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Prenylated benzophenone derivatives from Hypericum patulum.

Naonobu Tanaka1, Kanji Niwa2, Yuki Yano2

  • 1Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima, 770-8505, Japan. ntanak@tokushima-u.ac.jp.

Journal of Natural Medicines
|August 5, 2019
PubMed
Summary

Researchers discovered hypatulin C, a novel prenylated benzophenone from Hypericum patulum leaves. Its unique tricyclic structure and stereochemistry were determined using advanced spectroscopic and computational methods.

Keywords:
Hypatulin CHypericaceaeHypericum patulumPrenylated benzophenone

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Phytochemistry

Background:

  • Hypericum patulum is a plant species known to produce various bioactive compounds.
  • Prenylated benzophenones represent a class of natural products with diverse chemical structures and potential biological activities.

Purpose of the Study:

  • To isolate and characterize new prenylated benzophenones from Hypericum patulum.
  • To elucidate the chemical structure and absolute stereochemistry of the isolated compounds.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation through detailed spectroscopic analyses (NMR, MS).
  • Assignment of absolute stereochemistry using Electronic Circular Dichroism (ECD) spectroscopy and Time-Dependent Density Functional Theory (TDDFT) calculations.

Main Results:

  • A new prenylated benzophenone, hypatulin C (1), was isolated.
  • Hypatulin C (1) possesses a unique tricyclic [4.3.1.0^3,7]-decane core with four prenyl substituents.
  • A known analog, hypelodin B (2), was co-isolated.
  • The absolute stereochemistries of hypatulin C and hypelodin B were successfully assigned.

Conclusions:

  • The study successfully identified and characterized a novel prenylated benzophenone, hypatulin C.
  • The findings expand the knowledge of secondary metabolites from Hypericum species.
  • The applied spectroscopic and computational methods provide a robust framework for analyzing complex natural products.