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Galiridosid, ein Iridoidglucosid aus Galeopsis tetrahit L. (Labiatae)
Author(s) -
Sticher O.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530810
Subject(s) - chemistry , derivative (finance) , glucoside , stereochemistry , iridoid , lithium (medication) , selective catalytic reduction , catalytic hydrogenation , liquid ammonia , medicinal chemistry , ammonia , organic chemistry , catalysis , glycoside , medicine , financial economics , economics , endocrinology , alternative medicine , pathology
From fresh leaves of Galeopsis tetrahit L. ( Labiatae ) a compound observed earlier only by paper chromatography and known as ‘Tetrahit‐Pseudoindican’ or ‘Gal. tetr. 47’ has been isolated, and its constitution (II) as a new iridoid glucoside has been established. The name of galiridoside is proposed for this compound. Acetylation of galiridoside gave the tetraacetyl‐derivative III. Catalytic reduction of II by Pd/C gave dihydrogaliridoside (IV). Basic hydrolysis of II with Ba(OH) 2 gave desepoxydihydroxy‐galiridoside (VI). Reduction of galiridoside by lithium and ammonia yielded among other compounds a small amount of dideoxy‐aucubin (XI), isolated as its tetraacetate XII. The NMR. spectra of galiridoside and its derivatives support the proposed structure and configuration.