Glyceollins are a family of prenylated

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 (i.e. 6''H''- enzofuro ,2-chromene skeleton) which can be formed by coupling of the B rin ...

s found in ineffective types of nodule 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 ...

in response to symbiotic infection. It possesses two chiral centers and can be asymmetrically synthesized chemically at a gram level scale. Molecules found in the family are : *

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 ...

Glyceollin II 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 ...

Glyceollin III Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean (''Glycine max''). It has an antiestrogenic Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like est ...

Glyceollin IV 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 ...

Effects

They are

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 with an

antiestrogenic Antiestrogens, also known as estrogen antagonists or estrogen blockers, are a class of drugs which prevent estrogens like estradiol from mediating their biological effects in the body. They act by blocking the estrogen receptor (ER) and/or inh ...

activity.Glyceollins, a Novel Class of Antiestrogenic Phytoalexins. Syreeta L. Tilghman, Stephen M. Boué and Matthew E. Burow, Mol Cell Pharmacol 2010;2(4), pp. 155-160, Lygin ''et al.'' 2013 finds

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as crypto ...

activity against ''

Phytophthora sojae ''Phytophthora sojae'' is an oomycete and a soil-borne plant pathogen that causes stem and root rot of soybean. This is a prevalent disease in most soybean growing regions, and a major cause of crop loss. In wet conditions the pathogen produces z ...

'' and ''

Macrophomina phaseolina ''Macrophomina phaseolina'' is a Botryosphaeriaceae plant pathogen fungus that causes damping off, seedling blight, collar rot, stem rot, charcoal rot, basal stem rot, and root rot on many plant species. Hosts, symptoms, and signs One of the ...

'', and Kim ''et al.'' 2010 against ''

Aspergillus sojae ''Aspergillus sojae'' is a species of fungus in the genus ''Aspergillus''. In Japan, it is used to make the ferment ( ''kōji'') of soy sauce, miso, mirin, and other lacto-fermented condiments such as ''tsukemono''. Soy sauce condiment is produ ...

''. Kaplan ''et al.'' 1980 finds nematicidal activity against ''

Meloidogyne incognita ''Meloidogyne incognita'' (root-knot nematode - RKN), also known as the "southern root-nematode" or "cotton root-knot nematode" is a plant-parasitic roundworm in the family Heteroderidae. This nematode is one of the four most common species world ...

''. Parniske ''et al.'' 1991 finds an

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

effect. Glyceollin is a vital part of

immunity.

Metabolism

Lygin ''et al.'' 2013 find that

daidzein Daidzein (7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one) is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones a ...

is a precursor. . Glyceollin is a product of the

phenylpropanoid pathway The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

. Glycinol is the direct precursor of glyceollins through the action of a

prenyltransferase Prenyltransferases (PTs) are a class of enzymes that transfer allylic prenyl groups to acceptor molecules. Prenyl transferases commonly refer to isoprenyl diphosphate syntheses (IPPSs). Prenyltransferases are a functional category and include seve ...

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 ...

then transforms those prenylated precursors into glyceollins.

Inhibitors

Some

pathogens In biology, a pathogen ( el, πάθος, "suffering", "passion" and , "producer of") in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ ...

produce inhibitors. Ziegler & Pontzen 1982 find ''

Phytophthora megasperma ''Phytophthora megasperma'' is a species of water mould in the family Peronosporaceae. It is well known as a plant pathogen with many hosts. It often causes a plant disease called root rot.invertase Invertase is an enzyme that catalyzes the hydrolysis (breakdown) of sucrose (table sugar) into fructose and glucose. Alternative names for invertase include , saccharase, glucosucrase, beta-h-fructosidase, beta-fructosidase, invertin, sucrase, ma ...

, a mannanglycoprotein (a

glycoprotein Glycoproteins are proteins which contain oligosaccharide chains covalently attached to amino acid side-chains. The carbohydrate is attached to the protein in a cotranslational or posttranslational modification. This process is known as glycos ...

of mannan), which prevents glyceollin accumulation not by its enzymatic action but due to an effect of its

carbohydrate In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or ma ...

moiety.

References

Antiestrogens Pterocarpans {{aromatic-stub