Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp

Yaming Zhou; Abdessamad Debbab; Victor Wray; WenHan Lin; Barbara Schulz; Rozenn Trepos; Claire Pile; Claire Hellio; Peter Proksch; Amal H. Aly

doi:10.1016/j.tetlet.2014.02.062

Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp

Yaming Zhou, Abdessamad Debbab, Victor Wray, WenHan Lin, Barbara Schulz, Rozenn Trepos, Claire Pile, Claire Hellio, Peter Proksch, Amal H. Aly

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Abstract

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin- 3-yl)methyl)-1-methyl-3,4-dihydrobenzo[e][1,4]diazepine-2,5-dione (1) and a new meroterpenoid, austalide R (2), together with three known compounds (3-5). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR (1H, 13C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell line
L5178Y.

Original language	English
Pages (from-to)	2789-2792
Journal	Tetrahedron Letters
Volume	55
Issue number	17
Early online date	13 Mar 2014
DOIs	https://doi.org/10.1016/j.tetlet.2014.02.062
Publication status	Published - 23 Apr 2014

Keywords

Aspergillus
Marine natural products
Sponge-derived fungi
Tethya aurantium

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2014.02.062

tetrahedron letters 2014Accepted author manuscript (Post-print), 341 KBLicence: CC BY-NC-ND

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title = "Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp",

abstract = "Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin- 3-yl)methyl)-1-methyl-3,4-dihydrobenzo[e][1,4]diazepine-2,5-dione (1) and a new meroterpenoid, austalide R (2), together with three known compounds (3-5). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR (1H, 13C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell lineL5178Y.",

keywords = "Aspergillus, Marine natural products, Sponge-derived fungi, Tethya aurantium",

author = "Yaming Zhou and Abdessamad Debbab and Victor Wray and WenHan Lin and Barbara Schulz and Rozenn Trepos and Claire Pile and Claire Hellio and Peter Proksch and Aly, {Amal H.}",

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doi = "10.1016/j.tetlet.2014.02.062",

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T1 - Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp

AU - Zhou, Yaming

AU - Debbab, Abdessamad

AU - Wray, Victor

AU - Lin, WenHan

AU - Schulz, Barbara

AU - Trepos, Rozenn

AU - Pile, Claire

AU - Hellio, Claire

AU - Proksch, Peter

AU - Aly, Amal H.

PY - 2014/4/23

Y1 - 2014/4/23

N2 - Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin- 3-yl)methyl)-1-methyl-3,4-dihydrobenzo[e][1,4]diazepine-2,5-dione (1) and a new meroterpenoid, austalide R (2), together with three known compounds (3-5). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR (1H, 13C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell lineL5178Y.

AB - Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin- 3-yl)methyl)-1-methyl-3,4-dihydrobenzo[e][1,4]diazepine-2,5-dione (1) and a new meroterpenoid, austalide R (2), together with three known compounds (3-5). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR (1H, 13C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell lineL5178Y.

KW - Aspergillus

KW - Marine natural products

KW - Sponge-derived fungi

KW - Tethya aurantium

U2 - 10.1016/j.tetlet.2014.02.062

DO - 10.1016/j.tetlet.2014.02.062

M3 - Article

VL - 55

SP - 2789

EP - 2792

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp

Abstract

Keywords

UN SDGs

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