Characteristic α-Acid Derivatives from Humulus lupulus with Antineuroinflammatory Activities

Abstract

Twenty compounds, including 14 new α-acid derivatives, a new chromone, and five known compounds, were identified from the pistillate inflorescence of Humulus lupulus (hops), and their structures were elucidated via physical data analysis. The absolute configurations of new α-acid derivatives 1-11b were determined by comparing their computed and experimental electronic circular dichroism spectra using TDDFT and NMR spectroscopic data. A putative biosynthetic pathway for the identified components was deduced. Their antineuroinflammatory effects were assayed systematically, and their structure-activity relationships are discussed briefly. Among the identified compounds, compound 14 displayed moderate inhibitory effects against nitric oxide production with an IC value of 7.92 μM.

Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes

“…Li et al, 2017c) or xanthohumol and a-acid derivatives such as humulones in Humulus lupulus flowers (J. Li et al, 2017b;. Nevertheless, these compounds might only be slightly different from each other in terms of skeletons as illustrated in the following example: the compounds which structures are shown in Figure 4 were recently isolated from six different species of Euphorbia.…”

Quantitative Analysis of Prenylated Constituents in Commercial Hops Samples Using Ultrahigh-Performance Supercritical Fluid Chromatography

“…▶ Table 3 Percentage of prenylated hops compounds (1)(2)(3)(4)(5) in investigated samples (Prod1-6) (n = 3) determined via quantitation using the PDA signal at 220 nm. The calculated recommended daily intake of reference substances in μg per dietary product (Prod1-4) is given in parentheses.…”

“…Apart from this, a considerable number of pharmacological research studies has been conducted on hop strobile and its constituents regarding estrogenic activities, anticancer properties, and anti-inflammatory effects [3][4][5]. Some of these results have been…”

“…This prompted us to establish the first supercritical fluid chromatography-based protocol for the separation, identification, and quantitation of five prenylated constituents of hops. Hulupinic acid (1), a prominent oxidation product of hop acids, three flavanones, i.e., 8-prenylnaringenin (2), 6prenylnaringenin (3), and isoxanthohumol (4), as well as the chalcone xanthohumol (5) could be baseline separated in less than 5 minutes using a Viridis BEH 2-EP column (3.0 × 100 mm; 1.7 μm particle size) and a mobile phase consisting of CO 2 and isopropanol. Good results regarding selectivity, accuracy (recovery rates: 85.0-113.1 %), precision (intra-day ≤ 2.1 %, inter-day ≤ 3.5 %), and linearity (R 2 ≥ 0.99) were obtained for both photodiode array and mass detection.…”

Natural Inhibitors on Over-Activation of Microglia from Herbals

“…These active ingredients may be promising resources for the development of new antineuroinflammation drugs. [19][20][21][22][23][24][25][26][27][28] A large number of natural products have shown strong anti-neuroinflammatory activities in vitro, and some of them have been demonstrated effective in animal models. For example, we reported that pterostilbene, the major component of Chinese Dragon's Blood, could reduce LPS-induced learning and memory impairment evaluated by Morris water maze and Y-maze tests.…”