Cytisus Alkaloids

Cytisine, methylcytisine, and anagyrine were obtained from Cytisus laburnum (Leguminosae). All parts of the plant are poisonous because of the cytisine. It is one of the Cytisus alkaloids (95, 96). 

The most common tetracyclic alkaloid, (-)-sparteine, was isolated from Cytisus scoparius with (-)-isosparteine and (+)-lupanine. Sparteine sulfate has been used as an oxytocic. 

These tetracyclic and tricyclic quinolizidine alkaloids are commonly known as lupine alkaloids. The simple bicyclic alkaloids such as lupinine are produced from two lysine units via cadaverine. Tricyclic alkaloids such as cytisine are considered to be formed from tetracyclic alkaloids through anagyrine-type alkaloids (Fig. 5.2.7). 

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Mass spectral data have also been employed for biological studies aimed at determining the distribution of quinolizidine alkaloids within a plant. For instance, the analysis of stem sections of Lupinus polyphyllus and Cytisus scoparius by laser desorption mass spectrometry led to the conclusion that these alkaloids are restricted to the epidermis and probably also to the neighboring one or two subepidermal cell layers <1984MI230>. 

In addition to lupines, poison-hemlock and Nicotiana spp., other plant species of the genera Genista, Prosopis, Lobelia, Cytisus, Sophora, Pinus, Punica, Duboisia, Sedum, Withania, Carica, Hydrangea, Dichroa, Cassia, Ammondendron, Liparia, and Colidium contain potentially toxic and teratogenic piperidine alkaloids. Many plant species or varieties from these genera may be included in animal and human diets (Keeler and Crowe, 1984). 

Plant Part Alkaloid Concentration (mmol/kg fresh weight) Lupinus polyphyllus Cytisus scoparius ... 

L. angustifolius and is, like sparteine, probably found in all lupine species in different concentrations, from main compounds to mere traces. Lupanine is the main alkaloid in the seeds of Lupinus rotundiflorus, Lupinus exaltatus and Lupinus mexicanus. It has been discovered in considerable amounts in Lupinus mon-tanus and Lupinus madrensis, but only traces were noted in Lupinus elegans. Moreover, lupanine occurs in Cytisus scoparius and Leontice eversmannif-. ... 

Notes Physostigmine as synonymous name Scopolamine as synonymous name ° Narcotine as synonymous name In small concentrations in many species especially in Lupinus spp. The main alkaloid in Cytisus scoparius Low concentrations in natural sources. Synthetical theophy-Une is used. 

Wink, M., Witte, L., Hartmann, T., Theuring, C. and Volz, V. 1983. Accumulation of quinolizidine alkaloids in plants and cell suspension cultures Genera Lupinus, Cytisus, Baptisia, Genista, Laburnum, and Sophora. Planta Medica, 48 253-257. 

Quinolizidine alkaloids are mainly found in plants of the Leguminosae/Fabaceae family. They deter or repel feeding of herbivores, and are toxic to them by a variety of mechanisms. A number of plants (Laburnum, Cytisus, Lupinus) containing significant quantities of these alkaloids must be regarded as potentially toxic to humans, and are known to be responsible for human poisoning. 

Sparteine, lupanine, and other QA exhibit antiarrhythmic properties. Since only sparteine can be isolated easily from broom (Cytisus scoparius) it is the only lupin alkaloid that is commercially available and exploited in medicine as an antiarrhythmic drug. However, about 10% of all patients are unable to metabolize sparteine and suffer from sparteine intoxication. Because of these side effects and the availability of more reliable synthetic heart drugs, the use of sparteine in... 

For one group of alkaloids, the quinolizidine alkaloids, these experiments have already been performed (2,184,484,503,527). As mentioned before, QAs constitute the main secondary products of many members of the Leguminosae, especially in the genera Lapinas, Genista, Cytisus, Bapti-sia, Thermopsis, Sophora, Ormosia, and others (503). 

A dibasic alkaloid obtained from scoparium, the dried tops of broom, Sarothamnus scoparius (= Cytisus scoparius) (Legumino-sae). 

Cytisus scoparius (Scotch broom) contains the toxic alkaloid sparteine and related quinolizidine alkaloids, such as isosparteine and cytisine. Sparteine has been used as a marker of drug metabolism by CYP2D6 (28) and is covered in a separate monograph. 

Cytamen cyanocobalamin. cytarabine [ban, inn. jan, usan] (cytarabine hydrochloride [usan] Ara C Cytosar Cytosar-U ) is an antimetabolite cytotoxic ANTICANCER and ANTIVIRAL AGENT isolated from the mushroom Xerocomm nigromaculatus. It works by interfering with pyrimidine synthesis. Clinically, it can be used sys-temically in anticancer treatment mainly of acute leukaemia, cytidine diphosphate choline dticoline. cytidine diphosphocholine dticoline. cytisine is an alkaloid with CNS STIMULANT, RESPIRATORY STIMULANT and psychoactive properties. It has been used clinically as a respiratory stimulant in Russia. It is a common cause of poisoning by the seeds of Cytisus laburnum. 

COMMON BROOM Cytisus scoparius, L., Link, Family Fabaceae, is a shrub growing in Europe and Western Asia. The whole aerial part of the shrub, including the seeds, is poisonous due to the presence of the alkaloid sparteine. The sparteine content in the leaves and branch tips is at its highest in the month of May and decreases after flowering, which takes place in June. 

A quinolizidine alkaloid isolated from several brooms and lupins (Fabaceae), including Lupi-nus, Spartium and Cytisus. It has been used as an oxytocic and an anti-arrhythmia agent. Cardiac stimulant, higher doses - muscular trembling, inco-ordination, emesis, catharsis and finally paralysis of the respiratory and motor centres, cardiac arrest. 

Cytisus canariensis This Old Xbrld plant, introduced to Mexico, has been adopted as a shamanic drug by the Yaqui Indians (Di az, 1979 Fadiman 1965 Schultes Hofinann 1979). While the plant contains abundant cytisine, this alkaloid is not psychoptic. It is sometimes known in the literature as Genista canariensis. 

A survey has been contributed of the alkaloid content of 16 species of Spanish and Portuguese Leguminosae belonging to the Cytisus, Genista, Echinospartium, Stauracanthus, and Adenocarpus genera 13 quinolizidine or dipiperidine bases were identified, and their distribution in the various organs of the plants determined. 

Quinolizidine alkaloids occur in the species Lupinus, Cytisus and Genista of the papilionaceae. Lupinine 24, cytisine 25 and sparteine 26, the main alkaloid in common broom Cytisus... 

G. cinerea thus proves to be a plant of some chemotaxonomic interest, because its major alkaloidal constituents are esters of 13-hydroxylupanine, compounds which are characteristic of the genus Cytisus rather than of Genista. In Cytisus species, for instance, the biosynthetic sequence lupanine, 13-hydroxylupanine, 13-hydroxylupanine esters, is often observed. However, G. cinerea also contains alkaloids characteristic of the Genista genus, e.g. anagyrine and hystrine, although these are only present in very small amounts, and in fact anagyrine was not encountered in the extracts from some samples. ... 

Following the partial and total syntheses of a-isosparteine, the natural occurrence of Z-a-isosparteine in Lupinus cavdatus Kellogg was definitely established (310). More recently, the identity of Z-a-isospar-teine with genisteine has been confirmed (312). Genisteine was first considered, erroneously, to be an alkaloid of composition C16H28N2 (45, 46, 271), isolated from Cytisus scoparius L. For direct comparison and identification, recourse was had to additional derivatives aurichloride,... 

Grosser, G., L. Witte, V.P. Dedkov, and RC. Czygan. 1996. A survey of quinolizidine alkaloids and phenylethylamine tyramine in Cytisus scoparius (Leguminosae) from different origins. Z. Naturforsch. 51c 791-801. 

C12H20N2O, Mr 208.30, mp. 43-46°C, [a]o +15° (C2H5OH) racemate, mp. 50- 60 °C. A. is a piperidine alkaloid, occurring together with quinolizidine alkaloids in many Fabaceae genera (e.g., Ammodendron, Baptisia, Cytisus, Lupinus). Its Structure is closely related to that of anabasine. 

C14H22N2O, Mr 234.34, mp. 80.5-81 °C, [oId -7.5° (+5.2°) (C2H5OH). A tricyclic quinolizidine alkaloid of the sparteine type from 4 genera of the Fabaceae Cytisus, Diplotropis, Lupinus, Ormosia). A. exists as 2 optically active isomers The biosynthesis of A. in plants is assumed to involve ring opening and side chain degradation of lupanine as a precursor Ut. Waterman 8, 197-239. Planta Med. 59, 289 (1993). Pelletier 2, 105-148. 

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