Structural Revision of Hyperibrin B and Hyperscabrones H and I by Biosynthetic Considerations, NMR Analysis, and Chemical Synthesis

Xiaohui Wang, Xiao Bin Nie, Robert B. Grossman, Teng Fei Ji, Xing Wei Yang

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Previously, Gao et al. reported the isolation and structural determination of three natural products, hyperibrin B (HB), hyperscabrone H (HH), and hyperscabrone I (HI), fromHypericum 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.

Original languageEnglish
Pages (from-to)2059-2064
Number of pages6
JournalJournal of Natural Products
Volume84
Issue number7
DOIs
StatePublished - Jul 23 2021

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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