Pinocembrine: A bioactive flavanone from Teloxys graveolens

Camacho, Maria del Rayo; Sánchez, Berta; Quiroz, Héctor; Contreras, J. L.; Mata, Rachel

doi:10.1016/0378-8741(91)90022-6

Cited by 37 publications

(17 citation statements)

References 8 publications

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“…Previous studies have suggested some pharmacological activity for pinocembrin and pinostrobin including anti-cancer, antiinflammatory, anti-diabetic, and anti-oxidant activities (15)(16)(17)(18)(19)(20)(21)(22)(23). Understanding the role of each flavonoid enantiomer in the pharmacological activity described for the racemic mixtures is important as the combined effect of some enantiomers can be exaggerated or attenuated.…”

Section: Introductionmentioning

confidence: 99%

Pre-Clinical Pharmacokinetic and Pharmacodynamic Characterization of Selected Chiral Flavonoids: Pinocembrin and Pinostrobin

et al. 2015

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Purpose: Delineate the stereospecific pharmacokinetics and pharmacodynamics of the chiral flavonoids pinocembrin and pinostrobin. Objective: Characterize for the first time the stereoselective pharmacokinetics of two flavonoids, pinocembrin and pinostrobin and their bioactivity in several in vitro assays with relevant roles in heart disease, colon cancer, and diabetes etiology and pathophysiology. Methods: Chiral flavonoids were intravenously and orally administered to male Sprague-Dawley rats. Concentrations in serum and urine were characterized via stereospecific HPLC or LC/MS. Pure enantiomeric forms of each flavonoid were tested, where possible, to identify the stereospecific contribution to bioactivity in comparision to their racemates. Results: Short half-lives (0.2-6 h) in serum were observed, while a better estimation of half-life (3-26 h) and other pharmacokinetic parameters were observed using urinary data. The flavonoids are predominantly excreted via non-renal routes (fe values of 0.3-4.6 %), and undergo rapid and extensive phase II metabolism. Chiral differences in the chemical structure of these compounds result in significant pharmacodynamic differences. Conclusion: The importance of understanding the stereospecific pharmacokinetics and pharmacodynamics of two chiral flavonoids were delineated.This article is open to POST-PUBLICATION REVIEW. Registered readers (see “For Readers”) may comment by clicking on ABSTRACT on the issue’s contents page.

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Section: Introductionmentioning

confidence: 99%

Pre-Clinical Pharmacokinetic and Pharmacodynamic Characterization of Selected Chiral Flavonoids: Pinocembrin and Pinostrobin

et al. 2015

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“…The presence of these flavonoids in extracts of T. graveolens has been previously reported (Calzada et al, 2003;Del Rayo-Camacho et al, 1991). In our study pinocembrin (2) was the only active compound at the concentrations evaluated.…”

Section: Discussionmentioning

confidence: 80%

“…Del Rayo-Camacho et al (1991) showed that pinocembrin (2) exhibits fasciolicide, ovicide and larvicide activities on newly excysted Fasciola hepatica and on infective eggs of Ascaridia galli. Thus, our study contributes to the knowledge of the potential of pinocembrin (2) as a cysticidal agent.…”

Section: Discussionmentioning

confidence: 99%

“…Weber, commonly known as "epazote de zorrillo", which is widely used for the treatment of intestinal parasites and related gastrointestinal ailments, such as diarrhea and stomach pain (Aguilar et al, 1994;CONABIO, 1998). Also, pharmacological studies have reported its anthelmintic efficacy against Fasciola hepatica and Ascaridia galli (Calzada et al, 2003;Del Rayo-Camacho et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

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Cysticidal activity of extracts and isolated compounds from Teloxys graveolens: In vitro and in vivo studies

Palomares-Alonso

Rojas-Tomé

Rocha

et al. 2015

Experimental Parasitology

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“…Pinocembrin, also known as 5,7‐dihydroxyflavanone or dihydrochrysin, is a chiral flavonoid. As with many other flavonoids, it has been shown to have anti‐inflammatory, anti‐oxidant, neuroprotective, anti‐tumor and anti‐microbial activity (Del Rayo Camacho et al ., ; Meng et al ., ; Sala et al ., ; Santos et al ., ). Pinocembrin is also present in many currently marketed dietary supplements, in particular propolis, which is consumed by many Western people.…”

Section: Introductionmentioning

confidence: 99%

Chiral analytical method development and application to pre‐clinical pharmacokinetics of pinocembrin

Sayre

Takemoto

Martinez

et al. 2012

Biomedical Chromatography

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An analytical method enabling the detection and quantification of the individual enantiomers of racemic (±) pinocembrin is required to fully characterize its pharmacokinetic disposition. Direct resolution of the enantiomers of pinocembrin was achieved using a novel and simple reversed-phase high-performance liquid chromatography method with electrospray ionization and detection by mass spectrometry in rat serum. A Chiralcel® AD-RH column was employed to perform baseline separation with electrospray positive-mode ionization with selected ion monitoring detection. The standard curves were linear from 0.5 to 100 µg/mL for each enantiomer. The limit of quantification was 0.5 µg/mL. The assay was applied successfully to stereoselective serum disposition of pinocembrin enantiomers in rats. Pinocembrin enantiomers were detected in serum. Both enantiomers had a serum half-life of ~15 min in rats. Similar values of volume of distribution between the enantiomers were also observed: 1.76 L/kg for S-pinocembrin and 1.79 L/kg for R-pinocembrin. Total clearance was 5.527 L//h/kg for S-pinocembrin and 5.535 L/h/kg for R-pinocembrin, and the area under the curve was 1.821 µg h/mL for S-pinocembrin and 1.876 µg h/mL for R-pinocembrin. The large volume of distribution coupled with the short serum half-life suggests extensive distribution of pinocembrin into the tissues.

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Pinocembrine: A bioactive flavanone from Teloxys graveolens

Cited by 37 publications

References 8 publications

Pre-Clinical Pharmacokinetic and Pharmacodynamic Characterization of Selected Chiral Flavonoids: Pinocembrin and Pinostrobin

Pre-Clinical Pharmacokinetic and Pharmacodynamic Characterization of Selected Chiral Flavonoids: Pinocembrin and Pinostrobin

Cysticidal activity of extracts and isolated compounds from Teloxys graveolens: In vitro and in vivo studies

Chiral analytical method development and application to pre‐clinical pharmacokinetics of pinocembrin

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