Guaianolides cytotoxic activity

Examination of the Montenegro Achillea clavennae reveals the presence of three new chlorine-containing guaianolides 277-279 in addition to several known analogues (524). The first investigation of the Chinese medicinal plant Vernonia chinensis has uncovered the new chlorinated sesquiterpene lactones vemchinilides A (280), B (281), C (282) and E (283) (525). Vemchinilides B and E exhibit potent cytotoxic activity against the P-388 and A-549 cell lines. The structurally similar vemolide C (284) was found in the Cambodian traditional medicinal plant Vernonia cinera (fever, colic, malaria) (526). Indeed, vemolide C could be identical with vemchinilide A. 

Initially, this reaction was studied by Kupchan et al. to explain the cytotoxic activities of a-methylene sesquiterpene lactones [13]. By reaction of the guaianolide with an essential enzyme or receptor containing cysteine, a malfunctioning product might be formed that could kill the cell. In spite of several later studies, no drug based on this reaction has been registered until now,... 

Bruno M, Rosselli S, Maggio A, Raccuglia RA, Bastow KF, Lee K-H (2005) Cytotoxic activity of some natural and synthetic guaianolides. J Nat Prod 68(7) 1042-1046... 

A new guaianolide derivative, which possesses cytotoxic activity, was obtained from leaves and stems of Chrysanthemum boreale. It is effective in kidney carcinoma, melanoma, colon adenocarcinoma, prostate adenocarcinoma, and lung carcinoma. Chrysanthemum morifolium effectively inhibited the cytotoxicity and improved cell viability. It also stimulates the elevation of reactive oxygen species (ROS) level, increase in Bax/Bcl-2 ratio, cleavage of caspase-3, and PARP proteolysis [43, 44]. 

Eupatorium perfoliatum L. (Asteraceae), boneset also known as Indian sage, produces a number of sesquiterpene lactones possessing cytotoxic and immunostimulant activities [37, 38]. The sesquiterpenes lactones are guaianolides such as euperfolid, 11,13-dihydroeuperfolid, eufoliatin, eufoliatorin, or germacranolides such as euperfolitin and euperfolin [39]. 

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