A New Furofuran Lignan Diglycoside and Other Secondary Metabolites from the Antidepressant Extract of Castilleja tenuiflora Benth

Abstract

Castilleja tenuiflora has been used for the treatment of several Central Nervous System (CNS) diseases. Herein we report the antidepressant activity of the methanol extract from the leaves of this medicinal plant. The oral administration of MeOH extract (500 mg/kg) induced a significant (p < 0.05) decrement of the immobility parameter on Forced Swimming Test (FST) and an increment in the latency and duration of the hypnosis, induced by administration of sodium pentobarbital (Pbi, 40 mg/kg, i.p.). Chemical analysis of this antidepressant extract allowed the isolation of (+)-piperitol-4-O-xylopyranosyl-(1→6)-Oglucopyranoside. This new furofuran lignan diglycoside was named tenuifloroside (1) and its complete chemical structure elucidation on the basis of 1D and 2D NMR spectra analysis of the natural compound 1 and its peracetylated derivative 1a is described. This compound was found together with two flavones-apigenin and luteolin 5-methyl ether-a phenylethanoid- OPEN ACCESSMolecules 2015, 20 13128 verbascoside-and three iridoids-geniposide, caryoptoside and aucubin. All these compounds were purified by successive normal and reverse phase column chromatography. Tenuifloroside, caryoptoside and luteolin 5-methyl ether were isolated from Castilleja genus for the first time. These findings demonstrate that C. tenuiflora methanol extract has beneficial effect on depressive behaviors, and the knowledge of its chemical constitution allows us to propose a new standardized treatment for future investigations of this species in depressive illness.

Influence of spermine and nitrogen deficiency on growth and secondary metabolites accumulation in Castilleja tenuiflora Benth. cultured in a RITA® temporary immersion system

“…Of the 11 secondary metabolites identified in C. tenuiflora , three had already been reported for both in vitro cultures and wild plants (aucubin, verbascoside and isoverbascoside) and the other eight have been detected only in wild plants. This is the first time that the accumulation of the lignan tenuifloroside, which has antidepressant activity , has been detected in in vitro cultures of C. tenuiflora .…”

“…(Orobanchaceae) is a wild plant used in Mexican traditional medicine to relieve gastrointestinal diseases, and to “treat” nerves and tumors . This species synthesizes secondary metabolites such as iridoid glycosides , phenylethanoid glycosides (PhGs) , flavonoids , and lignans . These compounds have been shown to have valuable pharmacological activities such as cytotoxic , antioxidant , anti‐inflammatory , antiulcer and anti‐depressant effects .…”

“…shown to have valuable pharmacological activities such as cytotoxic [8], antioxidant [6], anti-inflammatory [4,9], antiulcer and anti-depressant effects [7,10].…”

Optimización de las condiciones de producción de cápsulas con microestacas para aumentar el tiempo de almacenamiento de la planta medicinal mexicana Castilleja tenuiflora (Orobanchaceae)

“…En plantas silvestres y cultivadas in vitro se ha evaluado la actividad antiinflamatoria y antiulcerogénica en pruebas con ratones (Carrillo-Ocampo et al, 2013;Sanchez et al, 2013), se han reportado sus efectos citotóxicos (Moreno-Escobar et al, 2011), antioxidantes (López-Laredo et al, 2012) y antidepresivos (Herrera-Ruiz etal., 2015). Dicha actividad biológica está relacionada con metabolitos secundarios como iridoides glicosilados (aucubina y bartsiósido) (Jiménez et al, 1995;Carrillo-Ocampo et al, 2013), feniletanoides glicosilados (verbascósidos e isoverbascósidos) (Gómez-Aguirre et al, 2012;Sanchez etal., 2013), flavonoides (apigenina y quercetina) (López-Laredo et al, 2012) y lignanos (Herrera-Ruiz et al, 2015), que fueron identificados tanto en plantas silvestres, cultivadas in vitro, como en plantas aclimatadas en condiciones de vivero (López-Laredo et al, 2012).…”

MORPHOGENESIS AND SECONDARY METABOLITES PRODUCTION IN THE MEDICINAL PLANT Castilleja tenuiflora Benth. UNDER NITROGEN DEFICIENCY AND STARVATION STRESS IN A TEMPORARY IMMERSION SYSTEM

“…(Orobanchaceae) is a wild plant used in traditional medicine to relieve gastrointestinal diseases, and "treat" nerves and tumors (Graham et al 2000;Alonso-Castro et al 2011). This species synthesizes secondary metabolites such as iridoid glycosides (aucubin, bartsioside, mussaenosidic acid, geniposidic acid, methyl 8-epi-loganin, geniposide, carioptoside, shanzhiside) (Jiménez et al 1995, Herrera-Ruiz et al 2015, phenylethanoid glycosides (verbascoside, isoverbascoside) (Gómez-Aguirre et al 2012), flavonoids (apigenin, quercetin glycosides, luteolin-5-methyl ether) HerreraRuiz et al 2015) and lignans (tenuifloroside) (HerreraRuiz et al 2015). These compounds have shown valuable pharmacological activities such as cytotoxic, antioxidant, anti-inflammatory, antiulcer and antidepressant effects (Moreno-Escobar et al 2011;Sanchez et al 2013;Herrera-Ruiz et al 2015).…”