Glycoperine — A new alkaloid from Haplophyllum perforatum

Chemistry of Natural Compounds
1974.0

Abstract

From the total alkaloids of the epigeal part of Haplophyllum perforatum collected in the Dzhungarian Ala-Tau, a new alkaloid glycoperine (C₁₉H₂₁NO₈) with mp 224-225°C (methanol), molecular weight 391, and [α]ᴅ -66.3° (pyridine) was isolated. Its structure was determined by spectral analyses (IR, UV, MS, NMR), alkaline fusion (yielding haplopine, confirming a 4,8-dimethoxyfuroquinoline nucleus), hydrolysis (producing haplopine and L-rhamnose), and calculation of the Klyne's Mᴅ value (indicating an α-glycosidic bond). Glycoperine is the first furoquinoline glycoalkaloid, with L-rhamnose attached to the 7-position of haplopine via an α-glycosidic bond. The partial synthesis of its acetyl derivative (by condensing 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl chloride with haplopine) yielded a product identical to the natural triacetyl derivative (II) in TLC, melting point, and spectral (MS, IR, NMR) data.

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