Aspiperidine oxide, a piperidine N-oxide from the filamentous fungus Aspergillus indologenus

Lene M. Petersen; Sara Kildgaard; Marcel Jaspars; Thomas O. Larsen

doi:10.1016/j.tetlet.2015.02.082

Aspiperidine oxide, a piperidine N-oxide from the filamentous fungus Aspergillus indologenus

Lene M. Petersen, Sara Kildgaard, Marcel Jaspars, Thomas O. Larsen^*

^*Corresponding author for this work

Chemistry

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

3 Citations (Scopus)

Abstract

A novel secondary metabolite, aspiperidine oxide, was isolated from the filamentous fungus, Aspergillus indologenus. The structure of aspiperidine oxide was determined from extensive 1D and 2D NMR spectroscopic analysis supported by high-resolution mass spectrometry. The structure revealed a rare piperidine N-oxide, not observed in filamentous fungi before. A biosynthetic pathway towards aspiperidine oxide is proposed, based on tentative identification of intermediates from UHPLC-DAD-HRMS data. (C) 2015 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1847-1850
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	14
Early online date	25 Feb 2015
DOIs	https://doi.org/10.1016/j.tetlet.2015.02.082
Publication status	Published - 1 Apr 2015

Keywords

Aspergillus indologenus
biosynthesis
N-Oxide
dipeptide
secondary metabolites
Niger
aculeatus
alkaloids

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title = "Aspiperidine oxide, a piperidine N-oxide from the filamentous fungus Aspergillus indologenus",

abstract = "A novel secondary metabolite, aspiperidine oxide, was isolated from the filamentous fungus, Aspergillus indologenus. The structure of aspiperidine oxide was determined from extensive 1D and 2D NMR spectroscopic analysis supported by high-resolution mass spectrometry. The structure revealed a rare piperidine N-oxide, not observed in filamentous fungi before. A biosynthetic pathway towards aspiperidine oxide is proposed, based on tentative identification of intermediates from UHPLC-DAD-HRMS data. (C) 2015 Elsevier Ltd. All rights reserved.",

keywords = "Aspergillus indologenus, biosynthesis , N-Oxide, dipeptide, secondary metabolites, Niger, aculeatus, alkaloids",

author = "Petersen, {Lene M.} and Sara Kildgaard and Marcel Jaspars and Larsen, {Thomas O.}",

note = "We kindly acknowledge Foundaci{\'o}n Medina, Granada, Spain for bioactivity testing of purified compounds. This study was supported by grant 09-064967 from the Danish Council for Independent Research, Technology, and Production Sciences.",

year = "2015",

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doi = "10.1016/j.tetlet.2015.02.082",

language = "English",

volume = "56",

pages = "1847--1850",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Aspiperidine oxide, a piperidine N-oxide from the filamentous fungus Aspergillus indologenus

AU - Petersen, Lene M.

AU - Kildgaard, Sara

AU - Jaspars, Marcel

AU - Larsen, Thomas O.

N1 - We kindly acknowledge Foundación Medina, Granada, Spain for bioactivity testing of purified compounds. This study was supported by grant 09-064967 from the Danish Council for Independent Research, Technology, and Production Sciences.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - A novel secondary metabolite, aspiperidine oxide, was isolated from the filamentous fungus, Aspergillus indologenus. The structure of aspiperidine oxide was determined from extensive 1D and 2D NMR spectroscopic analysis supported by high-resolution mass spectrometry. The structure revealed a rare piperidine N-oxide, not observed in filamentous fungi before. A biosynthetic pathway towards aspiperidine oxide is proposed, based on tentative identification of intermediates from UHPLC-DAD-HRMS data. (C) 2015 Elsevier Ltd. All rights reserved.

AB - A novel secondary metabolite, aspiperidine oxide, was isolated from the filamentous fungus, Aspergillus indologenus. The structure of aspiperidine oxide was determined from extensive 1D and 2D NMR spectroscopic analysis supported by high-resolution mass spectrometry. The structure revealed a rare piperidine N-oxide, not observed in filamentous fungi before. A biosynthetic pathway towards aspiperidine oxide is proposed, based on tentative identification of intermediates from UHPLC-DAD-HRMS data. (C) 2015 Elsevier Ltd. All rights reserved.

KW - Aspergillus indologenus

KW - biosynthesis

KW - N-Oxide

KW - dipeptide

KW - secondary metabolites

KW - Niger

KW - aculeatus

KW - alkaloids

U2 - 10.1016/j.tetlet.2015.02.082

DO - 10.1016/j.tetlet.2015.02.082

M3 - Article

VL - 56

SP - 1847

EP - 1850

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

ER -

Aspiperidine oxide, a piperidine N-oxide from the filamentous fungus Aspergillus indologenus

Abstract

Keywords

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