An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum.

Abstract:

:The CH(2)Cl(2) extract of aerial parts of Eupatorium perfoliatum L. exhibits antiprotozoal activity under in vitro conditions, especially against Plasmodium falciparum (IC(50)=2.7μg/ml). The search for active compounds yielded seven sesquiterpene lactones: Four structurally similar guaianolides, one dimeric guaianolide, and two germacranolides. The guaianolides differ in the degree of oxidation at C-14, ranging from a hydroxyl group up to a free carboxylic acid. The dimeric guaianolide, structurally closely related to the monomers, displays an unusual type of interguaianolide linkage between C-14 and C-4. Except for the germacranolide euperfolitin, all STLs described here were hitherto unknown. Furthermore, the flavonoid aglycones eupafolin, hispidulin, patuletin, and kaempferol were identified in the extract, which, except for kaempferol, have not been described as constituents of E. perfoliatum before. The dimeric guaianolide was shown to be the most active constituent against Plasmodium falciparum (IC(50) = 2.0μM) and was less cytotoxic against rat skeletal myoblasts (IC(50) = 16.2μM, selectivity index of about 8).

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Maas M,Hensel A,Costa FB,Brun R,Kaiser M,Schmidt TJ

doi

10.1016/j.phytochem.2011.01.025

subject

Has Abstract

pub_date

2011-05-01 00:00:00

pages

635-44

issue

7

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(11)00052-5

journal_volume

72

pub_type

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