Pigments of the Moss Paraleucobryum longifolium : Isolation and Structure Elucidation of Prenyl-Substituted 8,8'-Linked 9,10-Phenanthrenequinone Dimers.

Autor: Csupor D, Kurtán T, Vollár M, Kúsz N, Kövér KE, Mándi A, Szűcs P; Department of Botany and Plant Physiology, Institute of Biology , Eszterházy Károly University , Eszterházy tér 1 , H-3300 Eger , Hungary., Marschall M; Department of Botany and Plant Physiology, Institute of Biology , Eszterházy Károly University , Eszterházy tér 1 , H-3300 Eger , Hungary., Senobar Tahaei SA, Zupkó I, Hohmann J
Jazyk: angličtina
Zdroj: Journal of natural products [J Nat Prod] 2020 Feb 28; Vol. 83 (2), pp. 268-276. Date of Electronic Publication: 2020 Feb 20.
DOI: 10.1021/acs.jnatprod.9b00655
Abstrakt: In a search for new secondary metabolites from mosses, leucobryns A-E, axially chiral 9,10-phenanthrenequinone dimers, were isolated from Paraleucobryum longifolium ( 1 - 5 ), together with diosmetin triglycoside. Leucobryns B ( 2 ) and C ( 3 ) were proved to be homodimeric atropodiastereomers containing both axial and central chirality elements, while leucobryns D ( 4 ) and E ( 5 ) were found to be heterodimeric atropodiastereomers containing central chirality in only one of the two monomeric units. Axial chirality of the compounds was determined by ECD measurements and sTDA ECD calculations, while the central chirality elements were assigned by TDDFT-SOR calculations. Leucobryns represent the first 9,10-phenanthrenequinone dimers, the monomers of which are linked through their C-8 atoms. Leucobryns B-E contain an uncommon C 10 monoterpenoid side chain, in which isoprenoid units are joined by 3,4 linkages. Leucobryns A and B exhibited weak antiproliferative activity against several human cancer cell lines.
Databáze: MEDLINE