Secoiridoid ester from Centaurium spicatum with hepatoprotective activity

J Pharm Pharmacogn Res 3(3): 69-76, 2015.

Short Communication | Comunicación Corta

New secoiridoid ester of swertiamarin and secoxyloganic acid   with hepatoprotective activity from Centaurium spicatum L.

[Nuevo éster secoiridoide de swertiamarin y ácido secoxilogánico de Centaurium spicatum L.]

Ahmed E. Allam1*, Alaa M. Nafady1, Mohamed A. El-Shanawany2, Fumide Takano3, Tomihisa Ohta3

1Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut 71524, Egypt.2Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.3Laboratory of Pharmacognosy and Chemistry of Natural Products, School of Pharmaceutical Sciences, Kanazawa University, Kanazawa 920-1192, Japan.
Abstract

Context: Centaurium spicatum (L.) Fritsch (Gentianaceae) is an annual herb occurring in Southern Europe and Northern Africa where it is used in traditional medicine for treatment of numerous illness.

Aims: To isolate compounds from C. spicatum having hepatoprotective activity.

Methods: Structure elucidation of the new compound was established on the basis of 1D and 2D NMR analyses including 1H-, 13C- NMR, DEPT-135 NMR, HMQC, HMBC and H- H HOHAHA experiments in addition to FAB+ and HRFAB+ Mass spectrometry. In vivo transaminases inhibition activity was carried out.

Results: A new ester of swertiamarin and secoxyloganic acid (1) was isolated from C. spicatum in addition to its known components secoiridoids swertiamarin (2) and secoxyloganic acid (3). All tested secoiridoids have transaminases inhibition activity with different values for each compound 1, 2, 3 (86, 83, 81%) for SGOT and (96, 93, 91%) for SGPT, respectively.

Conclusions: The new ester compound from C. spicatum has hepatoprotective activity over than its components.

Keywords: Centaurium spicatum; ester of swertiamarin and secoxyloganic acid; hepatoprotective activity; NMR analysis.

Resumen

Contexto: Centaurium spicatum (L.) Fritsch (Gentianaceae) es una hierba anual que crece en el sur de Europa y norte de África, donde se utiliza en la medicina tradicional para el tratamiento de numerosas enfermedades.

Objetivos: Aislar compuestos a partir de C. spicatum con actividad hepatoprotectora.

Métodos: La elucidación estructural del nuevo compuesto fue establecida sobre las bases del analisis de RMN 1D y 2D que incluyó experimentos de 1H-, 13C- NMR, DEPT-135 NMR, HMQC, HMBC y H- H HOHAHA, además espectrometría de masas FAB+ and HRFAB+. También fue medida la actividad de transaminasas in vivo.

Resultados: Un nuevo éster del ácido swertiamarin y ácido secoxilogánico (1) de C. spicatum, además de compuestos secoiridoides  conocidos como swertiamarin (2) y ácido secoxilogánico (3).  Todos los secoididoides tuvieron actividad inhidora sobre transaminasas con diferentes valores para cada compuesto 1, 2, 3 (86, 83, 81%) para SGOT y (96, 93, 91%) para SGPT, respectivamente.

Conclusiones: El nuevo éster de C. spicatum tiene actividad hepatoprotectora superior a la de sus componentes.

Palabras Clave: Actividad hepatoprotectora; análisis por RMN; Centaurium spicatum; éster de swertiamarin y ácido secoxilogánico.

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Citation Format: Ahmed E. Allam, Alaa M. Nafady, Mohamed A. El-Shanawany, Fumide Takano, Tomihisa Ohta (2015) New secoiridoid ester of swertiamarin and secoxyloganic acid with hepatoprotective activity from Centaurium spicatum L. J Pharm Pharmacogn Res 3(3): 69-76.
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© 2015 Journal of Pharmacy & Pharmacognosy Research (JPPRes)