Dihydrostilbenes from Indigofera pulchra

Aliyu Musa; A. K. Haruna; M. Ilyas; Augustine Ahmadu; Simon Gibbons; M. Mukhlesur Rahman

doi:10.1177/1934578X0800300524

Dihydrostilbenes from Indigofera pulchra

Aliyu Musa, A. K. Haruna, M. Ilyas, Augustine Ahmadu, Simon Gibbons, M. Mukhlesur Rahman

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A mixture of two new dihydrostilbenes, 3-methoxy-4,5-methylenedioxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (1) and 3,5-dimethoxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (2), was isolated from Indigofera pulchra as an inseparable mixture. Several isolation strategies, including multiple preparative TLC, SPE and finally HPLC were undertaken in an attempt to separate these metabolites, but to no avail. Structure elucidation on the mixture was conducted and we were able to establish the structures of these compounds unambiguously by MS and a series of 1D and 2D-NMR analyses. The mixture of these dihydrostilbenes was analyzed by NMR spectroscopy and 1 and 2 were in a ratio of 52:48, respectively, and this was evaluated against a panel of methicillin-resistant Staphylococcus aureus (MRSA) and multidrug-resistant variants of this organism, including a strain over-expressing the NorA efflux pump; weak activity was observed.

Original language	English
Journal	Natural Product Communications
Volume	3
Issue number	5
DOIs	https://doi.org/10.1177/1934578X0800300524
Publication status	Published - 1 May 2008

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10.1177/1934578X0800300524

http://journals.sagepub.com/doi/10.1177/1934578X0800300524

Cite this

@article{1c2bc466059c47b484f3fb67cd67c88e,

title = "Dihydrostilbenes from Indigofera pulchra",

abstract = "A mixture of two new dihydrostilbenes, 3-methoxy-4,5-methylenedioxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (1) and 3,5-dimethoxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (2), was isolated from Indigofera pulchra as an inseparable mixture. Several isolation strategies, including multiple preparative TLC, SPE and finally HPLC were undertaken in an attempt to separate these metabolites, but to no avail. Structure elucidation on the mixture was conducted and we were able to establish the structures of these compounds unambiguously by MS and a series of 1D and 2D-NMR analyses. The mixture of these dihydrostilbenes was analyzed by NMR spectroscopy and 1 and 2 were in a ratio of 52:48, respectively, and this was evaluated against a panel of methicillin-resistant Staphylococcus aureus (MRSA) and multidrug-resistant variants of this organism, including a strain over-expressing the NorA efflux pump; weak activity was observed.",

author = "Aliyu Musa and Haruna, {A. K.} and M. Ilyas and Augustine Ahmadu and Simon Gibbons and Rahman, {M. Mukhlesur}",

year = "2008",

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T1 - Dihydrostilbenes from Indigofera pulchra

AU - Musa, Aliyu

AU - Haruna, A. K.

AU - Ilyas, M.

AU - Ahmadu, Augustine

AU - Gibbons, Simon

AU - Rahman, M. Mukhlesur

PY - 2008/5/1

Y1 - 2008/5/1

N2 - A mixture of two new dihydrostilbenes, 3-methoxy-4,5-methylenedioxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (1) and 3,5-dimethoxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (2), was isolated from Indigofera pulchra as an inseparable mixture. Several isolation strategies, including multiple preparative TLC, SPE and finally HPLC were undertaken in an attempt to separate these metabolites, but to no avail. Structure elucidation on the mixture was conducted and we were able to establish the structures of these compounds unambiguously by MS and a series of 1D and 2D-NMR analyses. The mixture of these dihydrostilbenes was analyzed by NMR spectroscopy and 1 and 2 were in a ratio of 52:48, respectively, and this was evaluated against a panel of methicillin-resistant Staphylococcus aureus (MRSA) and multidrug-resistant variants of this organism, including a strain over-expressing the NorA efflux pump; weak activity was observed.

AB - A mixture of two new dihydrostilbenes, 3-methoxy-4,5-methylenedioxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (1) and 3,5-dimethoxy-4′-O-(2ξ,3-dihydroxy-3-methylbutyl)-dihydrostilbene (2), was isolated from Indigofera pulchra as an inseparable mixture. Several isolation strategies, including multiple preparative TLC, SPE and finally HPLC were undertaken in an attempt to separate these metabolites, but to no avail. Structure elucidation on the mixture was conducted and we were able to establish the structures of these compounds unambiguously by MS and a series of 1D and 2D-NMR analyses. The mixture of these dihydrostilbenes was analyzed by NMR spectroscopy and 1 and 2 were in a ratio of 52:48, respectively, and this was evaluated against a panel of methicillin-resistant Staphylococcus aureus (MRSA) and multidrug-resistant variants of this organism, including a strain over-expressing the NorA efflux pump; weak activity was observed.

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DO - 10.1177/1934578X0800300524

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VL - 3

JO - Natural Product Communications

JF - Natural Product Communications

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IS - 5

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