Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort)

doi:10.1016/S0367-326X(03)00114-X

Fitoterapia

Volume 74, Issue 5, July 2003, Pages 439-444

https://doi.org/10.1016/S0367-326X(03)00114-X Get rights and content

Abstract

Repeated examination of the aerial parts of Hypericum perforatum yielded a new degradation product of hyperforin (1) namely deoxyfurohyperforin A (2), together with the previously identified furohyperforin (3), furoadhyperforin (4), furohyperforin A (5a and 5b), pyrano[7,28-b]hyperforin (6) and 3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)-cyclohexanone (7). The antimicrobial activity of the compounds 3, 5a and 5b, 6 and 7 was tested against Staphylococcus aureus, Candida albicans, Bacillus subtilis and Escherichia coli.

Introduction

Due to numerous pharmacological activities [1], Hypericum perforatum L. (Clusiaceae), St. John's Wort, one of the best known medicinal plants, is currently receiving considerable attention.

Among the active principles, hyperforin exhibiting antibiotic [2] and antidepressant properties [3], [4], [5], [6] is, beyond any doubt, one of the most important constituent of this species. Unfortunately, this compound, showing pronounced susceptibility to oxidative transformations, is very unstable. In a previous investigation, focused on the fractions of the crude EtOH extract of the aerial parts of H. perforatum with antibiotic activity, we have isolated two oxidized products of hyperforin [7] and one of adhyperforin [8], all of them formed by oxygenation of the C-6 side chain of (ad)hyperforin. In the meantime, furohyperforin was also isolated from H. perforatum by two groups, and was reported under two different names, furohyperforin [9] and orthoforin [10]. Verotta et al. [11] reported three additional oxygenated hyperforin analogues from the same source. Recently, three new hyperforin analogues, pyrano-[7,28-b]-hyperforin and 3-methyl-4,6-di(3-methyl-2-butenyl)-2-(2-methyl-1-oxopropyl)-3-(4-methyl-3-pentenyl)-cyclohexanone as well as its 6-methoxycarbonyl analogue were isolated from the aerial parts of H. perforatum [12].

In order to gain better insight into the degradation processes of this pharmacologically important molecule, we have repeated the investigation of the aerial parts of H. perforatum also focusing on the less active antibiotic fractions not studied before.

Section snippets

Plant material

H. perforatum (voucher 0799HP), deposited at the Institute for Medicinal Plant Research ‘Dr Josif Pančić’, Tadeuša Košćuška 1, Belgrade, Serbia and Montenegro was collected at mountain Ozren (southeast Serbia) during the flowering season in July 1999.

Extraction and isolation

A crude extract (107.9 g/kg of air-dried aerial parts) was obtained by extraction of 3.1 kg of plant material with 96% EtOH (2×5 l), followed by depigmentation with active charcoal, according the procedure described previously [7]. Using the same

Results and discussion

The aerial parts of H. perforatum, after extraction, followed by fractionation with supercritical CO₂ [7] in combination with Silica-gel CC and PTLC, yielded a new oxidation product, named deoxyfurohyperforin A (2), along with the known compounds 3, 4, 5a and 5b, 6, 7 identified by analogy of their ¹H and ¹³C NMR data to those reported [7], [8], [12].

Deoxyfurohyperforin A 2 (Fig. 1), C₃₂H₄₆O₄, was the deoxy analogue of 5a and 5b (furohyperforin A). The ¹H-NMR spectrum of 2 was similar to those

Acknowledgements

The authors from Serbia and Montenegro are grateful to the Ministry for Science, Technologies and Development of Republic of Serbia for financial support.

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Further degradation product of hyperforin from Hypericum perforatum (St. John's Wort)

Abstract

Introduction

Section snippets

Plant material

Extraction and isolation

Results and discussion

Acknowledgements

Life Sci

Phytochemistry

Antibiotiki (Moscow)

Pharmacopsychiatry

Pharmacopsychiatry

Pharmacopsychiatry