Dibenzofuran and pyranone metabolites from Hypericum revolutum ssp. revolutum and Hypericum choisianum

Winnie Ka Po Shiu; Simon Gibbons

doi:10.1016/j.phytochem.2008.12.016

Dibenzofuran and pyranone metabolites from Hypericum revolutum ssp. revolutum and Hypericum choisianum

Winnie Ka Po Shiu, Simon Gibbons

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28 Citations (SciVal)

Abstract

In a project to isolate and characterise anti-staphylococcal compounds from members of the genus Hypericum, a dibenzofuran and a pyranone were isolated from the dichloromethane and hexane extracts of Hypericum revolutum ssp. revolutum Vahl (Guttiferae) and Hypericum choisianum Wall. ex. N. Robson (Guttiferae), respectively. The structures of these compounds were elucidated by 1- and 2D-NMR spectroscopy and mass spectrometry as 3-hydroxy-1,4,7-trimethoxydibenzofuran (1) and 4-(3-O-3″)-3″-methylbutenyl-6-phenyl-pyran-2-one (2). The metabolites were evaluated against a panel of multidrug-resistant strains of Staphylococcus aureus. Compound 1 exhibited a minimum inhibitory concentration (MIC) of 256 μg/ml, whereas compound 2 was inactive at a concentration of 512 μg/ml.

Original language	English
Pages (from-to)	403-406
Number of pages	4
Journal	Phytochemistry
Volume	70
Issue number	3
Early online date	4 Feb 2009
DOIs	https://doi.org/10.1016/j.phytochem.2008.12.016
Publication status	Published - Feb 2009

Keywords

Antibacterial
Dibenzofuran
Guttiferae
Hypericum choisianum
Hypericum revolutum
MDR
MRSA
Pyran-2-one
Pyranone
Staphylococcus aureus

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10.1016/j.phytochem.2008.12.016

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title = "Dibenzofuran and pyranone metabolites from Hypericum revolutum ssp. revolutum and Hypericum choisianum",

abstract = "In a project to isolate and characterise anti-staphylococcal compounds from members of the genus Hypericum, a dibenzofuran and a pyranone were isolated from the dichloromethane and hexane extracts of Hypericum revolutum ssp. revolutum Vahl (Guttiferae) and Hypericum choisianum Wall. ex. N. Robson (Guttiferae), respectively. The structures of these compounds were elucidated by 1- and 2D-NMR spectroscopy and mass spectrometry as 3-hydroxy-1,4,7-trimethoxydibenzofuran (1) and 4-(3-O-3″)-3″-methylbutenyl-6-phenyl-pyran-2-one (2). The metabolites were evaluated against a panel of multidrug-resistant strains of Staphylococcus aureus. Compound 1 exhibited a minimum inhibitory concentration (MIC) of 256 μg/ml, whereas compound 2 was inactive at a concentration of 512 μg/ml.",

keywords = "Antibacterial, Dibenzofuran, Guttiferae, Hypericum choisianum, Hypericum revolutum, MDR, MRSA, Pyran-2-one, Pyranone, Staphylococcus aureus",

author = "Shiu, {Winnie Ka Po} and Simon Gibbons",

year = "2009",

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doi = "10.1016/j.phytochem.2008.12.016",

language = "English",

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T1 - Dibenzofuran and pyranone metabolites from Hypericum revolutum ssp. revolutum and Hypericum choisianum

AU - Shiu, Winnie Ka Po

AU - Gibbons, Simon

PY - 2009/2

Y1 - 2009/2

N2 - In a project to isolate and characterise anti-staphylococcal compounds from members of the genus Hypericum, a dibenzofuran and a pyranone were isolated from the dichloromethane and hexane extracts of Hypericum revolutum ssp. revolutum Vahl (Guttiferae) and Hypericum choisianum Wall. ex. N. Robson (Guttiferae), respectively. The structures of these compounds were elucidated by 1- and 2D-NMR spectroscopy and mass spectrometry as 3-hydroxy-1,4,7-trimethoxydibenzofuran (1) and 4-(3-O-3″)-3″-methylbutenyl-6-phenyl-pyran-2-one (2). The metabolites were evaluated against a panel of multidrug-resistant strains of Staphylococcus aureus. Compound 1 exhibited a minimum inhibitory concentration (MIC) of 256 μg/ml, whereas compound 2 was inactive at a concentration of 512 μg/ml.

AB - In a project to isolate and characterise anti-staphylococcal compounds from members of the genus Hypericum, a dibenzofuran and a pyranone were isolated from the dichloromethane and hexane extracts of Hypericum revolutum ssp. revolutum Vahl (Guttiferae) and Hypericum choisianum Wall. ex. N. Robson (Guttiferae), respectively. The structures of these compounds were elucidated by 1- and 2D-NMR spectroscopy and mass spectrometry as 3-hydroxy-1,4,7-trimethoxydibenzofuran (1) and 4-(3-O-3″)-3″-methylbutenyl-6-phenyl-pyran-2-one (2). The metabolites were evaluated against a panel of multidrug-resistant strains of Staphylococcus aureus. Compound 1 exhibited a minimum inhibitory concentration (MIC) of 256 μg/ml, whereas compound 2 was inactive at a concentration of 512 μg/ml.

KW - Antibacterial

KW - Dibenzofuran

KW - Guttiferae

KW - Hypericum choisianum

KW - Hypericum revolutum

KW - MDR

KW - MRSA

KW - Pyran-2-one

KW - Pyranone

KW - Staphylococcus aureus

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U2 - 10.1016/j.phytochem.2008.12.016

DO - 10.1016/j.phytochem.2008.12.016

M3 - Article

C2 - 19200564

AN - SCOPUS:62349124072

SN - 0031-9422

VL - 70

SP - 403

EP - 406

JO - Phytochemistry

JF - Phytochemistry

IS - 3

ER -

Dibenzofuran and pyranone metabolites from Hypericum revolutum ssp. revolutum and Hypericum choisianum

Abstract

Keywords

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