Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases

Loaiza, Juan Camilo Marín; Ernst, Ludger; Beuerle, Till; Theuring, Claudine; Céspedes, Carlos L.; Hartmann, Thomas

doi:10.1016/j.phytochem.2007.07.004

Cited by 19 publications

(8 citation statements)

References 29 publications

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“…The porous graphitic carbon column conditions were essential for confirming the presence of the heliotridine‐based rinderine along with the retronecine‐based lycopsamine and intermedine. Such co‐biosynthesis of the heliotridine and retronecine bases has only rarely been reported, for example 7‐angeloylheliotridine and senecionine from Pittocaulon velatum (Marín‐Loaiza et al ., ), but the co‐occurrence of monoesters of the retronecine, supinidine and isoretronecanol necine bases is not uncommon (El‐Shazly and Wink, ). In addition to the differences in alkaloid resolution, the most significant change in the ion chromatograms was that the N ‐oxides eluted before their free‐base counterparts when using the basic elution conditions and the porous graphitic carbon column.…”

Section: Resultsmentioning

confidence: 99%

Recognition of Pyrrolizidine Alkaloid Esters in the Invasive Aquatic Plant Gymnocoronis spilanthoides (Asteraceae)

Boppré

Colegate

2015

Phytochem. Anal.

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The butterflies proved to be reliable indicators for the presence of pro-toxic 1,2-dehydropyrrolizidine alkaloids in G. spilanthoides, the first aquatic plant shown to produce these alkaloids. The presence of the anti-herbivory alkaloids may contribute to the plant's invasive capabilities and would certainly be a consideration in any risk assessment of deliberate utilisation of the plant. The prolific growth of the plant and the structural diversity of its pyrrolizidine alkaloids may make it ideal for investigating biosynthetic pathways or for large-scale production of specific alkaloids.

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Section: Resultsmentioning

confidence: 99%

Recognition of Pyrrolizidine Alkaloid Esters in the Invasive Aquatic Plant Gymnocoronis spilanthoides (Asteraceae)

Boppré

Colegate

2015

Phytochem. Anal.

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“…Foi realizado ainda um processo de derivatização, como no procedimento realizado por Marín-Loaiza et al (2008), de uma determinada fração, para injeção em cromatógrafo gasoso acoplado a espectrômetro de massa (modelo GCMS-QP5050A, Shimadzu) em coluna DB5 (30 m x 0,25 µm x 0,25 µm).…”

Section: As Reuniões De Frações Semelhantes Foram Submetidas à Espectunclassified

Prospecção química de compostos produzidos por Senna alata com atividade alelopática

et al. 2010

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RESUMO -Senna alata é uma espécie daninha frequente em pastagens da região amazônica. Suas folhas apresentam propriedades medicinais capazes de influenciar a germinação e o desenvolvimento de outras plantas. Objetivou-se neste estudo a prospecção química e a avaliação da atividade alelopática dos compostos presentes nas folhas de S. alata. O material vegetal foi seco, triturado e submetido à extração exaustiva, com solução água:metanol (3:7). O extrato obtido foi então fracionado por coluna cromatográfica por via úmida. As frações mais puras foram submetidas à espectroscopia de Ressonância Magnética Nuclear, para determinação das fórmulas estruturais das moléculas. Na avaliação dos efeitos das substâncias químicas isoladas, utilizaram-se as concentrações de 50, 100, 150 e 200 ppm, tendo como eluente solução hidrometanólica (3:7 v/v). As frações foram adicionadas em placas de Petri e seus efeitos avaliados sobre a germinação de sementes e o alongamento da radícula e hipocótilo de três espécies daninhas de áreas de pastagens: Mimosa pudica, Senna obtusifolia e a própria S. alata. Os compostos com atividade alelopática encontrados em folhas de S. alata pertencem à classe dos flavonoides glicosilados, cujo núcleo aromático é um kaempferol, e causaram maior inibição sobre o crescimento da radícula e sobre a germinação de S. obtusifolia e M. pudica. Já os efeitos autotóxicos desse composto são pouco significativos para o desenvolvimento da plântula e nulos sobre a germinação.Palavras-chave: Leguminosae, aleloquímicos, RMN, flavonoides glicosilados, kaempferol.ABSTRACT -Senna alata is a weed species frequently found in pastures of the Amazonian region and whose leaves have medicinal properties. This study aimed to carry out a chemical prospecting and evaluation of the allelopathic activity of the compounds present in S. alata leaves. The plant material was dried, ground, and submitted to exhaustive extraction with water/methanol (3:7) solution. The crude extract obtained was fractioned by wet chromatography column. The purest fractions were submitted to Nuclear Magnetic Resonance Spectroscopy to determine their structures. To evaluate the effects of the isolated chemical substances, concentrations of 50, 100, 150 and 200 ppm were used in water/methanol solvents (3:7). The fractions were placed on Petri dishes and their effects were evaluated on seed germination and radicle and hypocotyl elongation of three pasture weeds: Mimosa pudica, Senna obtusifolia, and Senna alata itself. The compounds with allelopathic activity found in S. alata leaves belong to the flavonoid glycoside class, whose aromatic core is a kaempferol causing major inhibition on radicle elongation and germination of S. obtusifolia and M. pudica. The auto toxic effects of this compound are not very significant for seedling development and null for germination.

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“…Hydrogenation of the 1,2-double bond was performed as recently described by Marín-Loaiza et al (2008). Further purification was achieved by column chromatography on silica gel 60 (mesh 230-400) using the solvent system CH 2 Cl 2 /MeOH/NH 4 OH conc (83:15:2/ v:v:v).…”

Section: Methodsmentioning

confidence: 99%

Feeding Deterrence and Detrimental Effects of Pyrrolizidine Alkaloids Fed to Honey Bees (Apis mellifera)

et al. 2009

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Recent studies have shown the occurrence of plant derived pyrrolizidine alkaloids (PAs) in retail honeys and pollen loads, but little is known about how these compounds influence the fitness of foraging honey bees. In feeding experiments, we tested a mix of tertiary PAs and the corresponding N-oxides from Senecio vernalis, pure monocrotaline, and 1,2-dihydromonocrotaline in 50% (w/w) sucrose solutions. The bees were analyzed chemically to correlate the observed effects to the ingested amount of PAs. PA-N-oxides were deterrent at concentrations >0.2%. 1,2-Unsaturated tertiary PAs were toxic at high concentrations. The observed PAs mortality could be linked directly to the presence of the 1,2-double bond, a well established essential feature of PA cytotoxicity. In contrast, feeding experiments with 1,2-dihydromonocrotaline revealed no toxic effects. Levels of less than 50 microg 1,2-unsaturated tertiary PAs per individual adult bee were tolerated without negative effects. PA-N-oxides fed to bees were reduced partially to the corresponding tertiary PAs. Unlike some specialized insects, bees are not able to actively detoxify PAs through N-oxidation. To gain insight into how PAs are transmitted among bees, we tested for horizontal PA transfer (trophallaxis). Under laboratory conditions, up to 15% of an ingested PA diet was exchanged from bee to bee, disclosing a possible route for incorporation into the honey comb. In the absence of alternative nectar and pollen sources, PA-containing plants might exhibit a threat to vulnerable bee larvae, and this might affect the overall colony fitness.

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Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases

Cited by 19 publications

References 29 publications

Recognition of Pyrrolizidine Alkaloid Esters in the Invasive Aquatic Plant Gymnocoronis spilanthoides (Asteraceae)

Recognition of Pyrrolizidine Alkaloid Esters in the Invasive Aquatic Plant Gymnocoronis spilanthoides (Asteraceae)

Prospecção química de compostos produzidos por Senna alata com atividade alelopática

Feeding Deterrence and Detrimental Effects of Pyrrolizidine Alkaloids Fed to Honey Bees (Apis mellifera)

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