“Click” reaction mediated synthesis of costunolide and dehydrocostuslactone derivatives and evaluation of their cytotoxic activity

Abstract

As part of pharmacological-phytochemical integrated studies on medicinal plants from Indian flora, costunolide (1) and dehydrocostus lactone (2), were isolated as major phytochemicals from Saussurea lappa, a plant traditionally used in different Asian systems of medicine. A series of 1,4-disubstituted-1,2,3-triazoles conjugates were synthesized through diastereo selective Michael addition followed by regioselective Huisgen 1,3-dipolar cycloaddition reactions. All these triazolyl derivatives (5a-5j) & (7a-7j) were well characterized using modern spectroscopic techniques and evaluated for their anticancer activity against a panel of five human cancerous celllines. The results indicated that all the analogs displayed moderate cytotoxic activity.

Latest developments in coumarin-based anticancer agents: mechanism of action and structure–activity relationship studies

“…Besides the above-mentioned coumarin hybrids, coumarin-hydroxamic acid, 217 coumarin–ergosterol peroxide, 218 coumarin–formonontin, 219 coumarin–costunolide, 220 coumarin–curcuminoid, 221 coumarin–furan, 222 coumarin–maltol, 223 coumarin–carbazole, 224 coumarin–quinazoline, 225 coumarin-steroidal, 226,227 coumarin-sugar, 228–232 coumarin-thiazin-2-thione, 233 coumarin–thiophosphate, 234 coumarin-triazolothiadiazines, 235 N -heterocyclocoumarin, 236 hydroxymercapto-methylcoumarin, 237 triazole-tethered coumarin–isatin, 238 and others 239–241 also showed certain anticancer activities.…”

Application of triazoles in the structural modification of natural products

“…Kumar et al. 63 successfully synthesised 20 analogs of costunolide and dehydrocostuslactone and evaluated their anticancer activities. It is clear that majority of the derivatives synthesised displayed higher anticancer activity than the parent compounds, costunolide and dehydrocostuslactone against the tested cell lines.…”

Applications of Sesquiterpene Lactones: A Review of Some Potential Success Cases

“…Some species are rich sources of costunolide (3), such as essential oil of Saussurea lappa roots (yield ~3%), of which 52% was identified as costunolide ( 3) [86]. The total synthesis of costunolide (3) has been described using different methods/strategies [87][88][89].…”