Cyanidin can be synthesized in berry plants through the
shikimate pathway and
polyketide synthase (PKS) III. The shikimate pathway is a biosynthetic pathways that uses the starting materials
Phosphoenolpyruvic acid (PEP) and
Erythrose 4-phosphate to form
shikimic acid, which then further reacts to form specific
aromatic amino acids. L-
phenylalanine, which is necessary in the production of cyanidin, is synthesized through the shikimate pathway. In the synthesis of L-phenylalanine,
chorismate undergoes a
Claisen rearrangement by a
Chorismate mutase enzyme to form
prephenate. Prephenate undergoes dehydration, decarboxylation, and transamination with
Pyridoxal phosphate (PLP) and
alpha-Ketoglutaric acid to form L-phenylalanine (figure 1). L-phenylalanine then undergoes an elimination of the primary amine with
Phenylalanine ammonia-lyase (PAL) to form cinnamate. Through an oxidation with molecular oxygen and
NADPH, a hydroxyl group is added to the para position of the aromatic ring. The compound then reacts with
Coenzyme A (CoA), CoA ligase, and
ATP to attach CoA to the carboxylic acid group. The compound reacts with
naringenin-
chalcone synthase and three malonyl CoA molecules to add six carbon atoms and three more keto groups ring through
PKS III.
Aureusidin synthase catalyses the aromatization and cyclization of the newly added carbonyl groups and facilitates the release of CoA. The compound then spontaneously cyclizes to form
naringenin (figure 2). Naringenin is then converted to cyanidin through several oxidizing and reducing steps. First naringenin is reacted with two equivalents of oxygen,
alpha-Ketogluteratic acid, and flavanone 3-hydroxylase to form
dihydrokaempferol. The compound then reacts with NADPH and dihydroflavonol 4-reductase to form
leucopelargonidin, which is further oxidized with oxygen,
alpha-Ketogluteratic acid, and anthocyanidin synthase. This compound spontaneously loses a water molecule and a hydroxide ion to form cyanidin (figure 3). ==Activation==