In vitro anti-HIV and -HSV activity and safety of sodium rutin sulfate as a microbicide candidate

Tao, Jian; Hu, Qinxue; Yang, Jing; Li, Rurun; Li, Xiuyi; Lu, Chengping; Chen, Chao-Yin; Wang, Ling; Shattock, Robin J.; Ben, Kunlong

doi:10.1016/j.antiviral.2007.03.008

Cited by 90 publications

(66 citation statements)

References 30 publications

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“…Sulfated flavonoids have been identified as metabolites, and sulfated phenolic small molecules are attracting attention due to their high water solubility, and detoxification and enhanced biological effects (Correia-da-Silva, Sousa, & Pinto, 2014;Tao et al, 2007). Sodium rutin sulfate blocked the entry of HIV-1 into host cells by interacting with the virus envelope glycoprotein and inhibited HSV-1 replication although unsulfated rutin did not have any effect (Tao et al, 2007). Although sulfated flavonoids are not commercially available at this time, it will be necessary to compare the antiviral activity of flavonoids and sulfated flavonoids.…”

Section: Discussionmentioning

confidence: 99%

Comparison of the antiviral activity of flavonoids against murine norovirus and feline calicivirus

Seo

Jeon

et al. 2016

Food Control

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Section: Discussionmentioning

confidence: 99%

Comparison of the antiviral activity of flavonoids against murine norovirus and feline calicivirus

Seo

Jeon

et al. 2016

Food Control

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“…On the other hand, glucosides of eriodictyol and homoeriodictyol from Viscum coloratum have antioxidative activity (Yao et al, 2006). Additionally, it has been reported recently that sulfate-conjugated rutin showed anti-human immunodeficiency virus (HIV) activity (Tao et al, 2007), suggesting that sulfurcontaining modification might also affect anti-disease activities of chalcones and flavanones. Thus, technology to control the accumulation of chalcones and flavanones with various conjugation and modification moieties will be of interest to improve the availability of natural metabolites for human health protection.…”

Section: Discussionmentioning

confidence: 99%

Metabolite Profiling of Chalcones and Flavanones in Tomato Fruit

Iijima

Suda

Suzuki

et al. 2008

J. Japan. Soc. Hort. Sci.

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Tomato (Solanum lycopersicum) is one of a group of plants that accumulate chalcones and flavanones. However, the molecular diversity of chalcones, flavanones, and their conjugate metabolites has not been investigated intensively. Here, we report the profiling of chalcones and flavanones in fruits of the dwarf tomato cultivar MicroTom using liquid chromatography Fourier transform ion cyclotron resonance mass spectrometry (LC-FTICR-MS). We identified eriodictyol chalcone and eriodictyol aglycones, along with naringenin chalcone and naringenin aglycones. To our knowledge, this is the first report that demonstrates the presence of eriodictyol chalcone and eriodictyol in tomato. We detected 26 conjugate metabolites of chalcones and flavanones. Chemical information obtained simultaneously by LC-FTICR-MS, including m/z values, MS/MS spectra, UV absorption spectra, and retention times, facilitated the elucidation of molecular formulas and conjugate structures of the metabolites. Eriodictyol chalcone and eriodictyol conjugates had the same modification patterns seen in naringenin chalcone and naringenin conjugates. Chalcones and flavanones were much more abundant in tomato fruit peel than flesh. Accumulation profiles during ripening were classified into three groups. The first group included metabolites that showed the highest accumulation levels at the breaker stage, and then decreased during ripening. The second group included metabolites that accumulated to the highest levels at the turning stage, and then decreased at the red stage. The third group included metabolites that accumulated gradually during ripening, and showed the highest accumulation levels at the red stage. These accumulation profiles were mapped onto a putative modification pathway deduced from conjugate structures. Mapping revealed that the conjugate metabolites upstream of this pathway accumulated earlier, and those downstream accumulated later during ripening. This result demonstrated that chalcones and flavanones undergo sequential modification as ripening progresses.

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“…13 C NMR spectra of 40 mg/ml solution in D 2 O was recorded at 40°C with a Bruker Avance 600 MHz spectrometer (Germany), and the chemical shifts were expressed in ppm relative to the resonance of internal standard 2,2-dimethyl-2-silapentane-5-sulfonate (DSS).…”

Section: Characterization Of Sulfated Pop1mentioning

confidence: 99%

“…They were a kind of polysaccharides with sulfated groups replacing their hydroxyl groups, including natural sulfated polysaccharides extracted from plants or derivatives synthesized from natural polysaccharides [12,13]. Sulfated polysaccharides could not only enhance the water solubility but also change the chain conformation, resulting in the alteration of their biological activities [2,10,11].…”

Section: Introductionmentioning

confidence: 99%

Sulfated modification and cytotoxicity of Portulaca oleracea L. polysaccharides

Chen

Jin

et al. 2010

Glycoconj J

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A water-soluble polysaccharide (POP1) was isolated from Portulaca oleracea L. Four sulfated derivatives of POP1 (POP1-s1, POP1-s2, POP1-s3 and POP1-s4) were prepared by chlorosulfonic acid method with N,N-Dicyclohexylcarbodiimide (DCC) as a dehydration-condensation agent. FT-IR spectra and 13C NMR spectra indicated the sulfated groups had been introduced at the C-6 and C-2 positions of POP1. Sulfated derivatives had different degree of substitution (DS) ranging from 1.01 to 1.81, and different weight-average molecular mass (Mw) ranging from 41.4 to 48.5 KDa. Sulfated derivatives except POP1-s5 inhibited the growth of HepG2 cells and Hela cells in vitro significantly, which indicated that sulfated modification could enhance cytotoxicity of POP1 on tumor cells. Flow cytometric studies revealed that sulfated derivatives could mediate the cell-cycle arrest of Hela cells in the S phase.

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In vitro anti-HIV and -HSV activity and safety of sodium rutin sulfate as a microbicide candidate

Cited by 90 publications

References 30 publications

Comparison of the antiviral activity of flavonoids against murine norovirus and feline calicivirus

Comparison of the antiviral activity of flavonoids against murine norovirus and feline calicivirus

Metabolite Profiling of Chalcones and Flavanones in Tomato Fruit

Sulfated modification and cytotoxicity of Portulaca oleracea L. polysaccharides

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