New Dihydrobiflavones from the Moss Plagiomnium cuspidatum

Anhut, Siegbert; Seeger, Tassilo; Zinsmeister, Hans Dietmar; Geiger, Hans

doi:10.1515/znc-1989-3-403

Cited by 17 publications

(6 citation statements)

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“…ZINC000043552589, ZINC000003594862, ZINC000003947429 and ZINC000070691536 with docking energy −10.5, −9.8, −9.5 and −9.4 kcal/mol, respectively, with favorable binding affinity in the active pocket of SARS-CoV-2 M pro were considered for further analysis. Here, ZINC000043552589 was identified as 2,3-Dihydroamentoflavone, an amentoflavone-type bioflavonoid was first isolated from Cycas revoluta [ 53 ]. Likewise, ZINC000003594862 (Podocarpusflavon-B) was reported as an amentoflavone and extracted from Selaginella sinensis (Selaginellaceae) herb [ 54 ].…”

Section: Resultsmentioning

confidence: 99%

Exploration of natural compounds with anti-SARS-CoV-2 activityviainhibition of SARS-CoV-2 Mpro

Bharadwaj

Dubey

Yadava

et al. 2021

Briefings in Bioinformatics

148

114

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Coronavirus disease 2019 (COVID-19), caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), is a dreaded pandemic in lack of specific therapeutic agent. SARS-CoV-2 Mpro, an essential factor in viral pathogenesis, is recognized as a prospective therapeutic target in drug discovery against SARS-CoV-2. To tackle this pandemic, Food and Drug Administration-approved drugs are being screened against SARS-CoV-2 Mpro via in silico and in vitro methods to detect the best conceivable drug candidates. However, identification of natural compounds with anti-SARS-CoV-2 Mpro potential have been recommended as rapid and effective alternative for anti-SARS-CoV-2 therapeutic development. Thereof, a total of 653 natural compounds were identified against SARS-CoV-2 Mpro from NP-lib database at MTi-OpenScreen webserver using virtual screening approach. Subsequently, top four potential compounds, i.e. 2,3-Dihydroamentoflavone (ZINC000043552589), Podocarpusflavon-B (ZINC000003594862), Rutin (ZINC000003947429) and Quercimeritrin 6”-O-L-arabinopyranoside (ZINC000070691536), and co-crystallized N3 inhibitor as reference ligand were considered for stringent molecular docking after geometry optimization by DFT method. Each compound exhibited substantial docking energy >−12 kcal/mol and molecular contacts with essential residues, including catalytic dyad (His41 and Cys145) and substrate binding residues, in the active pocket of SARS-CoV-2 Mpro against N3 inhibitor. The screened compounds were further scrutinized via absorption, distribution, metabolism, and excretion - toxicity (ADMET), quantum chemical calculations, combinatorial molecular simulations and hybrid QM/MM approaches. Convincingly, collected results support the potent compounds for druglikeness and strong binding affinity with the catalytic pocket of SARS-CoV-2 Mpro. Hence, selected compounds are advocated as potential inhibitors of SARS-CoV-2 Mpro and can be utilized in drug development against SARS-CoV-2 infection.

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Section: Resultsmentioning

confidence: 99%

Exploration of natural compounds with anti-SARS-CoV-2 activityviainhibition of SARS-CoV-2 Mpro

Bharadwaj

Dubey

Yadava

et al. 2021

Briefings in Bioinformatics

148

114

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“…15,16 dihydroxyamentoflavone. 17 Analysis of both the ECD spectrum ( Figure S20, Supporting Information) and optical rotation indicated that biflavonoid 2 was present as a racemic mixture.…”

Section: Resultsmentioning

confidence: 99%

“…The proposed molecular formula of C 30 H 20 O 12 for compound 2 was confirmed by the assignment of the [M + H] + to the peak observed in the HRESIMS spectrum at m / z 573.1044. The structure of compound 2 was defined through extensive NMR analyses as the known biflavonoid 8-[5-(5,7-dihydroxy-4-oxochroman-2-yl)-2,3-dihydroxyphenyl)-2-(3,4-dihydroxyphenyl]-5,7-dihydroxy-4 H -chromen-4-one, or 2,3-dihydro-5′,3‴-dihydroxyamentoflavone . Analysis of both the ECD spectrum (Figure S20, Supporting Information) and optical rotation indicated that biflavonoid 2 was present as a racemic mixture.…”

Section: Results and Discussionmentioning

confidence: 99%

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Waterman¹,

Nugraha²,

Hendra³

et al. 2017

J. Nat. Prod.

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Ceratodon purpureus is a cosmopolitan moss that survives some of the harshest places on Earth: from frozen Antarctica to hot South Australian deserts. In a study on the survival mechanisms of the species, nine compounds were isolated from Australian and Antarctic C. purpureus. This included five biflavonoids, with complete structural elucidation of 1 and 2 reported here for the first time, as well as an additional four known phenolic compounds. Dispersion-corrected DFT calculations suggested a rotational barrier, leading to atropisomerism, resulting in the presence of diastereomers for compound 2. All isolates absorbed strongly in the ultraviolet (UV) spectrum, e.g., biflavone 1 (UV-A, 315-400 nm), which displayed the strongest radical-scavenging activity, 13% more efficient than the standard rutin; p-coumaric acid and trans-ferulic acid showed the highest UV-B (280-315 nm) absorption. The more complex and abundant 1 and 2 presumably have dual roles as both UV-screening and antioxidant compounds. They are strongly bound to Antarctic moss cell walls as well as located inside the cells of moss from both locations. The combined high stability and photoprotective abilities of these isolates may account for the known resilience of this species to UV-B radiation and its survival in some of the toughest locations in the world.

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“…The detailed extraction o f P. cuspidatum is de scribed in [11]. T he m ethanolic ex tract o f P. elatum was separated by repeated colum n and pap er ch ro m ato g rap h y w ith the solvent systems as listed in T able I. F inal purification o f the isolated com p o unds was achieved on Sephadex LH 20 w ith aqueous M eO H as eluent.…”

Section: E Xtraction and Isolationmentioning

confidence: 99%

Flavone-C-Glycosides from the Mosses Plagiomnium elatum and Plagiomnium cuspidatum

Anhut

Biehl

Seeger

et al. 1992

Zeitschrift Für Naturforschung C

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New Dihydrobiflavones from the Moss Plagiomnium cuspidatum

Abstract: In Plagiomnium cuspidatum the three new dihydrobiflavones 2,3-dihydro-5′-hydroxyam entoflavone, 2,3-dihydro-5′,3‴-dihydroxyamentoflavone and 2,3-dihydro-5′-hydroxyrobustaflavone were detected.

Cited by 17 publications

References 0 publications

Exploration of natural compounds with anti-SARS-CoV-2 activityviainhibition of SARS-CoV-2 Mpro

Exploration of natural compounds with anti-SARS-CoV-2 activityviainhibition of SARS-CoV-2 Mpro

Antarctic Moss Biflavonoids Show High Antioxidant and Ultraviolet-Screening Activity

Flavone-C-Glycosides from the Mosses Plagiomnium elatum and Plagiomnium cuspidatum

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