Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Asmaa Boufridi; David Lachkar; Dirk Erpenbeck; Mehdi A. Beniddir; Laurent Evanno; Sylvain Petek; Cécile Debitus; Erwan Poupon

doi:10.1071/CH16455

Back

Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Journal article

Peer reviewed

Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis

Asmaa Boufridi, David Lachkar, Dirk Erpenbeck, Mehdi A. Beniddir, Laurent Evanno, Sylvain Petek, Cécile Debitus and Erwan Poupon

Australian Journal of Chemistry, Vol.70(6), pp.743-750

2017

DOI: https://doi.org/10.1071/CH16455

Files and links (1)

url

https://doi.org/10.1071/CH16455View

Published Version

Abstract

Analytical chemistry

Natural products and bioactive compounds

Dactylospongia metachromia and Dactylospongia elegans collected from French Polynesia were studied with a particular focus on the variation of the diastereomeric ratio between ilimaquinone (4) and 5-epi-ilimaquinone (5). More than 100 samples, covering an area of 4100km(2), were studied to try to clarify this intriguing issue. Nuclear magnetic resonance appeared as the non-destructive, straightforward technique of choice for a relative quantitative study. A random distribution, unique at that point in nature, is observed and leads to biosynthetic considerations. Biological evaluation of both compounds was also performed and showed moderate discrepancies in cytotoxicity and apoptosis induction.

Details

Title: Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis
Authors: Asmaa Boufridi (Author) - University of Paris-Saclay
David Lachkar (Author) - University of Paris-Saclay
Dirk Erpenbeck (Author) - Ludwig-Maximilians-Universität München
Mehdi A. Beniddir (Author) - University of Paris-Saclay
Laurent Evanno (Author) - University of Paris-Saclay
Sylvain Petek (Author) - Institut de Recherche pour le Développement
Cécile Debitus (Author) - Institut de Recherche pour le Développement
Erwan Poupon (Author) - University of Paris-Saclay
Publication details: Australian Journal of Chemistry, Vol.70(6), pp.743-750
Publisher: C S I R O Publishing
DOI: 10.1071/CH16455
ISSN: 1445-0038
Organisation Unit: Centre for Bioinnovation; School of Science, Technology and Engineering; University of the Sunshine Coast, Queensland; School of Health - Biomedicine
Language: English
Record Identifier: 99650998502621
Output Type: Journal article

Metrics

3 Record Views

7 Times Cited - Web of Science

See more details

InCites Highlights

These are selected metrics from InCites Benchmarking & Analytics tool, related to this output

Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Multidisciplinary

UN Sustainable Development Goals (SDGs)

This output has contributed to the advancement of the following goals:

Source: InCites