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Penisimplinoids A-K, highly oxygenated andrastin-type meroterpenoids with diverse activities from the marine-derived fungus Penicillium simplicissimum. | LitMetric

Penisimplinoids A-K, highly oxygenated andrastin-type meroterpenoids with diverse activities from the marine-derived fungus Penicillium simplicissimum.

Bioorg Chem

Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China; Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, People's Republic of China. Electronic address:

Published: December 2024

AI Article Synopsis

  • Penisimplinoid A (1) is a unique compound derived from the marine fungus Penicillium simplicissimum, characterized by a complex polycyclic structure that hasn't been seen before.
  • Alongside penisimplinoid A, ten new related compounds (2-11) and one known analogue (12) were identified, and their molecular structures were confirmed using advanced techniques like X-ray diffraction and computational chemistry.
  • Biological tests indicated that some of these compounds, particularly 7 and 12, have anti-inflammatory properties, while compound 6 showed potential as a cancer treatment and compounds 7 and 11 promoted blood vessel formation (angiogenesis).

Article Abstract

Penisimplinoid A (1), the first andrastin-type meroterpenoid with an unprecedented 6/6/3/6/5/5 polycyclic systems, together with ten highly oxygenated andrastin-type meroterpenoids (2-11) and one known analogue (12), were co-isolated from the marine-derived fungus Penicillium simplicissimum. Their absolute configurations were determined by single-crystal X-ray diffraction analysis (Cu Kα), DP4+ probability analyses, and ECD quantum chemistry calculations. Biological evaluation revealed that 7 and 12 showed anti-inflammatory activities in the zebrafish assay, 6 exhibited cytotoxic activity against NCI-H446 tumor cells with an IC value of 6.49 μM, 7 and 11 exhibited significant promoting angio-genesis activities.

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Source
http://dx.doi.org/10.1016/j.bioorg.2024.107897DOI Listing

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