Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine

Abstract

Contrary to predictions based on earlier observations, it is now found that label from DL-[6-14C]lysine and from [6-14C]-Δ1-piperideine does not enter the three C5 segments of lupanine with equal efficiency. One of the C5 segments is labelled at a significantly higher level than the other two C5 segments, which show identical levels of labelling. A new biogenetic model is proposed, which is consistent with these new findings as well as with all other regio- and stereochemical evidence on the mode of incorporation of precursors that is available.

Characterization of the genetic factors affecting quinolizidine alkaloid biosynthesis and its response to abiotic stress in narrow‐leafed lupin (Lupinus angustifoliusL.)

“…LaL/ODC is involved in the first step of the QA biosynthetic pathway, the decarboxylation of lysine to the intermediate cadaverine (Bunsupa et al, ). A copper amine oxidase functions in the deamination of cadaverine to yield a pathway intermediate common to the formation of all QAs (Golebiewski & Spenser, ; Leistner & Spenser, ), with LaCAO recently identified as being involved in this reaction (Yang et al, ). After the formation of QAs such as lupanine, sparteine, multiflorine, and lupinine, further modification can yield a variety of structurally related QAs (Ohmiya, Saito, & Murakoshi, ; Saito, Suzuki, Takamatsu, & Murakoshi, ; Suzuki, Murakoshi, & Saito, ; Wink & Hartmann, ).…”

Lysine Decarboxylase Catalyzes the First Step of Quinolizidine Alkaloid Biosynthesis and Coevolved with Alkaloid Production in Leguminosae

“…QAs are synthesized through the cyclization of the cadaverine unit (Golebiewski and Spenser, 1988), which is produced through the action of Lys decarboxylase (LDC; EC 4.1.1.18) (Figure 1), via a postulated enzyme-bound intermediate . The various skeletons of QAs [e.g., bicyclic alkaloids such as (2)-lupinine and (+)-epilupinine or tetracyclic alkaloids such as (+)-multiflorine, (+)-lupanine, and (+)-matrine] are then further modified by tailoring reactions (e.g., dehydrogenation, oxygenation, esterification, and glycosylation) to yield hundreds of structurally related alkaloids (Ohmiya et al, 1995).…”

“…Some QAs exhibit beneficial pharmacological properties, such as cytotoxic, antiarrhythmic, oxytocic, hypoglycemic, and antipyretic activities, and thus can be used as drugs (Ohmiya et al, 1995). They can therefore serve as potential starting compounds in the development of new drugs and in pest control for plants .QAs are synthesized through the cyclization of the cadaverine unit (Golebiewski and Spenser, 1988), which is produced through the action of Lys decarboxylase (LDC; EC 4.1.1.18) (Figure 1), via a postulated enzyme-bound intermediate . The various skeletons of QAs [e.g., bicyclic alkaloids such as (2)-lupinine and (+)-epilupinine or tetracyclic alkaloids such as (+)-multiflorine, (+)-lupanine, and (+)-matrine] are then further modified by tailoring reactions (e.g., dehydrogenation, oxygenation, esterification, and glycosylation) to yield hundreds of structurally related alkaloids (Ohmiya et al, 1995).…”

Assessing the genotoxicities of sparteine and compounds isolated from Lupinus mexicanus and L. montanus seeds by using comet assay

“…However, the comet assay is very efficient at detecting genotoxic agents (Golebiewski and Spenser, 1988;Singh et al, 1988;Henderson et al, 1998;AlvarezMoya et al, 2001). Therefore, the comet assay proved to be ideal for assessing the genotoxicity of alkaloids.…”