Piperidine Alkaloids

Piperidine alkaloids are widespread among the Apiaceae, Solanaceae, Chenopodiaceae, Fabaceae, Crassulaceae, Lycopodiaceae, and Asteraceae. They are organic compounds containing saturated heterocyclic amine ring, i.e piperidine nucleus – a six membered ring consists of five methylene bridge (-CH₂-) and one amine (-NH₂-) bridge. Most of the alkaloids containing the piperidine rings, including pelletierine (Punica granatum), piperine (Piper nigrum et longum), and lobeline (Lobelia inflata) are derived from lysine. Piperidine alkaloids are of interest to many researchers because of their important biological activities.

Precursors of piperidine alkaloids

The precursor of piperidine alkaloids is a substrate for the piperidine alkaloid molecule as well as being the source of the piperidine alkaloid's nitrogen and skeleton. L-lysine is the precursor of piperidine alkaloids. It is α-ε-diaminocarbon acid, the homologue of L-ornithine, contains with one methylene group more than that. Lysine is formed from aspartic acid, one of the members of Krebs cycle. When the lysine loses its carboxyl group, the ε-amino group is retained in the ring. Lysine thus supplies C₅N-building block for piperidine alkaloids^[1].

Figure 1. Lysine, the precursor of piperidine skeleton.

Common piperidine alkaloids

The most important representative of piperidine alkaloids is piperine, which is responsible for the pungent taste of pepper. In addition, common piperidine alkaloids also include lobelin and lobelanine.

• Piperine

Black pepper is one of the most ancient spices and known as a preservative food additive. Piperine, the chief constituent, increases the bioavailability of numerous therapeutical drugs (e.g., propranolol, theophylline, curcumine, b-carotene) perhaps by increasing intestinal absorption or by exerting an antioxidant effect during the first pass through the liver. Piperine also has antidiarrheal, antipyretic, analgesic, insecticidal, antitumor, anti-inflammatory, and antidepressant properties.

Figure 2. The structure of piperine.

• Lobeline

Lobeline is obtained from the herb and seeds of Lobelia inflata. It strengthens and accelerates respiratory movements and thus is successfully used in chronic pneumonia, asthma, bronchitis, and laryngitis. Lobeline is also an effective drug in the treatment of central nervous system (CNS) disorders, such as Alzheimer's or Parkinson's disease.

Figure 3. The structure of lobeline.

• Lobelanine

Lobelanine is a chemical precursor in the biosynthesis of lobeline. It has many pharmacological activities (e.g., diuretic, respiratory stimulant, antibacterial and anticancer).

Figure 4. The structure of lobelanine.

What we offer

As a supplier of alkaloids, Alfa Chemistry has always shown great interest in the latest developments in piperidine alkaloids. Alfa Chemistry is committed to providing a wide range of piperidine alkaloids. If you do not find what you need, please contact us. We also offer product customization according to customer's detailed requirements.

Reference

1. Szoke, E.; et al. Alkaloids derived from lysine: piperidine alkaloids. Natural Products. 2013: 303-341.