Pterocarpans are derivatives of

isoflavonoid Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estro ...

s found in the family

Fabaceae The Fabaceae or Leguminosae,International Code of Nomenc ...

. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6''H''- enzofuro ,2-chromene skeleton) which can be formed by coupling of the B ring to the 4-one position. 2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in ''

Cicer arietinum The chickpea or chick pea (''Cicer arietinum'') is an annual legume of the family Fabaceae, subfamily Faboideae. Its different types are variously known as gram" or Bengal gram, garbanzo or garbanzo bean, or Egyptian pea. Chickpea seeds are high ...

'' and

glyceollin synthase In enzymology, a glyceollin synthase is an enzyme that catalyzes the last committed step in glyceollin biosynthesis. This enzyme has been classified as a cytochrome dependent monooxygenase. It uses cyclization of prenyl residue to convert gl ...

for the production of

glyceollin Glyceollins are a family of prenylated pterocarpans found in ineffective types of nodule in soybean in response to symbiotic infection. It possesses two chiral centers and can be asymmetrically synthesized chemically at a gram level scale. Mol ...

phytoalexin Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized ''de novo'' by plants t ...

s in

soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu an ...

Known compounds

* Bitucarpin A and B, isolated from the aerial parts of Mediterranean plants ''

Bituminaria morisiana ''Bituminaria morisiana'' is a perennial Mediterranean herb species in the genus ''Bituminaria''. Leaf, trifoliate with 3 linear, lanceolate, tomentose leaflets. White flowers in globose flowerheads. Fruit a tomentose legume. Flowers May–July. ...

'' and ''

Bituminaria bituminosa ''Bituminaria bituminosa'', the Arabian pea or pitch trefoil, is a perennial Mediterranean herb species in the genus '' Bituminaria''. The pterocarpans bitucarpin A and B can be isolated from the aerial parts of ''B. bituminosa''. It has sev ...

'' * Erybraedin A and B, isolated from the stems of ''

Erythrina subumbrans ''Erythrina subumbrans'' is a flowering plant species in the genus ''Erythrina ''Erythrina'' is a genus of plants in the pea family, Fabaceae. It contains about 130 species, which are distributed in tropical and subtropical regions worldwide. ...

'' and C, isolated from the leaves of ''

'' * Erythrabyssin II, erystagallin A, erythrabissin-1, and erycristagallin isolated from the stems of ''

'' * Glycinol, glyceollidin I and II,

s (

glyceollin I Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean. Glyceollin synthase is an enzyme responsible for the production of glyceollin. The five substrates of this enzyme are 2-dimethylallyl-(6aS ...

, II, III and IV), found in the

(''Glycine max'') *

Glycyrrhizol A Glycyrrhizol A is a prenylated pterocarpan and an isoflavonoid derivative. It is a compound isolated from the root of the Chinese licorice plant (''Glycyrrhiza uralensis''). It may has ''in vitro'' antibacterial An antibiotic is a type of ...

, isolated from the root of the Chinese licorice plant (''Glycyrrhiza uralensis'') * Maackiain, isolated from the roots of '' Maackia amurensis subsp. Buergeri'' * Medicarpin, found in ''

Medicago truncatula ''Medicago truncatula'', the barrelclover, strong-spined medick, barrel medic, or barrel medick, is a small annual legume native to the Mediterranean region that is used in genomic research. It is a low-growing, clover-like plant tall with trifol ...

'' * Morisianine, isolated from the seeds of ''

'' * Orientanol A, isolated from the wood of '' Erythrina orientalis'' * Phaseolin, found in

French bean Green beans are young, unripe fruits of various cultivars of the common bean ('' Phaseolus vulgaris''), although immature or young pods of the runner bean (''Phaseolus coccineus''), yardlong bean ( ''Vigna unguiculata'' subsp. ''sesquipedalis ...

seeds * Pisatin, found in ''

Pisum sativum The pea is most commonly the small spherical seed or the seed-pod of the flowering plant species ''Pisum sativum''. Each pod contains several peas, which can be green or yellow. Botanically, pea pods are fruit, since they contain seeds and d ...

'' * Striatine, isolated from aerial parts of ''

Mundulea striata ''Mundulea striata'' is a plant species in the genus ''Mundulea''. The pterocarpan Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes ...

'' * Trifolirhizin, found in ''

Sophora flavescens ''Sophora flavescens'', the shrubby sophora, is a species of plant in the genus '' Sophora'' of the family Fabaceae. This genus contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceania, and the ...

References

External links

Superpathway of pterocarpan biosynthesis (via formononetin) on metacyc.org

Pterocarpans on the Comparative Toxicogenomics Database
{{Pterocarpan *Pterocarpans