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Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol hydro-bromide].

ABSTRACT: X-ray crystallographic analysis of the title hydro-bromide salt, C(10)H(20)N(+)·Br(-), of (1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol defines the absolute and relative stereochemistry at the five chiral centres in steviamine, a new class of polyhydroxy-lated indolizidine alkaloid isolated from Stevia rebaudiana (Asteraceae) leaves. In the crystal structure, mol-ecules are linked by inter-molecular O-H?Br and N-H?Br hydrogen bonds, forming double chains around the twofold screw axes along the b-axis direction. Intra-molecular O-H?O inter-actions occur.

SUBMITTER: Thompson AL 

PROVIDER: S-EPMC2971327 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol hydro-bromide].

Thompson Amber L AL   Michalik Agnieszka A   Nash Robert J RJ   Wilson Francis X FX   van Well Renate R   Johnson Peter P   Fleet George W J GW   Yu Chu-Yi CY   Hu Xiang-Guo XG   Cooper Richard I RI   Watkin David J DJ  

Acta crystallographica. Section E, Structure reports online 20091028 Pt 11

X-ray crystallographic analysis of the title hydro-bromide salt, C(10)H(20)N(+)·Br(-), of (1R,2S,3R,5R,8aR)-3-hydroxy-meth-yl-5-methyl-octa-hydro-indolizine-1,2-diol defines the absolute and relative stereochemistry at the five chiral centres in steviamine, a new class of polyhydroxy-lated indolizidine alkaloid isolated from Stevia rebaudiana (Asteraceae) leaves. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯Br and N-H⋯Br hydrogen bonds, forming double chains around the  ...[more]

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