Andreas Tei

GLC and GLC-mS analysis of thiophene derivatives in plants and in in vitro cultures of Tagetes patula L. (Asteraceae).

The occurrence of thiophenic compounds in diverse plant organs and in in vitro root-, callus- and cell suspension cultures of Tagetes patula cv. Carmen was investigated using capillary GLC and GLC-MS. The separation of thiophenes by capillary GLC and the group specific MS fragmentation with the typical sulfur isotope peaks allowed the unequivocal assignment of individual thiophenes in complex mixtures, even when occurring in traces and in the presence of different geometrical isomers. The extracts of Tagetes patula cv. Carmen contained the following 8 thiophene compounds: 5-(3-buten-1-ynyl)-2,2′-bithienyl (BBT), 5′-methyl-5-(3-buten-1-ynyl)-2,2′-bithienyl (MeBBT), 5-(1-pentynyl)-2,2′-bithienyl (PBT), 5-(4-hydroxy-1-butynyl)-2,2′-bithienyl (BBTOH), 2,2′,5,2″-terthienyl (α-T), 5-(4-acetoxy- 1-butynyl)-2,2′-bithienyl (BBTOAc), 5-methylaceto-5′-(3-buten-1-ynyl)-2,2′-bithienyl (AcOCH2BBT), and 5-(3,4-diacetoxy-1-butynyl)-2,2′-bithienyl (BBT(OAc)2). The most complex thiophene profile, including the less common PBT was detected in aerial parts of freshly harvested plant material. Under in vitro conditions only the root cultures, but not callus or cell suspension cultures produced substantial amounts of irregular thiophenes confirming that roots are the main site of thiophene biosynthesis.

PYRROLIZIDINE ALKALOIDS FROM ECHIUM RAUWOLFII AND ECHIUM HORRIDUM (BORAGINACEAE)

Abstract Echimidine was isolated from Echium rauwolfii and Echium horridum and identified by MS, 1H-and 13C NMR as a major alkaloid. In addition, structures of 12 minor alkaloids were inferred from GLC and GLC-MS analyses: 7-angeloylretronecine, 7-tigloylretronecine, lycopsamine, 7-acetyllycopsamine, uplandicine, 7-angeloyllycopsamine, 7-tigloyllycopsamine, tigloyl isomer of echimidine, 7-angeloyl-9-(2-methylbutyryl)retronecine, 7-tigloyl-9-(2-methylbutyryl)retronecine, 7-angeloyl-9-(2,3-dihydroxybutyryl)retronecine, and 7-tigloyl-9-(2,3-dihydroxybutyryl)retronecine. Both species had similar alkaloid profiles. Alkaloid extracts exhibited antibacterial effects with a MIC of 1.7 mg/ml in E. coli. Microscopic examination of E. coli treated with different subtoxic alkaloid concentrations (13-52 μg/ml) revealed extensive filamentation.

TROPANE ALKALOIDS OF HYOSCYAMUS BOVEANUS, H. DESERTORUM, H. MUTICUS AND H.ALBUS FROM EGYPT

Abstract The alkaloid composition of Hyoscyam us boveanus, H. desertorum, H. muticus and H. albus was investigated by capillary GLC and GLC-mass spectrometry. Altogether 39 alkaloids of the tropane and pyrrolidine types were identified. Several alkaloids were found in the different species for the first time, e.g., 22 alkaloids in H. boveanus, 13 in H. desertorum, 24 in H. muticus and 4 in H. albus. 3β-Hyoscyamine, dehydrohyoscyamine, phyllalbine, 3α-phenylacetyltropane, phenylacetylscopine as well as phygrine and 2,3-diacetonyl-N-methyl-pyrrolidine are apparently new for the genus Hyoscyamus. Alkaloid profiles and alkaloid contents of flowers, fruits, leaves, stems and roots were determined and their chemoecological functions discussed.

Quinolizidine alkaloids from the east-african legume Dicraeopetalum stipulare harms

Abstract The alkaloid composition of leaves of Dicraeopetalum stipulare Harms was examined by capillary gas chromatography (GLC) and GLC-mass spectrometry. 5,6-Dehydrolupanine, anagyrine and cytisine figured as major and baptifoline, N -methylcytisine, lupanine, ammodendrine, N -formylcytisine and N -acetylcytisine as minor alkaloids. Sparteine, rhombifoline and 6β-hydroxylupanine were detected in trace amounts. Two new alkaloids were tentatively identified as 10-oxolupanine and 17-oxolupanine.

QUINOLIZIDINE ALKALOIDS OF PLATYCELPHIUM VOENSE (ENGL.) WILD (LEGUMINOSAE)

Abstract 13 Alkaloids were identified in leaves and twigs of Platycelphium vöense (a monotypic genus in the tribe Sophoreae) by capillary GLC and GLC-MS. Cytisine, N-methylcytisine, anagyrine and 5,6-dehydrolupanine figured as major and N-formylcytisine, N-acetylcytisine, baptifoline, thermopsine, isolupanine, and rhombifoline as minor alkaloids in both leaves and twigs. Lupanine occurred in considerable amount in the leaves and as a minor component in the twigs. The rare alkaloid, 6β-hydroxylupanine, was detected only in the leaves while N-ethylcytisine was shown to be a minor constituent of the twigs only.

Quinolizidine alkaloid profiles of two taxa of Teline maderensis.

Abstract The alkaloid composition of the aerial parts of two taxa of Teline maderensis was studied by capillary GLC and GLC-MS. N-Methylcytisine was the major alkaloid found in both plants. Contents of cytisine and lupanine were higher in T. maderensis var. paivae while anagyrine content was more pronounced in T. maderensis var. maderensis. The alkaloids dehydrocytisine, N-acetylcytisine and epibaptifoline appeared only in T. maderensis var. maderensis and N-formylcytisine was identified as a minor constituent in T. maderensis var. paivae, and detected only in trace amounts in the other variety of the plant.