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Mass spectral analysis of some derivatives and in vitro metabolites of steviol, the aglycone of the natural sweeteners, stevioside, rebaudioside a, and rubusoside
Author(s) -
Compadre C. M.,
Hussain R. A.,
Nanayakkara N. P. D.,
Pezzuto J. M.,
Kinghorn A. D.
Publication year - 1988
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200150405
Subject(s) - steviol , stevioside , aglycone , rebaudioside a , chemistry , metabolite , glycoside , stevia rebaudiana , mutagen , biochemistry , pulegone , stereochemistry , chromatography , food science , medicine , dna , alternative medicine , pathology , essential oil
Steviol ( ent ‐13‐hydroxykaur‐16‐en‐19‐oic acid), the aglycone of various plant‐derived glycoside sweeteners consumed by human populations, is known to be mutagenic toward Salmonella typhimurium strain TM677 when metabolically activated using a 9000 × g supernatant fraction derived from the liver of Aroclor 1254‐pretreated rats. Mass spectral analysis of this diterpenoid and some analogs revealed characteristic patterns reflecting differential stereochemistry at the C/D rings and variations in the nature of the substituents present. Such information has been used to help identify several in vitro metabolites of steviol in conditions known to produce a mutagenic response, when analyzed by human populations, is known to be mutagenic toward Salmonella typhimurium strain TM677 when metabolically be allylic oxidation and epoxidation. 15‐Oxosteviol, a product of oxidation of the major steviol metabolite, 15α‐hydroxysteviol, was found to be a direct‐acting mutagen.