S. Yu. Yunusov

Alkaloids of Peganum harmala

Dipegine (1) and dipeginol (2) were isolated fromPeganum harmala.The structures of these alkaloids were established by mass and IR spectra

Structure of sibirine

The new optically based sibirine with [α]D-22.5° (c 0.81; chloroform), M+ 183, has been isolated from the epigeal part of theNitraria sibirica by column chromatography. On the basis of the results of chemical transformations (acetylation, oxidation), analysis of spectral characteristics (UV, IR, mass, PMR, ORD), and also a comparison of the alkaloid with the N-methyl derivatives of nitramine and isonitramine, the structure of sibirine has been established as methyl-2-azaspiro[5.5] undecan-7-o1.

The roots ofDictamnus angustifolius

SummaryFrom the roots ofDictamnus angustifolius G. Don. collected in Chimgan at the end-of-fruit-bearing stage have been isolated alkaloids dictamnine, skimmianine, γ-fagarine, isodictamnine, isopteleine, and preskimmianine, the limonoid fraxinellone, and the steroid β-sitosterol. This is the first time that any of these substances, with the exception of dictamnine and skimmianine, have been found in this plant.

Alkaloids of Gentiana olivieri

SummaryThe separation of the chloroform fraction of the combined alkaloids ofG. olivieri according to basicities (pH 6.0 and 4.0) has yielded gentioflavine, gentiananine, and the new base oliveramine, C20H20N2O4. On the basis of its UV, IR, NMR, and mass spectra structure (I) has been put forward as the most probable for it.

Isonitramine — A new alkaloid from Nitraria sibirica

A benzene solution of the ether-soluble nonphenolic fraction of the combined alkaloids was separated according to basicity with c i t ra te-phosphate buffer solutions having pH values from 8 to 4 at intervals of 1 pH unit. By working up the ethereal fraction with pH 8 we isolated a white crystalline optically active base (I) with [~]D -30° (c 1.36; chloroform), mp 102-103°C, which we have called isonitramine.

Alkaloids of Haplophyllum perforatum

Summary1. From the epigeal part of the plantH. perforatum growing in the Dzhungarian Ala-Tau we have isolated the lignane eudesmin, the known alkaloids evoxine, flindersine, and 7-isopentenyloxy-γ-fagarine, and the new alkaloids haplamine, glycoperine, and methylevoxine. It has been shown that haplamine has the structure of 6-methoxyflindersine, glycoperine the structure of 7-hydroxy-4,8-dimethoxyfuranoquinoline 7-O-α-L-rhamnopyranoside, and methylevoxine the structure of 4,8-dimethoxy-7-(2′-hydroxy-3′-methoxy-3′-methylbutoxy)furanoquinoline.

Structure of norloline, loline, and lolinine

SummaryOn the basis of a study of the oxidation products, the course of the Hofmann degradation, the reduction of tetrahydrohemiloline methiodide, and other properties of the alkaloids investigated, it has been established that norloline has the structure of 6-amino-1, 5-oxypyrrolizidine, loline that of N-methyl-6-amino-1, 5-oxypyrrolizidine, and lolinine that of N-acetyl-N-methyl-6-amino-1, 5-oxypyrrolizidine.

Structure of the alkaloid schoberine

The structure of an alkaloid of a new type, schoberine, isolated from plants of the genusNitraria has been established by the x-ray structural method as perhydro-1,10-propano-4a,8a-diazaphenanthrene. Its chemical and spectral properties have been studied.

Alkaloids ofNitraria schoberi. Structure of nitraraine

The dehydration of nitraraine leads to the formation of 1-(2′,6′-dimethylbenzyl)-β-carboline, together with other products. Several isomeric 1-(dimethylbenzyl)-β-carbolines have been synthesized for comparison. The products of acylation, hydrogenation, and oxidation of the alkaloid nitraraine have been studied. The results obtained have shown its structure as (±)-16-hydroxymethylyohimb-16-ene.

Structures of nitramine and isonitramine — Alkaloids of a new type from plants of the genusNitraria

The proof of the structures of two isomeric alkaloids — nitramine and isonitramine — from two species of plants of the genusNitraria is given. Their diastereoisomerism with respect to the C7 asymmetric atom has been established. This is the first time that alkaloids with the structure of 2-azaspiro[5,5]undecan-7-ol have been found.