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Englerin A, a Selective Inhibitor of Renal Cancer Cell Growth, from Phyllanthus engleri
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Center for Cancer Research.
, ‡Developmental Therapeutics Program.
Section:Abstract
An extract from Phyllanthus engleri was identified in a bioinformatic analysis of NCI 60-cell natural product extract screening data that selectively inhibited the growth of renal cancer cell lines. Bioassay-guided fractionation yielded two new guaiane sesquiterpenes, englerins A (1) and B (2). Englerin A showed 1000-fold selectivity against six of eight renal cancer cell lines with GI50 values ranging from 1−87 nM. The structures of 1 and 2 and their relative stereochemistry were established by spectroscopic methods.
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
Chlorinated Englerins with Selective Inhibition of Renal Cancer Cell Growth
Rhone K. Akee, Tanya Ransom, Ranjala Ratnayake, James B. McMahon, and John A. BeutlerJournal of Natural Products2012 Article ASAPChlorinated Englerins with Selective Inhibition of Renal Cancer Cell Growth
Rhone K. Akee, Tanya Ransom, Ranjala Ratnayake, James B. McMahon, and John A. BeutlerJournal of Natural Products2012 Article ASAPThe chlorinated englerins (3–9) were isolated from Phyllanthus engleri and shown to selectively inhibit the growth of renal cancer cells. The compounds were shown to be extraction artifacts produced by exposure to chloroform decomposition products during ...
Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions
Noah Z. Burns, Michael R. Witten, and Eric N. JacobsenJournal of the American Chemical Society2011 Article ASAPDual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions
Noah Z. Burns, Michael R. Witten, and Eric N. JacobsenJournal of the American Chemical Society2011 Article ASAPA new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental ...
From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds
Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin PuJournal of the American Chemical Society2011 133 (30), 11780-11794From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds
Mark Turlington, Yuhao Du, Samuel G. Ostrum, Vishaka Santosh, Kathryne Wren, Tony Lin, Michal Sabat, and Lin PuJournal of the American Chemical Society2011 133 (30), 11780-11794(S)-1,1′-Binaphth-2-ol (BINOL) in combination with ZnEt2, Ti(OiPr)4, and biscyclohexylamine was found to catalyze the highly enantioselective (83–95% ee) addition of various 1,3-diynes to aldehydes of diverse structures. This method provides a convenient ...
A Brief Synthesis of (−)-Englerin A
Zhenwu Li, Mika Nakashige, and William J. ChainJournal of the American Chemical Society2011 133 (17), 6553-6556A Brief Synthesis of (−)-Englerin A
Zhenwu Li, Mika Nakashige, and William J. ChainJournal of the American Chemical Society2011 133 (17), 6553-6556Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic ...
Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A
Dmitry B. Ushakov, Vaidotas Navickas, Markus Ströbele, Cäcilia Maichle-Mössmer, Florenz Sasse, and Martin E. MaierOrganic Letters2011 13 (8), 2090-2093Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A
Dmitry B. Ushakov, Vaidotas Navickas, Markus Ströbele, Cäcilia Maichle-Mössmer, Florenz Sasse, and Martin E. MaierOrganic Letters2011 13 (8), 2090-2093An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by ...
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History
- Published In Issue January 01, 2009
- Article ASAPDecember 05, 2008
- Received: October 09, 2008
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