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Inactivation of the cytotoxic activity of repin, a sesquiterpene lactone from Centaurea repens.

Abstract：

:Prolonged ingestion of Yellow Starthistle (Centaurea solstitialis) and Russian Knapweed (Centaurea repens) by horses has been shown to result in a fatal neurodegenerative disorder called equine nigropallidal encephalomalacia (ENE). Bioassay-guided fractionation of extracts from Centaurea species using the PC12 cell line have led to the identification of one of several putative agents, which may contribute to ENE, namely, the sesquiterpene lactone (SQL) repin (1), previously linked to ENE due to its abundance in C. repens. To characterize the molecular basis of repin-induced neurotoxicity, the present study was designed to identify reactive functional groups that may contribute overall to its toxicity. The reaction of repin (1) with glutathione (GSH) led to the exclusive addition of GSH to the alpha-methylenebutyrolactone affording a GSH conjugate (3b) that lacked toxicity in the PC12 cell assay, while selective reduction of the alpha-methylenebutyrolactone double bond of 1 also resulted in an analogue (2) that was devoid of toxicity relative to the parent compound. Unlike repin, analogue 2 failed to decrease cellular dopamine levels in PC12 cells, further substantiating the requirement of the alpha-methylenebutyrolactone group. Results from this study are suggestive that GSH depletion by the SQL repin may be a primary event in the etiology of ENE, increasing the susceptibility to oxidative damage.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Tukov FF,Anand S,Gadepalli RS,Gunatilaka AA,Matthews JC,Rimoldi JM

doi

10.1021/tx049864e

subject

Has Abstract

pub_date

2004-09-01 00:00:00

pages

1170-6

issue

9

eissn

0893-228X

issn

1520-5010

journal_volume

17

pub_type

杂志文章

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