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Occurrence of Progesterone and Related Animal Steroids in Two Higher Plants#,
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Dedicated to the late Dr. John W. Daly of NIDDK, NIH, Bethesda, Maryland, for this pioneering work on bioactive natural products.
, Dedicated also to Drs. Peter Junior (formerly Heinrich Heine- University, Düsseldorf) and Nikolaus H. Fischer (formerly Louisiana State University and The University of Mississippi).
, * To whom correspondence should be addressed. Tel: (312) 355-1949. Fax: (312)-355-2693. E-mail: gfp@uic.edu., †Department of Medicinal Chemistry and Pharmacognosy and Program for Collaborative Research, University of Illinois at Chicago.
, ‡Institute for Tuberculosis Research, University of Illinois at Chicago.
,
Dominican University.
,
Innsbruck Medical University.
, §Previous address: Institute for Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-University Münster, Hittorfstrasse 56, 48149 Münster, Germany.
Section:Abstract
Previously, the presence of a wide variety of chemically diverse steroids has been identified in both flora and fauna. Despite the relatively small differences in chemical structures and large differences in physiological function of steroids, new discoveries indicate that plants and animals are more closely related than previously thought. In this regard, the present study gathers supporting evidence for shared phylogenetic roots of structurally similar steroids produced by these two eukaryotic taxa. Definitive proof for the presence of progesterone (3) in a vascular plant, Juglans regia, is provided. Additional evidence is gleaned from the characterization of five new plant steroids from Adonis aleppica: three 3-O-sulfated pregnenolones (6a/b, 7), a sulfated H-5β cardenolide, strophanthidin-3-O-sulfate (8), and spirophanthigenin (10), a novel C-18 oxygenated spirocyclic derivative of strophanthidin. The ab initio isolation and structure elucidation (NMR, MS) of these genuine minor plant steroids offers information on preparative metabolomic profiling at the ppm level and provides striking evidence for the conserved structural space of pregnanes and its congeners across the phylogenetic tree.
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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A. Douglas Kinghorn, Li Pan, Joshua N. Fletcher, and Heebyung ChaiJournal of Natural Products2011 Article ASAPAlong with compounds from terrestrial microorganisms, the constituents of higher plants have provided a substantial number of the natural product-derived drugs used currently in Western medicine. Interest in the elucidation of new structures of the ...
Compelling Computational Evidence for the Concerted Cyclization of the ABC Rings of Hopene from Protonated Squalene
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Lidia Smentek and B. Andes Hess, Jr.Journal of the American Chemical Society2010 132 (48), 17111-17117The long-standing question of what is the nature of the cyclization of squalene to form tetracyclic and pentacyclic triterpenes has been addressed computationally. Using the DFT method with an intrinsic reaction coordinate calculation, we find that the ...
Research Advances: Elastic Salt, and Plant Progesterone
Angela G. KingJournal of Chemical Education2010 87 (7), 660-661Research Advances: Elastic Salt, and Plant Progesterone
Angela G. KingJournal of Chemical Education2010 87 (7), 660-661This installment of Research Advances describes recent discoveries in properties of salt at the nanoscale, as well as the first discovery of the animal hormone progesterone in a plant.
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History
- Published In Issue March 26, 2010
- Article ASAPJanuary 28, 2010
- Received: November 15, 2009
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