Antioxidative Caffeoylquinic Acids and Flavonoids from Hemerocallis fulva Flowers

Abstract

Tumor necrosis factor-α (TNF-α)-induced reactive oxygen species (ROS) production in HepG2 was used to screen hepatocyte protective compounds from the flowers of Hemerocallis fulva. Three new polyphenols, n-butyl 4-trans-O-caffeoylquinate (1), kaempferol 3-O-{α-L-rhamnopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)]}-β-D-galactopyranoside (2), and chrysoeriol 7-O-[β-D-glucuronopyranosyl(1→2)(2-O-trans-feruloyl)-β-D-glucuronopyranoside (3), together with four caffeoylquinic acid derivatives (4-7), eight known flavones (8-15), one naphthalene glycoside, stelladerol (16), one tryptophan derivative (17), adenosine (18), and guanosine (19) were isolated from the bioactive fractions of the aqueous ethanol extract of H. fulva flowers. The structures of isolated compounds were characterized by means of spectroscopic data. Compounds 1-3 were described as first isolated natural products. Among the above-mentioned compounds, the caffeoylquinic acid derivatives are the major components with potent free radical scavenging activity in HepG2 cells and are for the first time isolated from H. fulva flowers. A convenient ultraperformance liquid chromatography (UPLC) method was also developed to simultaneously separate and identify caffeoylquinic acids and flavonoids promptly.

Dihydrocaffeic acid, a major microbial metabolite of chlorogenic acids, shows similar protective effect than a yerba mate phenolic extract against oxidative stress in HepG2 cells

“…Other authors have reported similar effects of phenolic extracts from plants rich in monocaffeoylquinic acids such as Hemerocallis fulva (Lin, Lu, Huang, & Chen, 2011) and Corema album (León-González et al, 2012), or rich in dicaffeoylquinic acids like Gymnaster koraiensis (Jho et al, 2013) decreasing ROS generation in HepG2 cells, partially preventing the GSH depletion, antioxidant enzyme dysregulation and oxidative damage to macromolecules induced by t-BOOH, in line with the effects elicited by the YMPE.…”

Hyperpigmentation mechanism of methyl 3,5-di-caffeoylquinate through activation of p38 and MITF induction of tyrosinase

“…Derivatives of caffeoylquinic acid have been used to cure various diseases in traditional oriental medicine and exhibit wide ranges of biological activities, such as anti-tumor [13], hepatoprotective [14,15], anti-inflammatory [16], anti-microbial [17], and antimutagenicity activities [18], indicating that theses derivatives may exert beneficial effects against various human diseases. In addition to inhibition of human immunodeficiency virus-1 integrase and its replication [19][20][21], the antioxidant activities of caffeoylquinic acid derivatives [15,22] were also reported.…”

“…In addition to inhibition of human immunodeficiency virus-1 integrase and its replication [19][20][21], the antioxidant activities of caffeoylquinic acid derivatives [15,22] were also reported. However, no previous study has examined the activity of methyl 3,5-di-caffeoylquinate (3,5-diCQM) (Fig.…”

Effects of phenolic constituents of daylily flowers on corticosterone- and glutamate-treated PC12 cells

“…The column temperature was set at 30 °C. A gradient mobile phase system consisting of acetonitrile:H 2 O (3:97 to 20:80 from 0 to 20 min, 20:80 to 80:20 from 20 to 22 min, 80:20 to 3:97 from 22 to 23 min, 3:97 from 23 to 27 min) with 0.1% formic acid as a modifier was used to elute the analytes after 2 μL of sample solution was applied onto the column whereas the detection wavelength was set at 340 nm [12]. The flow rate was 0.2 mL/min and the sample temperature was maintained at 4 °C.…”

“…In our previous in vivo screening study on the active ingredients of daylily flowers, the fraction containing ~60% flavonoids exhibited significant antidepressant-like effects whereas the fraction lack of flavonoids showed no effect in mice model by forced swimming test, tail suspension test and antagonism reserpine experiments [11]. However, daylily flowers contain various types of chemical ingredients including flavonoids, phenolic acids and derivatives, di- and tri-terpenes, essential oils, steroidal saponins, alkaloids, amino acids, polysaccharides and so on [12], the potential neurological effects of other constituents in daylily flowers are largely uninvestigated. Therefore, the objectives of this study were to separate the extracts of daylily flowers into different fractions and to evaluate the neuroprotective effects of each fraction using PC12 cell damage models induced by corticosterone and glutamate with also a view to identifying the active fractions and their potential effect on the neurotransmitter release in the cell culture medium.…”