Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity

Bernie V. Mcinerney; Richard P. Gregson; Michael J. Lacey; Raymond J. Akhurst; Graham R. Lyons; Stuart H. Rhodes; Donald R. J. Smith; Lutz M. Engelhardt; Allan H. White

doi:10.1021/np50075a005

Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity

Bernie V. Mcinerney^*, Richard P. Gregson, Michael J. Lacey, Raymond J. Akhurst, Graham R. Lyons, Stuart H. Rhodes, Donald R. J. Smith, Lutz M. Engelhardt, Allan H. White

^*Corresponding author for this work

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131 Citations (Scopus)

Abstract

Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3–b] pyrrole (compounds 1–3)or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.

Original language	English
Pages (from-to)	774-784
Number of pages	11
Journal	Journal of Natural Products
Volume	54
Issue number	3
DOIs	https://doi.org/10.1021/np50075a005
Publication status	Published - 1 May 1991
Externally published	Yes

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Mcinerney, Bernie V. ; Gregson, Richard P. ; Lacey, Michael J. ; Akhurst, Raymond J. ; Lyons, Graham R. ; Rhodes, Stuart H. ; Smith, Donald R. J. ; Engelhardt, Lutz M. ; White, Allan H. / Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity. In: Journal of Natural Products. 1991 ; Vol. 54, No. 3. pp. 774-784.

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title = "Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity",

abstract = "Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3–b] pyrrole (compounds 1–3)or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.",

author = "Mcinerney, {Bernie V.} and Gregson, {Richard P.} and Lacey, {Michael J.} and Akhurst, {Raymond J.} and Lyons, {Graham R.} and Rhodes, {Stuart H.} and Smith, {Donald R. J.} and Engelhardt, {Lutz M.} and White, {Allan H.}",

year = "1991",

month = may,

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doi = "10.1021/np50075a005",

language = "English",

volume = "54",

pages = "774--784",

journal = "Journal of Natural Products",

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Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity. / Mcinerney, Bernie V.; Gregson, Richard P.; Lacey, Michael J.; Akhurst, Raymond J.; Lyons, Graham R.; Rhodes, Stuart H.; Smith, Donald R. J.; Engelhardt, Lutz M.; White, Allan H.

In: Journal of Natural Products, Vol. 54, No. 3, 01.05.1991, p. 774-784.

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

TY - JOUR

T1 - Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity

AU - Mcinerney, Bernie V.

AU - Gregson, Richard P.

AU - Lacey, Michael J.

AU - Akhurst, Raymond J.

AU - Lyons, Graham R.

AU - Rhodes, Stuart H.

AU - Smith, Donald R. J.

AU - Engelhardt, Lutz M.

AU - White, Allan H.

PY - 1991/5/1

Y1 - 1991/5/1

N2 - Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3–b] pyrrole (compounds 1–3)or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.

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Biologically active metabolites from Xenorhabdus spp., part 1. dithiolopyrrolone derivatives with antibiotic activity

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