Potent virucidal effect of pheophorbide a and pyropheophorbide a on enveloped viruses

Bouslama, Lamjed; Hayashi, Kyoko; Lee, Jung‐Bum; Ghorbel, Abdelwahed; Hayashi, Toshimitsu

doi:10.1007/s11418-010-0468-8

Cited by 25 publications

(23 citation statements)

References 17 publications

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“…Consequently, PPa may block virus entry into cells by physically damaging the viral membrane integrity, thereby inhibiting the entry of an enveloped virus in the early stage of infection, consistent with the mechanism hypothesized by Bouslama and colleagues 35 . Furthermore, similar mechanisms in which a compound physically interacts with virion envelope lipids to inhibit fusion of the influenza virus with the cell membrane have also been reported in other articles, such as the studies by Colpitts 29 , Speerstra 36 , St Vincent 37 , Kim 32 , and He 38 .…”

Section: Discussionsupporting

confidence: 80%

The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids

Chen

Yang

et al. 2020

Biochemical Pharmacology

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The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids, Biochemical Pharmacology (2020), doi: https://doi. AbstractMarine environments are known to be a new source of structurally diverse bioactive molecules. In this paper, we identified a porphyrin derivative of Pyropheophorbide a (PPa) from the mussel Musculus senhousei (M. senhousei) that showed broad anti-influenza A virus activity in vitro against a panel of influenza A viral strains. The analysis of the mechanism of action indicated that PPa functions in the early stage of virus infection by interacting with the lipid bilayer of the virion, resulting in an alteration of membrane-associated functions, thereby blocking the entry of enveloped viruses into host cells. In addition, the anti-influenza A virus activity of PPa was further assessed in mice infected with the influenza A virus. The survival rate and mean survival time of mice were apparently prolonged compared with the control group which was not treated with the drug. Therefore, PPa and its derivatives may represent lead compounds for controlling influenza A virus infection.Keywords: Marine food, Musculus senhousei, Pyropheophorbide a, Anti-influenza A virus activity, Enveloped virus. the H5N1 pseudo-typed virus screening approach, we identified the traditional Chinese seafood M. senhousei as showing a good inhibitory activity toward influenza A virus (IAV). The preliminary mechanistic study indicated that the antiviral activity of this food resulted from the inhibition of virus entry during early infection. We then investigated the bioactive components of this mussel using a bioassay-guided approach, from which a porphyrin derivative named pyropheophorbide a (PPa) that showed significant anti-IAV activity in vitro was isolated and identified, indicating a potential application of this molecule in the development of new antiviral agents.IAVs are enveloped viruses, and the viral envelopes are derived from portions of the host cell membranes and function to cover the capsids to protect the packaged viral genome 7 . In addition to the lipid bilayer, the viral envelope also contains viral glycoproteins, such as hemagglutinin (HA), neuraminidase (NA) and the viral M2 protein. These components, including lipid bilayers and associated proteins, play important roles in the process of viral infection 8,9 . As a result, they are viewed as promising tools for the development of new anti-influenza A drugs 10 .The HA glycoprotein consisting of two subunits, HA1 and HA2, is located on the surface of the envelope and is responsible for binding to receptor sites on the host membrane (HA1) and mediating the fusion between viral and host membranes (HA2).Following fusion, the viral genome is able to enter and subsequently infect the host cells 11 .The lipid bilayer is a major component of the IAV envelope. To date, a number of molecules targeting virion envelope lipids to interfere with the fusion of viral-host cellular membranes have been reported 12,13 . These molecul...

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Section: Discussionsupporting

confidence: 80%

The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids

Chen

Yang

et al. 2020

Biochemical Pharmacology

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“…Pheophorbide a reportedly inhibits influenza A virus infection . Pheophorbide a and pyropheophorbide a also reportedly show antiviral activities against herpes simplex virus type 2 and influenza A virus, but not poliovirus . Given that herpes simplex virus type 2 and influenza A virus are envelope viruses whereas poliovirus is a non‐envelope virus, Bouslama et al .…”

Section: Discussionmentioning

confidence: 99%

“…Given that herpes simplex virus type 2 and influenza A virus are envelope viruses whereas poliovirus is a non‐envelope virus, Bouslama et al . speculate that pheophorbide a and pyropheophorbide a inhibit envelope viruses, targeting specific envelope proteins and thereby interfering with viral binding to the host cell receptors (). On the other hand, our present results suggest that pheophorbide a and pyropheophorbide a inhibit HCV infection not only during the viral binding/entry step but also during the post‐entry step (Table , Fig.…”

Section: Discussionmentioning

confidence: 99%

Antiviral activity of extracts from Morinda citrifolia leaves and chlorophyll catabolites, pheophorbide a and pyropheophorbide a, against hepatitis C virus

Ratnoglik

Aoki

Sudarmono

et al. 2014

Microbiology and Immunology

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The development of complementary and/or alternative drugs for treatment of hepatitis C virus (HCV) infection is still needed. Antiviral compounds in medicinal plants are potentially good targets to study. Morinda citrifolia is a common plant distributed widely in Indo-Pacific region; its fruits and leaves are food sources and are also used as a treatment in traditional medicine. In this study, using a HCV cell culture system, it was demonstrated that a methanol extract, its n-hexane, and ethyl acetate fractions from M. citrifolia leaves possess anti-HCV activities with 50%-inhibitory concentrations (IC 50 ) of 20.6, 6.1, and 6.6 mg/mL, respectively. Bioactivity-guided purification and structural analysis led to isolation and identification of pheophorbide a, the major catabolite of chlorophyll a, as an anti-HCV compound present in the extracts (IC 50 ¼ 0.3 mg/mL). It was also found that pyropheophorbide a possesses anti-HCV activity (IC 50 ¼ 0.2 mg/mL). The 50%-cytotoxic concentrations (CC 50 ) of pheophorbide a and pyropheophorbide a were 10.0 and 7.2 mg/mL, respectively, their selectivity indexes being 33 and 36, respectively. On the other hand, chlorophyll a, sodium copper chlorophyllin, and pheophytin a barely, or only marginally, exhibited anti-HCV activities. Time-of-addition analysis revealed that pheophorbide a and pyropheophorbide a act at both entry and the post-entry steps. The present results suggest that pheophorbide a and its related compounds would be good candidates for seed compounds for developing antivirals against HCV.

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“…Opuntia ficus-indica (L.) is used in other regions as laxative, anti-inflammatory, or against diarrhoea (Bullitta, 2007). It is also antacid, astringent, antidermatosic, emollient, antiseptic, vulnerary, analgesic, expectorant, antiviral, sedative, antioxidant (Lamjed, 2011;Bullitta, 2007). The current study was undertaken to highlight certain information, including physico-chemical aspects and safety of P.lentiscus and O.f.indica seed oils.…”

Section: Introductionmentioning

confidence: 99%

Acute Toxicity of <em>Opuntia Ficus Indica</em> and <em>Pistacia Lentiscus</em> Seed Oils in Mice

Boukeloua¹,

Belkhiri²,

Djerrou³

et al. 2012

Afr. J. Trad. Compl. Alt. Med.

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Opuntia ficus indica and Pistacia lentiscus L. seeds are used in traditional medicine. The objective of this study was to investigate the toxicity of the fixed oil of Opuntia ficus indica and Pistacia lentiscus L. seeds in mice through determination of LD 50 values, and also the physicochemical characteristics of the fixed oil of these oils. The acute toxicity of their fixed oil were also investigated in mice using the method of Kabba and Berhens. The fixed oil of Pistacia lentiscus and Opuntia ficus indica seeds were extracted and analyzed for its chemical and physical properties such as acid value, free fatty acid percentage (% FFA), iodine index, and saponification value as well as refractive index and density. LD 50 values obtained by single doses, orally and intraperitoneally administered in mice, were respectively 43 ± 0,8 ;[40.7-45.4 ] ml/kg body wt. p.o. and 2.72 ± 0,1 ;[2.52-2.92] ml/kg body wt. i.p. for Opuntia ficus indica ; and 37 ± 1 ; [34.4 -39.8 ] ml/kg body wt. p.o. and 2.52 ± 0,2 ;[2.22 -2.81 ] ml/kg body wt. i.p. for Pistacia lentiscus respectively. The yields of seed oil were respectively calculated as 20.25% and 10.41%. The acid and free fatty acid values indicated that the oil has a low acidity

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Potent virucidal effect of pheophorbide a and pyropheophorbide a on enveloped viruses

Cited by 25 publications

References 17 publications

The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids

The seafood Musculus senhousei shows anti-influenza A virus activity by targeting virion envelope lipids

Antiviral activity of extracts from Morinda citrifolia leaves and chlorophyll catabolites, pheophorbide a and pyropheophorbide a, against hepatitis C virus

Acute Toxicity of <em>Opuntia Ficus Indica</em> and <em>Pistacia Lentiscus</em> Seed Oils in Mice

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