Structural Revision of Hyperibrin B and Hyperscabrones H and I by Biosynthetic Considerations, NMR Analysis, and Chemical Synthesis
| Autor: | Robert B. Grossman, Teng-Fei Ji, Xing-Wei Yang, Xiaohui Wang, Xiao-Bin Nie |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Pharmacology
Biological Products Magnetic Resonance Spectroscopy Bicyclic molecule Molecular Structure Chemistry Stereochemistry Organic Chemistry Pharmaceutical Science Cyclohexanone Total synthesis Phloroglucinol Chemical synthesis Analytical Chemistry chemistry.chemical_compound Complementary and alternative medicine Drug Discovery Molecular Medicine Hypericum scabrum Hypericum |
| Zdroj: | Journal of natural products. 84(7) |
| ISSN: | 1520-6025 |
| Popis: | Previously, Gao et al. reported the isolation and structural determination of three natural products, hyperibrin B (HB), hyperscabrone H (HH), and hyperscabrone I (HI), from Hypericum scabrum. HB and HH had different NMR spectroscopic data, but they were assigned identical structures. Furthermore, these compounds should be derived from bicyclic polyprenylated acylphloroglucinols (BPAPs) via degradation, but the assigned structural features of the prenyl and prenylmethyl groups being cis and meta-substituted on the cyclohexanone core were not consistent with their biosynthetic origin. In this note, we revise the structures of HB, HH, and HI via NMR and MS spectroscopic analyses and biosynthetic considerations. We also complete a total synthesis of the revised structure of HB as well as its analogue, hyperibrin A, to further confirm the revision. The revised structures of HB, HH, and HI have not been reported. |
| Databáze: | OpenAIRE |
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