Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain

Marieke Vansteelandt; Elodie Blanchet; Maxim Egorov; Fabien Petit; Loïc Toupet; Arnaud Bondon; Fabrice Monteau; Bruno Bizec; Olivier P. Thomas; Yves François Pouchus; Ronan Le Bot; Olivier Grovel

doi:10.1021/np3007364

Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain

Marieke Vansteelandt
, Elodie Blanchet
, Maxim Egorov
, Fabien Petit
, Loïc Toupet
, Arnaud Bondon
, Fabrice Monteau
, Bruno Bizec
, Olivier P. Thomas
, Yves François Pouchus
, Ronan Le Bot
, Olivier Grovel

Laboratoire de Chimie marine-ISOMer
Atlanthera
Institut de Physique de Rennes
University of Rennes
Veterinary School of Nantes
Université Nice Sophia Antipolis

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

53 Citations (Scopus)

Abstract

A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.

Original language	English
Pages (from-to)	297-301
Number of pages	5
Journal	Journal of Natural Products
Volume	76
Issue number	2
DOIs	https://doi.org/10.1021/np3007364
Publication status	Published - 22 Feb 2013
Externally published	Yes

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

SDG 3 Good Health and Well-being

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10.1021/np3007364

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title = "Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain",

abstract = "A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.",

author = "Marieke Vansteelandt and Elodie Blanchet and Maxim Egorov and Fabien Petit and Lo{\"i}c Toupet and Arnaud Bondon and Fabrice Monteau and Bruno Bizec and Thomas, \{Olivier P.\} and Pouchus, \{Yves Fran{\c c}ois\} and Bot, \{Ronan Le\} and Olivier Grovel",

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doi = "10.1021/np3007364",

language = "English",

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T1 - Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain

AU - Vansteelandt, Marieke

AU - Blanchet, Elodie

AU - Egorov, Maxim

AU - Petit, Fabien

AU - Toupet, Loïc

AU - Bondon, Arnaud

AU - Monteau, Fabrice

AU - Bizec, Bruno

AU - Thomas, Olivier P.

AU - Pouchus, Yves François

AU - Bot, Ronan Le

AU - Grovel, Olivier

PY - 2013/2/22

Y1 - 2013/2/22

N2 - A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.

AB - A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.

UR - https://www.scopus.com/pages/publications/84876735793

U2 - 10.1021/np3007364

DO - 10.1021/np3007364

M3 - Article

SN - 0163-3864

VL - 76

SP - 297

EP - 301

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 2

ER -

Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain

Abstract

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