Triterpenic and Steroidal Compounds of Cnicus Benedictus

Abstract

Light petrol and chloroform extracts of the herba of C n i c u s b e n e d i c t u s yielded a-amyrenone; a-amyrine acetate; a-amyrine; oleanolic acid; multiflorenol acetat; mtlltiflorenol and sitosteryl-3 B-D-glucoside.Cnicus benedictus is a well known plant for its pharmacological activity. In a study by VANHAELEN and VANHAELEN FASTRE (1975) cynicin, arctigenin, trachelogenin, nortracheloside, 2-acetyl nortracheloside and salonitenolide were isolated from C. &~~~?~~C~U S .~A N H A E L E N FASTRE (1968) showed the antibacterial activity of cynicin. The presence of n-nonacosan, stigmasterol, sitosterol and a-amyrine were shown by KUBALA and LUDWICZAK (196Sa, b).In this study six triterpenic and a steroidal compounds were isolated from the light petrol and chloroform extracts of the herba of Cnicus benedictus, these were identified as a-amyrenone, a-amyrine acetate, a-amyrine, oleanolic acid, multiflorenol acetate, multiflorenol and sitosteryl-3p-D-glucoside by using UV, IR,, NMR and mass spectral methods as well as standard sample comparison. ExperimentalCnicus benedictus (Compositue) was collected from Urla (near Izmir) western p a n of Turkey in October 1974. It was identified by Prof. Dr. N. ZEYBEK (Ege University), a voucher sample is deposited in the herbarium of the University of Ege, Faculty of Sciences. The herba of the plant (2 kg) was extracted with light petrol and chloroform, 32 g and 90 g of the extracts were obtained respectively. Silica gel columns were used in order to fractionate the extracts.In this study melting points were taken in a Reichert-microscope instrument and uncorrected. The following instruments were used for the spectra: A Varian techtron model 635 for UV, Perkin-Elmer 557 for IR, Joel 100 Hz for NMR and LKB 9000 instrument (Sweden) for Mass.

Isolation and Identification of Two Phenolic Compounds from a Moderately Cytotoxic Fraction of Cousinia verbascifolia Bunge

“…[4567] Based on phytochemical studies on a few Cousinia species chemical constituents including acetylenes, triterpenes, steroids, sesquiterpene lactones, and flavonoids were reported. [891011121314151617] However, little information is available about the phytochemical and biological properties of the species grow in Iran. In a phytochemical study on the aerial parts of three Iranian species of the genus Cousinia ( Cousinia picheriana , Cousinia piptocephala , and Cousinia canescens ), all three species yielded guianolide class sesquiterpens including 10 (14), 11 (13)-guiadien, 12, 6-olide, 4 (15), 10 (14)-guiadien, 12, 6-olide, and 4 (15), 10 (14), 11 (13)-guiatrien, 12, 6-olide derivatives mainly differed in functions on C-3, C-4, C-15, and ester located on C-8.…”

Characterization of Secondary Metabolites in Two Cousinia species

“…But, the main compounds in CA were rutin (161.638 µg/mgextract), quinic acid (37.715 µg/mgextract), and isorhamnetin 3-O-rutinoside (37.273 µg/mgextract). To date, sesquiterpene lactones (C. picheriana, C. piptocephala, C. canescens), triterpenes (C. adenostica), steroids (C. canescens) and flavonoids (C. verbascifolia) have been isolated from Cousinia genus [2][3][4][5][6][7][8]24]. In the present study the preliminary qualitative analysis of secondery metobilities in C. iconica and C. aintabensis revealed the presence of carbohydrates, flavonoids, tannins, saponins and steroids which have a wide range of cytotoxic and antitumor effects.…”

Occurrence of triterpenyl acetates in soil and their potential as chemotaxonomical markers of Asteraceae

“…Multiflorenyl acetate was found in Cirsium sp. and Ixeris chinensis (Asteracae; Ulubelen and Berkan, 1977;Shiojima et al, 1994;Kataria, 1995;Jakupovic et al, 2011), as well as in Tabernaemontana longipes (Apocynaceae; Cicció-Alberti and Hoet, 1981), Euphorbia guyoniana (Euphorbiaceae; Haba et al, 2007), Sedum brevifolium and S. meyeri-johannis (Stevens et al, 1994a), and in Polypodium niponicum (Polypodiaceae; Ageta and Arai, 1983). -Amyrin acetate was described in 11 Asteraceae spp.…”

“…X Jordon-Thaden and Louda, 2003 Cirsium arvense X X X X X Dutta and Ray, 1972;Tulloch and Hoffman, 1982;Jakupovic et al, 2011 Hieracium pilosella L. X Jakupovic et al, 2011 Onopordum acanthium X Khalilova et al, 2003Khalilova et al, , 2004Shoeb et al, 2007 Picris echioides X Jakupovic et al, 2011 Picris hieracioides X X X X X X X X X X X Shiojima et al, 1989a;b;1995;Jakupovic et al, 2011 Solidago virga-aurea X Choi et al, 2004 Sonchus oleraceus L. X X X Jakupovic et al, 2011 Taraxacum officinale X Hänsel et al, 1980 Total (a) X X X X X X X X X X X (b) Asteraceae genera Artemisia (2) X X X X X X Lao et al, 1983;1984;Yang et al, 1994;Jakupovic et al, 2011 Cirsium (7) X X X X X X Dutta and Ray, 1972;Ulubelen and Berkan, 1977;Tulloch and Hoffman, 1982;Jakupovic et al, 2011 Inula (1) X X X Ahmad and Ismail, 1991;Jakupovic et al, 2011 Total (a)+(b) X X X X X X X X X X X X X X (c) Other taxa Acer X X van Bergen et al, 1997;Ding et al, 2010 Euphorbia X X X X X X X X Dutta and Ray, 1972;Ahmad and Fizza, 1986;Liu et al, 2001;Shi et al, 2005;Haba et al, 2007 Total (a)+(b)+(c) X X X X X X X X X X X X X X X a (a) Asteraceae species in Lake Aydat catchment; (b) Asteraceae genera in which triterpenyl acetates have been described; b numbers into parentheses refer to number of species of a given genera described in the catchment according to Antonetti et al (2006).…”

“…Because multiflorenyl acetate was described in Cirsium sp. and C. benedictus (Asteraceae; Ulubelen and Berkan, 1977;Kataria, 1995), it is tempting to suppose that one of the Cirsium spp. in the catchment could also produce multiflorenyl acetate.…”