Detail of "471-80-7"

CAS Number:
471-80-7
Name:
Kaur-16-en-18-oic acid,13-hydroxy-, (4a)-
Superlist Name:
Stevioside
Molecular Structure:
Formula:
C₂₀H₃₀O₃
Molecular Weight:
318.45
Deleted CAS:
13095-77-7,4574-62-3
Synonyms:
Kaur-16-en-18-oicacid, 13-hydroxy- (7CI,8CI);Steviol (6CI);(-)-Steviol;13-Hydroxykaurenoicacid;Ent-13-hydroxy-kauran-16-en-19-oic acid;NSC 226902;
Density:
1.17 g/cm³
Boiling Point:
464.5 °C at 760 mmHg
Flash Point:
248.8 °C

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Reference

Effects of Stevia rebaudiana natural products on rat liver mitochondria: Effects of Stevia rebaudiana natural products on rat liver mitochondria. Bracht, Ana Kelmer; Alvarez, Mauro; Bracht, Adelar (Univ. Maringa, Maringa, Brazil). Biochem. Pharmacol., 34(6), 873-82 (English) 1985. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) The effects of several natural products extd. from the leaves of S. rebaudiana on rat liver mitochondria were investigated. The compds. used were stevioside [57817-89-7] (a non-caloric sweetener), steviolbioside [41093-60-1], isosteviol [27975-19-5], and steviol [471-80-7]. Total aq. exts. of the leaves were also investigated. S. rebaudiana Natural products inhibited oxidative phosphorylation, ATPase [9000-83-3] activity NADH oxidase [9032-21-7] activity, succinate oxidase [9014-35-1] activity, succinate dehydrogenase [9002-02-2], and L-glutamate dehydrogenase [9029-12-3]. The ADP/O ratio was decreased. Substrate respiration (state II respiration) was increased at low concns. (￡0.5 mM) and inhibited at higher concns. (1 mM or more). In uncoupled mitochondria, inhibition of substrate respiration was the only effect obsd. Net proton ejection induced by succinate and swelling induced by several substrates were inhibited. Of the compds. investigated, the sweet principle stevioside was less active. Thus, in addn. to the inhibitory effects, S. rebaudiana natural products may also act as uncouplers of oxidative phosphorylation. The possible physiol. consequences of the ingestion of stevioside and S. rebaudiana aq. exts. are discussed.

Metabolically activated steviol, the aglycone of stevioside, is mutagenic: Metabolically activated steviol, the aglycone of stevioside, is mutagenic. Pezzuto, John M.; Compadre, Cesar M.; Swanson, Steven M.; Nanayakkara, N. P. Dhammika; Kinghorn, A. Douglas (Coll. Pharm., Univ. Illinois, Chicago, IL 60612, USA). Proc. Natl. Acad. Sci. U. S. A., 82(8), 2478-82 (English) 1985. CODEN: PNASA6. ISSN: 0027-8424. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Stevioside [57817-89-7] was not mutagenic as judged by utilization of Salmonella typhimurium strain TM677, either in the presence or in the absence of a metabolic activating system. Similar neg. results were obtained with several structurally related sweet-tasting glycosides. However, steviol [471-80-7], the aglycon of stevioside, was highly mutagenic when evaluated in the presence of a 9000 ′ g supernatant fraction derived from the livers of Aroclor 1254-pretreated rats. Expression of mutagenic activity was dependent on both pretreatment of the rats with Aroclor 1254 and addn. of NADPH; unmetabolized steviol was not active. The structurally related species, isosteviol, was not active regardless of metabolic activation. Similarly, chem. redn. of the unsatd. bond linking the C-16 and -17 positions of steviol resulted in the generation of 2 isomeric products, dehydrosteviol A and B, that were not mutagenic. In addn., ent-kaurenoic acid was inactive. It is therefore clear that a metabolite of an integral component of stevioside is mutagenic; structural features of requisite importance for the expression of mutagenic activity include OH at position 13 and an unsatd. bond joining the C atoms at positions 16 and 17. A potential metabolite of steviol, steviol-16a,17-epoxide, was synthesized chem. and found to be ineffective as a direct-acting mutagen. Thus, although stevioside itself appears innocuous, it would seem prudent to expeditiously and unequivocally establish the human metabolic disposition of this substance.

Detail of "471-80-7"

Kaur-16-en-18-oic acid,13-hydroxy-, (4a)-

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Reference