Cytotoxic Activity of Some Natural and Synthetic Guaianolides

Abstract

Several natural guaianolides and synthetic derivatives of repin (1) were tested and found to be active against tumor cell replication. Repin (1) and both mono- and di-halohydrin analogues (2, 7-9, 11, 12) showed significant antitumor potency. A more effective compound (17) was obtained by esterificating repin with the paclitaxel side chain.

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

“…Among the sesquiterpenoids, the seco-pseudoguaianolides paulitin (4) and isopaulitin (5) are the most efficient inhibitors of tumour cell proliferation (Table 2). Both compounds contain two α,β-unsaturated (C-O-CH= CH 2 ) systems, which was earlier found to determine the cytotoxicity of natural and synthetic sesquiterpene lactones (Bruno et al, 2005). Psilostachyin C (6), possessing only one C-O-CH=CH 2 moiety in the molecule, does not exhibit an antiproliferative effect.…”

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

“…Repin (209), chlorohyssopifolin C (212) and chlorohyssopifolin A (224) showed significant antitumor potency (Bruno et al, 2005c). Repin (209) showed also significant activity toward chick embryo sensory neurons and a causal relationship between repin and the necrosis of the neural cells in substantia nigra of horses leading to equine nigrostriatal encephalomalacia (ENE) disease has been suggested (Stevens et al, 1990).…”

Production of Valuable Lipophilic Compounds by Using Three Types of Interface Bioprocesses: Solid–Liquid Interface Bioreactor, Liquid–Liquid Interface Bioreactor, and Extractive Liquid-Surface Immobilization System

“…Epoxy groups in many terpenes are known to enhance various biological activities, including antibacterial 108 , antifungal 109 , and cytotoxic activities 110 . L/L-IBR has been used for producing optically active β-caryophyllene oxides through regio-and stereoselective epoxidation of β-caryophyllene Fig.…”