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

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.

Marine natural products

“…218 Three pairs of atropodiastereomers were obtained from another strain of P. steckii, comprising heterodimeric 591 and 592, and homodimeric 593 and 594, bis-isochromans, and isochroman/1,4-benzoquinone conjugates 595 and 596. 219 OSMAC manipulation of Pestalotiopsis heterocornis led to production of polyketides 643-650 and ceramide 651, 230 a P. neglecta culture yielded chromenes 652-655 and chromones 656 and 657, 231 (−)-tricinonoic acid 658 and polyketide 659 were isolated from Phaeosphaeria spartinae, 232 and deep-sea sediment-derived Phomopsis strains yielded tenellone-macrolides 660-662, 233 and chlorinated azaphilones 663-667. 234 Pleosporales strains were the source of phenalenone derivatives 668-670, 235 and polyketides 671 and 672.…”

“…218 Three pairs of atropodiastereomers were obtained from another strain of P. steckii , comprising heterodimeric 591 and 592 , and homodimeric 593 and 594 , bis-isochromans, and isochroman/1,4-benzoquinone conjugates 595 and 596 . 219 Deep-sea sediment and sediment-derived Penicillium strains have been the source of numerous metabolites. Deep-sea-derived compounds include chromone derivatives 597–604 , 220 meroterpenoids 605–607 , 221 p -terphenyls 608–610 , 222 drimane sesquiterpenes 611 and 612 , and polyketides 613–618 .…”

Novel Bioactive Natural Products from Marine-Derived Penicillium Fungi: A Review (2021–2023)

“…Penicisteckins A-F (120-125) (Figure 3) represented novel biaryl scaffolds containing both central and axial chirality elements and isolated from the beach-mud-derived P. steckii HNNU-5B18 [51].…”

Two Decarestrictine Analogs from the Soil‐Derived Fungus Penicillium sp. YUD18003 Associated with Gastrodia elata

“…The chemical research of fungal secondary metabolites has been a challenging and promising research area in recent years. [1,2] Nowadays, thousands of compounds with different structures have been isolated and identified from fungi. [3] Penicillium spp.…”

“…1 H and13 C-NMR spectroscopic data for compounds 1 and 2.No.1 a 2 b δ H (J in Hz) δ C , type δ H (J in Hz) δ C , type1174.1, C 170.1, C 2 2.47 dd (13.6, 2.8) 2.39-2.42 m 41.3, CH 2 6.13 d (15.a Data were recorded at 400 MHz for proton and at 100 MHz for carbon in CD 3 OD. b Data were recorded at 400 MHz for proton and at 100 MHz for carbon in CDCl 3 .…”