The Pyrrolizidine Alkaloids

Warren, F. L.

doi:10.1007/978-3-7091-7166-0_5

Cited by 4 publications

(5 citation statements)

References 98 publications

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“…This stereochemistry was supported by the agreement of C-i, C-7 and C-8 '3C-NMR signals of dihydroretrorsine (39. 4 senecionine; the physical and spectral data were identical to those reported in (11).…”

Section: Resultssupporting

confidence: 66%

“…The fractions 27-51 were subjected to chromatography as above resulting the alkaloid retrorsine; the physical and spectral data were identical with those described in (11).…”

Section: Resultsmentioning

confidence: 99%

“…The similar composition fractions (by TLC) 8 to 17 and 25 to 42 were gathered. The first fraction group after repeated purifications gave integerrimine identified for comparison of physical and spectral data with the already reported(11).…”

mentioning

confidence: 81%

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Pyrrolizidine Alkaloids fromSenecio subulatusandS. glandulosus

Pestchanker¹,

Ascheri²,

Giordano³

1985

Planta Med

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Die zur BlUtezeit in Bonn gesammelten oberirdischen Teile wurden luftgetrocknet, pulverisiert und anschlieBend in einer Soxhiet-Apparatur mit Methanol erschopfend extrahiert. Der eingedampfte Methanolextrakt wurde einer Flussig-Flussig-Extraktion unterworfen (7). Aus dem erhaltenen Rohextrakt konnte mittels Niederdrucksaulenchromatographie an Kieselgel 60 (0.04-0.63 mm) das Alkaloid isoliert werden. Glassäule im; 2.5 cm; 6 bar; Detektion: Dann'sche Probe. Als FlieBmittel diente em Gemisch aus CH2CI2/MeOH im Verhältnis 8:2. Es wurden 100 ml Fraktionen aufgefangen. Das Alkaloid konnte aus der vierten Fraktion isoliert werden. Es wurde in AcetonlMethanol/Petrolether umkristallisiert. Fp.: 112°C. Da sich die Substanz leicht zersetzt, konnte die optische Drehung nicht bestimmt werden. IR cm* 3460 und 3410 (OH); 3030 (= CH); 1625 (C = C); 1625 (N -0); ElMS : DE 150° C/300 iA/40 eV; mle (% rel. tnt.): [MJ 229.1057 (0.21); 197 [M -CH3OH] (2.98); 180 [197-OH] (1.32); 167 [197_CH2OJa (2.08); 110 [167-C3H5O] (53.0); 94 [197-C3H5NO3] (44.6); 82 [110-CO1 (66.3); 59 [197-C7H6O3] (100).Abstract: A new pyrrolizidine alkaloid dihydroretrorsine was isolated from roots of S. subulatus Don ex Hook et Am var. erectus together with the previously known senecionine and retrorsine. From the roots of S. glandulosus Don ex Hook et Am was isolated integerrimine and the mixture of the retrorsine and uraramine isomers. The structure of dihydoretrorsine was deduced by spectral and chemicals means.

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Section: Resultssupporting

confidence: 66%

“…The fractions 27-51 were subjected to chromatography as above resulting the alkaloid retrorsine; the physical and spectral data were identical with those described in (11).…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Pyrrolizidine Alkaloids fromSenecio subulatusandS. glandulosus

Pestchanker¹,

Ascheri²,

Giordano³

1985

Planta Med

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“…Ten years have elapsed since the pyrrolizidine alkaloids were reviewed in this series (387), and it is a not much shorter period since they formed the subject of an excellent account by LEONARD (329) and a masterly summary by BOIT (225). The intervening years have seen considerable activity in the isolation of new alkaloids, the determination of absolute structures, the synthesis of both the "necine" bases and "necic" acids, the study of the formation of these alkaloids in the plant and the effect of structure in hepatic cirrhosis.…”

Section: Introduction: Occurrence and Nature Of The Pyrrolizidine mentioning

confidence: 99%

“…This review follows systematically, and must be regarded as Part II of the original communication (387). The references to the original literature and the Chart numbers follow in sequence those of the previous review.…”

Section: Introduction: Occurrence and Nature Of The Pyrrolizidine mentioning

confidence: 99%