Coreolanceolins A–E, New Flavanones from the Flowers of Coreopsis lanceolate, and Their Antioxidant and Anti-Inflammatory Effects

Abstract

(1) Background: Many flavonoids derived from natural sources have been reported to exhibit antioxidant and anti-inflammatory effects. Our preliminary study suggested that Coreopsis lanceolata flowers (CLFs) include high flavonoid content; (2) Methods: CLFs were extracted in 80% (v/v) aqueous methanol and fractionated into ethyl acetate, n-butanol, and water fractions. Repeated column chromatographies for the organic fractions led to the isolation of seven flavanones. Quantitative analysis of the flavanones was carried out using reversed-phase high-performance liquid chromatography. All flavanones were evaluated for their antioxidant and pro-inflammatory inhibition effects; (3) Results: Spectroscopic analyses revealed the chemical structure of five new flavanones, coreolanceolins A–E, and two known ones. The content of the seven flavanones in extracts were determined from 0.8 ± 0.1 to 38.8 ± 0.3 mg/g. All flavanones showed radical scavenging activities (respectively 104.3 ± 1.9 to 20.5 ± 0.3 mg vitamin C equivalents (VCE)/100 mg and 1278.6 ± 26.8 to 325.6 ± 0.2 mg VCE/100 mg) in the DPPH and 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays and recovery activities in Caco-2 (59.7 to 41.1%), RAW264.7 (87.8 to 56.0%), and PC-12 (100.5 to 69.9%) cells against reactive oxygen species. Furthermore, all flavanones suppressed nitric oxide production (99.5% to 37.3%) and reduced iNOS and COX-2 expression in lipopolysaccharide-treated RAW 264.7 cells; (4) Conclusions: Five new and two known flavanones were isolated from CLF, and most of them showed high antioxidant and pro-inflammatory inhibition effects.

β-Glucogallin isolated from Fusidium coccineum and its enhancement of skin barrier effects

“…In a gradient-selected heteronuclear multiple bond coherence spectrum, a hemiacetal proton signal (δ H 5.97, H1′) showed a cross-peak with an ester carbon signal (δ C 166.4, C7), suggesting the presence of β-d-glucopyranose at the C7 position. A hemiacetal carbon signal (δ C 91.4, C1′), which is usually observed at δ C 101.8 in β-glucopyranose [12], was shifted upfield due to the ester-glycosylation effect. This evidence indicates that 1 was 1-(3,4,5-trihydroxybenzoate) 7-O-β-d-glucopyranoside, β-glucogallin (Fig.…”

“…Preparation of methanol (MeOH) extract from FC and solvent fractions and ethyl acetate (EtOAc) (SHE, 4.5 g) and normal-butanol (n-BuOH) (SHB, 19.0 g) fractions (Frs) followed procedures described in a previous study [12].…”

Metabolite Profiling and Dipeptidyl Peptidase IV Inhibitory Activity of Coreopsis Cultivars in Different Mutations

“…They are usually cultivated for ornamental purposes in gardens or on roadsides. The plants are in the range of 46–120 cm in height and the petals of the flowers are primarily yellow in color and are serrated [ 5 , 6 ]. The color and size of Coreopsis flowers have commercially important value and are the reason for Coreopsis breeding.…”

Constituents of Coreopsis lanceolata Flower and Their Dipeptidyl Peptidase IV Inhibitory Effects

“…Among them, C. lanceolate are ornamental plants commonly found in Korea in spring and summer. The shape of the yellow petals are split and jagged, and have a diameter 4-6 cm, which is larger than other species [ 5 , 6 ]. In the previous phytochemical studies on C. lanceolata , phenolics, flavonoids (aurones, chalcones, flavaons, flanavol) and acetylene compounds have been isolated from this plant [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ].…”

“…In the previous phytochemical studies on C. lanceolata , phenolics, flavonoids (aurones, chalcones, flavaons, flanavol) and acetylene compounds have been isolated from this plant [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ]. The C. lanceolata flower has been reported to have diverse biological activities, such as anti-cancer [ 5 ], anti-inflammatory [ 6 ], antioxidant [ 6 , 8 , 10 ], anti-allerginc [ 9 , 10 ], antileukemic [ 11 ] and nematicidal [ 12 ] effects. Because of the good efficacy of C. lanceolata , it has been traditionally used as an ingredient in herbal medicine, such as folk remedies to control fever in China and East Asia [ 8 ].…”