Alkaloids ofVeratrum lobelianum. the structure of germinalinine

Chemistry of Natural Compounds
1975.0

Abstract

Continuing the separation of the combined alkaloids (31.5 g) of the soluble metaphosphate part fractionated by Salzberger's method from Veratrum lobelianum, we chromatographed it on a silica gel column and separated the benzene eluate with a pH 4.0 acetate buffer, leading to the isolation of the new alkaloid germinalinine (III), C₃₉H₆₁NO₁₃, with mp 168-170°C (ether), [α]ᴰ -52.08° (pyridine). The IR spectrum of (III) showed absorption bands at 3490 cm⁻¹ (OH) and 1750, 1255 cm⁻¹ (ester C=O). Saponification of (III) gave the amino alcohol germine (IV) and l-2-methylbutyric, d-2,3-dihydroxy-2-methylbutyric, and acetic acids. Acetylation of (III) with acetic anhydride in pyridine yielded a derivative (V, mp 205-207°C) identical to germbudine triacetate (II), and methanolysis of (III) produced germbudine (I). Comparative NMR spectral analysis (19-CH₃ proton signal shifted 1 Hz downfield vs. germbudine (I)) and gentle methanolysis confirmed the acetic acid residue at C₇. Thus, germinalinine was structured as 7α-acetyl-3β-(d)-2,3-dihydroxy-2-methylbutyryl-15α-(l)-2-methylbutyrylgermine. Germbudine (for the first time) and the new alkaloid germinalinine (III) were isolated from V. lobelianum.

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