(+/-)-Heterocarpine, a hydroxymethylated isoquinoline alkaloid from Ceratocapnos heterocarpa
1998
Suau, R. | Posadas, N. | Silva, M.V. | Valpuesta, M.
Heterocarpine, a novel alkaloid from Ceratocapnos heterocarpa, has been characterised as (+)-1-hydroxymethyl-2-(3-hydroxy-4-methoxybenzyl)-7- hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline. The alkaloid was synthesized from the corresponding 3,4-dihydro isoquinoliniun salt. A key step in the process is the acid resin catalysed methanolysis of the 1-carbamoyl isoquinoline. The structural correlation of the hydroxymethylated alkaloids heterocarpine and malacitanine with their unsubstituted counterparts capnosine and caseamine, also present in the plant, might be of biosynthetic significance.
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