Pyrrolizidine alkaloids from Ageratum houstonianum Mill

Wiedenfeld, Helmut; Andrade‐Cetto, Adolfo

doi:10.1016/s0031-9422(01)00192-3

Cited by 26 publications

(15 citation statements)

References 14 publications

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“…Their PAs have been identified (Larson et al 1984;Kim et al 2001;Wiedenfeld and Andrade-Cetto 2001;Wiedenfeld et al 2006) and these species have also been part of nematode host studies and/or studies concerning nematicidal effects of plant extracts made from them (Moreno et al 1992;McSorley and Frederick 1994;Walker et al 1994;Brinkmann et al 1996;Lordello and Lordello 1996;Bernard and Jennings 1997;Dias et al 2000;Costa et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Effects of plants containing pyrrolizidine alkaloids on the northern root-knot nematode Meloidogyne hapla

2008

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1,2-Dehydropyrrolizidine alkaloids (PAs), known to be nematotoxic in vitro, represent a class of secondary plant metabolites from hundreds of plant species worldwide. Pot experiments with the commercially available PA-containing plants Ageratum houstonianum, Borago officinalis, Senecio bicolor, and Symphytum officinalis demonstrate that Meloidogyne hapla is not per se repelled by these plants as all species were infested with nematodes. However, the development of M. hapla juveniles was completely suppressed on A. houstonianum and S. bicolor. Soil in which A. houstonianum and S. bicolor were cultivated and incorporated contained 200-400 times less nematodes than soil treated with Lycopersicon esculentum.Depending on their qualitative composition of PAs at least some of these plants thus appear to be valuable tools for integrated root-knot nematode management.

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Section: Introductionmentioning

confidence: 99%

Effects of plants containing pyrrolizidine alkaloids on the northern root-knot nematode Meloidogyne hapla

2008

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“…The reaction mixture was extracted with EtOAc (3Â20 mL) and the combined organic extracts were washed with brine (10 mL (3)), 37.6 (C(1 0 )), 50.6 (NCH 2 Ph), 57.4 (C(4)), 58.0 (C(a)), 82.6 (C(5)), 119.1 (C(3 0 )), 127. 3,127.6,127.7,128.0,128.7,128.7 (o,m,, 132.4 (C(2 0 )), 139.6, 141.3 (i-Ph), 175.8 (C(2) TBAF (1.0 M in THF, 4.88 mL, 4.88 mmol) was added to a stirred solution of 28 (1.70 g, 3.25 mmol, >99:1 d.r.) at rt.…”

Section: (C(a)mentioning

confidence: 99%

“…The reaction mixture was extracted with EtOAc (3Â20 mL) and the combined organic extracts were washed with brine (10 mL C(3)), 33.9 (C(1 0 )), 51.9 (NCH 2 Ph), 55.0 (C(4)), 56.3 (C(a)), 84.4 (C(5)), 118.1 (C(3 0 )), 127. 3,127.7,127.7,127.9,128.5,128.8 (o,m, n-BuLi (2.2 M in hexanes, 2.60 mL, 5.74 mmol) was added dropwise to a stirred solution of i Pr 2 NH (0.94 mL, 6.70 mmol) in THF (15 mL) at 0 C, and the resultant mixture was stirred at 0 C for 30 min. A solution of 28 (1.00 g, 1.91 mmol, >99:1 d.r.)…”

Section: (C(a)mentioning

confidence: 99%

“…1). 3 Asymmetric and enantiospecific syntheses of 1-hydroxymethyl substituted pyrrolizidines have been actively pursued employing strategies such as chiral auxiliary approaches, 4 enantioselective catalysis, 5 diastereoselective reactions of enantiopure precursors derived from L-proline (e.g., hydrogenation of unsaturated azabicycles, 6 and radical 7 or transition metal 8 mediated cyclisations). 9 As part of our on-going research programme concerning the synthesis of azacyclic natural products, 10 we became interested in developing methodology for the synthesis of 1-hydroxymethyl pyrrolizidines.…”

Section: Introductionmentioning

confidence: 99%

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Asymmetric syntheses of (−)-hastanecine, (−)-turneforcidine and (−)-platynecine

et al. 2016

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a b s t r a c tConcise total asymmetric syntheses of three diastereoisomeric 1-hydroxymethyl-7-hydroxy substituted pyrrolizidines, (À)-hastanecine, (À)-turneforcidine and (À)-platynecine, are reported. The doubly diastereoselective conjugate additions of lithium (R)-or (S)-N-benzyl-N-(a-methylbenzyl)amide to tertbutyl (R,E)-4-(triethylsilyloxy)hepta-2,6-dienoate [which was prepared (in 96:4 e.r.) via Lewis acid mediated catalytic asymmetric allylation of tert-butyl (E)-4-oxobut-2-enoate] proceeded in both cases under the dominant control of the lithium amide reagent. Subsequent diastereoselective enolate allylations installed the required stereogenic centres, and the pyrrolizidine ring system was rapidly accessed by a two-step protocol (viz. ozonolysis and one-pot hydrogenolysis/double reductive cyclisation), to complete the asymmetric syntheses of (À)-hastanecine, (À)-turneforcidine and (À)-platynecine in 17, 8 and 24% overall yield, respectively, in eleven steps from commercially available 2,2-dimethoxyacetaldehyde in each case.

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“…LE and HE were each dissolved in 1 ml of CH 2 Cl 2 and analyzed by GC and GC-MS as described earlier [10,11].…”

Section: Case Reportmentioning

confidence: 99%

Veno-Occlusive Disease in a Fetus Caused by Pyrrolizidine Alkaloids of Food Origin

Rasenack

Müller²,

Kleinschmidt³

et al. 2003

Fetal Diagn Ther

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We report the occurrence of veno-occlusive disease in a preterm neonate who was symptomatic with hepatomegaly and ascites and was delivered by caesarean section for threatening fetal asphyxia and died shortly afterwards. Post mortem examination revealed veno-occlusive disease typical for pyrrolizidine alkaloid poisoning. The content of pyrrolizidine alkaloids in the liver could be confirmed. Analysis of a herbal mixture which was used for cooking in the family revealed high amounts of the respective alkaloids clarifying the source of the poison and the causal relationship.

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Pyrrolizidine alkaloids from Ageratum houstonianum Mill

Cited by 26 publications

References 14 publications

Effects of plants containing pyrrolizidine alkaloids on the northern root-knot nematode Meloidogyne hapla

Effects of plants containing pyrrolizidine alkaloids on the northern root-knot nematode Meloidogyne hapla

Asymmetric syntheses of (−)-hastanecine, (−)-turneforcidine and (−)-platynecine

Veno-Occlusive Disease in a Fetus Caused by Pyrrolizidine Alkaloids of Food Origin

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