Piceid is a
stilbenoid
Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Most stilbenoids are prod ...
glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.
The name was o ...
and is a major
resveratrol
Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...
derivative in grape juices. It can be found in the bark of ''
Picea sitchensis
''Picea sitchensis'', the Sitka spruce, is a large, coniferous, evergreen tree growing to almost tall, with a trunk diameter at breast height that can exceed 5 m (16 ft). It is by far the largest species of spruce and the fifth-larg ...
''. It can also be isolated from ''
Reynoutria japonica
''Reynoutria japonica'', synonyms ''Fallopia japonica'' and ''Polygonum cuspidatum'', is a species of herbaceous perennial plant in the knotweed and buckwheat family Polygonaceae. Common names include Japanese knotweed and Asian knotweed. It is ...
'' (
syn. ''Fallopia japonica''),
the Japanese knotweed (syn. ''Polygonum cuspidatum'').
Resveratrol
Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources ...
can be produced from piceid via the mold ''
Aspergillus oryzae
''Aspergillus oryzae'', also known as , is a filamentous fungus (a mold) used in East Asia to saccharify rice, sweet potato, and barley in the making of alcoholic beverages such as ''sake'' and '' shōchū'', and also to ferment soybeans for m ...
''.
[ as the fungus produces a potent ]beta-glucosidase
β-Glucosidase (EC 3.2.1.21; systematic name β-D-glucoside glucohydrolase) is an enzyme that catalyses the following reaction:
: Hydrolysis of terminal, non-reducing β-D-glucosyl residues with release of β-D-glucose
Structure
β-Glucosidase ...
.
''trans''-Piceid is the glucoside formed with ''trans''-resveratrol, while ''cis''-piceid is formed with ''cis''-resveratrol.
''trans''-Resveratrol-3-''O''-glucuronide is one of the two metabolites of ''trans''-piceid in rat.
Resveratrol glucoside from