scholarly journals Pyrrolizidine Alkaloid Profiles of Some Senecio Species from Egypt

2002 ◽  
Vol 57 (5-6) ◽  
pp. 429-433 ◽  
Author(s):  
Assem El-Shazly
Keyword(s):  
Mass Spectrometry ◽  
Pyrrolizidine Alkaloids ◽  
Pyrrolizidine Alkaloid ◽  
Plant Organs ◽  
Capillary Glc ◽  
Cultivated Species ◽  
Alkaloid Profiles ◽  
C Nmr

Alkaloid profiles of two Egyptian Senecio species (Senecio aegyptius var. discoideus and S. desfontainei) in addition to a cultivated species (S. cineraria) were studied using capillary GLC and GLC-mass spectrometry with respect to pyrrolizidine alkaloids (PAs). Four alkaloids were identified in S. aegyptius var. discoideus, 8 in S. desfontainei and 13 in S. cineraria. Some of these alkaloids have not been reported from these plants. The alkaloidal pattern of different plant organs (flowers, leaves, stem, root) were also investigated. Senecionine has been found to be a one of the major alkaloid in all studied species, it was isolated and its structure was elucidated by 1H- and 13C-NMR.

Analysis and chemotaxonomic significance of pyrrolizidine alkaloids from two Boraginaceae species growing in Algeria

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Houari Benamar ◽  
Abderrazak Marouf ◽  
Malika Bennaceur
Keyword(s):  
Mass Spectrometry ◽  
Pyrrolizidine Alkaloids ◽  
Pyrrolizidine Alkaloid ◽  
Fragment Ions ◽  
The Family ◽  
Kováts Indices ◽  
Chemotaxonomic Study ◽  
Botanical Classification ◽  
Alkaloid Profiles

Abstract In the current study the pyrrolizidine alkaloid profiles of the species Echium sabulicola ssp. decipiens (Pomel) Klotz and Solenanthus lanatus DC were studied in various extracts. In addition, a chemotaxonomic study within the genus and the family was carried out. The analysis was carried out by using gas chromatography coupled to mass spectrometry and by comparing the Kovats Indices and molecular and fragment ions with literature data. Twenty-three alkaloids were tentatively identified. The results showed the presence of already reported compounds as well as previously unreported ones leading both to a confirmation of the botanical classification of the two studied species and to a brand new path in the chemotaxonomy of Boraginaceae family. The presence of some pyrrolizidine alkaloids sets limits for the usage of these plants for medicinal purposes. The identified compounds confirm the botanical classification of the studied species as members of the Boraginaceae family and their presence advices against their use in the ethnopharmacological field.

scholarly journals Analysis of Pyrrolizidine Alkaloids in Queensland Honey: Using Low Temperature Chromatography to Resolve Stereoisomers and Identify Botanical Sources by UHPLC-MS/MS

Toxins ◽  
2019 ◽  
Vol 11 (12) ◽  
pp. 726 ◽  
Author(s):  
Natasha L. Hungerford ◽  
Steve J. Carter ◽  
Shalona R. Anuj ◽  
Benjamin L. L. Tan ◽  
Darina Hnatko ◽  
...  
Keyword(s):  
Low Temperature ◽  
Pyrrolizidine Alkaloids ◽  
Pyrrolizidine Alkaloid ◽  
Plant Secondary Metabolites ◽  
Diverse Group ◽  
Botanical Origin ◽  
Region Of Origin ◽  
Chronic Liver Damage ◽  
Chromatographic Resolution ◽  
Alkaloid Profiles

Pyrrolizidine alkaloids (PAs) are a diverse group of plant secondary metabolites with known varied toxicity. Consumption of 1,2-unsaturated PAs has been linked to acute and chronic liver damage, carcinogenicity and death, in livestock and humans, making their presence in food of concern to food regulators in Australia and internationally. In this survey, honey samples sourced from markets and shops in Queensland (Australia), were analysed by high-resolution Orbitrap UHPLC-MS/MS for 30 common PAs. Relationships between the occurrence of pyrrolizidine alkaloids and the botanical origin of the honey are essential as pyrrolizidine alkaloid contamination at up to 3300 ng/g were detected. In this study, the predominant alkaloids detected were isomeric PAs, lycopsamine, indicine and intermedine, exhibiting identical MS/MS spectra, along with lesser amounts of each of their N-oxides. Crucially, chromatographic UHPLC conditions were optimised by operation at low temperature (5 °C) to resolve these key isomeric PAs. Such separation of these isomers by UHPLC, enabled the relative proportions of these PAs present in honey to be compared to alkaloid levels in suspect source plants. Overall plant pyrrolizidine alkaloid profiles were compared to those found in honey samples to help identify the most important plants responsible for honey contamination. The native Australian vines of Parsonsia spp. are proposed as a likely contributor to high levels of lycopsamine in many of the honeys surveyed. Botanical origin information such as this, gained via low temperature chromatographic resolution of isomeric PAs, will be very valuable in identifying region of origin for honey samples.

scholarly journals Pyrrolizidine Alkaloid Profiles of the Senecio cineraria Group (Asteraceae)

2007 ◽  
Vol 62 (7-8) ◽  
pp. 467-472 ◽  
Author(s):  
Rosa Tundis ◽  
Monica R. Loizzo ◽  
Giancarlo A. Statti ◽  
Nicodemo G. Passalacqua ◽  
Lorenzo Peruzzi ◽  
...  
Keyword(s):  
Pyrrolizidine Alkaloids ◽  
Pyrrolizidine Alkaloid ◽  
Alkaloid Profiles

Alkaloid profiles of five Senecio species (Asteraceae), including S. ambiguus subsp. ambiguus, S. ambiguus subsp. nebrodensis, S. gibbosus subsp. bicolor, S. gibbosus subsp. gibbosus, and S. gibbosus subsp. cineraria, were studied. Eleven pyrrolizidine alkaloids were identified and their content was evaluated by GLC-MS and GLC analysis. Otosenine and florosenine were found to be the major alkaloids in all studied species. It is interesting that only S. ambiguus subsp. nebrodensis was characterized by a high content of the alkaloids jacobine, jacoline, jaconine, and jacozine

Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae)

1999 ◽  
Vol 54 (5-6) ◽  
pp. 295-300 ◽  
Author(s):  
Assem El-Shazly ◽  
M. Abdel-All ◽  
Andreas Tei ◽  
Michael Wink
Keyword(s):  
Microscopic Examination ◽  
Pyrrolizidine Alkaloids ◽  
Antibacterial Effects ◽  
E Coli ◽  
Alkaloid Extracts ◽  
Alkaloid Profiles ◽  
C Nmr

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.

Quinolizidine Alkaloid Profiles of Lupinus varius orientalis, L. albus albus, L. hartwegii, and L. densiflorus

2001 ◽  
Vol 56 (1-2) ◽  
pp. 21-30 ◽  
Author(s):  
Assem El-Shazly ◽  
Abdel-Monem M. Ateya ◽  
Michael Wink
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Bacillus Subtilis ◽  
New World ◽  
Indole Alkaloids ◽  
Quinolizidine Alkaloids ◽  
World Species ◽  
Capillary Glc ◽  
First Time ◽  
Alkaloid Profiles

Abstract Alkaloid profiles of two Lupinus species growing naturally in Egypt (L. albus albus [synonym L. term is], L. varius orientalis) in addition to two New World species (L. hartwegii, L. densiflorus) which were cultivated in Egypt were studied by capillary GLC and GLC-mass spectrometry with respect to quinolizidine alkaloids. Altogether 44 quinolizidine, bipiperidyl and proto-indole alkaloids were identified; 29 in L. albus, 13 in L. varius orientalis, 15 in L. hartwegii, 6 in L. densiflorus. Some of these alkaloids were identified for the first time in these plants. The alkaloidal patterns of various plant organs (leaves, flowers, stems, roots, pods and seeds) are documented. Screening for antimicrobial activity of these plant extracts demonstrated substantial activity against Candida albicans, A spergillus flavus and Bacillus subtilis.

Biosynthesis of Pyrrolidine Alkaloid-Derived Pheromones in the Arctiid Moth, Creatonotos transiens: Stereochemical Conversion of Heliotrine

1988 ◽  
Vol 43 (9-10) ◽  
pp. 737-741 ◽  
Author(s):  
M. Wink ◽  
D. Schneider ◽  
L. Witte
Keyword(s):  
Developmental Stages ◽  
Pyrrolizidine Alkaloid ◽  
Major Metabolite ◽  
Arctiid Moth ◽  
Capillary Glc ◽  
Creatonotos Transiens ◽  
C Nmr

Abstract In larvae and later developmental stages of Creatonotos transiens, which had been reared on the pyrrolizidine alkaloid 7S-heliotrine, a new major metabolite was detected by capillary GLC. The structure of this metabolite was determined by GLC-MS (EI, CI-MS) and 13C NMR to be 7Rheliotrine and 7R-heliotrine-N-oxide. 7R-Heliotrine is likely to be the direct precursor for the pheromone R( - )-hydroxydanaidal.

Tropane Alkaloids of Hyoscyamus boveanus, H. desertorum, H. muticus and H. albus from Egypt

1997 ◽  
Vol 52 (11-12) ◽  
pp. 729-739 ◽  
Author(s):  
Assem El-Shazly ◽  
Andreas Tei ◽  
Ludger Witte ◽  
Mäher El-Domiaty ◽  
Michael Wink
Keyword(s):  
Mass Spectrometry ◽  
Tropane Alkaloids ◽  
Alkaloid Composition ◽  
Capillary Glc ◽  
First Time ◽  
Alkaloid Contents ◽  
Alkaloid Profiles

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.

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