Cytotoxic guaianolide from Anthemis segetalis (Asteraceae)

Abstract

Two epimeric guaianolides were isolated from the aerial parts of Anthemis segetalis. These compounds have not been detected in any Anthemis species so far. One of them was tested for cytotoxicity against human cervical cancer (HeLa) and murine melanoma (B16) cell lines showing appreciable activity.

Phytochemical investigation of Pimpinella serbica

“…These data were compatible with the structures of apiole and dillapiole, which were identified as major components in previous investigations of the essential oils of the plant. 7,8 By comparing the 1 H NMR spectrum of compound 1 to the spectrum of apiole isolated in our study of the Malabaila aurea essential oils, 9 The molecular formula of compound 2 can be deduced as C13H16O5, based on [M+H + ] ion at m/z 253.1082. Its 1 H and 13 C spectra (Figures S11-12) were similar to those of 1, except that in spectra of compound 3 there are three signals corresponding to methoxy groups, and aromatic proton at C-6 is missing.…”

“…Nothoapiole (1-allyl-2,3,6-trimethoxy-4,5-(methylenedioxy)bezene) (2): 1 H NMR and 13 C NMR data in Table I 19) 225 ( 9) 221 ( 6) 207 ( 22) 191 ( 6) 179 ( 14) 164 ( 5) 151 ( 10) 121 ( 5) 77 (9) Falcarindiol ((3R,8S,Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol) (3): [α] 20 ; D = +228° (c 0.2, CH2Cl2). 1 H NMR and 13 C NMR data in Table II…”

Natural sesquiterpenoids

“…Known guaianolides have been isolated from Anthemis segetalis, 373 Lactuca aculeata 233,374 and Lactuca altaica. 375 A biomimetic total synthesis of (+)-ainsliadimer A has been accomplished, 376 whilst a synthesis of the guaianolide ring system has been achieved, starting from (R)-(À)-carvone.…”

Molecular authentication of Anthemis deserti Boiss. (Asteraceae) based on ITS2 region of nrDNA gene sequence

“…The genus Anthemis (family: Asteraceae) includes approximately 210 species (Bremer and Humphries, 1993) distributed in Europe, south west Asia, and north and north east Africa, is medicinally important genus as evident from the several pharmacological studies (Quarenghi et al, 2000, Stamatis et al, 2003, Uzel et al, 2004, Akgul and Saglikoglu, 2005, Buruk et al, 2006, Magro et al, 2006, Karioti et al, 2007, Karioti et al, 2008, Karioti et al, 2009, Papaioannou et al, 2007, Réthy et al, 2007, Collu et al, 2008, Di Giorgio et al, 2008, Hajdú et al, 2010, Vucković et al, 2010, Seol et al, 2010, Kilic et al, 2011, Conforti et al, 2012, Formisano et al, 2012, Samadi et al, 2012). In Saudi Arabia, the genus Anthemis is represented by 17 species viz., Anthemis arvensis L., A. bornmuelleri Stoj.…”

“…The essential oils of water-distilled vegetative parts of A. pseudocotula possess medicinally important molecules such as 1,8-cineole, camphor, artemisiaketone, filifolene (Kilic et al, 2011). A. arvensis and A. cotula possess pharmacologically important linear sesquiterpene lactones (Vucković et al, 2010).…”