Pterocarpan

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Pterocarpan chemical structure. It consists of a 1-benzofuran moiety (dotted blue circle) fused to a 2H-chromene moiety (dotted green circle). The systematic name for it is 6H-[1]benzofuro[3,2-c]chromene. The new numbering of the resulting moiety is shown with red numbers. Pterocarpan.png
Pterocarpan chemical structure. It consists of a 1-benzofuran moiety (dotted blue circle) fused to a 2H-chromene moiety (dotted green circle). The systematic name for it is 6H-[1]benzofuro[3,2-c]chromene. The new numbering of the resulting moiety is shown with red numbers.

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 (i.e. 6H-[1]benzofuro[3,2-c]chromene skeleton) which can be formed by coupling of the B ring to the 4-one position. [1]

Contents

2'-hydroxyisoflavone reductase is the enzyme responsible for the conversion in Cicer arietinum [2] and glyceollin synthase for the production of glyceollins, phytoalexins in soybean. [3]

Known compounds

Medicarpin chemical structure Medicarpin structure.svg
Medicarpin chemical structure
Phaseolin - a prenylated pterocarpan - chemical structure Phaseolin structure.svg
Phaseolin a prenylated pterocarpan chemical structure
Glyceollin III - a prenylated pterocarpan - chemical structure Glyceollin III.svg
Glyceollin III a prenylated pterocarpan chemical structure

Related Research Articles

<i>Bituminaria</i> Genus of legumes

Bituminaria is small genus of perennial herbs in the bean family.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

<i>Maackia amurensis</i> Species of legume

Maackia amurensis, commonly known as the Amur maackia, is a species of tree in the family Fabaceae that can grow 15 metres (49 ft) tall. The species epithet and common names are from the Amur River region, where the tree originated; it occurs in northeastern China, Korea, and Russia.

In enzymology, an isoflavone 7-O-methyltransferase is an enzyme that catalyzes the chemical reaction

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 glyceollidins into glyceollins.

<span class="mw-page-title-main">Apigeninidin</span> Chemical compound

Apigeninidin is a chemical compound belonging to the 3-deoxyanthocyanidins and that can be found in the Patagonian plant Ephedra frustillata and in the soybean. Apigeninidin is one of the principal pigments found in sorghum. Extremely high level of apigeninidin (49 mg/g) has been documented in sorghum leaf sheath. Like all anthocyanidins it exists in a variety of tautomers depending on pH and hydration, several of these bare the distinctive pyrylium core.

<span class="mw-page-title-main">Prenylflavonoid</span>

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

<span class="mw-page-title-main">Barbigerone</span> Chemical compound

Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

Glyceollins are a family of prenylated pterocarpans found in ineffective types of nodule in soybean in response to symbiotic infection.

<span class="mw-page-title-main">Glyceollin I</span> Chemical compound

Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.

<i>Bituminaria bituminosa</i> Species of legume

Bituminaria bituminosa, the Arabian pea or pitch trefoil, is a perennial Mediterranean herb species in the genus Bituminaria.

<span class="mw-page-title-main">Glycinol (pterocarpan)</span> Chemical compound

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean. It is formed by the cyclisation of daidzein.

<span class="mw-page-title-main">Phaseolin (pterocarpan)</span> Chemical compound

Phaseolin is a prenylated pterocarpan found in French bean seeds and in the stems of Erythrina subumbrans.

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. It is endemic to Sardinia where it is restricted to high mountain areas, such as Monte Albo and Monte Corrasi.

<span class="mw-page-title-main">Glyceollin III</span> Chemical compound

Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean. It has an antiestrogenic effect. In soil, it has an antifungal activity against Aspergillus sojae.

Erythrina orientalis is a plant species in the genus Erythrina. This plant is a climbing herb that grows up to 6 m long, and has compound leaves with petioles that are 5–6 cm long. Its leaflets emerge in groups of three, and are 7–9 cm long and 5–8 cm wide. The plant's young leaves, flowers and pods are consumed as vegetables.

Mundulea striata is a plant species in the genus Mundulea.

7-<i>O</i>-Methylluteone Chemical compound

7-O-Methylluteone is a prenylated isoflavone. It can be found in the bark of Erythrina burttii.

<i>Erythrina burttii</i> Species of legume

Erythrina burttii is a flowering plant species in the genus of Erythrina found in Kenya and Ethiopia.

<span class="mw-page-title-main">Pisatin</span> Chemical compound

Pisatin (3-hydroxy-7-methoxy-4′,5′-methylenedioxy-chromanocoumarane) is the major phytoalexin made by the pea plant Pisum sativum. It was the first phytoalexin to be purified and chemically identified. The molecular formula is C17H14O6.

References

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