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Abstract
The steroidal alkaloid 3β, 20α-diamino-pregn-5-ene (kurchamine) obtained from the stem bark of Holarrhena antidysenterica is reported to have appreciable amoebicidal activity. Its three stereoisomers namely 3α, 20β-diamino-pregn-5-ene, 3β, 20β-diamino-pregn-5-ene and 3α,20α-diamino-pregn-5-ene and their intermediate stereoisomeric monoamino pregnene alkaloids namely 3β-amino-pregn-5-ene-20-one, 3α-amino-pregn-5-ene-20-one, 20α -amino-pregn-5-ene-3β-ol, 20β-amino-pregn-5-ene-3β-ol were synthesized. The natural stereoisomer and synthesized diamino and monoamino stereoisomers were N-methylated and all the compounds were evaluated for amoebicidal activity comparison. The natural stereoisomer 3β,20α-diamino-pregn-5-ene (kurchamine) was found to be superior than other stereoisomers and N-methylation was found to have insignificant effect on amoebicidal activity of stereoisomers. Stereoisomers of kurchamine, the natural pregnene alkaloid of Holarrhena antidysenterica (stem bark) and their intermediate monoamino stereoisomers were synthesized from 16-dehydropregnenolone acetate (16-DPA). Kurchamine and synthesized stereoisomers along with their N-methylated analogs were evaluated for their antiamoebic activity.
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