Isolation and structure determination of a lignan from the bark of<b><i>Salix alba</i></b>

Du, Qizhen; Jerz, Gerold; Shen, Lianqing; Xiu, Lili; Winterhalter, Peter

doi:10.1080/14786410601083845

Cited by 17 publications

(17 citation statements)

References 10 publications

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“…The 13 C-NMR spectrum ( Table 1 ), coupled with HSQC analysis, exhibited the signals of twenty-two carbons in total, comprising three methyls, two oxymethylenes [δ C 64.3 (C-9′) and 66.7 (C-9)], nine methines (including five aromatic methanes), and eight quaternary carbons [including a carboxyl group at δ C 172.7 and seven aromatic quaternary carbons]. Detailed analysis of the NMR data indicated that compound 2 closely resembled threo -dihydroxydehydrodiconiferyl alcohol [ 20 , 21 , 22 ], with the only difference of the hydroxyl group at C-9 being replaced by an acetoxy group in 2 . This deduction was consistent with the molecular formula and in accord with the significant HMBC correlations ( Figure 2 ) from δ H 4.33 and 4.44 (C-9) to δ C 172.7.…”

Section: Resultsmentioning

confidence: 99%

Phenolics from Mikania micrantha and Their Antioxidant Activity

et al. 2017

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A phytochemical study on the aerial parts of Mikania micrantha led to the isolation of two new phenolic compounds, benzyl 5-O-β-d-glucopyranosyl-2,5-dihydroxybenzoate (1) and (7S,8R)-threo-dihydroxydehydrodiconiferyl alcohol 9-acetate (2), together with twelve known compounds, benzyl 2-O-β-d-glucopyranosyl-2,6-dihydroxybenzoate (3), 4-allyl-2,6-dimethoxyphenol glucoside (4), (+)-isolariciresinol (5), icariol A2 (6), 9,10-dihydroxythymol (7), 8,9,10-trihydroxythymol (8), caffeic acid (9), p-coumaric acid (10), ethyl protocatechuate (11), procatechuic aldehyde (12), 4-hydroxybenzoic acid (13), and hydroquinone (14). Their structures were elucidated on the basis of extensive spectroscopic analysis. Except 8 and 9, all the other compounds were isolated from this plant species for the first time. The antioxidant activity of those isolated compounds were evaluated using three different assays. Compounds 1, 2, 3, 9, 10, 13, and 14 demonstrated significant 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from SC50 0.31 to 4.86 µM, which were more potent than l-ascorbic acid (SC50 = 10.48 µM). Compounds 5, 9, 11, and 12 exhibited more potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (SC50 = 16.24–21.67 µM) than l-ascorbic acid (39.48 µM). Moreover, the ferric reducing antioxidant power (FRAP) of compounds 2, 5, 9, and 11 were discovered to be also comparable to or even more potent than l-ascorbic acid.

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Section: Resultsmentioning

confidence: 99%

Phenolics from Mikania micrantha and Their Antioxidant Activity

et al. 2017

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“…Metabolomics for the study of willow is still in its infancy with a handful of studies focusing on the phytochemical properties of willow bark and leaves (Du et al, 2007 ; Förster et al, 2010 ; Agnolet et al, 2012 ), the inhibitory compounds in lignocellulosic willow wood chips hydrolysates (Zha et al, 2014 ), and the chemical composition of the cuticular wax in relation to biomass productivity (Teece et al, 2008 ). These studies report on the accumulation of primary and secondary metabolites in the aerial parts of AMF willows.…”

Section: Introductionmentioning

confidence: 99%

Metabolic responses of willow (Salix purpurea L.) leaves to mycorrhization as revealed by mass spectrometry and 1H NMR spectroscopy metabolite profiling

Chamoun

Jabaji

2015

Front. Plant Sci.

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The root system of most terrestrial plants form symbiotic interfaces with arbuscular mycorrhizal fungi (AMF), which are important for nutrient cycling and ecosystem sustainability. The elucidation of the undergoing changes in plants' metabolism during symbiosis is essential for understanding nutrient acquisition and for alleviation of soil stresses caused by environmental cues. Within this context, we have undertaken the task of recording the fluctuation of willow (Salix purpurea L.) leaf metabolome in response to AMF inoculation. The development of an advanced metabolomics/bioinformatics protocol employing mass spectrometry (MS) and 1H NMR analyzers combined with the in-house-built metabolite library for willow (http://willowmetabolib.research.mcgill.ca/index.html) are key components of the research. Analyses revealed that AMF inoculation of willow causes up-regulation of various biosynthetic pathways, among others, those of flavonoid, isoflavonoid, phenylpropanoid, and the chlorophyll and porphyrin pathways, which have well-established roles in plant physiology and are related to resistance against environmental stresses. The recorded fluctuation in the willow leaf metabolism is very likely to provide AMF-inoculated willows with a significant advantage compared to non-inoculated ones when they are exposed to stresses such as, high levels of soil pollutants. The discovered biomarkers of willow response to AMF inoculation and corresponding pathways could be exploited in biomarker-assisted selection of willow cultivars with superior phytoremediation capacity or genetic engineering programs.

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“…Salix species have been used to treat pain, inflammation, and fever since ancient times (Du et al, 2007;Freischmidt et al, 2012). Moreover, Salix species also have anti-oxidant (Alam et al, 2006), anti-inflammatory (Li et al, 2008), antiobesity (Han et al, 2003), and anti-tumor (Sultana et al, 2004) effects.…”

Section: Introductionmentioning

confidence: 99%

Anti-oxidant and anti-inflammatory effects of Salix Koreensis Andersson in DC. leaf methanol extract in vitro models

Kim¹,

Kim²

2016

TANG [HUMANITAS MEDICINE]

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Oxidative rancidity in foods causes undesirable changes in nutritive value, aroma, flavor, and color. Salix Koreensis Andersson in DC. (SK) has anti-oxidative and anti-inflammatory effects and is traditionally used to treat neuralgia, edema, pain, and inflammatory diseases. However, the regulatory effects of SK on oxidative and inflammatory reactions have not been elucidated. In this context, we scientifically validated the anti-oxidative and anti-inflammatory activities of SK leaf (SKL). The methanol extract of SKL was evaluated for in vitro anti-oxidative activities. SKL showed increased superoxide dismutase (SOD)-like activity and 1, 1-diphenyl-2-picrylhydrazyl radical scavenging activity. The in vitro anti-oxidant and antiinflammatory activities of SKL were also investigated in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. LPS resulted in decreased SOD activities compared with the unstimulated cells, but SKL significantly increased SOD activities reduced by LPS. In addition, LPS-induced nitric oxide, tumor necrosis factor-α, and interleukin-6 productions were significantly and dose-dependently reduced by SKL in RAW264.7 macrophages without inducing cytotoxicity. In conclusion, these results indicate that SKL will be able to be effectively used as a food additive with anti-oxidative and anti-inflammatory effects.

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Isolation and structure determination of a lignan from the bark ofSalix alba

Abstract: A lignan, sisymbrifolin (1) found in the fruits of Solanum sisymbriflolium has been isolated from the bark extract of Salix alba (Salicaceae). Its structure was elucidated by its direct spectrum data of ESI-MS and one- and two-dimensional NMR spectroscopy for the first time.

Cited by 17 publications

References 10 publications

Phenolics from Mikania micrantha and Their Antioxidant Activity

Phenolics from Mikania micrantha and Their Antioxidant Activity

Metabolic responses of willow (Salix purpurea L.) leaves to mycorrhization as revealed by mass spectrometry and 1H NMR spectroscopy metabolite profiling

Anti-oxidant and anti-inflammatory effects of Salix Koreensis Andersson in DC. leaf methanol extract in vitro models

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