Zeylanone epoxide isolated from Diospyros anisandra stem bark inhibits influenza virus in vitro

Cetina-Montejo, Lisseth; Ayora-Talavera, Guadalupe; Borges-Argáez, Rocı́o

doi:10.1007/s00705-019-04223-y

Cited by 15 publications

(14 citation statements)

References 31 publications

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“…Extracts of the originating plant, Plumbago zeylanica , were shown to possess inhibitory activities against Coxsackie virus B3, influenza A virus, and herpes simplex virus type 1 Kupka [ 58 ]. The pure zeylanone epoxide was reported to have inhibited influenza virus replication in vitro [ 59 ].…”

Section: Resultsmentioning

confidence: 99%

High Throughput Virtual Screening to Discover Inhibitors of the Main Protease of the Coronavirus SARS-CoV-2

et al. 2020

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We use state-of-the-art computer-aided drug design (CADD) techniques to identify prospective inhibitors of the main protease enzyme, 3CLpro of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) causing COVID-19. From our screening of over one million compounds including approved drugs, investigational drugs, natural products, and organic compounds, and a rescreening protocol incorporating enzyme dynamics via ensemble docking, we have been able to identify a range of prospective 3CLpro inhibitors. Importantly, some of the identified compounds had previously been reported to exhibit inhibitory activities against the 3CLpro enzyme of the closely related SARS-CoV virus. The top-ranking compounds are characterized by the presence of multiple bi- and monocyclic rings, many of them being heterocycles and aromatic, which are flexibly linked allowing the ligands to adapt to the geometry of the 3CLpro substrate site and involve a high amount of functional groups enabling hydrogen bond formation with surrounding amino acid residues, including the catalytic dyad residues H41 and C145. Among the top binding compounds we identified several tyrosine kinase inhibitors, which include a bioflavonoid, the group of natural products that binds best to 3CLpro. Another class of compounds that decently binds to the SARS-CoV-2 main protease are steroid hormones, which thus may be endogenous inhibitors and might provide an explanation for the age-dependent severity of COVID-19. Many of the compounds identified by our work show a considerably stronger binding than found for reference compounds with in vitro demonstrated 3CLpro inhibition and anticoronavirus activity. The compounds determined in this work thus represent a good starting point for the design of inhibitors of SARS-CoV-2 replication.

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Section: Resultsmentioning

confidence: 99%

High Throughput Virtual Screening to Discover Inhibitors of the Main Protease of the Coronavirus SARS-CoV-2

et al. 2020

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“…Different plants of the genus Diospyros (family Ebenaceae) have been used in traditional medicine because of their high biological activity, including their antioxidant, anti-inflammatory, antipyretic, analgesic, antimicrobial, antifungal, antiprotozoal and insecticidal activities ( 33 – 36 ). In particular, D. anisandra has been attributed with numerous properties, including antimicrobial activity against multi-resistant strains of Mycobacterium tuberculosis ; ixodicidal activity against the tick Rhipicephalus microplus ; antiviral potential against the influenza virus; and anthelmintic activity ( 13 – 15 , 32 , 37 ).…”

Section: Discussionmentioning

confidence: 99%

Anthelmintic Activity of Extracts and Active Compounds From Diospyros anisandra on Ancylostoma caninum, Haemonchus placei and Cyathostomins

et al. 2020

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The present study aimed to evaluate the anthelmintic activity of leaf and bark extracts of Diospyros anisandra collected during different seasons and their major constituents on eggs of Ancylostoma caninum, Haemonchus placei , and cyathostomins. Specifically, the eclosion inhibition of the methanolic extracts of the leaves and bark of D. anisandra collected during the dry and rainy seasons (600–37.5 μg/ml) were evaluated in addition to the fractions, sub-fractions (300–37.5 μg/ml) and active major constituents (150–2.3 μg/ml). The rainy season bark extract had the highest percentage of eclosion inhibition (PEI) against the evaluated nematodes (≥ 90% at 75 μg/ml) along with high ovicidal activity (90.0 to 93.4% at 75 μg/ml). The purification of the rainy season bark extract showed that its biological activity came from the non-polar n -hexane fraction (≥ 93% at 75 μg/ml). The bioguided fractionation pointed to sub-fraction 5 as having the highest anthelmintic activity against the three evaluated genera of nematodes (PEI ≥ 93% at 37.5 μg/ml). Gas chromatography and mass spectrometry revealed that the major constituent in sub-fraction 5 was plumbagin. Upon evaluation, plumbagin was confirmed to be responsible for the anthelmintic activity of D. anisandra , with a PEI ≥ 90% at 2.3 μg/ml on the three evaluated nematodes. Additionally, the compounds betulin and lupeol in the bark of D. anisandra were evaluated but presented low anthelmintic activity (PEI ≤ 5.3% at 2.3 μg/ml). In conclusion, the rainy season bark extract of D. anisandra exerts a high ovicidal activity against the eggs of the three studied nematodes. Plumbagin is the active compound responsible for this activity and represents a potential alternative for the control of different genera of gastrointestinal nematodes given the current scenario of anthelmintic resistance.

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“…Cetina and coworkers discovered that the naphthoquinone compound zeylanone epoxide (1Q), isolated from Diospyros anisandra , could exert activity against influenza-A and -B viruses. Compound (1Q) could reduce viral titers and block the extra-nuclear transport of viral nucleoprotein, and could be a promising drug against influenza viruses ( Cetina-Montejo et al, 2019 ). Liu and his team established that acetylshikonin (2Q) could inactivate viral particles directly at relatively low concentrations to block the uptake or entry of coxsackievirus A16 (CVA16) in vitro .…”

Section: Quinonesmentioning

confidence: 99%

Research progress on the antiviral activities of natural products and their derivatives: Structure–activity relationships

Guo

Ma²,

Wang³

et al. 2022

Front. Chem.

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Viruses spread rapidly and are well-adapted to changing environmental events. They can infect the human body readily and trigger fatal diseases. A limited number of drugs are available for specific viral diseases, which can lead to non-efficacy against viral variants and drug resistance, so drugs with broad-spectrum antiviral activity are lacking. In recent years, a steady stream of new viral diseases has emerged, which has prompted development of new antiviral drugs. Natural products could be employed to develop new antiviral drugs because of their innovative structures and broad antiviral activities. This review summarizes the progress of natural products in antiviral research and their bright performance in drug resistance issues over the past 2 decades. Moreover, it fully discusses the effect of different structural types of natural products on antiviral activity in terms of structure–activity relationships. This review could provide a foundation for the development of antiviral drugs.

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Zeylanone epoxide isolated from Diospyros anisandra stem bark inhibits influenza virus in vitro

Cited by 15 publications

References 31 publications

High Throughput Virtual Screening to Discover Inhibitors of the Main Protease of the Coronavirus SARS-CoV-2

High Throughput Virtual Screening to Discover Inhibitors of the Main Protease of the Coronavirus SARS-CoV-2

Anthelmintic Activity of Extracts and Active Compounds From Diospyros anisandra on Ancylostoma caninum, Haemonchus placei and Cyathostomins

Research progress on the antiviral activities of natural products and their derivatives: Structure–activity relationships

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