Literature DB >> 33715562

Flavonoids and Acid-Hydrolysis derivatives of Neo-Clerodane diterpenes from Teucrium flavum subsp. glaucum as inhibitors of the HIV-1 reverse transcriptase-associated RNase H function.

Benedetta Fois1, Angela Corona1, Enzo Tramontano1,2, Simona Distinto1, Elias Maccioni1, Rita Meleddu1, Pierluigi Caboni1, Costantino Floris3, Filippo Cottiglia1.   

Abstract

Bioassay-guided fractionation of the ethyl acetate extract from Teucrium flavum subsp. glaucum, endowed with inhibitory activity towards the HIV-1 reverse transcriptase-associated RNase H function, led to the isolation of salvigenin (1), cirsimaritin (2) and cirsiliol (3) along with the neo-clerodanes teuflavin (4) and teuflavoside (5). Acid hydrolysis of the inactive teuflavoside provided three undescribed neo-clerodanes, flavuglaucins A-C (7-9) and one known neo-clerodane (10). Among all neo-clerodanes, flavuglaucin B showed the highest inhibitory activity towards RNase H function with a IC50 value of 9.1 μM. Molecular modelling and site-directed mutagenesis analysis suggested that flavuglaucin B binds into an allosteric pocket close to RNase H catalytic site. This is the first report of clerodane diterpenoids endowed with anti-reverse transcriptase activity. Neo-clerodanes represent a valid scaffold for the development of a new class of HIV-1 RNase H inhibitors.

Entities:  

Keywords:  HIV; RNase H; Teucrium flavum; flavonoids; neo-clerodane diterpenes; reverse transcriptase

Year:  2021        PMID： 33715562      PMCID： PMC7952052          DOI： 10.1080/14756366.2021.1887170

Source DB:  PubMed          Journal:  J Enzyme Inhib Med Chem        ISSN： 1475-6366            Impact factor:   5.051


  29 in total

1.  High resolution structures of HIV-1 RT from four RT-inhibitor complexes.

Authors:  J Ren; R Esnouf; E Garman; D Somers; C Ross; I Kirby; J Keeling; G Darby; Y Jones; D Stuart
Journal:  Nat Struct Biol       Date:  1995-04

2.  Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase.

Authors:  Vijay P Sonar; Angela Corona; Simona Distinto; Elias Maccioni; Rita Meleddu; Benedetta Fois; Costantino Floris; Nilesh V Malpure; Stefano Alcaro; Enzo Tramontano; Filippo Cottiglia
Journal:  Eur J Med Chem       Date:  2017-02-24       Impact factor: 6.514

3.  Identification of HIV-1 reverse transcriptase dual inhibitors by a combined shape-, 2D-fingerprint- and pharmacophore-based virtual screening approach.

Authors:  Simona Distinto; Francesca Esposito; Johannes Kirchmair; M Cristina Cardia; Marco Gaspari; Elias Maccioni; Stefano Alcaro; Patrick Markt; Gerhard Wolber; Luca Zinzula; Enzo Tramontano
Journal:  Eur J Med Chem       Date:  2012-02-05       Impact factor: 6.514

Review 4.  Molecular aspects of the RT/drug interactions. Perspective of dual inhibitors.

Authors:  Simona Distinto; Elias Maccioni; Rita Meleddu; Angela Corona; Stefano Alcaro; Enzo Tramontano
Journal:  Curr Pharm Des       Date:  2013       Impact factor: 3.116

5.  Combo of two HIV vaccines fails its big test.

Authors:  Jon Cohen
Journal:  Science       Date:  2020-02-07       Impact factor: 47.728

6.  Structural basis of the allosteric inhibitor interaction on the HIV-1 reverse transcriptase RNase H domain.

Authors:  Martin T Christen; Lakshmi Menon; Nataliya S Myshakina; Jinwoo Ahn; Michael A Parniak; Rieko Ishima
Journal:  Chem Biol Drug Des       Date:  2012-08-31       Impact factor: 2.817

7.  New insights into the interaction between pyrrolyl diketoacids and HIV-1 integrase active site and comparison with RNase H.

Authors:  Angela Corona; Francesco Saverio di Leva; Giuseppe Rigogliuso; Luca Pescatori; Valentina Noemi Madia; Frederic Subra; Olivier Delelis; Francesca Esposito; Marta Cadeddu; Roberta Costi; Sandro Cosconati; Ettore Novellino; Roberto di Santo; Enzo Tramontano
Journal:  Antiviral Res       Date:  2016-09-20       Impact factor: 5.970

8.  Basic quinolinonyl diketo acid derivatives as inhibitors of HIV integrase and their activity against RNase H function of reverse transcriptase.

Authors:  Roberta Costi; Mathieu Métifiot; Suhman Chung; Giuliana Cuzzucoli Crucitti; Kasthuraiah Maddali; Luca Pescatori; Antonella Messore; Valentina Noemi Madia; Giovanni Pupo; Luigi Scipione; Silvano Tortorella; Francesco Saverio Di Leva; Sandro Cosconati; Luciana Marinelli; Ettore Novellino; Stuart F J Le Grice; Angela Corona; Yves Pommier; Christophe Marchand; Roberto Di Santo
Journal:  J Med Chem       Date:  2014-04-11       Impact factor: 7.446

9.  HIV-1 drug resistance before initiation or re-initiation of first-line antiretroviral therapy in low-income and middle-income countries: a systematic review and meta-regression analysis.

Authors:  Ravindra K Gupta; John Gregson; Neil Parkin; Hiwot Haile-Selassie; Amilcar Tanuri; Liliana Andrade Forero; Pontiano Kaleebu; Christine Watera; Avelin Aghokeng; Nicholus Mutenda; Janet Dzangare; San Hone; Zaw Zaw Hang; Judith Garcia; Zully Garcia; Paola Marchorro; Enrique Beteta; Amalia Giron; Raph Hamers; Seth Inzaule; Lisa M Frenkel; Michael H Chung; Tulio de Oliveira; Deenan Pillay; Kogie Naidoo; Ayesha Kharsany; Ruthiran Kugathasan; Teresa Cutino; Gillian Hunt; Santiago Avila Rios; Meg Doherty; Michael R Jordan; Silvia Bertagnolio
Journal:  Lancet Infect Dis       Date:  2017-12-05       Impact factor: 25.071

10.  From cycloheptathiophene-3-carboxamide to oxazinone-based derivatives as allosteric HIV-1 ribonuclease H inhibitors.

Authors:  Serena Massari; Angela Corona; Simona Distinto; Jenny Desantis; Alessia Caredda; Stefano Sabatini; Giuseppe Manfroni; Tommaso Felicetti; Violetta Cecchetti; Christophe Pannecouque; Elias Maccioni; Enzo Tramontano; Oriana Tabarrini
Journal:  J Enzyme Inhib Med Chem       Date:  2019-12       Impact factor: 5.051
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  1 in total

Review 1.  Retroviral RNase H: Structure, mechanism, and inhibition.

Authors:  Tatiana V Ilina; Teresa Brosenitsch; Nicolas Sluis-Cremer; Rieko Ishima
Journal:  Enzymes       Date:  2021-09-24
  1 in total

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