The Inhibition of Superoxide Anion Generation by Neutrophils from Viscum articulactum

Leu, Yann‐Lii; Kuo, Shih-Ming; Hwang, Tsong‐Long; Chiu, Sherry Yueh‐Hsia

doi:10.1248/cpb.52.858

Cited by 33 publications

(30 citation statements)

References 20 publications

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“…These data showed that compound 1 had the 1,3-diphenylpropane skeleton. In addition, d C 154.7 (C-6Ј), 151.7 (C-2Ј), 133.9 (C-3Ј), 146.6 (C-3Љ) and methoxyl protons d H 3.74, 3.82, 3.85, 3.88 also showed 3 J correlations, respectively. Above these data, the nucleus of compound 1 could be determined.…”

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confidence: 93%

“…The known compounds, (2S)-5,7,3Ј,4Ј-tetrahydroxyfla- 3) 5,7-dihydroxychromone (14), 10) 5-hydroxychromone-7-O-glucoside (15), 10) methyl-3-O-feruloylquinate (16), 11) 4-O-cinnamoylquinic acid (17), 3) oleanolic acid (18), 3) betulinic acid (19), 12) b-amyrin acetate (20), 3) lupeol (21), 13) b-sitostenone (22), 14) stigmasterol (23)ϩb-sitosterol (24) mixtures, 15) 15) cinnamic acid (27), 16) coumaric acid (28), 15) ferulic acid (29), 15) caffeic acid (30), 15) 4-hydroxybenzaldehyde (31), 3) 4-hydroxybenzoic acid (32), 3) vanillin (33), 3) vanillic acid (34), 17) protocatechuic acid (35), 3) syringaldehyde (36), 17) acetovanillone (37), 18) 2,6-dimethoxy-p-benzoquinone (38), 19) 2-deoxyepi-inositol (39), 3) thymine (40) 20) and uracil (41) 21) were also isolated and identified by comparison of their spectral data with corresponding literature values.…”

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confidence: 99%

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

et al. 2006

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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...

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

et al. 2006

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“…The methanolic extract of V. cinerea is known to possess triterpenes 33 , sesquiterpenes 34 , flavonoids, and phenylpropanoids 14 . Immunological activities of terpenes and flavonoids found in several plants have been reported [35][36][37] . Some sesquiterpenes, especially sesquiterpenes lactones, show a wide range of biological activities, such as anti-bacterial, anti-tumour, anti-virus, cytotoxic, and immune inhibition 32 .…”

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confidence: 99%

Anti-inflammatory activity of a Vernonia cinerea methanolic extract in vitro

Saraphanchotiwitthaya¹,

Sripalakit²

2015

ScienceAsia

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Vernonia cinerea Less. (Asteraceae) is a herbaceous plant commonly found in SE Asia. Different parts of V. cinerea have been used in various folklore medicine applications, including reducing inflammation and detoxification. This study investigates the effects of V. cinerea methanolic extract on the mouse immune system in vitro. Cytokine detection of ConA-stimulated splenocytes using ELISA, mitogen-induced splenocyte proliferation, and phagocytic activity were assayed. The results show that the extract shifted the Th1/Th2 balance towards a Th2 type response. Additionally, Th1-and Th2-related cytokine production correlated with lymphocyte proliferation by selective activation of T-cells into Th2-cells and suppression of Th1-cell proliferation. Our results confirmed the traditional applications of V. cinerea on immune-related remedies and anti-inflammation, suggesting a potential therapeutic application of this plant in the treatment of diseases associated with Th1-related cytokine production and inflammation.

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“…Its UV absorption bands at 330 (sh) and 284 nm indicated the presence of a flavanone skeleton. 20 Its IR absorptions at 3424 and 1648 cm −1 inferred the hydroxyl and carbonyl groups, respectively. The 1 H NMR spectrum of 1 (Table 1) showed the presence of three mutually coupled protons at δ C NMR spectra (Table 1) also showed 1 to be a flavanone diglycoside possessing a furanosyl and a pyranosyl moiety.…”

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confidence: 99%

“…The glucose moiety was determined to have a β-configuration at H-1'' due to a large coupling constant for the anomeric proton of the sugar unit at δ H 5.62 (1H, d, J = 7.5 Hz), 20 and the apiose unit was also determined to have a β-configuration at C-1''' due to the chemical shift of its anomeric carbon signal in the 13 C NMR at δ C 110.9. 21,22 Comparison of the 13 C NMR spectra of 1 with those of (2S)-pinocembrin 7-O-[β-D-apiosyl(1→2)]-β-Dglucoside revealed they were very similar, except for the glucose C-6'' signal in 1 was downfield from δ C 61.0 to 68.5, suggesting that the interglycosyl linkage is apiosyl-(1→6)-glucose, 20,23 which was confirmed by the presence of the HMBC correlation between H-1''' and C-6'' ( Figure 2). The glycosidation position was further determined by the presence of the three-bond HMBC correlation between the glucosyl anomeric proton H-1'' and C-7 of ring A.…”

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confidence: 99%