Strukturrevision des 4-Hydroxyaloin: 10-Hydroxyaloine A und B als Haupt-In vitro-Oxidationsprodukte der diastereomeren Aloine1

Hans W. Rauwald; Karsten Lohse

doi:10.1055/s-2006-961448

Planta Med 1992; 58(3): 259-262
DOI: 10.1055/s-2006-961448

Paper

Strukturrevision des 4-Hydroxyaloin: 10-Hydroxyaloine A und B als Haupt-In vitro-Oxidationsprodukte der diastereomeren Aloine¹

Structure Revision of 4-Hydroxyaloin: 10-Hydroxyaloins A and B as Main In Vitro-Oxidation Products of the Diastereomeric Aloins¹ Hans W. Rauwald² ^, ⁴ , Karsten Lohse²

²Institut für Pharmazeutische Biologie der Universitat Frankfurt am Main, Georg-Voigt-StraBe 16, D(W)-6000 Frankfurt/M., Federal Republic of Germany
⁴Prof. Dr. Liselotte Langhammer, Freie Universität Berlin, in memoriam

1 XVIII. Mitt.: Neue Untersuchung über lnhaltsstoffe aus Aloe- und Rhamnus-Arten. XVII. Mitt. s. Lit. (1). Vorgetragen am 27.10.1989 beim “16th Annual Symposium on Pharmacognosy and Natural Products Chemistry” in Utrecht/Niederlande. s. Lit. (1)

Abstract

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Abstract

A reinvestigation of the anthrone derivative 4-hydroxyaloin as main product of the mild in vitro-oxidation of aloin has led to the revision of the proposed structure as the aloin-analogous oxanthrone derivative, the new 10-hydroxyaloin, which was prepared from aloin by an improved procedure in ammonia at pH 9. 10-Hydroxyaloin was separated into its C10-diastereomers A and B by analytical and preparative chromatographic methods. Their structures were elucidated by spectroscopic methods (FAB-MS; ¹H/¹³C-NMR; CD), which show that 10-hydroxyaloin A is the 10R,1′R compound and that 10-hydroxyaloin B has the 10S,1′R-configuration.

Key words

Aloe - quinonoids - anthranoids - 10-hydroxyaloins A/B - oxanthrone derivatives - aloins - anthrone derivatives - stability

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