Flavonoids from <i>Matteuccia struthiopteris</i> and Their Anti-influenza Virus (H1N1) Activity

Li, Bo; Yang, Ni; Zhu, Lingjuan; Wu, Fengbo; Yan, Fei; Zhang, Xue; Yao, Xin‐Sheng

doi:10.1021/np500879t

Cited by 32 publications

(21 citation statements)

References 27 publications

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“…449.14422 [M + H] + ). The UV absorption bands at λ max 281 and 322 nm suggested the presence of a flavanone skeleton in 1 [ 9 ]. The 1 H-NMR spectrum of 1 ( Table 1 , see the Supplementary Materials ) exhibited a pair of meta-positioned aromatic protons at δ H 6.28 and 6.24 (each, 1H, d, J = 2.5 Hz) in ring A, an AA’XX’ coupling system at δ H 7.30 and 6.79 (each, 2H, d, J = 8.4 Hz) in ring B.…”

Section: Resultsmentioning

confidence: 99%

“…However, only incomplete 1D-NMR data of 1 was given in the literature 10, which was also differ greatly from our data ( Table 1 ). The electronic circular dichroism (CD) spectrum of 1 ( Figure 3 ) showed a negative Cotton effect at 282 nm (π→π * electronic transition) and a positive Cotton effect at 338 nm (n→π * electronic transition), suggesting that the absolute configuration at C-2 was S [ 9 , 11 ]. Thus, the structure of 1 was fully elucidated, and it was named hostaflavanone A.…”

Section: Resultsmentioning

confidence: 99%

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Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance

et al. 2017

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Two new phenolic glucosides, hostaflavanone A (1) and anti-1-phenylpropane-1,2-diol-2-O-β-d-glucopyranoside (2), together with six known compounds, anti-1-phenylpropane-1,2-diol (3), phenethyl-O-β-d-glucopyranoside (4), phenethanol-β-d-gentiobioside (5), phenethyl-O-rutinoside (6), (1S, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (7), and (1R, 3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (8), were isolated from the flower of Hosta plantaginea, and their structures were elucidated by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), and circular dichroism (CD) analyses. The cyclooxygenases (COX-1 and COX-2) inhibition and antioxidant activities of compounds 1 and 4–6 were investigated, and they showed moderate cyclooxygenases inhibition activities. Moreover, only compound 1 exhibited moderate antioxidant activity, with an IC50 value of 83.2 μM, while 4–6 showed insignificant activity with IC50 values of 282, 257, and 275 μM, respectively. This is the first report of compounds 3 and 5–8 from the Liliaceae family. The chemotaxonomic significance of the isolated compounds was also summarized.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance

et al. 2017

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“…This study investigated chemically the owers of H. plantaginea and isolated two avonol glycosides, plantanones A (1) and B (2) along with 10 known ones (3)(4)(5)(6)(7)(8)(9)(10)(11)(12).…”

Section: Discussionmentioning

confidence: 99%

Anti-inflammatory and antioxidant activities of flavonoids from the flowers of Hosta plantaginea

Yang

et al. 2018

RSC Adv.

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“…The natural flavonoid quercetin has the ability to mediate host antiviral interaction against hepatitis C virus replication and virion production . Further, several flavonoid glycosides show potent anti‐influenza inhibitory effects, including influenza virus A/WSN/33 and A/PR/8/34 in‐vitro and in‐vivo . Several bioinformatics studies elucidate the potential inhibitory effect of flavonoids on IAV‐H1N1 through direct interaction with the viral‐NA protein.…”

Section: Discussionmentioning

confidence: 99%

“…34 Further, several flavonoid glycosides show potent anti-influenza inhibitory effects, including influenza virus A/WSN/33 and A/PR/8/34 in-vitro and in-vivo. 35,36 Several bioinformatics studies elucidate the potential inhibitory effect of flavonoids on IAV-H1N1 through direct interaction with the viral-NA protein. Based on the structure-activity relationship of flavonoids and flavones, the molecular docking analysis between active ligands and H1N1-NA provides several stabilized compounds with hydrogen bond and hydrophobic interaction.…”

Section: Discussionmentioning

confidence: 99%

Guava flavonoid glycosides prevent influenza A virus infection via rescue of P53 activity

Khalil

Maksoud

Roshdey

et al. 2018

Journal of Medical Virology

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Influenza is a highly infectious disease caused by three types of viruses, including influenza A virus (IAV), influenza B virus, and, rarely, influenza C virus. IAV is a major, global public health threat, causing approximately 500 000 deaths per year worldwide. The new strains of IAV have emerged due to a mutation called antigenic shift, which results in a new subtype of the virus that shows resistance to common antiviral drugs. Here, guava and lemon extracts, including green leaves and flowers, were investigated for their activity against IAV replication in human A549 cells. Concomitantly, the cytotoxicity of a potent extract on host-cell multiplication was assessed. Our results reveal that guava extracts inhibit IAV replication, indicated by viral nucleoprotein expression profile and traditional plaque assay. Interestingly, treatment with guava extract inactivates Akt protein kinase and stimulates the pro-apoptotic protein P53, at early stages of infection. Furthermore, purified guava flavonoid glycosides (GFGs) show competitive inhibition of IAV-virus replication via early regulation of IL-1β and IL-8 in association with P53 gene expression. The docking analysis of GFGs and the protein structure of upstream targets for the Akt signaling pathway indicates a sufficient interaction and stabilization with Gbr2 protein. These data indicate that treatment with GFGs disturbs IAV replication via activation of P53 and its apoptotic related factors after infection. Collectively, these data show that targeting of essential host kinases that are involved in the replication cycle of IAV and rescue of P53 activity by GFGs could represent a new strategy to eradicate IAV.

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Flavonoids from Matteuccia struthiopteris and Their Anti-influenza Virus (H1N1) Activity

Cited by 32 publications

References 27 publications

Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance

Chemical Constituents from the Flower of Hosta plantaginea with Cyclooxygenases Inhibition and Antioxidant Activities and Their Chemotaxonomic Significance

Anti-inflammatory and antioxidant activities of flavonoids from the flowers of Hosta plantaginea

Guava flavonoid glycosides prevent influenza A virus infection via rescue of P53 activity

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