ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp

  • J Nat Prod. 2023 Nov 24;86(11):2580-2584. doi: 10.1021/acs.jnatprod.3c00174.
Karen Harms  1 ,  Pathompong Paomephan  1  2 ,  Thitiya Boonpratuang  3 ,  Rattaket Choeyklin  3  4 ,  Chuenchit Boonchird  2 ,  Frank Surup  1  5
Affiliations
  • 1. Department Microbial Drugs, Helmholtz Centre for Infection Research, and German Centre for Infection Research (DZIF), Partner Site Hannover-Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
  • 2. Department of Biotechnology, Faculty of Science, Mahidol University, 272 Thanon 4 Rama VI, Thung Phaya Thai, Ratchathewi, Bangkok 10400, Thailand.
  • 3. National Biobank of Thailand (NBT), National Science and Technology Development Agency (NSTDA), 144 Thailand Science Park, Phahonyothin Road, Khlong Nueng, Khlong Luang, Pathum Thani 12120, Thailand.
  • 4. Biodiversity-Based Economy Development Office (Public Organization), The Government Complex Commemorating His Majesty the King's 80th Birthday Anniversary 5 December 2007 Ratthaprasasanabhakdi Building, ninth Floor, Chaengwattana Road, Thung Song Hong, Lak Si, Bangkok 10210, Thailand.
  • 5. Institute of Microbiology, Technische Universität Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany.
PMID: 37931226 DOI: 10.1021/acs.jnatprod.3c00174
Abstract

Metabolites 1 and 2, isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak Antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against Cancer cell lines. Their planar structures were elucidated by high-resolution electrospray ionization mass spectrometry and NMR spectroscopy as clavilactone J, known from the basidiomycete Ampulloclitocybe clavipes, and its new 1,4-benzoquinone derivative. A detailed analysis of the ROESY correlations in 1 confirmed the recent revision of the relative configuration of clavilactone J. However, specific rotation and Cotton effects observed by electronic circular dichroism were contrary to those of the clavilactones; thus, we assigned a rare antipodal absolute configuration.