2. Academic Validation
  3. Penicisteckins A-F, Isochroman-Derived Atropisomeric Dimers from Penicillium steckii HNNU-5B18

Penicisteckins A-F, Isochroman-Derived Atropisomeric Dimers from Penicillium steckii HNNU-5B18

  • J Nat Prod. 2021 Nov 26;84(11):2953-2960. doi: 10.1021/acs.jnatprod.1c00787.
Xiao-Zhen Wu 1 2,  Wen-Jun Huang 1,  Wei Liu 2,  Attila Mándi 3,  Qingbo Zhang 2,  Liping Zhang 2,  Wenjun Zhang 2,  Tibor Kurtán 3,  Cheng-Shan Yuan 1 2,  Changsheng Zhang 2
Affiliations

Affiliations

  • 1 State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
  • 2 Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Institutions of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China.
  • 3 Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.
PMID: 34787427 DOI: 10.1021/acs.jnatprod.1c00787
Abstract

Penicisteckins A-D (1-4), two pairs of atropodiastereomeric biaryl-type hetero- and homodimeric bis-isochromans with 7,5'- and 7,7'-linkages and a pair of atropodiastereomeric 2-(isochroman-5-yl)-1,4-benzoquinone derivatives [penicisteckins E (5) and F (6)], were isolated from the Penicillium steckii HNNU-5B18. Their structures including the absolute configuration were determined by extensive spectroscopic and single-crystal X-ray diffraction analysis and TDDFT-ECD calculations. Both the bis-isochromans and the isochroman/1,4-benzoquinone conjugates represent novel biaryl scaffolds containing both central and axial chirality elements. The monomer anserinone B (8) exhibited potent Antibacterial activities against Staphylococcus aureus ATCC 29213 and methicillin-resistant Staphylococcus aureus with minimal inhibition concentration values ranging from 2 to 8 μg mL-1. Plausible biosynthetic pathways of 1-6 are proposed, which suggest how the absolute configurations of the isolates were established during the biosynthetic scheme.

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