3 research outputs found
Photosensitizing anthraquinones from Heterophyllaea lycioides (Rubiaceae)
Seven 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 7-chlorobisoranjidiol and 5-chlorosoranjidiol were confirmed by their synthesis from 5,5´-bisoranjidiol and soranjidiol, respectively. Type I photosensitizing properties (superoxide anion radical generation, O2?ÂŻ) were assessed by using the nitroblue tetrazolium assay. When lycionine and chlorinated derivatives were irradiated, they enhanced the O2?ÂŻ production with respect to the control; 7-chlorobisoranjidiol stood out by generating an increase of 20%, whereas the other anthraquinones only produced a slight increase of 7%.Fil: Dimmer, Jesica Ayelen. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; ArgentinaFil: Núñez Montoya, Susana Carolina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; ArgentinaFil: Mendoza, Caterine S.. Universidad de San Francisco Xavier de Chuquisaca. Facultad de Ciencias QuĂmico FarmacĂ©uticas y BioquĂmicas. Departamento de Farmacia; BoliviaFil: Cabrera, Jose Luis. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; Argentin
Chemical and bioactivity of flavanones obtained from roots of Dalea pazensis Rusby
Two new prenylated flavanones, pazentin A (3′,4′-dihydroxy-6,2′-diprenylpinocembrin, 1) and pazentin B [4′-hydroxy-2′-methoxy-5′-(1‴, 1‴-dimethylallyl)-6-prenylpinocembrin, 2] together with two known ones (3 and 4) previously isolated from other Dalea species were obtained from the benzene extract of Dalea pazensis Rusby roots. The compounds were evaluated in vitro for their inhibition on mushroom tyrosinase enzyme and in relation to their effect on melanogenesis in B16 murine melanoma cells, by using a spectrophotometric method. The information obtained could be relevant to the knowledge of the structure-activity relationship for these flavonoids with the aim to explore the rational design for skin-whitening agents.Fil: Santi, MarĂa Daniela. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; Argentina. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; ArgentinaFil: Peralta, Mariana Andrea. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; ArgentinaFil: Mendoza, Caterine S.. Universidad Mayor Real y Pontificia de San Francisco Xavier de Chuquisaca. Facultad de Cs. Quimico Farmaceuticas y BioquĂmicas; Bolivia. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; ArgentinaFil: Cabrera, Jose Luis. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; ArgentinaFil: Ortega, MarĂa Gabriela. Universidad Nacional de Cordoba. Facultad de Ciencias Quimicas. Departamento de Farmacia. Catedra de Farmacognosia; Argentina. Consejo Nacional de Investigaciones CientĂficas y TĂ©cnicas. Centro CientĂfico TecnolĂłgico Conicet - CĂłrdoba. Instituto Multidisciplinario de BiologĂa Vegetal. Universidad Nacional de CĂłrdoba. Facultad de Ciencias Exactas FĂsicas y Naturales. Instituto Multidisciplinario de BiologĂa Vegetal; Argentin