Literature DB >> 16321028

A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra.

Chen Li1, Dongho Lee, Tyler N Graf, Sharnelle S Phifer, Yuka Nakanishi, Jason P Burgess, Soedarsono Riswan, Fransisca M Setyowati, Achmad M Saribi, Djaja D Soejarto, Norman R Farnsworth, Joseph O Falkinham, David J Kroll, A Douglas Kinghorn, Mansukh C Wani, Nicholas H Oberlies.   

Abstract

[chemical reaction: see text]. Three new ent-trachylobane diterpenoids (1-3) were isolated and structures elucidated from Mitrephora glabra Scheff. (Annonaceae). Mitrephorone A (1) possesses a hexacyclic ring system with adjacent ketone moieties and an oxetane ring, both of which are unprecedented among trachylobanes. All compounds were evaluated for cytotoxicity against a panel of cancer cells, where 1 displayed the most potent and broadest activity, and against a battery of antimicrobial assays, where all compounds were approximately equipotent.

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Year:  2005        PMID： 16321028      PMCID： PMC2442714          DOI： 10.1021/ol052498l

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Bioactive constituents of the roots of Licania intrapetiolaris.

Authors:  N H Oberlies; J P Burgess; H A Navarro; R E Pinos; D D Soejarto; N R Farnsworth; A D Kinghorn; M C Wani; M E Wall
Journal:  J Nat Prod       Date:  2001-04       Impact factor: 4.050

2.  Quinone-methide triterpenoids from Glyptopetalum sclerocarpum.

Authors:  Uthai Sotanaphun; Rutt Suttisri; Vimolmas Lipipun; Rapepol Bavovada
Journal:  Phytochemistry       Date:  1998-11-20       Impact factor: 4.072

Review 3.  Anti-staphylococcal plant natural products.

Authors:  Simon Gibbons
Journal:  Nat Prod Rep       Date:  2004-03-01       Impact factor: 13.423

4.  New diterpenes from Croton insularis.

Authors:  Konstantia Graikou; Nektarios Aligiannis; Alexios-Léandros Skaltsounis; Ioanna Chinou; Sylvie Michel; François Tillequin; Marc Litaudon
Journal:  J Nat Prod       Date:  2004-04       Impact factor: 4.050

5.  A novel alkaloid from Mitrephora maingayi.

Authors:  Rong Yu; Bo-Gang Li; Qi Ye; Guo-Lin Zhang
Journal:  Nat Prod Res       Date:  2005-06       Impact factor: 2.861

6.  New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.

Authors:  Feras Q Alali; Tamam El-Elimat; Chen Li; Amjad Qandil; Ahmad Alkofahi; Khaled Tawaha; Jason P Burgess; Yuka Nakanishi; David J Kroll; Hernán A Navarro; Joseph O Falkinham; Mansukh C Wani; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2005-02       Impact factor: 4.050

7.  5-Oxonoraporphines from Mitrephora cf. maingayi.

Authors:  N H Lee; Y J Xu; S H Goh
Journal:  J Nat Prod       Date:  1999-08       Impact factor: 4.050

8.  Antimicrobial diterpenes from the stem bark of Mitrephora celebica.

Authors:  J R Zgoda-Pols; A J Freyer; L B Killmer; J R Porter
Journal:  Fitoterapia       Date:  2002-08       Impact factor: 2.882

9.  Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia.

Authors:  Jian-Qiao Gu; Tyler N Graf; Dongho Lee; Hee-Byung Chai; Qiuwen Mi; Leonardus B S Kardono; Fransisca M Setyowati; Rachman Ismail; Soedarsono Riswan; Norman R Farnsworth; Geoffrey A Cordell; John M Pezzuto; Steven M Swanson; David J Kroll; Joseph O Falkinham; Monroe E Wall; Mansukh C Wani; A Douglas Kinghorn; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2004-07       Impact factor: 4.050

10.  Diterpenoids from the roots of Salvia hypargeia.

Authors:  A Ulubelen; N Evren; E Tuzlaci; C Johansson
Journal:  J Nat Prod       Date:  1988 Nov-Dec       Impact factor: 4.050
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  12 in total

1.  Synthesis of (-)-Mitrephorone A via a Bioinspired Late Stage C-H Oxidation of (-)-Mitrephorone B.

Authors:  Lukas Anton Wein; Klaus Wurst; Peter Angyal; Lara Weisheit; Thomas Magauer
Journal:  J Am Chem Soc       Date:  2019-12-03       Impact factor: 15.419

2.  Isolation and synthesis of antiproliferative eupolauridine alkaloids of Ambavia gerrardii from the Madagascar Dry Forest.

Authors:  Ende Pan; Shugeng Cao; Peggy J Brodie; Martin W Callmander; Richard Randrianaivo; Stephan Rakotonandrasana; Etienne Rakotobe; Vincent E Rasamison; Karen TenDyke; Yongchun Shen; Edward M Suh; David G I Kingston
Journal:  J Nat Prod       Date:  2011-04-19       Impact factor: 4.050

3.  Proliferation of antibiotic-producing bacteria and concomitant antibiotic production as the basis for the antibiotic activity of Jordan's red soils.

Authors:  Joseph O Falkinham; Thomas E Wall; Justin R Tanner; Khaled Tawaha; Feras Q Alali; Chen Li; Nicholas H Oberlies
Journal:  Appl Environ Microbiol       Date:  2009-03-13       Impact factor: 4.792

4.  Bioactive constituents of the stem bark of Mitrephora glabra.

Authors:  Chen Li; Dongho Lee; Tyler N Graf; Sharnelle S Phifer; Yuka Nakanishi; Soedarsono Riswan; Fransisca M Setyowati; Achmad M Saribi; Djaja D Soejarto; Norman R Farnsworth; Joseph O Falkinham; David J Kroll; A Douglas Kinghorn; Mansukh C Wani; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2009-11       Impact factor: 4.050

5.  Relaxant effect of Ent-7α-hydroxytrachyloban-18-oic acid, a trachylobane diterpene from Xylopia langsdorfiana A. St-Hil. & Tul., on tracheal smooth muscle.

Authors:  Italo R R Martins; Rosimeire F Dos Santos; Ana C de C Correia; Gislaine A de Oliveira; Cibério L Macêdo; Fabio de S Monteiro; Paula F Dos Santos; Fabiana de A Cavalcante; Josean F Tavares; Bagnólia A da Silva
Journal:  J Smooth Muscle Res       Date:  2013

6.  Cytotoxic compounds from the leaves and stems of the endemic Thai plant Mitrephora sirikitiae.

Authors:  Natthinee Anantachoke; Duangporn Lovacharaporn; Vichai Reutrakul; Sylvie Michel; Thomas Gaslonde; Pawinee Piyachaturawat; Kanoknetr Suksen; Samran Prabpai; Narong Nuntasaen
Journal:  Pharm Biol       Date:  2020-12       Impact factor: 3.503

7.  Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation.

Authors:  Bushra Abdulkarim Moharam; Ibrahim Jantan; Juriyati Jalil; Khozirah Shaari
Journal:  Molecules       Date:  2010-11-03       Impact factor: 4.411

Review 8.  An Overview of Saturated Cyclic Ethers: Biological Profiles and Synthetic Strategies.

Authors:  Qili Lu; Dipesh S Harmalkar; Yongseok Choi; Kyeong Lee
Journal:  Molecules       Date:  2019-10-21       Impact factor: 4.411

9.  In vitro and in vivo antitumor effect of trachylobane-360, a diterpene from Xylopia langsdorffiana.

Authors:  João Carlos Lima Rodrigues Pita; Aline Lira Xavier; Tatyanna Kelvia Gomes de Sousa; Vivianne Mendes Mangueira; Josean Fechine Tavares; Robson José de Oliveira Júnior; Robson Cavalcante Veras; Hilzeth de Luna Freire Pessoa; Marcelo Sobral da Silva; Sandra Morelli; Veridiana de Melo Rodrigues Ávila; Teresinha Gonçalves da Silva; Margareth de Fátima Formiga Melo Diniz; Marianna Vieira Sobral Castello-Branco
Journal:  Molecules       Date:  2012-08-10       Impact factor: 4.411

10.  Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.

Authors:  Michael Schneider; Matthieu J R Richter; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2020-10-06       Impact factor: 15.419
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