Chariezza Lei J.

Sanglad

BS Chemistry-IV

Retronecine

The Chemistry of Retronecine

Retronecine is a pyrrolizidine alkaloid (PA) found in a variety of plants in the genera

Senecio and Crotalaria, and the family Boraginaceae. Retronecine is a heterocyclic organic
compound and an unsaturated base. Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is,
damaging to the liver. It is composed of a necine base (amino alcohols) and one or more necic
acids (mono- or dicarboxylic aliphatic acids), which are responsible for their structural diversity.
It is usually found in the form of tertiary bases or pyrrolizidine alkaloids N-oxides (PANO), which
are water soluble. Amino alcohols, or necines, are derived from pyrrolizidine. The pyrrolizidine
core, comprising two saturated five-membered rings with a nitrogen atom between them,
sometimes displays a double bond which frequently results in enhanced toxicity.

Advantages of Retronecine

Retronecine, a pyrrolizidine alkaloid is known to be used in the production of honey.

Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores.
Disadvantages of Retronecine

Retronecine can pose a life threat to humans and animals once they are present in a variety
of foodstuff. This compound has become known for its toxicity, as per several outbreaks that were
registered, mainly in developing countries. Retronecine, a pyrrolizidine alkaloid have little or no
known therapeutic value and are exceptionally toxic. PA were associated to skin cancer and
ultimately trigger the formation of tumors, since they can lead to photosensitization in animals
upon their consumption and metabolism. It has been shown before that this compound induces
liver tumors in rodents via formation of DNA adducts, thus may also be genotoxic and tumorigenic
to humans. The potential role of this compound in diseases such as cancer, pulmonary
hypertension, congenital anomalies and liver diseases has been reviewed before wherein these
alkaloids are genotoxic and can slowly initiate diseases.

Uses

Retronecine as one type of PA is also used as a defense mechanism for some organisms
such as Utetheisa ornatrix. Utetheisa ornatrix caterpillars obtain these toxins from their food
plants and use them as a deterrent for predators. This protect them from most of their natural
enemies. The toxins stay in these organisms even when they metamorphose into adult moths,
continuing to protect them throughout their adult stage.

This compound can also be use in the production of honey.

Effects

 Effects on Human Health

The symptoms are characterized by upper abdominal discomfort that develops rapidly and
progresses to swelling of the abdomen resulting in increased girth, sometimes accompanied by a
reduction in the quantity of urine excreted and swelling of the feet. The disease is called veno-
occlusive disease (VOD). There may be vomiting of blood. Some patients may have only vague
symptoms and the only sign of the disease may be persistent enlargement of the liver. The liver is
usually the target organ.

Consumption of crops containing retronecine can cause large-scale outbreaks of toxic

disease in both man and farm animals.