Pyrrolizidine alkaloids from Canarian endemic plants and their biological effects

Domínguez, Dulce M.; Reina, Matı́as; Santos‐Guerra, Arnoldo; Santana, Omar; Agulló, Teresa; López-Balboa, Carmen; González-Coloma⊥, Azucena

doi:10.1016/j.bse.2007.08.015

Cited by 35 publications

(21 citation statements)

References 42 publications

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“…Senecioninae: gynuroids 5, 20, 21 5 20, 21 Smith and Culvenor (1981), Robins (1982), Mattocks (1986), Rizk (1990), Ahmad et al (1994), Hartmann and Witte (1995), Dominguez et al (2008) Kleinia petraea (R.E.Fr. )…”

Section: Biosynthetic and Ecological Interpretation Of Pa Diversitymentioning

confidence: 97%

The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae

2010

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Pyrrolizidine alkaloids are characteristic secondary metabolites of the Asteraceae and some other plant families. They are especially numerous and diverse in the tribe Senecioneae and form a powerful defense mechanism against herbivores. Studies into the evolution of pyrrolizidine alkaloid biosynthesis using Senecio species have identified homospermidine synthase as the enzyme responsible for the synthesis of the first specific intermediate. These studies further indicated that the homospermidine synthase-encoding gene was recruited following gene duplication of deoxyhypusine synthase and that this occurred independently in several different angiosperm lineages. A review of published pyrrolizidine alkaloid data shows that the Senecioneae are characterized by a large qualitative and quantitative variation in pyrrolizidine alkaloid profiles and that these data demonstrate little phylogenetic signal. This suggests that although the first steps of this pathway are highly conserved, the diversification of secondarily derived pyrrolizidine alkaloids is extremely plastic.

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Section: Biosynthetic and Ecological Interpretation Of Pa Diversitymentioning

confidence: 97%

The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae

2010

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“…PAs of about 15 species from this genus have been investigated which accumulate PAs from retronecine type [11,28,29,60,87,[89][90][91][92][93]96,99]. However, in earlier papers [47,97,98], the structure of major compounds in Echium vulgare were wrongly assigned to heliosupine and 3'-acetylheliosupine by means of paper chromatography and/or mass spectrometry.…”

Section: Genus Echiummentioning

confidence: 99%

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

2014

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Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs) are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014) of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

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“…4-Hydroxybenzaldehyde (19) reduced food ingestion but not biomass gain, suggesting metabolic alterations and showed fumigant toxicity against Sitophilus oryzae (Lee et al, 2001). None of the PAs tested exhibited postingestive toxicity against S. littoralis (Domínguez et al, 2008). S. littoralis larvae avoid PA poisoning by rapid and efficient excretion of the absorbed tertiary alkaloid (Lindigkeit et al, 1997).…”

Section: Resultsmentioning

confidence: 95%

“…The jacaranone derivative 16 was moderately active against L. decemlineata and M. persicae with lower potency than 14. The pyrrolizidine alkaloids 20 and 21 have been reported as antifeedants against L. decemlineata but not S. littoralis or the aphid species (Domínguez et al, 2008). In contrast, 23 was the most effective antifeedant against S. littoralis and L. decemlineata with moderate action against M. persicae.…”

Section: Resultsmentioning

confidence: 97%

“…A number of insect species from different taxa present adaptations that evolved to sequester, store and utilize plant PAs against their predators and parasitoids (Van Dam et al, 1995;Hartmann, 1999;Hartmann and Ober, 2000;Eisner et al, 2002). Ethanolic extracts of some PA-producing plants were generally more active insect antifeedants than their alkaloidal extracts (Domínguez et al, 2008). Thus, the non-alkaloidal fraction of Senecio species may be an important part of their defence.…”

Section: Introductionmentioning

confidence: 98%

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Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae

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Pyrrolizidine alkaloids from Canarian endemic plants and their biological effects

Cited by 35 publications

References 42 publications

The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae

The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

Bioactive compounds from transformed root cultures and aerial parts of Bethencourtia hermosae

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