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The Amaryllidaceae alkaloids are a family of amino acid derived alkaloids with many biological activities; examples include haemanthamine, haemanthidine, galanthamine, lycorine, and maritidine. Central to the biosynthesis of the majority of these alkaloids is a  C-C  phenol-coupling reaction that can have  para-para', para-ortho' , or  ortho-para'  regiospecificity. Through comparative transcriptomics of  Narcissus  sp.  aff. pseudonarcissus, Galanthus  sp., and  Galanthus elwesii  we have identified a  para-para' C-C  phenol coupling cytochrome P450, CYP96T1, capable of forming the products (10b R ,4a S )-noroxomaritidine and (10b S ,4a R )-noroxomaritidine from 4′- O -methylnorbelladine. CYP96T1 was also shown to catalyzed formation of the  para-ortho'  phenol coupled product,  N -demethylnarwedine, as less than 1% of the total product.  CYP96T1  co-expresses with the previously characterized norbelladine 4′- O -methyltransferase. The discovery of CYP96T1 is of special interest because it catalyzes the first major branch in Amaryllidaceae alkaloid biosynthesis. CYP96T1 is also the first phenol-coupling enzyme characterized from a monocot.

CYP96T1 of Narcissus sp. aff. pseudonarcissus Catalyzes Formation of the Para-Para' C-C Phenol Couple in the Amaryllidaceae Alkaloids