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Benzylisoquinoline

Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified within numerous compounds of pharmaceutical interest, such as moxaverine; but most notably it is found within the structures of a wide variety of plant natural products, collectively referred to as benzylisoquinoline alkaloids. This class is exemplified in part by the following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, tubocurarine.

Biosynthesis

(S)-Norcoclaurine (higenamine) has been identified as the central 1-benzyl-tetrahydro-isoquinoline precursor from which numerous complex biosynthetic pathways eventually emerge. These pathways collectively lead to the structurally disparate compounds comprising the broad classification of plant natural products referred to as benzylisoquinoline alkaloids (BIA), which have been comprehensively discussed by Hagel. The biosynthesis of (S)-norcoclaurine, which is catalyzed by (S)-norcoclaurine synthase, is accomplished by the stereoselective condensation of dopamine and 4-hydroxyphenylacetaldehyde (4-HPAA); each of these compounds is prepared by multiple enzymatic transformations from L-tyrosine.

It is of interest to note that early studies initially identified norlaudanosoline (tetrahydropapaveroline) as the purported central precursor for the biosynthesis of BIAs. However, more than two decades later it was finely unequivocally established that (S)-norcoclaurine was the central precursor for the biosynthesis of the structurally diverse BIAs.

Examples of benzylisoquinoline alkaloids

File:Benzylisoquinoline structure in Papaverin.svg|Papaverine File:Benzylisoquinoline structure in Noscapine.svg|Noscapine File:Benzylisoquinoline structure in Apomorphone.svg|Apomorphine (one additional ring closure) File:Benzylisoquinoline structure in Morphine.svg|Morphine (two additional ring closures) File:Benzylisoquinoline structure in Berberine.svg|Berberine (one additional ring closure with incorporated N-methyl) File:Benzylisoquinoline structures in Tubocurarine.svg|Tubocurarine (composed of two benzylisoquinoline units)

References

References

  1. (1989). "(S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis". Phytochemistry.
  2. (2015). "Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants". BMC Plant Biol.
  3. (2013). "Benzylisoquinoline alkaloid metabolism: A century of discovery and a brave new world". Plant Cell Physiol..
  4. (1964). "Alkaloid biosynthesis> Part IV. 1-Benzylisoquinolines as precursors of thebaine, codeine, and morphine". J Chem Soc.
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