89647-87-0Relevant articles and documents
Cynaropicrin and inhibition of NF-κB activation: A structure activity relationship study
Li, Jing,Yoshida, Yusuke,Kurita, Manami,Usuki, Toyonobu
, p. 1518 - 1521 (2019/04/25)
Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. This natural product has various biological activities including anti-inflammatory properties and antitrypanosomal activity. It was also found to suppress photoaging of the skin by inhibiting the transcription activity of nuclear factor-kappa B (NF-κB). In this paper, nine chemical derivatives of cynaropicrin were prepared, and the structure activity relationship (SAR) study for NF-κB inhibition by measuring relative light units (RLU) was conducted.
Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives
Usuki, Toyonobu,Sato, Makiko,Hara, Shihori,Yoshimoto, Yukiko,Kondo, Ryosuke,Zimmermann, Stefanie,Kaiser, Marcel,Brun, Reto,Hamburger, Matthias,Adams, Michael
, p. 794 - 798 (2014/02/14)
Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). In this Letter, chemical derivatization of cynaropicrin and the structure-activity-relationship (SAR) study against T. brucei is described.
11,16 Oxetane lactones. Spectroscopic evidences and conformational analysis
Macías, Francisco A.,Vi?olo, Victor M.I.,Fronczek, Frank R.,Massanet, Guillermo M.,Molinillo, José M.G.
, p. 7747 - 7755 (2007/10/03)
Sesquiterpene lactones constitute a wide group of compounds with several biological activities, including allelopathic. The naturally occurring sesquiterpene lactones dehydrocostuslactone and cynaropicrin have been modified in three different ways: preparation of 11,13-oxetane lactones, addition of a second Michael acceptor and reduction of the α-methylene-γ-lactone in order to future structure-activity relationship (SAR) studies. We have obtained all oxetane lactones stereoisomers at C-11 and C-16 positions. This fact has allowed us to establish some correlations between experimental data, derived by NMR and X-ray analysis, and the configuration at C-11 and C-16, which could be a useful tool to establish the stereochemistry as well as to confirm the presence of an oxetane ring on similar compounds. Comparative conformational analyses as a key aspect in the biological behaviour of those compounds in future structure-activity relationship (SAR) studies are presented.
Studies on Sesquiterpene Glycosides from Crepis japonica BENTH.
Miyase, Toshio,Ueno, Akira,Noro, Tadataka,Kuroyanagi, Masanori,Fukushima, Seigo
, p. 4451 - 4456 (2007/10/02)
Nine new guaianolide-type glycosides, crepisides A(II), B(III), C(IV), D(V), E(VI), F(VII), G(VIII), H(IX) anf I(X), have been isolated from Crepis japonica BENTH., together with a known glycoside, glucozaluzanin C(I).The structures of II-X were established on the basis of chemical and spectral data.Keywords - Crepis japonica; Compositae; sesquiterpene glycoside; guaianolide; crepiside
SESQUITERPENE LACTONE GLYCOSIDES FROM CREPIS CAPILLARIS
Kisiel, Wanda
, p. 1955 - 1958 (2007/10/02)
Four new sesquiterpene lactone glucosides, in addition to known compounds, have been isolated from the roots of Crepis capillaris and their stuctures elucidated on the basis of spectral analysis and hydrolytic studies.Key Word Index-Crepis capillaris; Compositae; sesquiterpene lactone glycosides; guaianolides.
GUAIANOLIDES FROM TRICHOLEPIS GLABERRIMA
Singhal, Ashok Kumar,Chowdhury, Pritish Kumar,Sharma, Ram Prakash,Baruah, Jogendra Nath,Herz, Werner
, p. 462 - 463 (2007/10/02)
Cynaropicrin and 11,13-dihydrodesacylcynaropicrin were isolated from Tricholepis glaberrima. - Key Word Index - Tricholepis glaberrima; Compositae; sesquiterpene lactones; guaianolides.
