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Synthesis and biosynthesis of isocordoin.

Title: Synthesis and biosynthesis of isocordoin.
Authors: Vitali A; Ferrari F; Monache GD; Bombardelli E; Botta B
Source: Planta medica [Planta Med] 2001 Jul; Vol. 67 (5), pp. 475-7.
Publication Type: Letter; Research Support, Non-U.S. Gov't
Language: English
Journal Info: Publisher: George Thieme Country of Publication: Germany NLM ID: 0066751 Publication Model: Print Cited Medium: Print ISSN: 0032-0943 (Print) Linking ISSN: 00320943 NLM ISO Abbreviation: Planta Med Subsets: MEDLINE
Imprint Name(s): Publication: Stuttgart ; New York : George Thieme; Original Publication: Stuttgart, Hippokrates Verlag.
MeSH Terms: Antineoplastic Agents, Phytogenic/*chemical synthesis ; Catechols/*chemical synthesis ; Chalcone/*analogs & derivatives ; Rosales/*chemistry; Acetophenones/chemistry ; Benzaldehydes/chemistry ; Chalcone/chemistry ; Chalcone/metabolism ; Dimethylallyltranstransferase/metabolism ; Resorcinols/chemistry ; Biotransformation ; Cell Line ; Chalcones ; Culture Techniques
Abstract: In the search of a convenient synthesis for isocordoin (1), a potential anticancer natural product, 2',4'-dihydroxychalcone was inoculated in cell suspension cultures of Morus nigra, which were expected to contain an active prenyltransferase. After 24 hours the target compound was easily isolated from the metabolite extract. Optimization of the biotransformation resulted in a 85% yield of the prenyl derivative.
Substance Nomenclature: 0 (Acetophenones); 0 (Antineoplastic Agents, Phytogenic); 0 (Benzaldehydes); 0 (Catechols); 0 (Chalcones); 0 (Resorcinols); 0 (isocordoin); 25515-43-9 (2',4'-dihydroxychalcone); 5S5A2Q39HX (Chalcone); EC 2.5.1.1 (Dimethylallyltranstransferase); UC3V356VZC (resacetophenone)
Entry Date(s): Date Created: 20010808 Date Completed: 20011101 Latest Revision: 20131121
Update Code: 20260130
DOI: 10.1055/s-2001-15814
PMID: 11488468
Database: MEDLINE

Letter; Research Support, Non-U.S. Gov't