Alkaloids ofArundo donax

Chemistry of Natural Compounds
1976.0

Abstract

We investigated the alkaloids of the epigeal part of Arundo donax (giant reed) from the "Subtropik" sovkhoz in Shaartuz region, Tadzhik SSR. From 60 kg of plant material, 0.18% ether-soluble and 0.04% chloroform-soluble bases were obtained via chloroform extraction. Donaxine (I) was isolated from ether-soluble bases by acetone treatment, and column chromatography of the mother liquor on Al₂O₃ yielded new alkaloid donaxaridine (II, mp 175-176°C, [α]ᴅ ± 0°, C₁₁H₁₄N₂O₂) and known donaxarine (III, mp 218-220°C, [α]ᴅ ± 0°, C₁₃H₁₆N₂O₂). Spectroscopic (IR, UV, NMR, mass) and chemical analyses (acetylation, oxidation, condensation) revealed donaxaridine as 3-(β-methylaminoethyl)dihydroxyindole and donaxarine as oxindole-3-spiro-6'-(2',3'-dimethyltetrahydro-1,3-oxazine). Additionally, we re-evaluated l-cycloprotobuxine-C (I, mp 195-197°C, [α]ᴅ -62°, C₂₇H₄₃N₂), previously thought to be the levorotatory form of cycloprotobuxine-C (II). Comparison with an authentic sample showed physicochemical differences, indicating it is a stereoisomer. Mass spectrometry, NMR (methyl proton shifts), and saponification rate studies suggested the C₂₀ N(CH₃)₂ has α orientation and C₃ NH-CH₃ has e-axial orientation, leading to the structure 20α-dimethylamino-4,4,14a-trimethyl-3α-methylamino-9α,19-cyclo-5α-pregnane.

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