Relationship between polyphenol content and anti‐influenza viral effects of berries

Sekizawa, Haruhito; Ikuta, Kazufumi; Mizuta, Katsumi; Takechi, Seiichi; Suzutani, Tatsuo

doi:10.1002/jsfa.6031

Cited by 33 publications

(27 citation statements)

References 13 publications

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“…The cytotoxicity of each compound (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) was evaluated by cell proliferation assay. Flavones (8)(9), flavonols (11)(12)(13) and 16 exhibited relatively high cytotoxic effects when compared with other flavonoids, although their selectivity index (CC 50 /IC 50 ) was larger than 500. Interestingly, they all have planar pai-conjugated systems.…”

Section: Cytotoxicities Of Natural Flavonoids and Gallic Acid Derivatmentioning

confidence: 99%

“…We reported that epigallocatechin gallate, a major green tea catechin, and its fatty acid derivatives directly inhibit various types of influenza virus including neuraminidase inhibitor resistant viruses [6,7]. Natural flavonoids in pomegranate [8], berries [9], and plant seeds [10] have also been reported to be effective for inhibition of virus infection. However, little is known about the antiviral activity of coffee extracts [10,11], despite its status as the most-consumed drink in the world.…”

Section: Introductionmentioning

confidence: 99%

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Potential Anti-Influenza Virus Agents Based on Coffee Ingredients and Natural Flavonols

Kaihatsu¹

2014

Nat Prod Chem Res

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Natural phenolic compounds have been reported to directly inhibit influenza virus. Nonetheless, there have been no reports on the direct inhibitory effects of coffee ingredients. Here, we fractionated the hydrophobic and hydrophilic components of coffee. The hydrophobic fraction directly inhibited both a seasonal influenza A/Puerto Rico/8/24(H1N1) virus and a neuraminidase-resistant influenza A/Yokohama/77/2008(H1N1) virus infection in a dosedependent manner, while the hydrophilic fraction did not show any inhibitory effects, even at concentrations above 100 µg/ml. The HPLC profile of the hydrophobic fraction indicated that caffeine is the major component. Indeed, caffeine alone showed comparable anti-influenza virus activity. Interestingly, caffeic acid also inhibited viral infection, while chlorogenic acid, which is an ester of caffeic acid and (-)-quinic acid, showed no obvious antiviral effect at less than 2 mg/ml. We previously reported a method for enhancing the anti-influenza virus activity of epigallocatechin gallate, a major tea catechin, by lipase-catalyzed acylation. Using this methodology, we synthesized fatty acid esters of caffeic acid and evaluated their influenza virus-inhibitory effects. It was found that dioctanoyl ester of caffeic acid exhibited approximately 38-fold higher direct antiviral activity. To understand the essential structure required for virus inhibition, we further examined the antiviral activity of natural flavonoids containing either the caffeic acid skeleton or its analogous structure. Flavonols (quercetin, myricetin and morin) and hexahydrobenzophenone containing extended planar pi-conjugated systems efficiently inhibited the virus infection. Flavonoids possessing both radical scavenging activity and cytotoxicity tended to show higher antiviral activity, probably due to their affinity with viral surface factors. On the other hand, there was no apparent correlation between their antiviral activity and antioxidative activity. These findings provide insight into the design of anti-influenza virus agents from natural polyphenols.

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Section: Cytotoxicities Of Natural Flavonoids and Gallic Acid Derivatmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Potential Anti-Influenza Virus Agents Based on Coffee Ingredients and Natural Flavonols

Kaihatsu¹

2014

Nat Prod Chem Res

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“…Therefore, cranberry extracts may also represent a source of potential compounds that would prevent viral attachment to target cells as well. Indeed, antiviral activities of cranberry extracts have been reported against Reovirus ( Lipson et al, 2007 ), Enterovirus ( Su et al, 2010 ), and even against IV ( Weiss et al, 2005 ; Oiknine-Djian et al, 2012 ; Sekizawa et al, 2013 ). However, a lack of mechanistic studies and the standardization of productive processes to maintain comparable bioactive components concentrations, have limited the development of cranberry products as antivirals against IV infections.…”

Section: Introductionmentioning

confidence: 99%

The Cranberry Extract Oximacro® Exerts in vitro Virucidal Activity Against Influenza Virus by Interfering With Hemagglutinin

et al. 2018

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The defense against influenza virus (IV) infections still poses a series of challenges. The current antiviral arsenal against influenza viruses is in fact limited; therefore, the development of new anti-influenza strategies effective against antigenically different viruses is an urgent priority. Bioactive compounds derived from medicinal plants and fruits may provide a natural source of candidates for such broad-spectrum antivirals. In this regard, cranberry (Vaccinium macrocarpon Aiton) extracts on the basis of their recognized anti-adhesive activities against bacteria, may provide potential compounds able to prevent viral attachment to target cells. Nevertheless, only few studies have so far investigated the possible use of cranberry extracts as an antiviral tool. This study focuses on the suitability of a cranberry extract as a direct-acting anti-influenza compound. We show that the novel cranberry extract Oximacro® inhibits influenza A and B viruses (IAV, IBV) replication in vitro because of its high content of A-type proanthocyanidins (PAC-A) dimers and trimers. Mechanistic studies revealed that Oximacro® prevents attachment and entry of IAV and IBV into target cells and exerts a virucidal activity. Oximacro® was observed to interact with the ectodomain of viral hemagglutinin (HA) glycoprotein, thus suggesting the interference with HA functions and a consequent loss of infectivity of IV particles. Fluorescence spectroscopy revealed a reduction in the intrinsic fluorescence of HA protein after incubation with purified dimeric PAC-A (PAC-A2), thus confirming a direct interaction between HA and Oximacro® PAC-A2. In silico docking simulations further supported the in vitro results and indicated that among the different components of the Oximacro® chemical profile, PAC-A2 exhibited the best binding propensity with an affinity below 10 nM. The role of PAC-A2 in the anti-IV activity of Oximacro® was eventually confirmed by the observation that it prevented IAV and IVB replication and caused the loss of infectivity of IV particles, thus indicating PAC-A2 as the major active component of Oximacro®. As a whole, these results suggest Oximacro® as a potential candidate to create novel antiviral agents of natural origin for the prevention of IV infections.

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“…bioregulatory functions involved in the maintenance and improvement of health), which are attributed to the presence of various bioactive components. For example, flavonoids, a category of polyphenols that includes catechins from green tea, have been reported to have anti‐influenza virus effects …”

Section: Introductionmentioning

confidence: 99%

Anti‐influenza virus effects of cocoa

et al. 2015

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Relationship between polyphenol content and anti‐influenza viral effects of berries

Cited by 33 publications

References 13 publications

Potential Anti-Influenza Virus Agents Based on Coffee Ingredients and Natural Flavonols

Potential Anti-Influenza Virus Agents Based on Coffee Ingredients and Natural Flavonols

The Cranberry Extract Oximacro® Exerts in vitro Virucidal Activity Against Influenza Virus by Interfering With Hemagglutinin

Anti‐influenza virus effects of cocoa

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