26931-94-2Relevant academic research and scientific papers
Sesquiterpene lactones from Centaurea arbutifolia
Gonz'alez, Antonio G.,Bermejo, Jaime,Toledo, Francisco,Daza, Lina Rosa
, p. 1895 - 1897 (1981)
The investigation of the aerial parts of Centaurea arbutifolia afforded four new sesquiterpene lactones; two germacranolides and two elemanolides, plus aguerin A. Their structures were elucidated by spectroscopic methods and by partial synthesis.
Antibacterial evaluation of cnicin and some natural and semisynthetic analogues
Bruno, Maurizio,Rosselli, Sergio,Maggio, Antonella,Raccuglia, Rosa Angela,Napolitano, Francesco,Senatore, Felice
, p. 277 - 281 (2003)
Some ester derivatives of salonitenolide have been prepared from cnicin, a germacranolide sesquiterpenoid. The compounds were tested for their antibacterial activity. The 8,15-diesters showed a good activity, comparable with that of cnicin. The 15-monoester compounds were not very active showing that esterification at the C-8 position is an important structural feature for antibacterial properties.
Synthetic study of cnicin: Synthesis of the side chain and its esterification
Kurita, Manami,Tanigawa, Miho,Narita, Shuhei,Usuki, Toyonobu
supporting information, p. 5899 - 5901 (2016/12/09)
Cnicin is a germacranolide sesquiterpene lactone that possesses potent inhibitory activity against the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT). Although cnicin has an interesting structure and attractive biological activity, synthetic studies of cnicin have not yet been reported. This report describes the synthesis of the protected side chain carboxylic acid moiety at C8 of cnicin via two routes starting from L-ascorbic acid. In addition, esterification between the synthetic side chain and salonitenolide derivative, which can be achieved via hydrolysis of cnicin and protection of the primary alcohol, was conducted. Thus, a semi-synthesis of cnicin was achieved.
Rearrangement of germacranolides. Synthesis and absolute configuration of elemane and heliangolane derivatives from cnicin
Rosselli, Sergio,Maggio, Antonella,Raccuglia, Rosa Angela,Bruno, Maurizio
, p. 2690 - 2694 (2007/10/03)
A study of the Cope rearrangement of 15-oxo-germacranolides to 15-oxo-elemanolides has been carried out. The synthesis of two natural elemanolides, isolated from Centaurea paui, and an efficent isomerization of the C-4/C-5 double bond of 15-oxo-germacranolides to form heliangolides are reported. The absolute configuration of all the compounds has been ascertained. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae
Barrero, Alejandro F.,Oltra, J. Enrique,Raslan, Delio S.,Saude, Denia A.
, p. 726 - 729 (2007/10/03)
Incubations of the fungi Cunninghamella echinulata and Rhizopus oryzae with the sesquiterpene lactones (+)-costunolide (1), (+)-cnicin (2), (+)- salonitenolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5), and (-)-eremantholide C (6) were performed. Incubation of 1 with C. echinulata afforded Δ(11(13))-dihydrogenation and Δ(1(10))-epoxidation products (7- 10). C. echinulata also hydrolyzed the side chain of 2, and transformed 4 into (+)-11α,13-dihydrodehydrocostuslactone (12), a new natural product. R. oryzae converted 4 into both Δ(11(13))-dihydrogenation and Δ(10(14))- epoxidation products (16 and 17). Both fungi transformed 5 into (-)-16-(1- methyl-1-propenyl)eremantholanolide (13), providing experimental evidence for the biosynthesis of the eremantholide hemiketal unit. Compounds 3 and 6 were not metabolized by either fungus under the test conditions.
