Natural cis-solamin is a mixture of two tetra-epimeric diastereoisomers: biosynthetic implications for Annonaceous acetogenins.
The anti-tumour natural product cis-solamin has been shown to occur as a mixture two of tetra-epimeric diastereoisomers 1A and 1B, whereas solamin (6) was isolated as a single diastereoisomer; the biosyntheses of 1A/B and 6 are likely to involve enzyme-mediated cyclohydrations of the bis-epoxide acetogenins anti-diepomuricanin A2 and syn-diepomuricanin A1 respectively, where addition of water occurs regioselectively at either C15 or C20.
Hu
Yulai
Y
School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.
Cecil
Alex R L
AR
Frank
Xavier
X
Gleye
Christophe
C
Figadère
Bruno
B
Brown
Richard C D
RC
D054378:Acetogenins; D001558:Benzethonium / Q000737:chemistry* / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism; D005233:Fatty Alcohols / Q000737:chemistry* / Q000378:metabolism*; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism*; D029562:Magnoliaceae / Q000378:metabolism*; D008958:Models, Molecular; D013237:Stereoisomerism
D054378:Acetogenins; D004852:Epoxy Compounds; D005233:Fatty Alcohols; D007783:Lactones; D001558:Benzethonium