Lupinus albus

Vanillin, CgHgOj, is one of the most important synthetic perfumes. It is the active odorous ingredient of the vanilla pod, in which it occurs to the extent of about 2 per cent., appearing on the surface of the bean as a fine white crystalline efflorescence. It occurs naturally also in Sumatra benzoin (about 1 per cent.), Siam benzoin (15 per cent.), and the balsams of Tolu and Peru (traces). Numerous other bodies have been recorded as containing it, such as asafoetida, beetroot and asparagus, the seeds of Lupinus albus, the seeds of Sosa canina, etc. 

J. F. Johnson, D. L. Allan, C. P. Vance, and G. Weiblen, Root carbon dioxide fixation by phosphorus-deficient Lupinus albus. Plant Physiol. 7/2 19 (1996). 

M. Kamh, W. J. Horst, F. Amer, and H. Mostafa, Exudation of organic anions by white lupin Lupinus albus L.) and their role in phosphate mobilization from... 

J. Gerke, W. Romer, and A. Jungk, The excretion of citric and malic acid by proteoid roots of Lupinus albus L. effects on soil solution concentrations of phosphate, iron, and aluminium in the proteoid rhizosphere in samples of an oxisol and a luvi.sol. Z. Pflatizenerndrhr. Bodenk. /57 289 (1994). 

Neumann G, Massonneau A, Langlade N, Dinkelaker B, Hengeler C, Romheld V, Martinoia E (2000) Physiological aspects of cluster root function and development in phosphorus-deficient white lupin (Lupinus albus L.). Ann Bot 85 909-919. doi http //aob.oxfordjournals.org/cgi/ content/abstract/85/6/909... 

Shane MW, De Vos M, De Roock S, Lambers H (2003a) Shoot P status regulates cluster-root growth and citrate exudation in Lupinus albus grown with a divided root system. Plant Cell Environ 26 265-273. doi http //www.blackwell-synergy.com/doi/abs/10.1046/ j. 1365-3040.2003.00957.x... 

All these data support the idea that QA may function as chemical defense compounds. We also tested whether this chemical defense is relevant for the survival of a lupin plant. Lupins offer a unique chance to explore this question experimentally plant breeders have selected "sweet" varieties, which have a very low alkaloid content. These varieties can be compared to semi-bitter or bitter ones. We have grown Lupinus albus strains that differ in their alkaloid content in our experimental garden and greenhouse and have monitored their susceptibility to attack by plant pests. As can be seen from Figure 2, "sweet" lupins are preferentially eaten by rabbits (Cuniculus europaeus) or are infested by aphids (Aphidae) or leaf miners (Agromyzidae). Literature data also support the assumption that alkaloid-rich lupins are much more resistant to plant pests than "sweet" varieties (30-32). We conclude therefore, that QA are indeed important for the fitness of a lupin plant and that they constitute a major part of its chemical defense system, in which... 

Lupinus albus Albine Angustifoline Lupanine Sparteine... 

Bellester, D. R., Brunser, M. T Saitua, M. T Egana, E. 0 Yanez, E. O. and Owen, D. F. 1984. Safety evaluation of sweet lupin Lupinus albus cv. Multolupa). II. Nine-month feeding and multigeneration study in rats. Journal of Chemistry and Toxicology, 22 45 8. 

Yovo, K., Huguet, F Pothier, J., Durand, M. K., Breteau, M. and Narcisse, G. 1984. Comparative pharmacological study of sparteine and its ketonic derivative lupanine from seeds of Lupinus albus L. Planta Medica, 50 420 24. 

Wysocka, W. and Przybyl, A. 1993. (-l-)-Angustifoline A Minor Alkaloid from Lupinus albus. Planta Medica, 59 289. 

Wysocka, W. and Brukwicki, T. 1991. Minor alkaloids of Lupinus albus 13a-hydroxy-5-dehydromultiflorine and 13(3-hydroxy-5-dehydromultiflorine. Planta Medica, 57 579-580. 

Wysocka, W., Brukwicki, T., Macioszek, E. and Wolski, W. 1988. The influence of the isolation method on the quantitative and qualitative composition of the alkaloids from Lupinus albus seeds. In Proceedings 5th International Lupin Conference, July 5-8, 1988 (Twardowski, T., ed.). Poznan, Polish Academy of Sciences, Institute of Bioorganic Chemistry. 

Wysocka, W. 1995. (+)-sparteine A new minor alkaloid from Lupinus albus L. Science of Legumes, 2 137-140. 

Baer von, D. and P6rez, I. 1990. Quality standard proposition for commercial grain of white lupin (Lupinus albus). In 6th International Lupin Conference. Proceedings, pp. 158-167. Temuco-Pucon ILA. 

Aniszewski, T., Drozdov, S. N., Kholoptseva, E. S., Kurets, V. K., Obshatko, L. A., Popov, E. G. and Talanov, A. V. 2001. Effects of light and temperature parameters on net photosynthetic carbondioxide fixation by whole plants of five lupin species Lupinus albus L., Lupinus angustifolius L., Lupinus luteus L., Lupinus mutabilis Sweet, and Lupinus polyphyllus Lindl.). Acta Agriculturae Scandinavica, 51 17-27. 

Wink, M. and Witte, L. 1984. Turnover and transport of quinolizidine alkaloids Diurnal variation of lupanine in the phloem sap, leaves and fruits of Lupinus albus L. Planta, 161 519-524. 

Beside this dermatoxic activity pederin (147) has various biological activities (92). When administered in appropriate doses to partially hepatectomized rats, this compound stimulates development of hepatic tissues. The inhibitory effect at the cellular level has been found in chicken heart fibroblast cultures, and mice embryo, dog kidney, HeLa, and KB cell lines. In plants, root growth of Lupinus albus is inhibited and mitosis in Allium cepa blocked at the metaphasic stage. Also, pederin (147) inhibits protein synthesis and growth of yeast cells. In addition, the treatment of rat ascites sarcoma with purified extracts of P. fuscipes produces almost complete regression. 

The formation of phytoalexins such as glyceollins and phaseollins requires C-prenylation by a range of pterocarpan prenyltransferase (PTP) activities, with dimethylallyl pyrophosphate (DMAPP) as the prenyl donor. For glyceollins and phaseollins, prenylation occurs at position C-2 or C-4 of glycinol or C-10 of 3,9-dihydroxypterocarpan. ° ° However, there are differing activities in other species. For example, in Lupinus albus (white lupin) a prenyltransferase acting at the C-6, -8, and -3 positions of isoflavones has been identified.PTPs have also been characterized in detail for the formation of prenylated flavanones in Sophora flavescens (see, e.g., Ref. 207). However, no cDNA clones for flavonoid-related prenyltransferases have been published to date. 

Shibuya, Y. et al.. New isoflavone glucosides from white lupine (Lupinus albus L.), Zeitschrift fuer Naturforschung C, 46, 513, 1991. 

Lupins are low in most minerals, with the exception of Mn. Lupinus albus is known to be an Mn accumulator and it has been suggested that high Mn might be the explanation for a reduced voluntary feed intake in some farm animals fed diets containing this species of lupin. However, excessive Mn levels in lupins do not appear to be the cause of reduced feed intake. 

Moschini, M., Masoero, F., Prandini, A., Fusconi, G., Morlacchini, M. and Piva, G. (2005) Raw pea (Pisum sativum), raw faba bean (Vicia faba var. minor) and raw lupin (Lupinus albus var. multitalia) as alternative protein sources in broiler diets. Italian Journal of Animal Science 4,59-69. 

Table 4.1.17A. Lupinseed meal sweet white (IFN 5-27-717). The ground whole seed of the species Lupinus albus, Lupinus angustifolius or Lupinus luteus. It has to contain less than 0.3g total alkaloids/kg. The species of seed must be listed after the name Sweet lupin seeds, ground . (From CFIA, 2007.) ...

Marschener, P., Crowley, D.E. Iron stress and pyoverdin production by a fluorescent pseudomonad in the rhizosphere of white lupin (Lupinus albus L.) and barley (Hordeum vulgare L.) Appl Environ Microbiol... 

Cantharidin (Figure 13), isolated from Spanish fly (Lylta vesicatoria L.), inhibits the growth of very young lupin (Lupinus albus L.) seedlings, Medico sativa L., Raphanus sativus L. and Brassica napus L. and Brassica napus L. seed germination at 20 ppm. It also inhibits the growth of wheat coleoptiles, com, tobacco and bean plants (241, 242). 

Wink, M. 1983. Inhibition of seed germination by quinolizidine alkaloids. Aspects of allelopathy in Lupinus albus L Planta 158, 365-368... 

The above structure is very different from that of the galactan associated with pectin in the seeds of Lupinus albus. This was shown to have a chain-length of 120 units.64 As no molecular weight measurements have been carried out on this material, it is not known whether the molecule is linear or branched. 

Lipoaldehydes, II, 123 Lipositol, III, 47, 343 Lithium aluminum hydride, for hydrogenation of 1,2-epoxides, V, 22 Lithium chloride, influence upon the activity of pancreatic amylase, V, 237 Lithium hypochlorite, III, 137 Liver, fat conversion by isolated, II, 141 ketogenesis in isolated, II, 155 Lobry de Bruyn-Alberda van Ekenstein transformation, III, 113 Locust bean mucilage, IV, 267 Lucerne seed, emulsins, V, 63 Lucerne seed, mucilage, IV, 266, 267 Lupinus albus, galactan from seed of, II, 248... 

Its enantiomer, (+)-sparteine, is also a natural product, but is more easily obtained by resolution and reduction of the racemic lactam 6164 (obtained from the bitter lupin Lupinus albus). Nonetheless, (+)-60 is much less readily available than (-)-60, and its general use in synthesis is impractical at present. Sparteine s two diastereoisomers a-isosparteine 64 and (3-isosparteine 65 also occur naturally, though they are more conveniently obtained by isomerisation of (-)-sparteine 60 via the enamines 62 and 63.65 Although both... 

SCHROEDER, G., ZAHRINGER, U., HELLER, W EBEL, J., GRISEBACH, H Biosynthesis of antifungal isoflavonoids in Lupinus albus. Enzymatic prenylation of genistein and 2 -hydroxygenistein. Arch Biochem. Biophys., 1979,194,535-536. 

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