Chemical Constituents and Biological Activities of Cirsium leucopsis, C. sipyleum, and C. eriophorum

Abstract

Two endemic Cirsium species, C. leucopsis DC. and C. sipyleum O. Schwarz, and C. eriophorum (L.) Scop. growing in Turkey were investigated to establish their secondary metabolites, fatty acid compositions, and antioxidant and anticholinesterase potentials. Spectroscopic methods were used to elucidate the structures of thirteen known compounds (p-hydroxy-benzoic acid, vanillic acid, cisepoxyconiferyl alcohol, syringin, balanophonin, 1′-O-methyl-balanophonin, apigenin, kaempferol-3- O-β-D-glucopyranoside, kaempferol-3-O-α-L-rhamnopyranoside, taraxasterol, taraxasterol acetate, β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside). cis-Epoxyconiferyl alcohol and 1′-O-methylbalanophonin were isolated for the first time from Cirsium species. Palmitic acid (47:1%) was found to be the main fatty acid of C. leucopsis, linoleic acid in both C. sipyleum (42:1%) and C. eriophorum (37:8%). Assays of b-carotene bleaching, scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals, 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium (ABTS) cation radicals, and superoxide anion radicals, as well as cupric reducing antioxidant capacity (CUPRAC) were used to determine the antioxidant activities of the extracts and isolated compounds. Vanillic acid, balanophonin, and kaempferol-3-O-α-L-rhamnopyranoside exhibited strong antioxidant activity. Taraxasterol was a potent inhibitor of acetyl- and butyrylcholinesterase activity, respectively.

Antimicrobial and Antioxidant Efficacy of the Lipophilic Extract of Cirsium vulgare

“…The values are higher than those reported by Karasakal et al, who reported lower CUPRAC values (0.18 mmol/g) after 80% methanol extraction in the C. vulgare varieties [39]. On the contrary, Boga et al reported that acetone and methanol extracts and isolated compounds from two endemic Cirsium species and C. eriophorum grown in Turkey [40] did not show CUPRAC activity. Higher CUPRAC activities in the methanol, ethyl acetate, and diethyl ether extracts compared to those of the hexane extract could be explained by differences in solvent polarity, similar to the results found for the TEAC and FRAP capacities of the previously mentioned extracts.…”

Plant cell culture extract of Cirsium eriophorum with skin pore refiner activity by modulating sebum production and inflammatory response

“…In the present article, we showed that C. eriophorum cell cultures were promising sources of bioactive molecules, including phenols, typically present in plants of the genus Cirsium and the genus Cynara (family of Asteraceae; Boğa et al, 2015; D'Antuono et al, 2018). For this purpose, the phenolic profile and dosage were investigated by using an UHPLC‐Orbitrap platform in MS and MS/MS levels.…”

“…The growing demand for plant‐derived ingredients in cosmetics is indeed driven by a significant reduction of the side effects and the chance to use them in unlimited amounts (Juliano & Magrini, 2018). Plants of the genus Cirsium (family of Asteraceae) have been extensively used in the food and biomedical applications (Das, Behera, & Pramanik, 2017), due to their content of active phytochemicals, such as flavonoid glycosides, phenolic acids, sterols, triterpenes and lignans (Boğa et al, 2015), with known antimicrobial, anti‐inflammatory and antiphlogistic activities (Dini & Laneri, 2019; Inui, Aoshima, Nishiyama, & Itami, 2011; Jeong, Jung, & Choi, 2008). In this study, a new potential dermo‐cosmetic ingredient was obtained by Cirsium eriophorum cell suspension cultures and, after a chemical characterization, it was tested in vitro on skin cell cultures and in vivo on oily and acne‐prone skins.…”

Herbal Therapy for the Treatment of Seborrhea Dermatitis

“…Some of the compounds contained include p-hydroxybenzoic acid, vanillic acid, balanophonin, apigenin, taraxasterol, -Sitosterol, and kaempferol-3-O-β-D-glucopyranosid. 41 Cirsium eriophorum cell culture extract had been investigated for its role in sebum regulation, stratum corneum desquamation, and anti-inflammation. The extract could regulate important markers related to sebum secretion and pore enlargement, such as the enzyme 5α-reductase which plays a role in sebum production, and KLK5 (Kallikrein-related peptidase 5) which plays a role in exfoliation and antimicrobial response.…”