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PYRROLIDIZINE ALKALOIDS
Thesinine, a pyrrolidizine, is one of the few non-toxic pyrrolidizine alkaloids produced by plants, and is responsible for the deep blue colour of the flowers of Borage. It tastes sweet, honey-like and is one of the few blue but edible compounds.
Borage also produces the pyrrolizidine alkaloids Intermedine and its enantiomorph Lycopsamine, and their 7-acetyl derivatives. Lycopsamine is also present in Comfrey . Pyrrolizidine alkaloids are metabolically activated within the liver and there will alkylate both proteins and DNA molecules; they are therefore hepatotoxic causing liver damage, as well as mutagenic and carcinogenic. Substantial ingestion results in inhibition of neurons and paralysis.
Amabiline and Supinine are other pyrrolizidine alkaloids (PA) manufactured within Borage. Both are structurally similar to Indicine, another natural PA found in the plant world. Amabiline is hepatotoxic as are many PAs. Supinine has a low concentration in Borage.
Caterpillar moths of species Hyalurga syma sequester all these poisonous pyrrolizidine alkaloids from the borage that they consume when in this larval stage, and escape un-harmed if caught by orb-weaving spiders Nephila clavipeswho would normally eat them. This averse reaction by the spiders is though to be due to the PAs within the moths which are poisonous to the spiders.
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