6/6/6/6 tetracyclic core, isolated from Penicillium canescens.•Absolute stereochemistry was determined by theoretical ECD calculation and X-ray diffraction.•(−)-Penicanesin A shows potential cytotoxicity against HL-60 and SW480 cells. Seven unreported multioxidized aromatic polyketides were discovered from a soil-derived fungus Penicillium canescens along with seven known compounds. (−)-Penicanesin A shows potential cytotoxicity against human cancer cell lines HL-60 and SW480 with IC50 values at 13.8 ± 0.6 and 12.5 ± 0.9 μM respectively, whereas the enantiomer (+)-penicanesin A is less active.