A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth

Maribel Herrera-Ruiz, Ricardo López-Rodríguez, Gabriela Trejo-Tapia, Blanca Eda Domínguez-Mendoza, Manases González-Cortazar, Jaime Tortoriello, Alejandro Zamilpa

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Abstract

© 2015 by the authors; licensee MDPI. 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)-O-glucopyranoside. 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 - 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.
Original languageAmerican English
Pages (from-to)13127-13143
Number of pages17
JournalMolecules
DOIs
StatePublished - 1 Jul 2015

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Orobanchaceae
Luteolin
Methyl Ethers
Lignans
geniposide
metabolites
Metabolites
hypnosis
pentobarbital sodium
Antidepressive Agents
Methanol
ethers
methyl alcohol
Iridoids
Flavones
Apigenin
Column chromatography
central nervous system
Hypnosis
constitution

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Herrera-Ruiz, M., López-Rodríguez, R., Trejo-Tapia, G., Domínguez-Mendoza, B. E., González-Cortazar, M., Tortoriello, J., & Zamilpa, A. (2015). A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth. Molecules, 13127-13143. https://doi.org/10.3390/molecules200713127
Herrera-Ruiz, Maribel ; López-Rodríguez, Ricardo ; Trejo-Tapia, Gabriela ; Domínguez-Mendoza, Blanca Eda ; González-Cortazar, Manases ; Tortoriello, Jaime ; Zamilpa, Alejandro. / A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth. In: Molecules. 2015 ; pp. 13127-13143.
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Herrera-Ruiz, M, López-Rodríguez, R, Trejo-Tapia, G, Domínguez-Mendoza, BE, González-Cortazar, M, Tortoriello, J & Zamilpa, A 2015, 'A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth', Molecules, pp. 13127-13143. https://doi.org/10.3390/molecules200713127

A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth. / Herrera-Ruiz, Maribel; López-Rodríguez, Ricardo; Trejo-Tapia, Gabriela; Domínguez-Mendoza, Blanca Eda; González-Cortazar, Manases; Tortoriello, Jaime; Zamilpa, Alejandro.

In: Molecules, 01.07.2015, p. 13127-13143.

Research output: Contribution to journalArticle

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T1 - A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth

AU - Herrera-Ruiz, Maribel

AU - López-Rodríguez, Ricardo

AU - Trejo-Tapia, Gabriela

AU - Domínguez-Mendoza, Blanca Eda

AU - González-Cortazar, Manases

AU - Tortoriello, Jaime

AU - Zamilpa, Alejandro

PY - 2015/7/1

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N2 - © 2015 by the authors; licensee MDPI. 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)-O-glucopyranoside. 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 - 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.

AB - © 2015 by the authors; licensee MDPI. 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)-O-glucopyranoside. 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 - 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.

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Herrera-Ruiz M, López-Rodríguez R, Trejo-Tapia G, Domínguez-Mendoza BE, González-Cortazar M, Tortoriello J et al. A new furofuran lignan diglycoside and other secondary metabolites from the antidepressant extract of Castilleja tenuiflora Benth. Molecules. 2015 Jul 1;13127-13143. https://doi.org/10.3390/molecules200713127