title: New erythritol derivatives from the fertile form of Roccella montagnei.
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 IC50value of 68.39 ± 3.46 μM.
authors.affiliation: Department of Chemistry, Ho Chi Minh City University of Pedagogy, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 748342, Viet Nam.
authors.forename: Thuc Huy
authors.initials: TH
authors.lastname: Duong
authors.affiliation: Department of Organic Chemistry, University of Science, National University - Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, Ho Chi Minh City 748355, Viet Nam.
authors.forename: Bui Linh Chi
authors.initials: BLC
authors.lastname: Huynh
authors.affiliation: Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Rd., Patumwan, Bangkok 10330, Thailand.
authors.forename: Warinthorn
authors.initials: W
authors.lastname: Chavasiri
authors.affiliation: Institute of Chemistry of Rennes, ISCR, UMR CNRS 6226, University of Rennes 1, 2 Av. du Pr. Léon Bernard, Rennes Cedex 35043, France.
authors.forename: Marylene
authors.initials: M
authors.lastname: Chollet-Krugler
authors.affiliation: Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Rd., Patumwan, Bangkok 10330, Thailand.
authors.forename: Van Kieu
authors.initials: VK
authors.lastname: Nguyen
authors.affiliation: Department of Basic Science, Ho Chi Minh City University of Medicine and Pharmacy, 217 Hong Bang Street, Dist. 5, Ho Chi Minh City 749051, Viet Nam.
authors.forename: Thi Hoai Thu
authors.initials: THT
authors.lastname: Nguyen
authors.affiliation: Department of Science and Environment, Roskilde University, P.O. Box 260, DK-4000 Roskilde, Denmark.
authors.forename: Poul Erik
authors.initials: PE
authors.lastname: Hansen
authors.affiliation: Institute of Chemistry of Rennes, ISCR, UMR CNRS 6226, University of Rennes 1, 2 Av. du Pr. Léon Bernard, Rennes Cedex 35043, France; Institute of Electronics and Telecommunications of Rennes (IETR), UMR CNRS 6164, University of Rennes 1, 263 Av. du Général Leclerc, Rennes Cedex 35042, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Le Pogam
authors.affiliation: Life Science Department, The Natural History Museum, Cromwell Road, SW7 5BD London, England, UK.
authors.forename: Holger
authors.initials: H
authors.lastname: Thüs
authors.affiliation: Institute of Chemistry of Rennes, ISCR, UMR CNRS 6226, University of Rennes 1, 2 Av. du Pr. Léon Bernard, Rennes Cedex 35043, France. Electronic address: joel.boustie@univ-rennes1.fr.
authors.forename: Joël
authors.initials: J
authors.lastname: Boustie
authors.affiliation: Department of Organic Chemistry, University of Science, National University - Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, Ho Chi Minh City 748355, Viet Nam. Electronic address: kimphiphung@yahoo.fr.
authors.forename: Kim Phi Phung
authors.initials: KPP
authors.lastname: Nguyen
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification; D001203:Ascomycota / Q000737:chemistry*; D045744:Cell Line, Tumor; D004896:Erythritol / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D008011:Lichens / Q000737:chemistry*; D015394:Molecular Structure; D012459:Salicylates / Q000737:chemistry / Q000302:isolation & purification; D014744:Vietnam
chemical_list: D000970:Antineoplastic Agents; D012459:Salicylates; C000616897:orsellinylmontagnetol A; D004896:Erythritol
keywords: Cytotoxicity; Lichen; Montagnetol; Montagnetol derivatives; Roccella montagnei (fertile form); Stereochemistry