A new triterpenic diester from the aerial parts of Chrysanthemum macrocarpum

Abstract

A new triterpenic diester, 3,21-dipalmitoyloxy-16β,21α-dihydroxy-β-amyrine(1), along with two natural cyclitols, conduritol C (2) and viburnitol (3), four known triterpenes (4-7), and seven known flavonoids (8-14) were isolated from the aerial parts of Chrysanthemum macrocarpum. Their structures were established on the basis of extensive 1D and 2D NMR ( 1 H, 13 C, COSY, HMBC, HSQC, and ROESY) and ESIMS studies. The chloroform fraction, taraxasterol (4) and β-sitosterol ( 7) were investigated for their antibacterial activity against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa and Klebsiella pneumoniae. The chloroform fraction and taraxasterol (4) showed a weak antibacterial activity and were evaluated for their cytotoxic activity against human colon cancer HT-29 cells and human prostate carcinoma PC3 cells. The results indicated that both the chloroform fraction and taraxasterol (4) inhibited cell proliferation of both PC3 and HT-29 cells.

Cytotoxic activity and chemical constituents ofAnthemis mirheydari

“…The same research group described the anti-tubercular activity of 1 and 2 against Mycobacterium tuberculosis with the MIC values of 64 and464 mg/mL, respectively (Akihisa et al 2005). As for the anticancer activity of compound 1, it has shown cytotoxicity against PC3 (human prostate cancer) (IC 50 15.8 mg/mL) and HT-29 (human colon cancer) (IC 50 38.3 mg/mL) (Boutaghane et al 2013), and MCF-7 (breast cancer) (IC 50 53.3 mM) cells (Lee et al 2010) in previous studies; however, in another study on KB (human nasopharyngeal carcinoma) and P388 (murine leukaemia) cells, no anticancer effect was observed for this compound (Villarreal et al 1994). Our findings in human leukaemia cells are in agreement with the later report, which has also used leukaemia cells for cytotoxicity assays (Villarreal et al 1994).…”

Identification of Bioactive Compounds in Polar and Nonpolar Extracts of Araujia sericifera

“…In order to unambiguously identify several polar metabolites, an aliquot of the fruit methanolic extract was subjected to a solid-phase extraction (SPE) C 18 cartridge and was eluted firstly with 100 % H 2 O, followed by 100 % MeOH. The methanolic fraction (F-2) was further purified by reversed-phase HPLC to give viburnitol (21, SF meth 2-1) [15], trigonelline (22, SF meth 2-2) [16], and conduritol F (23, SF meth 2-3, also known as L-leuchanthemitol) [17] (▶ Fig. 1).…”

The chemistry and biological activities of natural products from Northern African plant families: from Aloaceae to Cupressaceae

“…It is also used in food avoring and as a herbal tea by the Touaregs. [83][84][85][86] From the aerial parts of this plant were isolated and characterized three new metabolites: a triterpenic diester (100) and two natural cyclitols, conduritol C (101) and viburnitol (102), in addition to four known triterpenes (103-106) and seven known avonoids (107)(108)(109)(110)(111)(112)(113). Compound 100 was identied as 3,21dipalmitoyloxy-16b,21a-dihydroxy-b-amyrine and compounds 101 and 102 were determined to be cyclohex-5-ene 1b,2b,3b,4atetraol (conduritol C) and cyclohexa-1b,2a,3b,4a,5a-pentaol (viburnitol), respectively.…”

“…The compounds are, neopulchellin (114), 6a-hydroxyneopulchellin (115), b-sitosterol-3-O-b-D-glucoside (116), apigenin (117), quercetin (118), eupafolin (119), kaempferol-3-methoxy-7-O-a-L-rhamnoside (120), apigenin-7-O-b-D-glucopyranoside (121), a-amyrin (122) and b-sitosterol (123). 83 The antiproliferative activity of these compounds was evaluated against two human cell lines (breast (MCF7) and colon (HCT116)). Compounds 114 and 115 isolated from the chloroform extract indicated the highest cytotoxicity with IC 50 values of 0.43, 0.32 mg mL À1 against MCF7 and 0.46, 0.34 mg mL À1 against HCT116, respectively.…”