Alkaloids ofRhinopetalum bucharicum the structure of rhinoline

Chemistry of Natural Compounds
1979.0

Abstract

From the epigeal part of Rhinopetalum bucharicum (Liliaceae) collected in the Darvaza range of the Pamir-Alai in the flowering period, 0.2% combined alkaloids were isolated by chloroform extraction. Silica gel column chromatography yielded solanidine, a new alkaloid rhinoline (C₃₅H₅₇NO₇, mp 255-257°C, [α]ₚ -53.2°), and another base (mp 301-302°C). The IR spectrum of rhinoline showed absorption bands for hydroxy groups, -CH₃/-CH₂-, N-CH₃, C=CH, and glycoalkaloids. Rhinoline formed pentaacetylrhinoline via acetylation, and hydrolysis gave aglycone rhinolidine (C₂₈H₄₇NO₂, mp 199-201°C, [α]ₚ -52.9°) and D-glucose. IR, MS, and NMR data indicated rhinolidine has a Δ⁵-3β-OH group, C₁₅ α-axial OH, trans-linked B/C and C/D rings, and an edpetilidine skeleton. Klyne's rule showed a β-glycosidic bond, so rhinoline was proposed as rhinolidine 3β-D-glucopyranoside. From Korolkowia sewerzowii, mother liquors were chromatographed to isolate korsidine, sevedine, korseverinine, and a new base (C₃₀H₄₇NO₂, mp 241-243°C); its IR spectrum showed OH, N-CH₃, C=C, and MS peaks characteristic of steroid alkaloids.

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