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Establishment of Configurations for the Two Diastereomeric C-Glucosylanthrones Aloin A and Aloin B

✍ Scribed by Prof. Dr. Hans W. Rauwald; Karsten Lohse; Dr. Jan W. Bats

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 249 KB
Volume: 28
Category: Article
ISSN: 0044-8249
DOI: 10.1002/anie.198915281

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✦ Synopsis

Aloin [lo-( P-D-glucopyranosyl)-l ,8-dihydroxy-3-hydroxymethyl-9( 1 OH)-anthracenone] is the principal component and principal active ingredient in the world-wide used pharmaceutical agents Aloe burbadensis and Aloe rapensis. It is known to be present in at least 68 aloe species."] Aloin was first isolated in 1851,['] but the correct molecular formula was not established until 1945,[31 and only in 1952 was the compound shown to be a C-glucosylanthrone derivative.I41 The suggestion that aloin might exist in stereoisomeric was confirmed by HPLC separation into the two diastereomers aloin B (1) and aloin A (2) in 1979.[5961 Partial synthesis"] and 'H NMR a n a l y ~i s " ~ proved that the anthrone system is attached @ with respect to the D-glucosyl residues in both aloins. It follows that 1 and 2 must differ 0 ?H

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