Franz-Christian Czygan

Soluble phenolic constituents from Cuscuta reflexa and Cuscuta platyloba

Abstract Phytochemical analysis of the phanerogamic parasites C. reflexa and C. platyloba yielded characteristic patterns of soluble phenolic constituents. Whereas C. reflexa contained mainly caffeic acid depsides, C. platyloba was characterized by the accumulation of flavonoids of the flavonol-type. The phenolic patterns proved to be stable in both Cuscuta ssp. irrespective of different host plants employed in the experiments. Segmentation of growing Cuscuta shoots showed different concentrations of phenolic compounds. In contrast to the flavonoids that gradually declined from the meristematic apex towards the haustoria, the hydroxycinnamic acid derivatives were found to be enriched in the haustorial region in addition to their high concentration in the stem apex. The high concentration of phenylpropanoids in the apex, as well as the accumulation of caffeic acid depsides in the haustorial regions, were correlated to an enchanced activity of PAL in the respective segments.

Alkaloids of the genus Poecilanthe (Leguminosae: Papilionoideae)

Abstract The presence of alkaloids in the genus Poecilanthe is reported for the first time. Epilupinine, 4β-hydroxyepilupinine, dihydrolusitanine, dihydroammodendrine, lusitanine, N -methylcytisine, cytisine, lupanine, N -formylcytisine, anagyrine, baptifoline, camoensidine and four novel alkaloids were found as major alkaloids in leaves and seeds of the genus Poecilanthe . Tashiromine, acetylepilupinine, ammodendrine, α-isolupanine, 5,6-dehydrolupanine, aphyllidine, aphylline, thermopsine, epibaptifoline, rhombifoline, tinctorine, 11-allylcytisine, acetylbaptifoline and at least seven unknown compounds were found as minor alkaloids in the extracts studied. The co-occurence of different types of quinolizidine (bicyclic lupinine-type, lupanine-type, leontidine-type and α-pyridone-type) and bipiperidyl alkaloids appears to be a good chemotaxonomic marker for the genus. The presence of alkaloids in Poecilanthe suggests a relationship of this genus with the tribes Sophoreae or Brongniartieae rather than with the Dalbergieae. The alkaloidal data indicate that the genus can be divided into two phytochemical groups: one group of species accumulating mainly α-pyridone alkaloids and a second group accumulating bicyclic quinolizidine alkaloids, with α-pyridones being totally absent.

Über die Alkaloidzusammensetzung der oberirdischen Teile von Laburnum watereri (Kirchn.) Dipp.

Summary The alkaloid composition of the overground parts (leaves, petioles, stems, flowers, fruits and seeds) of Laburnum watereri (hybrid of Laburnum alpinum × L. anagyroides ) and its seasonal changes (from march to november) have been studied by different chromatographic (TLC, capillary GC) and spectroscopic (GC/MS, HRMS, 1 H-NMR, 13 C-NMR, IR, UV) methods. Seeds only contain cytisine. Besides cytisine, traces of methylcytisine and ammodendrine 12 further alkaloids could be identified in the fruits, among which β-isosparteine, 14e-hydroxysparteine and epi-baptifoline have been found for the first time in the genus Laburnum . Following the seasonal changes of the alkaloid composition of the fruits, an increase of epibaptifoline and ammodendrine was established during ripening, while the content of the main compound cytisine strongly declined. The highest total amount of alkaloids (with 80 to 90% cytisine) was found in the buds in the spring. During the further development of the leaves, the cystine content decreases and a methylation of this alkaloid begins. In summer the alkaloid concentration reaches the lowest level. In the course of July epi-baptifoline (erroneously reported as methylcytisine in literature) increases and becomes the main alkaloid for the following 6 months.

Equisetumpyrone, a styrylpyrone glucoside in gametophytes from Equisetum arvense

Abstract A new styrylpyrone was isolated from vegetative gametophytes of Equisetum arvense. Its structure was determined spectroscopically to be 3,4-dihydro

Lupin alkaloids from Lupinus polyphyllus

Abstract Twenty-nine quinolizidine alkaloids have been found and characterized from the combined leaf/hypocotyl extracts of Lupinus polyphyllus . Twelve have not been found previously in this plant and the structure of 10 has been unambiguously assigned from a combination of mass spectroscopy and NMR data, and by direct comparison with synthetic material for the N -carboxymethyl ester, N -carboxyethyl ester and N -formyl derivatives of angustifoline. The co-occurrence of 13α-hydroxylupanine and its 13β-isomer is reported for the first time in a quinolizidine alkaloid-accumulating species.

Phenolic constituents as taxonomic markers in the genus Cuscuta (Cuscutaceae)

Phytochemical analysis of nine species of the genus Cuscuta yielded characteristic patterns of soluble phenolic constituents that can be used as taxonomic markers. The specific patterns proved to be stable in all Cuscuta ssp. irrespective of host plant or localities.

A survey of alkaloids in the genera Harpalyce and Brongniartia (Fabaceae—Brongniartieae)

Abstract The presence of alkaloids in six species of Brongniartia and three species of Harpalyce is reported. This survey revealed remarkable qualitative differences in the alkaloid profiles of these two genera. B. discolor, B. lupinoides, B. sousae and B. intermedia showed a typical α-pyridone pattern, with cytisine, anagyrine and baptifoline as major alkaloids. In leaves of the first three species ormosanine-type alkaloids occurred additionally. B. flava and B. vazquezii are devoid of α-pyridones, but accumulate lupanine, hydroxylated lupanines and ester alkaloids. All three species of Harpalyce were similar in accumulating α-pyridones, but H. formosa differed from H. brasiliana and H. pringlei in the presence of epilupinine. In general the alkaloid profiles of Brongniartia and Harpalyce show similarities to those of the Australian genera Hovea, Lamprolobium, Plagiocarpus and Templetonia and support therefore the actual concept of the enlarged tribe Brongniartieae.

Ester alkaloids of Genista cinerea subspecies Cinerea

Abstract Two ester alkaloids, cineverine and a new compound, for which we suggest the name cineroctine, were isolated from twigs of Genista cinerea subsp. cinerea . Their structures were determined by spectroscopic methods to be 13α-(3′, 4′-dimethoxybenzoyl)oxylupanine (cineverine) and 13α-(3-hydroxy- cis -oct-5-enoyl)oxylupanine (cineroctine), 13- O -axial derivatives of lupanine. The distribution of these ester alkaloids amongst the different species of the section Spartioides of the genus Genista is recorded.

A SURVEY OF QUINOLIZIDINE ALKALOIDS AND PHENYLETHYLAMINE TYRAMINE IN CYTISUS SCOPARIUS (LEGUMINOSAE) FROM DIFFERENT ORIGINS

Distribution and content of the quinolizidine alkaloids and phenylethylamine tyramine in various organs of Cytisus scoparius taken from different localities in Germany, Russia, Italy and France were analyzed by capillary GLC. Sparteine and sparteine-derivatives like 11,12- dehydrosparteine are predominant in shoots and flowers whereas lupanine-type alkaloids are mainly accumulated in seeds, pods and roots. During the year no changes within the alkaloid pattern of the young developing shoots could be observed, but the total alkaloid amount increases remarkably at the end of the vegetation period. With respect to the date of harvest only a limited variation of the alkaloid profile and content could be found in shoots, flowers and roots taken from different geographical origins. In comparison the alkaloid pattern of seeds and pods varied considerably which seemed to be correlated with the different states of maturity and not with the geographical origin. Phenylethylamine tyramine is accumulated in flowers, green pods and young developing shoots. In young developing shoots the tyramine content declined drastically during the vegetation period.

A Survey of Alkaloids in Spartium junceum L. (Genisteae-Fabaceae)

Abstract The alkaloid pattern of Spartium junceum has been investigated. Cytisine, N-methylcytisine, anagyrine, rhombifoline and epi-baptifoline occur as major compounds in most of the samples studied. Considerable quantitative differences were found between various parts of the plant. The alkaloid content changed strongly dependent on the seasons. Only a limited variation can be ascribed to geographical origin.