Phytochemical and biological characterization of Agrimonia eupatoria L.: an approach to structure-activity

G Costa; V Francisco; J Liberal; A Figueirinha; T Cruz; I Figueiredo; C Lopes; T Batista

doi:10.1055/s-0031-1282843

Planta Medica, Inhaltsverzeichnis

Phytochemical and biological characterization of Agrimonia eupatoria L.: an approach to structure-activity

G Costa ¹, V Francisco ³, J Liberal ³, A Figueirinha ⁴, T Cruz ³, I Figueiredo ², C Lopes ³, T Batista ²

¹Faculdade de Farmácia, Universidade de Coimbra, Azinhaga de Santa Comba, 3000–548 Coimbra, Portugal
²Centro de Estudos Farmacêuticos, Universidade de Coimbra, Azinhaga de Santa Comba, 3000–548 Coimbra, Portugal
³Centro de Neurociências e Biologia Celular, Azinhaga de Santa Comba 3004–517 Coimbra, Portugal
⁴Departamento de Ambiente-IPV, Campus Politécnico de Repeses-3504–510 Viseu, Portugal

Abstract

Plant polyphenols are well-known antioxidants, and recent studies have reported that they play an important role in prevention and treatment of oxidative-related disorders, such as inflammatory diseases and cancer.

In this work, a phenol-rich fraction from Agrimonia eupatoria dry aerial parts (AePRF) was studied. Results revealed p-coumaric and ellagic acid derivatives, flavonol and flavone glycosides, and monomers and oligomers of flavan-3-ols (proanthocyanidins).

Some key features in molecular structure of flavonoids seem to be crucial to anti-inflammatory mechanisms: 4-oxo functional group and C2-C3 double bond at C-ring, 5- and 7-OH on A-ring and also OH functions on B-ring¹. Polymerization degree of proanthocyanidins plays a significant role in bioactivity, since dimers and higher oligomers are more effective than monomers, in inhibiting NO production. On the other hand, catechol moiety increases antioxidant activity, leading to presume that catechin-type proanthocyanidins are very active².

Anti-inflammatory effect was evaluated in LPS-stimulated Raw 264.7 macrophage cell line by measuring the nitric oxide (NO) production through the Griess assay and AePRF cytotoxicity was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Moreover, antioxidant capacity was determined by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Total phenols and total flavonoids were also evaluated, and phenolic compounds were identified by high performance liquid chromatography, coupled to photodiode-array and electrospray ionization mass spectrometry detectors.

Anti-inflammatory and antioxidant activities verified, as well as the phenolic profile established corroborate the traditional use of AePRF in inflammatory-related pathologies, since generous amount of the cited compounds were found in the phenol-rich fraction studied.

Keywords: anti-inflammatory, antioxidant, phenolic, agrimonia, eupatoria

Acknowledgement: This work was supported by FEDER/COMPETE (FCOMP-01–0124-FEDER-011096) and FCT, by the project PTDC/SAU-FCF/105429/2008 and the PhD fellowship SFRH/BD/46281/2008. A special thank to LEM/UC integrated in RNEM of Portugal for the HPLC/MS analyses.

References: 1. Takano-Ishikawa et al. (2006) Phytomedicine 13: 310–7

2. Terra et al.(2007)J Agric Food Chem 55: 4357–65