Targeted isolation of indole alkaloids from Streptomyces sp. CT37

Qing Fang; Fleurdeliz Maglangit; Morgane Mugat; Caroline Urwald; Kwaku Kyeremeh; Hai Deng

doi:10.3390/molecules25051108

Targeted isolation of indole alkaloids from Streptomyces sp. CT37

Qing Fang, Fleurdeliz Maglangit, Morgane Mugat, Caroline Urwald, Kwaku Kyeremeh, Hai Deng^* (Corresponding Author)

^*Corresponding author for this work

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Abstract

Four compounds (1–4) were isolated from the extracts of Streptomyces sp. CT37 using bioassay in conjunction with mass spectrometric molecular networking (MN) driven isolation. Their complete structures were established by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), and 1D and 2D nuclear magnetic resonance (NMR) data. Legonimide 1 was identified as a new alkaloid containing a rare linear imide motif in its structure, while compounds 2–4 were already known and their structures were elucidated as 1H-indole-3-carbaldehyde, actinopolymorphol B, (2R,3R)-1-phenylbutane-2,3-diol, respectively. The biosynthetic pathways of 1–4 were proposed based on the reported biogenesis of indole alkaloids in literature. Bioactivity tests for 1 and 2 revealed moderate growth inhibition activity against Candida albicans ATCC 10231 with MIC95 values of 21.54 µg/mL and 11.47 µg/mL, respectively. View Full-Text

Original language	English
Article number	1108
Number of pages	10
Journal	Molecules
Volume	25
Issue number	5
Early online date	2 Mar 2020
DOIs	https://doi.org/10.3390/molecules25051108
Publication status	Published - Mar 2020

Bibliographical note

Q.F. is grateful to the University of Aberdeen Elphinstone Scholarship and Scottish Funding Council/ScotCHEM for financial support through the PEER/PERCE Funding. F.M. thanks the University of the Philippines for the Faculty, Reps, and Staff Development Program (FRAS DP) for the PhD grant fellowship. H.D. and K.K. thank the financial supports of Leverhulme Trust-Royal Society Africa award (AA090088) and the jointly funded UK Medical Research Council-UK Department for InternationalmDevelopment (MRC/DFID) Concordat agreement African Research Leaders Award (MR/S00520X/1).

Keywords

legonimide
indole alkaloids
imide
streptomyces sp CT37
natural products
antifungal
Legonimide
Imide
Antifungal
Natural products
Streptomyces sp. CT37
Indole alkaloids
CT37
NEOCARAZOSTATIN
DISCOVERY
CHEMICAL-CONSTITUENTS
METABOLISM
Streptomyces sp
BIOSYNTHESIS
MICROBIAL NATURAL-PRODUCTS
RESISTANCE
DERIVATIVES

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Cite this

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title = "Targeted isolation of indole alkaloids from Streptomyces sp. CT37",

abstract = "Four compounds (1–4) were isolated from the extracts of Streptomyces sp. CT37 using bioassay in conjunction with mass spectrometric molecular networking (MN) driven isolation. Their complete structures were established by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), and 1D and 2D nuclear magnetic resonance (NMR) data. Legonimide 1 was identified as a new alkaloid containing a rare linear imide motif in its structure, while compounds 2–4 were already known and their structures were elucidated as 1H-indole-3-carbaldehyde, actinopolymorphol B, (2R,3R)-1-phenylbutane-2,3-diol, respectively. The biosynthetic pathways of 1–4 were proposed based on the reported biogenesis of indole alkaloids in literature. Bioactivity tests for 1 and 2 revealed moderate growth inhibition activity against Candida albicans ATCC 10231 with MIC95 values of 21.54 µg/mL and 11.47 µg/mL, respectively. View Full-Text",

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author = "Qing Fang and Fleurdeliz Maglangit and Morgane Mugat and Caroline Urwald and Kwaku Kyeremeh and Hai Deng",

note = "Q.F. is grateful to the University of Aberdeen Elphinstone Scholarship and Scottish Funding Council/ScotCHEM for financial support through the PEER/PERCE Funding. F.M. thanks the University of the Philippines for the Faculty, Reps, and Staff Development Program (FRAS DP) for the PhD grant fellowship. H.D. and K.K. thank the financial supports of Leverhulme Trust-Royal Society Africa award (AA090088) and the jointly funded UK Medical Research Council-UK Department for InternationalmDevelopment (MRC/DFID) Concordat agreement African Research Leaders Award (MR/S00520X/1).",

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AU - Maglangit, Fleurdeliz

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AU - Urwald, Caroline

AU - Kyeremeh, Kwaku

AU - Deng, Hai

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PY - 2020/3

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N2 - Four compounds (1–4) were isolated from the extracts of Streptomyces sp. CT37 using bioassay in conjunction with mass spectrometric molecular networking (MN) driven isolation. Their complete structures were established by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), and 1D and 2D nuclear magnetic resonance (NMR) data. Legonimide 1 was identified as a new alkaloid containing a rare linear imide motif in its structure, while compounds 2–4 were already known and their structures were elucidated as 1H-indole-3-carbaldehyde, actinopolymorphol B, (2R,3R)-1-phenylbutane-2,3-diol, respectively. The biosynthetic pathways of 1–4 were proposed based on the reported biogenesis of indole alkaloids in literature. Bioactivity tests for 1 and 2 revealed moderate growth inhibition activity against Candida albicans ATCC 10231 with MIC95 values of 21.54 µg/mL and 11.47 µg/mL, respectively. View Full-Text

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SN - 1420-3049

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JO - Molecules

JF - Molecules

IS - 5

M1 - 1108

ER -

Targeted isolation of indole alkaloids from Streptomyces sp. CT37

Abstract

Bibliographical note

Keywords

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