Itosides J−N from <i>Itoa orientalis</i> and Structure−Anti-COX-2 Activity Relationship of Phenolic Glycosides

Chai, Xing Yun; Song, Yuelin; Xu, Zheng Ren; Shi, Huicheng; Bai, Changcai; Bi, Dan; Wen, Jing; Li, Fei Fei; Tu, Peng

doi:10.1021/np800014s

Cited by 31 publications

(13 citation statements)

References 17 publications

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“…A variety of biological activities of plants have been found to be associated with the presence of phenolic glycosides [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. For example, A. plantanifolium , which contains the glycoside 2-(1-hydroxy-6-oxo-cyclohex-2-ene-1-carboxymethyl)-phenyl-4,6- O -[( S )-4,4’,5,5’,6,6’-hexahydroxydiphenoyl]-β-D-glucopyranose is used for the treatment of rheumatalgia, paralysis and cardianeuria [ 9 ], and is also used to promote the healing of wounds [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Wang

Chiou

et al. 2010

Molecules

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The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl α-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of β-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results.

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Section: Introductionmentioning

confidence: 99%

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Wang

Chiou

et al. 2010

Molecules

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“…Ag NPs were then immobilized onto the P2VP brush layer. As the pyridine groups in P2VP chains have strong affinity toward metal ions, 20 Ag ions were absorbed on P2VP chains by soaking the brush-coated substrate in an AgNO 3 aqueous solution. We Fig.…”

Section: Resultsmentioning

confidence: 99%

Localized surface plasmon-enhanced nanosensor platform using dual-responsive polymer nanocomposites

Choi

Yoo

et al. 2013

Nanoscale

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The fast and accurate identification of unknown liquids is important for the safety and security of human beings. Recently, sensors based on the localized surface plasmon resonance (LSPR) effect demonstrated an outstanding sensitivity in detecting chemical and biological species. In the present study, we suggest that a dual-responsive nanocomposite composed of two polymer brushes and two noble metal nanoparticles provides a significantly improved selectivity (improvement of a factor of 30 in figure-of-merit) for distinguishing diverse liquids compared to a single-responsive LSPR sensor. The dual-responsive LSPR sensor platform was realized by the synergic combinations of two hydrophobic and hydrophilic polymer brushes, which respond differently depending on the degree of interaction between the polymer brushes and the surrounding liquids. Moreover, the mixing ratio of two solvents can also be estimated with high accuracy using the dual-nanocomposite LSPR sensor, suggesting that this approach would be highly practical for in situ process monitoring systems that can instantly detect the change of solvent composition.

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“…Several biological properties have been attributed to this phenolic glycoside: antimalarial activity (Kaou et al, 2010;Sashidhara et al, 2013), antidiabetic potential (Sashidhara et al, 2014), anti-inflammatory activity against COX-2 (Chai et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Bioassay-Guided Isolation of Nigracin, Responsible for the Tissue Repair Properties of Drypetes Klainei Stem Bark

et al. 2020

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Drypetes klainei Pierre ex Pax is used in Cameroon by Baka people in the wound healing process and for the treatment of burns. In a previous paper we demonstrated the ability of both water (WE) and defatted methanol (DME) extracts to accelerate scratch wound closure in fibroblast cultures, thus validating the traditional use of D. klainey stem bark in the treatment of skin lesions. In this work we carried out a bioassay-guided fractionation of the most active DME, which exhibited in vitro efficacy in accelerating wound healing process, in order to isolate and identify the compound/s responsible for the assessed biological activity. HPLC was used for the metabolite profiling of DME and fractions (analytical) and for the isolation of the bioactive compound (semi-preparative). MS analyses and NMR spectroscopy were used for identifying the isolated compound. The abilities of treatments in accelerating wound healing were studied on murine fibroblasts in terms of cell viability and cell migration (scratch wound-healing assay). The results obtained allowed to unambiguously identify the isolated bioactive compound as nigracin, a known phenolic glycoside firstly isolated and characterized from bark and leaves of Populus nigra in 1967. However, this is the first time that nigracin is identified in the Drypetes genus and that a wound healing activity is demonstrated for this molecule. Specifically, we demonstrated that nigracin significantly stimulates fibroblast growth and improves cell motility and wound closure of fibroblast monolayer in a dose-dependent manner, without any toxicity at the concentrations tested, and is still active at very low doses. This makes the molecule particularly attractive as a possible candidate for developing new therapeutic options for wound care.

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Itosides J−N from Itoa orientalis and Structure−Anti-COX-2 Activity Relationship of Phenolic Glycosides

Cited by 31 publications

References 17 publications

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

A Simple Preparation of 2,3,4,6-Tetra-O-acyl-Gluco-, Galacto- and Mannopyranoses and Relevant Theoretical Study

Localized surface plasmon-enhanced nanosensor platform using dual-responsive polymer nanocomposites

Bioassay-Guided Isolation of Nigracin, Responsible for the Tissue Repair Properties of Drypetes Klainei Stem Bark

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