Literature DB >> 32292314

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984-2019).

Maryam Fattahian1, Mustafa Ghanadian1,2, Zulfiqar Ali2, Ikhlas A Khan2.   

Abstract

Diterpene compounds specially macrocyclic ones comprising jatrophane, lathyrane, terracinolide, ingenane, pepluane, paraliane, and segetane skeletons occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs. They possess diverse complex skeletons and a broad spectrum of therapeutically relevant biological activities including anti-inflammatory, anti-chikungunya virus, anti-HIV, cytotoxic, and multidrug resistance-reversing activities as well as curative effects on thrombotic diseases. Among macrocyclic diterpenes of Euphorbia, the discovery of jatrophane and modified jatrophane diterpenes with a wide range of structurally unique polyoxygenated polycyclic derivatives and as a new class of powerful inhibitors of P-glycoprotein has opened new frontiers for research studies on this genus. In this review, an attempt has been made to give in-depth coverage of the articles on the naturally occurring jatrophanes and rearranged jatrophane-type diterpenes isolated from species belonging to the Euphorbiaceae family published from 1984 to March 2019, with emphasis on the biogenesis, isolation methods, structure, biological activity, and structure-activity relationship. © Springer Nature B.V. 2020.

Entities:  

Keywords:  Chromatography; Euphorbia; Jatrophane diterpenes; Multidrug resistance; Natural products; Rearranged Jatrophanes

Year:  2020        PMID: 32292314      PMCID: PMC7152985          DOI: 10.1007/s11101-020-09667-8

Source DB:  PubMed          Journal:  Phytochem Rev        ISSN: 1568-7767            Impact factor:   7.741


  136 in total

Review 1.  Multidrug resistance reversal agents.

Authors:  Jacques Robert; Christian Jarry
Journal:  J Med Chem       Date:  2003-11-06       Impact factor: 7.446

2.  Macrocyclic diterpenoids from the Iranian plant Euphorbia bungei Boiss.

Authors:  Yalda Shokoohinia; Giuseppina Chianese; Behzad Zolfaghari; Seyed-Ebrahim Sajjadi; Giovanni Appendino; Orazio Taglialatela-Scafati
Journal:  Fitoterapia       Date:  2010-10-30       Impact factor: 2.882

Review 3.  Euphorbia diterpenes: isolation, structure, biological activity, and synthesis (2008-2012).

Authors:  Andrea Vasas; Judit Hohmann
Journal:  Chem Rev       Date:  2014-07-18       Impact factor: 60.622

4.  Microtubule interactions with chemically diverse stabilizing agents: thermodynamics of binding to the paclitaxel site predicts cytotoxicity.

Authors:  Rubén M Buey; Isabel Barasoain; Evelyn Jackson; Arndt Meyer; Paraskevi Giannakakou; Ian Paterson; Susan Mooberry; José M Andreu; J Fernando Díaz
Journal:  Chem Biol       Date:  2005-12

5.  Jatrophane diterpenes from Euphorbia mellifera and their activity as P-glycoprotein modulators on multidrug-resistant mouse lymphoma and human colon adenocarcinoma cells.

Authors:  Inês Valente; Mariana Reis; Noélia Duarte; Julianna Serly; Joséph Molnár; Maria-José U Ferreira
Journal:  J Nat Prod       Date:  2012-10-25       Impact factor: 4.050

6.  Jatrophane diterpenes as P-glycoprotein inhibitors. First insights of structure-activity relationships and discovery of a new, powerful lead.

Authors:  Gabriella Corea; Ernesto Fattorusso; Virginia Lanzotti; Orazio Taglialatela-Scafati; Giovanni Appendino; Mauro Ballero; Pierre-Noël Simon; Charles Dumontet; Attilio Di Pietro
Journal:  J Med Chem       Date:  2003-07-17       Impact factor: 7.446

7.  Jatrophane diterpenes as modulators of multidrug resistance. Advances of structure-activity relationships and discovery of the potent lead pepluanin A.

Authors:  Gabriella Corea; Ernesto Fattorusso; Virginia Lanzotti; Riccardo Motti; Pierre-Noël Simon; Charles Dumontet; Attilio Di Pietro
Journal:  J Med Chem       Date:  2004-02-12       Impact factor: 7.446

Review 8.  Inhibition of the multidrug resistance P-glycoprotein: time for a change of strategy?

Authors:  Richard Callaghan; Frederick Luk; Mary Bebawy
Journal:  Drug Metab Dispos       Date:  2014-02-03       Impact factor: 3.922

9.  Jatrophane diterpenoids from Euphorbia helioscopia and their lipid-lowering activities.

Authors:  Jun Li; Hui-Hui Li; Wen-Qiong Wang; Wei-Bin Song; Yi-Ping Wang; Li-Jiang Xuan
Journal:  Fitoterapia       Date:  2018-05-24       Impact factor: 2.882

10.  12,17-Cyclojatrophane and Jatrophane Constituents of Euphorbia welwitschii.

Authors:  Mariana A Reis; Vânia André; M Teresa Duarte; Hermann Lage; Maria-José U Ferreira
Journal:  J Nat Prod       Date:  2015-11-12       Impact factor: 4.050

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  2 in total

Review 1.  New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017-2022.

Authors:  Cristina Forzato; Patrizia Nitti
Journal:  Plants (Basel)       Date:  2022-08-29

2.  Gene discovery and virus-induced gene silencing reveal branched pathways to major classes of bioactive diterpenoids in Euphorbia peplus.

Authors:  Tomasz Czechowski; Edith Forestier; Sandesh H Swamidatta; Alison D Gilday; Amy Cording; Tony R Larson; David Harvey; Yi Li; Zhesi He; Andrew J King; Geoffrey D Brown; Ian A Graham
Journal:  Proc Natl Acad Sci U S A       Date:  2022-05-18       Impact factor: 12.779

  2 in total

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