Cynaratriol, a sesquiterpene lactone fromCentaurea musimomum

Abstract

The title compound [systematic name: 3,8-dihydr­oxy-3-(hydroxy­meth­yl)-9-methyl-6-methyl­enedeca­hydro­azuleno[4,5-b]furan-2(3H)-one], C15H22O5, is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the mol­ecular structure, assigned by 1H NMR and MS spectroscopy, as well as the the 11β-hydroxy­methyl, 3β-hydr­oxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O—H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the mol­ecular skeleton.

Guaianolide Sesquiterpene Lactones from Centaurothamnus maximus

“…papposa , C. granata , C. pullata and C. maroccana [ 43 ]. In addition, guaianolides and elemanolides have been isolated from Centaurea, including four guaianolides and cynaratriol from C. musimomum [ 44 ]; centaurpensin and 13-acetyl solstitian A from C. solstitialis [ 45 ]; cebellin M from C. bella [ 46 ]; the elemanolideshierapolitanins A, B, C, and D isolated from C. hierapolitana [ 22 ]; and 13- N -proline melitensin and 13- N -proline-6α, 8α, 15-trihydroxy elema-1,3-diene-oic acid from C. polyclada [ 47 ].…”

Secondary metabolites of three endemic Centaurea L. species

“…Various Centaurea species have certain biological activities, such as antifungal, 4 antimicrobial, 5 anti-ulcerogenic, 6 anti-inflammatory, 7 antioxidant, 8 antiviral, 9 anti-Helicobacter pylori, 10 anticancer and cytotoxic. 11 The genus was also the subject of interest of several phytochemical investigations for their potentially active constituents, particularly sesquiterpene lactones [12][13][14][15][16] and flavonoids. 17,18 As a part of ongoing and systematic investigations on the composition of the plants of this genus, [19][20][21][22][23][24] the chemical constituents of the extracts of the aerial parts of three species: C. tomorosii Micevski, C. soskae Hayek and C. galicicae Micevski, all are endemic to Balkan Peninsula, were investigated.…”

Cytotoxic and antioxidant properties of essential oil of Centaurea behen L. in vitro

“…In addition, it has been stated that Centaurea species exerts a vide range of biological effects including anti-microbial, anti-fungal, antiplasmodial (Karamenderes et al 2006;Kaskoos 2013), anti-ulcerogenic, anti-oxidant, anti-viral, antiprotozoal and anti-cancer properties (Ugur et al 2009a(Ugur et al , b, 2010Erol-Dayi et al 2011;Kilic 2013;Pires Tania et al 2018). Moreover, Centaurea was also a source of some phytochemical studies for its potentially active substance especially flavonoids (Flamini et al 2004;Mishio et al 2006) and sesquiterpene lactones (Gonzalez et al 1984;Medjroubi et al 2005;López-Rodriguez et al 2009). In another study, Escher et al (2018) identified chlorogenic, caffeic, ferulic, and p-coumaric acids, isoquercitrin, and coumarin as major compounds of Centaurea genus also.…”