Main Structural and Stereochemical Aspects of the Antiherpetic Activity of Nonahydroxyterphenoyl‐Containing <i>C</i>‐Glycosidic Ellagitannins

Quideau, Stéphane; Varadinova, T.; Karagiozova, Diana; Jourdes, Michaël; Pardon, Patrick; Baudry, Christian; Genova, Petia; Diakov, Theodore; Petrova, Rozalina

doi:10.1002/cbdv.200490021

Cited by 72 publications

(52 citation statements)

References 53 publications

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“…The 1 H-NMR spectroscopic data of the crude extract of S. cymosum showed signals characteristic of phenolic compounds as the major constituents. Phenolic compounds have received considerable attention because of their therapeutic effects and their favorable antiviral activity (Quideau et al, 2004;Likhitwitayawuid, 2005;Tareq et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Soares¹,

Robaina²,

Mendes³

et al. 2012

Rev. bras. farmacogn.

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Organic extracts of 36 species of marine algae (sixteen species of Rhodophyta, eight species of Ochrophyta and twelve species of Chlorophyta) from seven locations on the Brazilian coast were evaluated for their anti-HSV-1 and anti-HSV-2 activity resistant to Acyclovir (ACV). Activity tests in crude extracts, followed by the identification of the major compounds present, were performed for all species. The chemical profiles of all crude extracts were obtained by 1 H-NMR and 13 C-NMR spectroscopy. The percentage of extracts with antiviral activity was higher for HSV-1 (86.1%) than for HSV-2 (55.5%). The green algae Ulva fasciata and Codium decorticatum both showed the highest activity (99.9%) against HSV-1, with triacylglycerols and fatty acids as the major components. The red alga Laurencia dendroidea showed good activity against HSV-1 (97.5%) and the halogenated sesquiterpenes obtusol and (-)-elatol were identified as the major components in the extract. Against HSV-2, the green alga Penicillus capitatus (Chlorophyta) and Stypopodium zonale (Ochrophyta) were the most active (96.0 and 95.8%). Atomaric acid, a meroditerpene, was identified as the major secondary metabolite in the S. zonale extract. These results reinforce the role of seaweeds as important sources of compounds with the potential to enter into the pipeline for development of new drugs against herpes simplex.

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Section: Discussionmentioning

confidence: 99%

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Soares¹,

Robaina²,

Mendes³

et al. 2012

Rev. bras. farmacogn.

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“…1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), a naturally occurring polyphenolic compound abundant in several medicinal plants, was found to exhibit anti-influenza virus activity at non-cytotoxic concentrations. A number of in vitro and in vivo studies have previously shown that PGG exhibits a wide range of biological activities [41], including anti-inflammatory [16], antioxidant [29], anti-angiogenic [25], antitumor [14], antibacterial activity [40], and a broad range of antiviral activity against respiratory syncytial virus (RSV) [39], Hepatitis B virus (HBV) [18] and Herpes simplex virus (HSV) [27][28]31]. Moreover, it has been shown to have an inhibitory effect on viral enzymes such as integrase and reverse transcriptase of human immunodeficiency virus (HIV-1) [1], and NS3 protease of Hepatitis C Virus (HCV) [9].…”

Section: Introductionmentioning

confidence: 99%

Antiviral activity and possible mechanisms of action of pentagalloylglucose (PGG) against influenza A virus

et al. 2011

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Influenza A virus (IAV) infection is a major public health threat leading to significant morbidity and mortality. The emergence of drug-resistant virus strains highlights urgent needs to develop novel antiviral drugs with alternative modes of action. Pentagalloyl glucose (PGG), a natural occuring polyphenolic compound, possesses broad spectrum of biological activities. In this study, we found PGG has anti-influenza virus activity and investigated its possible mechanism(s) of action in vitro.

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“…Therefore, these two compounds are the likely main polyphenolic constituents in the seed of camu-camu fruit. Vescalagin and castalagin have been isolated from several plants belonging to Fagaceae, Combretaceae, Lythraceae and Myrtaceae (Quideau et al, 2004). Camu-camu belongs to the family Myrtaceae; however, this is the first report of the presence of vescalagin and castalagin in camu-camu.…”

Section: Resultsmentioning

confidence: 92%

Antioxidative Constituents in Camu-camu Fruit Juice Residue

Kaneshima¹,

Myoda²,

Toeda³

et al. 2013

FSTR

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Camu-camu (Myrciaria dubia, Myrtaceae) is a tropical fruit, and is known to be rich in vitamin C. The fruit is mainly used in juice or vinegar production, and large amounts of byproduct, composed of seed and peel, is generated as agricultural and industrial waste. Our studies on camu-camu seed and peel revealed that the seed contains large amounts of polyphenols (400 mg/g). Further studies on the seed resulted in the isolation of vescalagin and castalagin, C-glycosidic ellagitannins with a hexahydroxydiphenoyl group and a nonahydroxyterphenoyl group attached to the open chain d-glucose, as the main polyphenolic constituents. The structures of these tannins were characterized by their 1 H-and 13 C-NMR spectra and mass spectrum. The two C-glycosidic ellagitannins represent about 15% of the polyphenolics in the seed of camu-camu fruit, and are likely responsible for the anti-oxidative activity of the seed extract's anti-oxidative activity.Keywords: camu-camu, Myrciaria dubia, seed, polyphenol, vescalagin, castalagin, NMR *To whom correspondence should be addressed. E-mail: t1myouda@bioindustry.nodai.ac.jp IntroductionTropical fruits have been attracting attention from the food industry because of their unique appearance, flavor and nutritional value. Camu-camu (Myrciaria dubia, Myrtaceae) is a tropical fruit, and has recently been used for processed food in advanced countries. Camu-camu is a bushy tree native to the Amazon rainforest, mainly in Peru (Rodrigues et al., 2004). Its fruit is known to be rich in vitamin C, with higher levels reported than those of acerola fruit (Bradfield and Roca, 1964). Camu-camu fruit has a characteristically mild flavor, but its high acid content induces a bitter taste. Therefore, it is mainly consumed as a juice or used as an ingredient in prepared foods (Villachica, 1997;Franco and Janzantti, 2005). During juice production, byproduct, composed of peel and seed, is generated as agricultural and industrial waste on a large scale. Therefore, utilization of this residue is recommended from both a commercial and ecological point of view.In a previous paper (Myoda et al., 2010), we reported that the seed extract of camu-camu fruit contains a large amount of polyphenols (400 mg/g), approximately four and ten times that of the residues of acerola and passion fruit juice production, respectively (Oliveira et al., 2009). We also reported that the lipophilic fraction of the seed extract showed antimicrobial activity against Staphylococcus aureus at 1.0 mg/ mL. On the other hand, the hydrophilic fraction exhibited strong 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity (IC 50 = 32.2 μg/mL), and the polyphenol content of the fraction was shown to be responsible for the activity. In this paper, we report the polyphenolic constituents in the seed extract of camu-camu fruit and their contributions to the anti-oxidative activity. Materials and MethodsMaterials and chemicals Dried powder of seeds obtained from camu-camu juice production was obtained from Empresa Agroindustrial del ...

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Main Structural and Stereochemical Aspects of the Antiherpetic Activity of Nonahydroxyterphenoyl‐Containing C‐Glycosidic Ellagitannins

Cited by 72 publications

References 53 publications

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Antiviral activity and possible mechanisms of action of pentagalloylglucose (PGG) against influenza A virus

Antioxidative Constituents in Camu-camu Fruit Juice Residue

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