Sesquiterpene lactones cytotoxicity

Composites -have been reported (8) to contain a wide variety of sesquiterpene lactones and lactones of this type have been previously found in both Russian knapweed and yellow starthistle (9,10,11,12). The wide range of biological activity associated with sesquiterpene lactones, e.g., cytotoxicity, phytotoxicity, antineoplasticity, etc. (8) suggested the possibility that these compounds may play a role in the allelopathy of both Russian knapweed and yellow starthistle. 

Effects of Sesquiterpene Lactones on Seed Germination. Sesquiterpene lactones are common constituents of the Asteraceae but are also found in other angiosperm families and in certain liverworts (31,32). These highly bitter substances exhibit a wide spectrum of biological activities (J 3) which include cytotoxicity, anti-tumor, anti-microbial, insecticidal (34) and molluscicidal (35) properties. Furthermore, they are known causes for livestock poisoning and contact dermatitis in humans (33). Structure-activity relationship studies on sesquiterpene lactones have demonstrated that biological activity frequently depend on the presence of the cr... 

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. 

Huo J, Yang S-P, Ding J, Yue J-M (2004) Cytotoxic Sesquiterpene Lactones from Eupatorium lindleyanum. J Nat Prod 67 1470... 

Chen X, Zhan Z-J, Zhang X-W, Ding J, Yu J-M (2005) Sesquiterpene Lactones with Potent Cytotoxic Activities from Vernonia chinensis. Planta Med 71 949... 

B. gaudichaudiana, which is commonly used for diabetes. Elephantopus scaber contains hydroxylated germacranolides, such as molephantin and molephantinin, which cause diuresis, antipiresis, eliminate bladder stones, and have cytotoxic and antitumor properties. From the Tithonia genus, T, diversifolia is widely used in Mexico and often has been identified erroneously as Arnica montana. Because of this confusion it is used as European arnica to treat hematomas and muscular cramps. The genus is rich in sesquiterpene lactones.11... 

Encelin from Montanoa speciosa is inhibitory to growth and development of fungal cells of Mucor rouxii. Other cytotoxic sesquiterpene lactones from Montanoa tomentosa ssp. microcephala have been reported.45,46 A number of kaurane diterpenes and e/tf-kauranoids have been reported that are potentially useful because of their cytotoxicity against human tumor cells, anti-HIV activity, and trypanosomicidal activity.47 56 New structures are frequently discovered, and probably we will learn new effects in humans and animals in the future.57,58 Paradoxically, these plant natural products probably have specific and important effects in the plants, but we are still ignorant of these roles. 

TOPQU, G., CORDELL, G.A., FARNSWORTH, N.R. FONG, N.H., Studies on zoapatle. VIII. Novel cytotoxic sesquiterpene lactones from Montanoa tomentosa ssp. microcephala., J. Pharm. Sci., 1988, 77,553-556. 

Eudesmanolide sesquiterpene lactones (G6 G6 C40L) include a variety of variously cytotoxic compounds. The antifeedants alantolactone and isoalantolactone (helenin being a mixture of the two) (C6 ] C5 C40L=CH2) are antimicrobial. The pro-apoptotic activity of these compounds may derive from the reactivity of the a-methylene-y-butyrolactone ring... 

Hymenin (sesquiterpene lactone) Parthenium confertum (Asteraceae) Apoptotic [cytotoxic, phosphatidylserine migration]... 

Sesquiterpene lactones isolated from T. densum ssp. sivasicum were evaluated for cytotoxic activity against human epidermoid (KB) cells. Tavulin, spiciformin and dentatin A were found to be active with the IC50 values of 3.2, 2.9 and 2.4 pgml, respectively, whereas tanachin was inactive [36]. 

Organic and aqueous feverfew powdered leaf extracts were found to inhibit IL-1-induced prostaglandin E2 release from synovial cells, IL-2-induced thymidine uptake by lymphoblasts, and mitogen-induced uptake of thymidine by peripheral blood mononuclear cells (PBMCs) (23). Parthenolide also inhibited thymidine uptake by PBMCs. Both parthenolide and the extracts were cytotoxic to the PBMCs and synovial cells thus, the anti-inflammatory effects of feverfew may be secondary to cytotoxicity. These results reflect those of previous researchers who found parthenolide and other sesquiterpene lactones to be cytotoxic to cultures of human fibroblasts, human laryngeal carcinoma cells, and human cells transformed with simian virus 40 (24). 

Lee K, Huang E, Piantadosi C, Pagano JS, Geissman TA. Cytotoxicity of sesquiterpene lactones. Cancer Res 1971 31 1649-1654. 

Schmidt, T.J. and Heilmann, J. (2002) Quantitative structure-cytotoxicity relationships of sesquiterpene lactones derived from partial charge (Q)-based fractional accessible surface area descriptors (Q frASAs). Quant. Struct. -Act. Relat., 21, 276-287. 

Table 8. Cytotoxic Activity (in ICgo values pM + sd n=3) of the Sesquiterpene Lactones Isolated from T. praeteritum ssp. praeteritum Against the Human Cell Lung Carcinoma Cell Line (GLC4) and the Human Colorectal Cancer Cell Line (COLO 320)...

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