Accumulation of Quinolizidine Alkaloids in Plants and Cell Suspension Cultures: Genera Lupinus, Cytisus, Baptisia, Genista, Laburnum, and Sophora

Abstract

The patterns of quinolizidine alkaloids in cell cultures of 10 species of Fabaceae were analyzed by high-resolution GLC and GLC-MS and compared with the alkaloids present in the leaves of the respective plants. Lupanine was produced in all 10 cell suspension cultures as the main alkaloid. It was accompanied by sparteine, tetrahydrorhombifoline, 17-oxosparteine, 13-hydroxylupanine, 4-hydroxylupanine, 17-oxolupanine, and 13-hydroxylupanine esters as minor alkaloids in some species. The alkaloid patterns of the plants differed markedly in that alpha-pyridone alkaloids were the major alkaloids in the genera Cytisus, Genista, Laburnum and Sophora but were not accumulated in the cell cultures. These data further support the assumption that the pathway leading to lupanine is the basic pathway of quinolizidine alkaloids biosynthesis and that the other alkaloids are derived from lupanine.

Evidence for a wide‐spread occurrence of the genes of quinolizidine alkaloid biosynthesis

“…3.1. Induction of alkaloid accumulation in ceil suspension cultures of alkaloid-producing species Photoheterotrophic, chloroplast-containing cell suspension cultures to Lupinus polyphylus, Cytisus scoparius and other Fabaceae accumulate quinolizidine alkaloids such as lupanine at a concentration usually l-3 orders of magnitude lower than the alkaloid level of the differentiated plant [4,5], similarly to the situation in many other cell culture systems [l l-131. However, the activity of the enzymes of lupanine biosynthesis, lysine decarboxylase (3,141 and oxosparteine synthase [7,8], which are localized in the chloroplast [9], is similar to, or lower only by one order magnitude than, the respective enzyme activities in the plant [15].…”

“…Upon application of the com~unds which induce alkaloid accumulation in lupins (table 1) we could observe a significant increase in quinolizidine alkaloids 2-72 h after the treatment (table 2). These alkaloids could be unambiguously identified by GLC/MS and authentic reference compounds [5,6,10] as lupanine, the major alkaloid, along with sparteine, tetrahydrorhombifoline, and 17-oxosparteine as minor alkaloids. The activity of oxosparteine synthease was not significantly influenced by the inducers.…”

Antibacterial Activity of Naturally Occurring Compounds from Selected Plants

“…No data No data alkaloids (l-sparteine, sarothamnine, genisteine, lupanine, oxysparteine) (Wink et al, 1983) …”

“…No data No data alkaloids ( Wink et al, 1983) were air-dried under shade at room temperature and then ground into small pieces which were stored into paper bags at room temperature.…”

Alkaloids of Adenocarpus hispanicus (Lam.) DC Varieties

“…Twentyfour alkaloids were detected by direct com parison (mass spec trum , retention index) with authentic m aterial or by comparison of their mass spectral data with lit erature data. The alkaloid pattern of Adenocarpus hispanicus is characterized by the co-occurrence of the pyrrolizidine alkaloids N-acetylnorloline (2), decorticasine (3) and N-butyrylnorloline (5), the bipiperidyl alkaloid ammodendrine (13) and a large number of quinolizidine alkaloids. a-Isosparteine (4), sparteine (6), ß-isosparteine (10), 11,12-dehydrosparteine (11), 8 e-hydroxysparteine (15), 17-oxosparteine (16), a-isolupanine (18), lupanine (20), aphylline (21), m ultiflorine (22) and 17-oxolupanine (23) could be identified unam big uously by their specific retention indices and their mass spectral data.…”