The Inhibition of Superoxide Anion Generation in Human Neutrophils by Viscum coloratum

Abstract

In clinical use, Taxillus genus plants could be placed by Viscum genus plants. But, they belong to different genera of Loranthaceae. The genus of Viscum, the plants of Loranthaceae family, are photosynthetic shrubby, hemiparasites on the tree branches. Viscum coloratum has commonly been used for Chinese medicine as a curative for a number of ailments such as hemorrhage, pleurisy, gout, heart disease, epilepsy, arthritis and hypertension.1,2) In our research, we found oleanolic acid showed significantly anti-inflammatory activitiy in V. articulatum.3) Oleanolic acid concentration-dependently inhibited superoxide anion generation by human neutrophils in response to fMLP (formyl-L-methionyl-Lleucyl-L-phenylalanine), but not to PMA (phorbol myristate acetate). It suggested that the inhibitory effect of oleanolic acid was through protein kinase C-independent pathway.In a previous screening for the inhibitory activities on superoxide anion generation in fMLP-stimulated human neutrophils by Viscum and Taxillus medicinal plants, V. coloratum also exhibited the strong inhibition. From V. coloratum, two new and thirty-nine known compounds were isolated and characterized. This paper deals with the structural determination of two new compounds, viscolin (4Ј,4Љ-dihydroxy-2Ј,3Ј,6Ј,3Љ-tetramethoxy-1,3-diphenylpropane) (1) and (2S)-7,4Ј-dihydroxy-5,3Ј-dimethoxyflavanone (2) by spectral analysis. The inhibitory activities of crude extract and pure compounds on neutrophils stimulated by fMLP/CB were also tested. Results and DiscussionThe crude extract and partitioned layers were examined for their anti-inflammatory effect using neutrophils. The chloroform soluble layer revealed significantly anti-inflammatory activities and the butanol soluble layer demonstrated slight functions in the results (Table 1). The resultant chloroform and butanol fractions were repeatedly subjected to silica gel and reverse phase column chromatographies and yielded two new compounds, viscolin (1) and (2S)-7,4Ј-dihydroxy-5,3Ј-dimethoxyflavanone (2).Viscolin (1) was a pale yellow needles, and its chemical formula, C 19 H 24 O 6 , was gained by HR-EI-MS (high resolution electron impact mass). UV spectrum of viscolin (1) revealed the maximum absorption at 282 and 229 (sh) nm and the absorption band at 3393 cm Ϫ1 showed hydroxyl group in its IR spectrum.In the 1 H-NMR spectrum (Table 2) of viscolin (1), four methoxyl signals appeared at d 3.88, 3.85, 3.82 and 3.74, respectively. In the aromatic region, an ABX splitting pattern and one singlet signals showed at d 6.83, 6.72, 6.70 and 6.31 indicated a tri-substituted and a penta-substituted phenyl moieties in 1. In addition, there were three mutual coupled methylene signals showed at d 2.62, 2.60 and 1.79 confirmed One new 1,3-diphenylpropane, viscolin (1), and one new flavanone, (2S)-7,4-dihydroxy-5,3-dimethoxyflavanone (2), together with thirty-nine known compounds, which included eleven known flavanones, two chromones, fourteen benzenoids, one inositol, two pyrimidines, four triterpenoids and five steroids...

Development of a sensitive ultra high performance liquid chromatography with tandem mass spectrometry method for the simultaneous quantification of nine active compounds in rat plasma and its application to a pharmacokinetic study after administration of

“…Viscum coloratum, also known as Hujisheng, is a well-known herb commonly used as a traditional Chinese medicine (TCM) to prevent and treat hemorrhage, heart disease, epilepsy, arthritis, cancer, and hypertension [1][2][3][4]. Currently, preparations of its extract are used worldwide to treat several diseases, such as diabetes, hypertension, and cancer [5][6][7][8][9].…”

“…Based on phytochemical analysis, V. coloratum has been shown to contain flavonoids, lectins, alkaloids, sterols, and triterpenes [12][13][14]. Its flavonoids, serving as quantitative markers, have been reported to have antitumor and anti-inflammatory activities [15][16][17].…”

A Diversity‐Oriented Approach to Diphenylalkanes by Strategic Utilization of [2+2+2] Cyclotrimerization, Cross‐Enyne Metathesis and Diels–Alder Reaction

“…For example, viscolin 1 ( Figure 1) is a naturally occurring 1,3-diphenylpropane, isolated from the Viscum coloratum, [1] a hemiparasite herb used in Chinese medicine as a curative for a number of ailments such as hemorrhage, pleurisy, gout, heart disease, epilepsy, arthritis, and hypertension.…”

An Efficient Synthesis of a Potent Anti-inflammatory Agent, Viscolin, and Its Inducible Nitric Oxide Synthase Inhibitory Activity

“…Viscolin was identified from Viscum coloratum (Loranthaceae), 1) which was usually used as folk medicines for the treatment of a number of ailments such as hemorrhage, gout, heart disease, epilepsy, arthritis and hypertension. 2,3) The anti-inflammatory potentials of viscolin 1 had been reported to display significant inhibition of superoxide anion generation (O 2 ·− ) and elastase release induced with N-formyl-methionyl-leucephenyl alanine combined with cytochalasin B (fMLP/CB) in human neutrophils with IC 50 values of 0.58±0.03 and 4.93±0.54 μg/ mL, respectively.…”