2221-82-1Relevant articles and documents
(+)-β-FRULLANOLIDE AND (+)-BROTHENOLIDE, TWO NEW SESQUITERPENE LACTONES FROM THE LIVERWORT FRULLANIA BROTHERI STEPH.
Takeda, Reiji,Ohta, Yoshimoto,Hirose, Yoshio
, p. 1461 - 1464 (1980)
Two new sesquiterpene lactones, named (+)-β-frullanolide and (+)-brothenolide, were isolated from liverwort Frullania brotheri Steph.The absolute structures of these lactones have been established.
Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome
Chen, Hao,Hu, Wenhui,Ou, Yitao,Sun, Ping,Wu, Dan,Wu, Nannan,Yang, Zhongjin
supporting information, (2020/07/16)
Parthenolide (PTL) can target NLRP3 inflammasome to treat inflammation and its related disease, but its cytotoxicity limits further development as an anti-inflammatory drug. A series of PTL analogs and their Michael-type adducts were designed and synthesi
Easy Access to Alkoxy, Amino, Carbamoyl, Hydroxy, and Thiol Derivatives of Sesquiterpene Lactones and Evaluation of Their Bioactivity on Parasitic Weeds
Cala, Antonio,Zorrilla, Jesús G.,Rial, Carlos,Molinillo, José M. G.,Varela, Rosa M.,Macías, Francisco A.
, p. 10764 - 10773 (2019/10/22)
It has been hypothesized that the α-methylene-?-lactone moiety of sesquiterpene lactones is a key unit for their bioactivity. As a consequence, modifications of these compounds have been focused on this fragment. In the work reported here, two sesquiterpene lactones, namely, dehydrocostuslactone and β-cyclocostunolide, a eudesmanolide obtained by controlled cyclization of costunolide, were chosen for modification by Michael addition at C-13. On applying this reaction to both compounds, it was possible to introduce the functional groups alkoxy, amino, carbamoyl, hydroxy, and thiol to give products in good to high yields, depending on the base and solvent employed. In particular, the introduction of a thiol group at C-13 in both compounds was achieved with outstanding yields (>90%) and this is unprecedented for these sesquiterpene lactones. The bioactivities of the products were evaluated on etiolated wheat coleoptile elongation and germination of seeds of parasitic weeds, with significant activity observed on Orobanche cumana and Phelipanche ramosa. The structure-activity relationships are discussed.
Genepolide, a sesterpene γ-lactone with a novel carbon skeleton from mountain wormwood (Artemisia umbelliformis)
Appendino, Giovanni,Taglialatela-Scafati, Orazio,Romano, Adriana,Pollastro, Federica,Avonto, Cristina,Rubiolo, Patrizia
experimental part, p. 340 - 344 (2009/12/10)
The sesterpene γ-lactone genepolide (5) has been isolated from a Swiss horticultural variety of mountain wormwood (Artemisia umbelliformis) developed as a thujones-free alternative to native Western Alps wormwoods for the production of liqueurs. Genepolid