New erythritol derivatives from the fertile form of Roccella montagnei

Thuc Huy Duong 1 Bui Linh Chi Huynh 2 Warinthorn Chavasiri 3 Marylene Chollet-Krugler 4 Van Kieu Nguyen 3 Thi Hoai Thu Nguyen 5 Poul Erik Hansen 6 Pierre Le Pogam 4, 7 Holger Thüs 8 Joël Boustie 4 Kim Phi Phung Nguyen 2, *
* Auteur correspondant
1 Ho Chi Minh City University of Pedagogy
2 Ecole des Sciences Naturelles Ho Chi Minh Ville
3 Chulalongkorn University (THAILAND)
4 ISCR - Institut des Sciences Chimiques de Rennes
5 University of Medicine and Pharmacy (VIETNAM)
6 Roskilde University
7 IETR - Institut d'Electronique et de Télécommunications de Rennes
8 Life Sciences dpt. - Genomics & Microbial Biodiversity div.
Natural History Museum
Abstract : Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC50 value of 68.39 ± 3.46 μM.
Keywords : cytotoxicity Lichen Montagnetol Montagnetol derivatives Roccella montagnei (fertile form) Stereochemistry
Type de document :
Article dans une revue
Phytochemistry, Elsevier, 2017, 137, pp.156-164. 〈10.1016/j.phytochem.2017.02.012〉
Domaine :
Liste complète des métadonnées

Littérature citée [87 références]  Voir  Masquer  Télécharger
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01501264
Contributeur : Laurent Jonchère <>
Soumis le : lundi 23 octobre 2017 - 10:15:24
Dernière modification le : jeudi 5 avril 2018 - 12:30:20
Document(s) archivé(s) le : mercredi 24 janvier 2018 - 18:55:20

Fichier

New erythritol derivatives_acc...
Fichiers produits par l'(les) auteur(s)

Identifiants

Collections

UNIV-NANTES | INC-CNRS | UR1-UFR-SPM | ISCR-CORINT | UR1-UFR-ISTIC | IETR | ISCR | SUP_IETR | CENTRALESUPELEC | UNIV-RENNES

Citation

Thuc Huy Duong, Bui Linh Chi Huynh, Warinthorn Chavasiri, Marylene Chollet-Krugler, Van Kieu Nguyen, et al.. New erythritol derivatives from the fertile form of Roccella montagnei. Phytochemistry, Elsevier, 2017, 137, pp.156-164. 〈10.1016/j.phytochem.2017.02.012〉. 〈hal-01501264〉

Exporter

BibTeX TEI DC DCterms EndNote

Partager

Métriques

Consultations de la notice

201

Téléchargements de fichiers

43