Norlaudanosoline

Norlaudanosoline is a chemical compound that belongs to the class of alkaloids. It is also known as tetrahydroprotoberberine and is a precursor in the biosynthesis of many other pharmacologically active alkaloids.

Chemistry

Norlaudanosoline is a tetrahydroprotoberberine, which is a subclass of isoquinoline alkaloids. It has a tetracyclic structure, which is composed of two benzene rings (A and B), one dihydroisoquinoline ring (C), and one tetrahydrofuran ring (D). The compound is chiral and exists in two enantiomeric forms.

Biosynthesis

The biosynthesis of norlaudanosoline begins with the condensation of dopamine and 4-hydroxyphenylacetaldehyde, catalyzed by the enzyme norcoclaurine synthase. This reaction forms (S)-norcoclaurine, which is then methylated by norcoclaurine 6-O-methyltransferase to form (S)-coclaurine. (S)-Coclaurine is then converted to (S)-N-methylcoclaurine by coclaurine N-methyltransferase. The final step in the biosynthesis of norlaudanosoline is the conversion of (S)-N-methylcoclaurine to norlaudanosoline by N-methylcoclaurine 3'-hydroxylase.

Pharmacology

Norlaudanosoline has been found to have several pharmacological effects. It has been shown to have anti-inflammatory, anti-oxidant, and anti-cancer activities. It also has been found to have neuroprotective effects and may have potential in the treatment of neurodegenerative diseases.

See also

• Alkaloid
• Isoquinoline
• Norcoclaurine synthase
• Pharmacology