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The Amaryllidaceae alkaloids (+)-tazettine [(+)-(3S,4aS,6aS,13bS)-3-methoxy-5-methyl-3,4,4a,5,6,6a-hexahydro-8H,11H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indol-6a-ol, C18H21NO5] and partially hydrated (+)-3-epimacronine [(+)-(3S,4aS,6aR,13bS)-3-methoxy-5-methyl-3,4,4a,5,6,6a-hexahydro-8H,11H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indol-8-one 0.066-hydrate, C18H19NO5.0.066H2O] have been extracted from Galanthus plicatus subsp. byzantinus, while (+)-3-O-demethylcriwelline [(+)-(3R,4aS,6aS,13bS)-5-methyl-3,4,4a,5,6,6a-hexahydro-8H,11H-[1,3]dioxolo[6,7][2]benzopyrano[3,4-c]indole-3,6a-diol, C17H19NO5] has been isolated from the plant Galanthus gracilis. These compounds have the ring skeleton of the tazettine or [2]benzopyrano[3,4-c]indole subgroup. (+)-3-O-Demethylcriwelline is a new alkaloid and is the 3-O-demethyl C3-epimer of (+)-tazettine. The geometrical features of the compounds differ predominantly in the conformations of the pyrrolidine and pyran rings.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, I, II, III

fcf

Structure factor file (CIF format)
Contains datablock I

fcf

Structure factor file (CIF format)
Contains datablock II

fcf

Structure factor file (CIF format)
Contains datablock III

CCDC references: 130565; 130566; 130567

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