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

Authors
  • Csupor, Dezső1, 1
  • Kurtán, Tibor2
  • Vollár, Martin1
  • Kúsz, Norbert1
  • Kövér, Katalin E.2
  • Mándi, Attila2
  • Szűcs, Péter3
  • Marschall, Marianna3
  • Senobar Tahaei, Seyyed A.1
  • Zupkó, István1
  • Hohmann, Judit1, 1
  • 1 University of Szeged, Hungary , (Hungary)
  • 2 University of Debrecen, Hungary , (Hungary)
  • 3 Eszterházy Károly University, Hungary , (Hungary)
Type
Published Article
Journal
Journal of Natural Products
Publisher
American Chemical Society
Publication Date
Feb 20, 2020
Volume
83
Issue
2
Pages
268–276
Identifiers
DOI: 10.1021/acs.jnatprod.9b00655
PMID: 32077277
PMCID: PMC7316407
Source
PubMed Central
License
Unknown

Abstract

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 C10 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.

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