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- Title
Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols.
- Authors
Xie, Jin-Yan; Li, Pengfei; Yan, Xi-Tao; Gao, Jin-Ming
- Abstract
The search for lead compounds with anti-neuroinflammatory activity from structurally 'optimized' natural products is a crucial and promising strategy in the quest to discover safe and efficacious agents for treating neurodegenerative diseases. A phytochemical investigation on the aerial portions of Hypericum elatoides led to the isolation of five nitrogenous polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperelanitriles A–D (1–4) and hyperelamine A (5). Their structures were determined by spectroscopic analysis, ECD and NMR calculations, and X-ray crystallography. To the best of our knowledge, compounds 1–4 represent the first examples of acylphloroglucinols featuring an α-aminonitrile moiety, while 5 is a rare enamine-containing PPAP. Further, the synthesis of these naturally occurring PPAP-based nitriles or amines was accomplished. Compound 5 exhibited inhibitory activity against LPS-activated NO production in BV-2 cells, potentially through the suppression of TLR-4/NF-κB signaling. Here we show the isolation, structural elucidation, synthesis, and bioactive evaluation of compounds 1–5. Natural products are a rich source of lead compounds in drug discovery. Here, the authors report the discovery and synthesis of five nitrogenous polycyclic polyprenylated acylphloroglucinols named hyperelanitriles A–D and hyperelamine A from the plant Hypericum elatoides with anti-inflammatory activity against lipopolysaccharides-activated nitric oxide production.
- Subjects
HYPERICUM; DRUG discovery; X-ray crystallography; DOSAGE forms of drugs; NATURAL products; ENAMINES; ASYMMETRIC dimethylarginine
- Publication
Communications Chemistry, 2024, Vol 7, Issue 1, p1
- ISSN
2399-3669
- Publication type
Article
- DOI
10.1038/s42004-023-01091-1