New quinolizidine alkaloids from cadia purpurea

Eijk, J. L. van; Radema, M. H.; Versluis, Cees

doi:10.1016/s0040-4039(00)93815-2

Cited by 17 publications

(6 citation statements)

References 2 publications

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“…The mass spectrum of GLC-peak 16 (Fig. 2B) (M 280) with its characteristic fragment ions at m/z 262 and m/z 245 can be easily classified as a dihydroxylupanine [16,17]. However its mass spectrum differs significantly from the spectra of the known 12,13-dihydroxylupanine and 10,1 3-dihydroxylupanine.…”

Section: Resultsmentioning

confidence: 98%

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Quinolizidine Alkaloid Composition of Plants and of Photomixotrophic Cell Suspension Cultures ofSarothamnus scopariusandOrobanche rapum-genistae

Witte

Hartmann

1981

Planta Med

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The alkaloid composition of Sarothamnus scoparius cell cultures, plants and of its root parasite Orobanche rapum-genistae were analyzed by capillary gas-liquid chromatography (GLC) and capillary GLC/mass spectrometry. S. scoparius plants were found to contain the already known isosparteine, sparteine, 17-oxosparteine, lupanine and other quinolizidine alkaloids such as ammodendrine, N-methylangustifoline, alpha-isolupanine, 5,6-dehydrolupanine, 4-hydroxylupanine, 17-oxolupanine and five 13-hydroxylupanine esters. Two new alkaloids could be identified, a dehydrosparteine (presumably the 11,12-dehydroderivative) and a dihydroxylupanine (presumably 4,13-dihydroxylupanine). The distribution of these alkaloids within the different plant organs is reported. Orobanche rapum-genistae plants contain the already known sparteine, lupanine and 13-hydroxylupanine and 12 other lupin alkaloids, which are present in the Sarothamnus host plant. Photomixotrophic cell suspension cultures of S. scoparius accumulate lupanine as the main alkaloid. On tissue differentiation (bud formation) the cultures accumulate sparteine as well as lupanine. Whereas sparteine is stored in the cells, lupanine is excreted into the medium. Alkaloid formation of the cell cultures is positively correlated with chlorophyll content of the cells. The alkaloid pattern found in S. scoparius supports the hypothesis that lupanine biosynthesis is the common route of quinolizidine alkaloid biosynthesis from which the other alkaloids such as sparteine are derived.

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Section: Resultsmentioning

confidence: 98%

“…Subsequently these structures could be unequivocally confirmed by GLC/MS measurements (Table I) with the exception of the ester alkaloids. The ester alkaloids (17)(18)(19)(20)(21)(22), which were present in traces, could be identified by co-chromatography with reference compounds [12] only.…”

Section: Resultsmentioning

confidence: 99%

Quinolizidine Alkaloid Composition of Plants and of Photomixotrophic Cell Suspension Cultures ofSarothamnus scopariusandOrobanche rapum-genistae

Witte

Hartmann

1981

Planta Med

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“…High resolution mass spectrum of (4) gave a weak molecular ion, M at m/z 373 with an accurate mass determination corresponding to C20H27N304. The prominent peak at mlz 262, 111 a. m. u. lower than the molecular ion and the above spectroscopic properties were reminiscent of the spectral behaviour of pyrrole-2-carboxylic acid esters of oxosparteines (6,7,8). The ester nature of (4) was confirmed by hydrolysis of (4) with KOH which furnished an amino alcohol and pyrrole-2-carboxylic acid.…”

Section: Resultsmentioning

confidence: 84%

Two Novel Minor Alkaloids From EthiopianCalpurnia aureaSsp.aurea

Asres¹,

Phillipson²,

Mascagni³

1986

Planta Med

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Two novel minor quinolizidine alkaloids 4 beta-hydroxy-13alpha- O-(2'-pyrrolylcarbonyl)-lupanine (digittine) and its amino alcohol, 4 beta, 13alpha-dihydroxylupanine, have been isolated from Ethiopian Calpurnia aurea ssp. aurea. The structures of these alkaloids were determined by chemical transformation and by means of spectroscopic techniques (UV, IR, CD, MS, (1)H-NMR and (13)C-NMR) including two dimensional NMR.

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“…The 2-substituted piperidin-6-one pattern is noteworthy, as it is found as a part of some natural products (e.g., cadiamine [19] and other natural products from Leguminosae), as well as in some biologically interesting peptidomimetic molecules (e.g., conformationally restrained peptides as potent integrin antagonists [20] ). Concerning oxopipecolic acid derivatives more particularly, they constitute, for example, a part of posatireline, [21] a TRH-like drug prescribed for the treatment of senile dementia.…”

Section: Regioselective Oxidation Of the Oxazolidine System With Potamentioning

confidence: 99%

Reductive and Oxidative Transformations of the N‐(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

et al. 2004

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New quinolizidine alkaloids from cadia purpurea

Cited by 17 publications

References 2 publications

Quinolizidine Alkaloid Composition of Plants and of Photomixotrophic Cell Suspension Cultures ofSarothamnus scopariusandOrobanche rapum-genistae

Quinolizidine Alkaloid Composition of Plants and of Photomixotrophic Cell Suspension Cultures ofSarothamnus scopariusandOrobanche rapum-genistae

Two Novel Minor Alkaloids From EthiopianCalpurnia aureaSsp.aurea

Reductive and Oxidative Transformations of the N‐(Cyanomethyl)oxazolidine System to Expand the Chiral Pool of Piperidines

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