Seneciphylline N-oxide

The Uses of Seneciphylline N-oxide

Seneciphylline N-oxide is a pyrrolizidine alkaloid that is naturally found in the extracts of Adenostyles alliariae, a plant that is native to the western Alps. Seneciphylline N-oxide is highly toxic to mammals and is also a suspected mutagen.

Definition

ChEBI: Spartioidine N-oxide is a pyrrolizine alkaloid that is 13,19-didehydrosenecionane carrying a hydroxy substituent at position 12, two oxo substituents at positions 11 and 16 and an N-oxido substituent. It has a role as a Jacobaea metabolite. It is a macrocyclic lactone, an olefinic compound, an organic heterotricyclic compound, a pyrrolizine alkaloid, a tertiary alcohol and a tertiary amine oxide. It is functionally related to a spartioidine.

General Description

Seneciphylline-N-oxide is a pyrrolizidine alkaloid isolated from Senecio vulgaris. Pyrrolizidine alkaloids are secondary metabolites, produced by several plant species as protection against insect herbivores. Approximately 6000 plant species worldwide may contain pyrrolizidine alkaloids. They are mainly found in the families of the Boraginaceae, Asteraceae and Fabaceae. The PA-content depends on several factors (species, plant organ, harvest, storage, extraction procedures). Contents vary from trace amounts up to 19 % based on dry weight. These alkaloids occur in two forms, as tertiary base PAs and their N-oxide (PANO).

Biological Activity

Seneciphylline N-Oxide is a dehydrogenation product of Senecionine N-oxide. Seneciphylline N-Oxide is a natural compound isolated from root cultures of Senecio erucifolius (Asteraceae).

Source

They are common food contaminants in herbs, tea, salad, leafy vegetables and honey. Feed can be contaminated so that the plant products find their way in the food chain indirectly also over meat, milk and eggs. Pyrrolizidine alkaloids have adverse health effects and were classified as genotoxic, carcinogen and hepatotoxic.