Glyceollin Explained

Glyceollins are a family of prenylated pterocarpans found in ineffective types of nodule in soybean in response to symbiotic infection.^[1]

It possesses two chiral centers and can be asymmetrically synthesized chemically at a gram level scale.^[2]

Molecules found in the family are :

• Glyceollin I
• Glyceollin II
• Glyceollin III
• Glyceollin IV

Effects

They are phytoalexins with an antiestrogenic activity.^[3] Lygin et al. 2013 finds antifungal activity against Phytophthora sojae and Macrophomina phaseolina, and Kim et al. 2010 against Aspergillus sojae. Kaplan et al. 1980 finds nematicidal activity against Meloidogyne incognita. Parniske et al. 1991 finds an antibacterial effect. Glyceollin is a vital part of soybean immunity.

Metabolism

Lygin et al. 2013^[4] find that daidzein is a precursor.^[5] 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 produce inhibitors. Ziegler & Pontzen 1982 find Phytophthora megasperma produces an extracellular invertase, a mannanglycoprotein (a glycoprotein of mannan), which prevents glyceollin accumulation not by its enzymatic action but due to an effect of its carbohydrate moiety.

Notes and References

1. Soybean root response to symbiotic infection: Glyceollin accumulation in an ineffective type of nodule with an early loss of the peribacteroid membrane. Werner, D., R.B. Mellor, M.G. Hahn and H. Grisebach (1985), Z. Naturforsch., 40, 171-181.
2. Luniwal. Amarjit. Khupse. Rahul. Reese. Michael. Liu. Jidong. El-Dakdouki. Mohammad. Malik. Neha. Fang. Lei. Erhardt. Paul. 2011-09-16. Multigram Synthesis of Glyceollin I. Organic Process Research & Development. 15. 5. 1149–1162. 10.1021/op200112g. 1083-6160.
3. 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,
4. Lygin . Anatoliy V. . Zernova . Olga V. . Hill . Curtis B. . Kholina . Nadegda A. . Widholm . Jack M. . Hartman . Glen L. . Lozovaya . Vera V. . Glyceollin is an Important Component of Soybean Plant Defense Against Phytophthora sojae and Macrophomina phaseolina . . . 103 . 10 . 2013 . 0031-949X . 10.1094/phyto-12-12-0328-r . 984–994 . 12170923 . 23617338. free .
5. Bauters . Lander . Stojilković . Boris . Gheysen . Godelieve . Pathogens pulling the strings: Effectors manipulating salicylic acid and phenylpropanoid biosynthesis in plants . . British Society for Plant Pathology (W-B) . 2021-08-19 . 22 . 11 . 1464-6722 . 10.1111/mpp.13123 . 1436–1448 . 34414650 . 8518561 . free. .