Photosensitizing anthraquinones from Heterophyllaea lycioides (Rubiaceae)

DIMMER, JESICA A.; NÚÑEZ MONTOYA, SUSANA C.; MENDOZA, CATERINE S.; CABRERA, JOSÉ L.

PHYTOCHEMISTRY

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2017 vol. 137 p. 94 - 94

0031-9422

even anthraquinones were isolated from aerial parts of Heterophyllaea lycioides (Rusby) Sandwith (Rubiaceae), including three derivatives that have not been described before: a hetero-bianthraquinone identified as (R)-2-hydroxymethyl-2´methyl-1,1´,6,6´-tetrahydroxy-5,5´ bianthraquinone (lycionine), and two mono-chlorinated derivatives related to soranjidiol. One of them is a homo-bianthraquinone: (R)-7-chloro-2,2´-dimethyl-1,1´,6,6´-tetrahydroxy-5,5´ bianthraquinone (7-chlorobisoranjidiol), whereas the second halogenated derivative corresponds to a monomeric structure: 5-chloro-1,6-dihydroxy-2-methyl anthraquinone (5-chlorosoranjidiol). The four known compounds were already isolated from another species of this genus, H. pustulata, and they were identified as 5,5´-bisoranjidiol, soranjidiol, pustuline and heterophylline. Structural elucidation was performed by means of an extensive spectroscopic analysis, including 1D and 2D NMR data as well as by HRMS analysis. Chemical structures of