Glycinol (pterocarpan)
Encyclopedia
Glycinol is a pterocarpan
Pterocarpan
Pterocarpans are derivatives of isoflavonoids found in the Fabaceae family. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes Pterocarpans are derivatives of isoflavonoids found in the Fabaceae family. It is a group of compounds which can be described as...

, a type of natural phenol. It is a phytoalexin
Phytoalexin
Phytoalexins are antimicrobial substances synthesized de novo by plants that accumulate rapidly at areas of incompatible pathogen infection. They are broad spectrum inhibitors and are chemically diverse with different types characteristic of particular plant species...

 found in the soybean
Soybean
The soybean or soya bean is a species of legume native to East Asia, widely grown for its edible bean which has numerous uses...

 (Glycine max). It is formed by the cyclisation of daidzein
Daidzein
Daidzein belongs to the group of isoflavones. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs like the Thai Kwao Krua or Pueraria mirifica, Kudzu or Pueraria lobata, and in food sources such as soybeans and soy products like tofu and textured...

. It has antiestrogenic activities.

It can be synthethised chemically and possesses a chiral center.

Glycinol is the direct precursor of glyceollin
Glyceollin
Glyceollins are a family of prenylated pterocarpan found in ineffective types of nodule in soybean in response to symbiotic infection. They are phytoalexins with an antiestrogenic activity.Molecules found in the family are :* Glyceollin I* Glyceollin II...

s through the action of a prenyltransferase
Prenyltransferase
Prenyltransferases are a class of enzymes that transfer allylic prenyl groups to acceptor molecules. Prenyl transferases commonly refer to prenyl diphosphate synthases....

.

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen.
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