Glyceollins are a family of prenylated pterocarpans 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. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...

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 II *

Glyceollin III Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean (''Glycine max''). It has an antiestrogenic effect. In soil, it has an antifungal An antifungal medication, also known as an antimycotic medication, is a pharmace ...

* Glyceollin IV

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 ...

s with an antiestrogenic 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 ...

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 ...

'' 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 th ...

'', and Kim ''et al.'' 2010 against '' Aspergillus sojae''. 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 worldwid ...

''. 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 ...

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. Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase. Glyceollin synthase then transforms those prenylated precursors into glyceollins.

Inhibitors

Some

pathogens In biology, a pathogen (, "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. The term ...

produce inhibitors. Ziegler & Pontzen 1982 find '' Phytophthora megasperma'' produces an extracellular

invertase β-Fructofuranosidase is an enzyme that catalyzes the hydrolysis (breakdown) of the table sugar sucrose into fructose and glucose. Sucrose is a fructoside. Alternative names for β-fructofuranosidase include invertase, saccharase, glucosucrase ...

, a mannanglycoprotein (a

glycoprotein Glycoproteins are proteins which contain oligosaccharide (sugar) 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 a ...

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

carbohydrate A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' ...

moiety.

References

Antiestrogens Pterocarpans {{aromatic-stub