Pyrrolizidine alkaloids from Crotalaria aegyptiaca

Roeder, E.; Sarg, Taha; El-Dahmy, S.; Ghani, Abdul

doi:10.1016/0031-9422(91)80041-x

Cited by 14 publications

(11 citation statements)

References 12 publications

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“…Following isolation of the putative junceine and trichodesmine from seed extract, using preparative and semi-preparative reversed phase HPLC, their identities were confirmed by comparison of their 1 H and 13 C NMR data with literature reports. 12–14 Based upon HPLC-ESI/MS/MS, only a minor amount of the previously reported 4 senecionine (MH + m/z 336, peak 16, Figure 2) was observed in these analyses. Contrary to this previous report 4 there were no HPLC-ESI/MS indications of the related, macrocyclic diester dehydropyrrolizidine alkaloids riddelliine or seneciphylline.…”

Section: Resultsmentioning

confidence: 76%

Dehydropyrrolizidine Alkaloids, Including Monoesters with an Unusual Esterifying Acid, from Cultivated Crotalaria juncea (Sunn Hemp cv.‘Tropic Sun’)

Colegate

Gardner

Joy

et al. 2012

J. Agric. Food Chem.

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Cultivation of Crotalaria juncea L. (Sunn Hemp cv. ‘Tropic Sun’) is recommended as a green manure crop in a rotation cycle to improve soil condition, help control erosion, suppress weeds and reduce soil nematodes. Because C. juncea belongs to a genus that is known for the production of toxic dehydropyrrolizidine alkaloids, extracts of the roots, stems, leaves and seeds of ‘Tropic Sun’ were analyzed for their presence using HPLC-ESI/MS. Qualitative analysis identified previously unknown alkaloids as major components along with the expected macrocyclic dehydropyrrolizidine alkaloid diesters, junceine and trichodesmine. The dehydropyrrolizidine alkaloids occurred mainly as the N-oxides in the roots, stems and, to a lesser extent, leaves, but mainly as the free bases in the seeds. Comprehensive spectrometric and spectroscopic analysis enabled elucidation of the unknown alkaloids as diastereoisomers of isohemijunceine, a monoester of retronecine with an unusual necic acid. The dehydropyrrolizidine alkaloid content of the roots, stems, leaves of immature plants was estimated to be 0.05, 0.12 and 0.01% w/w respectively while seeds were estimated to contain 0.15% w/w.

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Section: Resultsmentioning

confidence: 76%

Dehydropyrrolizidine Alkaloids, Including Monoesters with an Unusual Esterifying Acid, from Cultivated Crotalaria juncea (Sunn Hemp cv.‘Tropic Sun’)

Colegate

Gardner

Joy

et al. 2012

J. Agric. Food Chem.

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“…One of these appears to be a crosemperine stereoisomer (27), and the others by MS interpretation are alkyl analogues of crosemperine in which the isopropyl side chain has been replaced by an ethyl group (23) and a methyl group (18). This latter alkaloid croaegyptine (18) has previously been reported to co-occur with crosemperine (26) in C. aegyptiaca (46). Our analysis of C. noVae-hollandiae subsp.…”

Section: Resultsmentioning

confidence: 90%

Pyrrolizidine Alkaloids in Crotalaria Taxa from Northern Australia: Risk to Grazing Livestock

Fletcher¹,

McKenzie²,

Blaney³

et al. 2008

J. Agric. Food Chem.

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Crotalaria species containing hepatotoxic pyrrolizidine alkaloids grow widely in pastures in northern Australia and have sporadically poisoned grazing livestock. The diverse Crotalaria taxa present in these pastures include varieties, subspecies, and chemotypes not previously chemically examined. This paper reports the pyrrolizidine alkaloid composition and content of 24 Crotalaria taxa from this region and assesses the risk of poisoning in livestock consuming them. Alkaloids present in C. goreensis , C. aridicola subsp. densifolia, and C. medicaginea var. neglecta lack the esterified 1,2-unsaturated functionality required for pyrrole adduct formation, and these taxa are not hepatotoxic. Taxa with high levels of hepatotoxic alkaloids, abundance, and biomass pose the greatest risk to livestock health, particularly C. novae-hollandiae subsp. novae-hollandiae, C. ramosissima , C. retusa var. retusa, and C. crispata . Other species containing moderate alkaloid levels, C. spectabilis and C. mitchellii , also pose significant risk when locally abundant.

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“…The combination of capillary GLC and MS is the method of choice for the separation and identification of complex pyrrolizidine alkaloid mixtures. Retention index RI data, molecular weight [M + ], and group-specific MS fragmentations provide sufficient information for an unequivocal identification of most PAs, which are present as trace components, or of geometrical isomers. − Thirteen PAs were detected in the reduced alkaloidal extract of E. setosum and 18 in E. vulgare (Tables and ). The major alkaloid in both extracts was identified as echimidine ( 1 ) (see above), while retronecine ( 3 ), 7-angeloylretronecine ( 4 ), 9-angeloylretronecine ( 5 ), 7-tigloylretronecine ( 6 ), 9-senecioylretronecine ( 7 ), 9-tigloylretronecine ( 8 ), and echihumiline ( 9 ) were unambiguously identified by their specific RI s and MS. Alkaloids 10 − 19 were only tentatively identified, inasmuch as amounts were too limited for a thorough spectroscopic analysis.…”

Section: Resultsmentioning

confidence: 99%

“…The MS of 10 exhibited significant ions at m/z 137, 124, 111, 106, and 80 (base peak); these fragments are characteristic for 1,2unsaturated necines with a monoester at C-7. 18,20,21 The fragment ion at m/z 137 is probably due to loss of the acid attached at C-7 (M -C 5 H 10 O 2 ). The fragments m/z 85 and 57 indicated that this acid is saturated and has two mass units more than angelic acid (or its isomers tiglic or senecic acid).…”

Section: Resultsmentioning

confidence: 99%