Steviol

13 - Hydroxykaur -16 -en -19- acid

Crystalline solid

215 ° C

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Steviol is a naturally occurring, chiral diterpene from the group of Kauranes or Kaurene. It is found in the leaves of the South American plant Stevia rebaudiana in the form of various glycosides ( stevioside ). The glycosides have a strong sweet taste. In contrast to the strong sweet steviol stevioside is tasteless.

• 4.1 toxicity

Occurrence

Steviol comes in the form of its glycosides present in stevia. From 1 kg of the dried drug up to 60 g glycosides can be extracted.

Production and representation

Steviol can be obtained from the glycosides by enzymatic hydrolysis with the enzyme diastase. The acid-catalyzed hydrolysis fails because steviol thereby rearranges to Isosteviol.

Properties

Physical Properties

[ α ] D -65 ° ( CHCl3 ).

Chemical Properties

Steviol is temperature resistant up to 200 ° C.

Biological Significance

Steviol is structurally related to gibberellins. Accordingly, it is weakly grew promoting. A mutant of the fungus Gibberella fujikuroi converted to steviol in 13 - Hydroxygibberellin. Steviol inhibited oxidative phosphorylation in rat mitochondria and acts as a repellent against the aphid Schizapis graminum.

Toxicity

Ames test (S9 activation, chromosome aberration, micronucleus assay and the HPRT test): to steviol was found to be weakly mutagenic and genotoxic in in vitro studies. The effect of metabolites of steviol - such as the 15 - Oxosteviol - attributed. Due to missing data steviol glycosides are not yet listed in North America as a sweetener.

Proof

Steviol can be analyzed by HPLC.