Geranylated flavonoids displaying SARS-CoV papain-like protease inhibition from the fruits of Paulownia tomentosa

Cho, Jung Keun; Long, Marcus J. C.; Lee, Kon Ho; Kim, Dae Wook; Ryu, Hyung Won; Yuk, Heung Joo; Park, Ki Hun

doi:10.1016/j.bmc.2013.03.027

Cited by 207 publications

(146 citation statements)

References 12 publications

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“…2). This suggests that increasing inhibitor concentration led to a decrease in V max and an increase in K m (Cho et al 2013), indicating that compounds 2 and 5-7 were mixed-type inhibitors. The K i values of compounds 1-7 were also measured using Dixon plots ( Fig.…”

Section: Resultsmentioning

confidence: 92%

Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity

Sun

Yan

et al. 2014

Arch. Pharm. Res.

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Fourteen compounds were isolated from a methanol extract of Polygonum multiflorum roots, and their structures were elucidated by comparing spectroscopic data to published spectra. The inhibitory effects of the isolated compounds on soluble epoxide hydrolase (sEH) were then evaluated. Compounds 1-7 inhibited sEH activity potently, with IC50 values ranging from 6.2 ± 0.5 to 48.6 ± 3.1 μM. Moreover, a kinetic analysis of compounds 1-7 revealed that the inhibitory actions of compounds 1, 3 and 4 were non-competitive, whereas those of compounds 2 and 5-7 were mixed-type.

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Section: Resultsmentioning

confidence: 92%

Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity

Sun

Yan

et al. 2014

Arch. Pharm. Res.

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“…18) Several geranyl-substituted flavanones that were isolated from P. tomentosa as minor components showed inhibitory activity against papain-like protease of coronavirus of severe acute respiratory syndrome (SARS). 19) As polyphenolic compounds, the activity of flavonoids is commonly attributed to their antioxidant, anti-inflammatory activities. 20) We showed that the antiviral effect of apigenin against EV71 infection was unlikely related to the antioxidant properties since similar compounds failed to inhibit EV71 infection.…”

Section: )mentioning

confidence: 99%

Antiviral Activity of Paulownia tomentosa against Enterovirus 71 of Hand, Foot, and Mouth Disease

Chen

et al. 2015

Biological ^|^ Pharmaceutical Bulletin

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The bark, leaves, and flowers of Paulownia trees have been used in traditional Chinese medicine to treat infectious and inflammatory diseases. We investigated the antiviral effects of Paulownia tomentosa flowers, an herbal medicine used in some provinces of P. R. China for the treatment of skin rashes and blisters. Dried flowers of P. tomentosa were extracted with methanol and tested for antiviral activity against enterovirus 71 (EV71) and coxsackievirus A16 (CAV16), the predominant etiologic agents of hand, foot, and mouth disease in P. R. China. The extract inhibited EV71 infection, although no effect was detected against CAV16 infection. Bioactivity-guided fractionation was performed to identify apigenin as an active component of the flowers. The EC 50 value for apigenin to block EV71 infection was 11.0 µM, with a selectivity index of approximately 9.3. Although it is a common dietary flavonoid, only apigenin, and not similar compounds like naringenin and quercetin, were active against EV71 infection. As an RNA virus, the genome of EV71 has an internal ribosome entry site that interacts with heterogeneous nuclear ribonucleoproteins (hnRNPs) and regulates viral translation. Cross-linking followed by immunoprecipitation and reverse transcription-polymerase chain reaction (RT-PCR) analysis showed that EV71 RNA was associated with hnRNPs A1 and A2. Apigenin treatment disrupted this association, indicating that apigenin suppressed EV71 replication through a novel mechanism by targeting the trans-acting factors. This study therefore validates the effects of Paulownia against EV71 infection. It also yielded mechanistic insights on apigenin as an active compound for the antiviral activity of P. tomentosa against EV71 infection.

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“…The antioxidant Š mejkal et al 2007a, b;Zima et al 2010), antibacterial (Navrátilová et al 2013;Š mejkal et al 2008b), antiphlogistic , cytotoxic (Kollár et al 2011;Š mejkal et al 2007a, and severe acute respiratory syndrome coronavirus papain-like protease (SARS-CoV PLpro) activities (Cho et al 2013) of isolated geranylated flavonoids have been described recently, together with their inhibitory effect on both human acetylcholinesterase and butyrylcholinesterase (Cho et al 2012). The great ability of several geranylated flavanones to interact with bacterial sialidase isolated from Clostridum perfringens (Cp-NanI), a bacterium causing various gastrointestinal diseases, has recently been reported (Lee et al 2014).…”

Section: P Tomentosa Flavonoids and Their Biological Activitymentioning

confidence: 99%

“…Prenylated flavonoids 55-59, modified with an unusual 3,4-dihydro-2H-pyran moiety, have been found to inhibit the severe acute respiratory syndrome corona virus PLpro enzyme more effectively than their parent compounds, the precursors from which were they derived (Cho et al 2013).…”

Section: P Tomentosa Flavonoids and Their Biological Activitymentioning

confidence: 99%

Phytochemical profile of Paulownia tomentosa (Thunb). Steud.

Schneiderová

Šmejkal

2014

Phytochem Rev

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Paulownia tomentosa, a member of the plant family Paulowniaceae and a rich source of biologically active secondary metabolites, is traditionally used in Chinese herbal medicine. Flavonoids, lignans, phenolic glycosides, quinones, terpenoids, glycerides, phenolic acids, and miscellaneous other compounds have been isolated from different parts of P. tomentosa plant. Recent interest in this species has focused on isolating and identifying of prenylated flavonoids, that exhibit potent antioxidant, antibacterial, and antiphlogistic activities and inhibit severe acute respiratory syndrome coronavirus papain-like protease. They show cytotoxic activity against various human cancer cell lines and inhibit the effects of human cholinesterase, butyrylcholinesterase, and bacterial neuraminidases. Most of the compounds considered here have never been isolated from any other species of plant. This review summarizes the information about the isolated compounds that are active, their bioactivities, and the structure-activity relationships that have been worked out for them. major flavonoid of citrus, activity reviewed by Khan and Zill-E-Huma (2014) 114 R1= R2= R3=R4= H 121 R1= R2=R3=R4 = H 115 R1= OH (6S), R2= R3=R4= H 122 R1= OH (6S), R2=R3= R4= H 116 R1= R3=R4= H, R2= OH (7R) 123 R1= R3=R4= H, R2= OH (7R) 117 R1= R2=R4= H, R3= OH (8R) 124 R1= R2=R4= H, R3= OH (8R) 118 R1= R2=R3= H, R4= OH (9R) 125 R1= R2=R3= H, R4= OH (9R) 119 R1= R3=R4= H, R2= OAc (7R) 126 R1= R2=R4= H, R3= OAc (8R) 120 R1= R2=R4= H, R3= OAc (8R) 127 R1= R2=R3= H, R4= OAc (9R)

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Geranylated flavonoids displaying SARS-CoV papain-like protease inhibition from the fruits of Paulownia tomentosa

Cited by 207 publications

References 12 publications

Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity

Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity

Antiviral Activity of Paulownia tomentosa against Enterovirus 71 of Hand, Foot, and Mouth Disease

Phytochemical profile of Paulownia tomentosa (Thunb). Steud.

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