Quinolizidine alkaloids Fabaceae

This group of alkaloids primarily is found in the subfamily Papilionoideae of the family Fabaceae quinolizidine alkaloids are the most commonly encountered alkaloids in this family (Howard and Michael, 1986 Kinghom and Ba-landrm, 1984). Quinolizidine alkaloids have been reported from all plant parts, but in most plants, they are synthesized in young photosynthetic tissues (Wink, 1987). 

Fabaceae. Quinolizidine alkaloidal evolution proceeded by skeletal specialization in tropical regions and by variation of oxidation level in temperate regions (10). 

Wink, M. and Carey, D.B. (1994). Variability of quinolizidine alkaloid profiles of Lupinus argenteus (Fabaceae) from North America, Biochem. Systematics EcoL, 22, 663-669. 

Lopez et al. reported the isolation of three quinolizidine alkaloids such as lupanine (30), 13-a-hydroxylupanine (31), and 17-oxo-lupanine (32) from Lupinus perennis Wild, (family Fabaceae) all these three isolates were found to have potent activity in enhancing glucose-induced insulin release from isolated rat islet cells in a glucose concentration-dependent manner. While the synthetic compound 2-thionosparteine... 

Table 28 Quinolizidine alkaloid frequencies in plant populations of Fabaceae in the boreal zone during 1999-2003...

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. 

Figure 1.7 Example of the complicated biochemistry and physiology of alkaloid formation quinolizidine alkaloids (QAs) in lupins (genus Lupinus, Fabaceae). QAs are formed in ieaf chioropiasts and exported via the phloem all over the plant. QAs predominantly accumulate in vacuoles of epidermal tissue. Organs important for survival and reproduction, such as flowers and seeds, store especially high amounts of defence alkaloids. (See Plate 6 in colour plate section.)...

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. 

A number of unusual quinolizidine alkaloids have been isolated from various leguminous plants now classified in the Fabaceae, such as lamprolobine (59) from Lamprolobium fruticosum 182], and podopetaline (60), a new member of the Ormosia group of alkaloids that was isolated from Podopetalum ormondii [831. Other genera, including Templetonia and Hovea, have been found to produce well-known leguminous alkaloids such... 

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. 

CijHjoNjOj. Mr 260.34, mp. 210 C, (aJc -147.7° (C2H5OH). Tetracyclic quinolizidine alkaloid of the sparteine type with an a-pyridone structure from several genera of the Fabaceae (e. g., Baptisia, Caulophyl-lum, Sophora). In analogy to 13-hydroxylupanine, esters of B. occasionally occur, and generally as the acetates. The 13-epimer epi-baptifoline (mp. 215 C, [o]d 138.9°) is often found together with B. . 

Mr 264.37, mp. 178-180 C, [a]p +51.8 (C2H5OH). A quinolizidine alkaloid of the sparteine type from many genera of the Fabaceae. It is mildly toxic [LD50 (rat i.p.) 199 mg/kg]. 13-H. is pur rted to have antiarrhythmic and hypotensive activities. Not only the 13/3- but also the 13a-isomer occur as natural pr ucts in plantsthe latter being more abundant. 

C,oH NO, Mr 169.27, mp. 68.5-69.2°C, bp. 269-270 °C, [alo -21° (C2H5OH) racemate, mp. 63 - 64°C (59 °C). L. and the 5-epimer epi-lupinine mp. 77-78°C, [alo +32° (CjHjOH)) are quinolizidine alkaloids of which only few members contain the bicyclic lupinine type structure. They occur in several Fabaceae genera . L. is also a component of the Che-nopodiaceae Anabasis aphylla. In addition, esters of epi-lupinine with acetic, coumaric, and ferulic acid are known as natural products. Several syntheses, some enantiosclective, of these simple quinolizidine alkaloids have been reported. ... 

C.sHjjNjO, Mr 246.35, mp. 108-109 °C, [a]g -317° (CHgOH). A quinolizidine alkaloid of the sparteine type from some Lupinus species and Cadia ellisiana (Fabaceae). Analogous to lupanine a I3a-hydroxy derivative (C15H22N2O2, Mr 262.35) of M. is also known. It is found in Lupinus albus and L. cosentinii. A depressive activity of M. on the central nervous system has been described. ... 

C20H33N3, Mr 315.50, oil, [a][)-ll°. A quinolizidine alkaloid of the ormosanine type. It occurs together with several isomers and other structures derived from the same skeleton in some South American Fabaceae species of the genus Ormosia (see also ormosanine). Ut Waterman 8, 197-239. 

Korir E, Kiplimo JJ, Crouch NR, Moodley N, Koorbanally NA. Quinolizidine alkaloids from Sophora veltina subsp zimbabweensis (Fabaceae Sophoieae). Nat Prod Common 2012 7(8) 999-1003. 

Alkaloids are important not only for individuals and species but also for the populations. A species is an evolutionarily independent population or group of populations. In the population of the same species can be individuals with different content of alkaloids. Fabaceae populations demonstrate that individual plants, even in the same species, differ largely when their quinolizi-dine alkaloid (QAs" ) content is checked. Also, individuals were found with no indication of quinolizidine alkaloids (QAs ). Probably the same situation occurs in all other alkaloids and species populations. Especially in animals, the sequestered alkaloids from their food make this phenomenon clearly observable. The problem of alkaloid research in populations is that scientists... 

Quinolizidine alkaloids are found in several tribes of the Fabaceae. These compounds have been implicated in acute intoxication and death of grazing stock. Since sweet lupin varieties have gained considerable importance as a stock food in some countries, monitoring of quinolizidine alkaloid levels is necessary since high levels may lead to fodder rejection or intoxications. 

Alkaloids of the genus Baptisia (Fabaceae) have been studied by Mabry and co-workers (Mears and Mabry, 1971 Waller and Nowacki, 1978). These compounds are highly variable within this genus, which contains about 16 species and occurs widely in the eastern half of North America. Hundreds of populations of these species have been studied. Several quinolizidine alkaloids are found in Baptisia species (Fig. 30.11). 

Baumel, P., L. Witte, F. Czygan, and P. Proksch, Transfer of quinolizidine alkaloids from various host plants of the Fabaceae to parasitizing Cuscuta species, Biochem. Syst. Ecol., 22, 647-656 (1964). 

Matrine (29) is a quinolizidine alkaloid isolated from several species of the genus Sophora (Fabaceae), mainly S. alopecuroides L. and S.flavescens Aiton. The latter has widely been used by traditional Chinese medicine, and its pharmacological properties were correlated to matrine contents [115, 116],... 

Figure 1.11. The three tribes of Fabaceae with quinolizidine alkaloids. The Sophoreae are close to the original stock of all Fabaceae. The more advanced tribes (Phaseoleae, Vicieae, and Trifolieae) are either entirely alkaloid-free or accumulate alkaloids of different origin, as in some species of Phaseoleae, Loteceae, Hedysaraceae, and Galegeae, although more primitive, are without alkaloids of the quinolizidine type. Probably an independent evolutionary line of the Fabaceae evolved which was not directly related to Sophoreae, Genisteae, and Podalyrieae tribes (Nowacki, 1960). Courtesy of the journal.

Quinohzidine alkaloids, hypothetically derived from quinolizidine (10-18), are a special group of bicyclic, tricyclic and tetracyclic secondary metabolites of some legumes, especially legumes of the genera Lupinus, Baptisia, Thermopsis, Genista, Cytisus, Chamae-cytisus. Laburnum and Sophora (Fabaceae), which occur as a complex mixture of several compounds. Quinolizidine alkaloids are... 

Quinolizidine alkaloids occur in seeds (beans) of certain species of lupines Lupinus spp., Fabaceae), including domesticated varieties. In Europe, Africa and America, lupines have been used as valuable pulses for human nutrition and feeding livestock from ancient times. Native species growing in south-western Europe are white lupine (L. albus), blue (narrow leaf) lupine (I. angustifolius) and yellow lupine (L. luteus). Yellow lupine is currently grown in Western Australia, particularly for feed, and for human nutrition in many countries of Asia. Beans of pearl (Andean) lupine (I. mutabilis), called tarhui or tarwi, are eaten as pulses by South American Indians of the Andes region and also used as an oil crop (mainly in Chile). 

Quinolizidine alkaloids are found in many species of the Fabaceae, Ber-beridaceae, Leguminosae, and Solanaceae and are derived from lysine (67, 68). Some quinolizidine alkaloids are very toxic insecticides that have the potential of commercial use for the control of insects. For example, the alkaloid ryanodine, which is found in the stems and roots of Ryania speciosa, is effective as both an insect contact and stomach insecticide and is particularly effective against Lepidoptera. It has been used to control the codling moth without affecting parasites and predators of the moth (69). 

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