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Facile constructed meroterpenoids with novel hexadecahydroacephenanthrylene carbon skeleton using the biotransformation and chemical synthesis method.
- Source :
-
Bioorganic chemistry [Bioorg Chem] 2024 Dec; Vol. 153, pp. 107871. Date of Electronic Publication: 2024 Oct 06. - Publication Year :
- 2024
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Abstract
- Bioaspermeroterpenoid A (1), the first meroterpenoid with an unprecedented hexadecahydroacephenanthrylene carbon skeleton, together with two analogues bioaspermeroterpenoids B and C (2 and 3) were co-isolated from the biotransformation extract of aspermeroterpene C by the fungus Penicillium herquei GZU-31-6. On the other hand, bioaspermeroterpenoid Aa (1a) featuring the same hexadecahydroacephenanthrylene carbon skeleton was synthesized from the precursor aspermeroterpene C by the nucleophilic addition reaction in the presence of CH <subscript>3</subscript> ONa. Furthermore, bioaspermeroterpenoids A and C showed good inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells with IC <subscript>50</subscript> values of 26.08 and 7.50 µM, respectively, compared to the positive control (Indomethacin, IC <subscript>50</subscript> 24.1 µM). Especially, bioaspermeroterpenoids A and C also significantly suppressed the protein expression of iNOS and COX-2 at the concentration of 12.5 μM.<br />Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Hui Cui reports was provided by Hui Cui. Hui Cui reports a relationship with Guangzhou University of Chinese Medicine that includes: non-financial support. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br /> (Copyright © 2024 Elsevier Inc. All rights reserved.)
- Subjects :
- Mice
RAW 264.7 Cells
Animals
Structure-Activity Relationship
Molecular Structure
Penicillium metabolism
Penicillium chemistry
Dose-Response Relationship, Drug
Nitric Oxide Synthase Type II metabolism
Nitric Oxide Synthase Type II antagonists & inhibitors
Cyclooxygenase 2 metabolism
Nitric Oxide biosynthesis
Nitric Oxide antagonists & inhibitors
Nitric Oxide metabolism
Lipopolysaccharides pharmacology
Lipopolysaccharides antagonists & inhibitors
Biotransformation
Terpenes chemistry
Terpenes pharmacology
Terpenes chemical synthesis
Terpenes metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 153
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 39383809
- Full Text :
- https://doi.org/10.1016/j.bioorg.2024.107871