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 estr ...

s found in the family

Fabaceae Fabaceae () or Leguminosae,International Code of Nomen ...

. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6''H''- enzofuro

,2-c The comma is a punctuation mark that appears in several variants in different languages. Some typefaces render it as a small line, slightly curved or straight, but inclined from the vertical; others give it the appearance of a miniature fille ...

hromene 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, cultivated for its edible seeds. Its different types are variously known as gram," Bengal gram, garbanzo, garbanzo bean, or Egypt ...

'' and

glyceollin synthase In enzymology, 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 glyceol ...

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. Mo ...

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 ...

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. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...

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 seve ...

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

Erythrina subumbrans ''Erythrina subumbrans'', common names Tton Tong or Dadap, 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 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,1 ...

, 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 properties. In one study, the str ...

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

Medicarpin Medicarpin is a pterocarpan, a derivative of isoflavonoids. Natural occurrences Medicarpin is found in ''Medicago truncatula'' and ''Swartzia madagascariensis''. It can also be found in ''Maackia amurensis'' cell cultures. The root nodule form ...

, 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 trif ...

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

'' * Orientanol A, isolated from the wood of '' Erythrina orientalis'' * Phaseolin, found in French bean seeds * Pisatin, found in ''

Pisum sativum Pea (''pisum'' in Latin) is a pulse or fodder crop, but the word often refers to the seed or sometimes the pod of this flowering plant species. Peas are eaten as a vegetable. Carl Linnaeus gave the species the scientific name ''Pisum sativum ...

'' * Striatine, isolated from aerial parts of '' Mundulea striata'' * Trifolirhizin, found in '' Sophora flavescens''

References

External links

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

Pterocarpans on the Comparative Toxicogenomics Database
{{Pterocarpan *Pterocarpans