Glyceollin
Group of plant chemicals
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[3] with an antiestrogenic activity.[4] Lygin et al. 2013[5] finds antifungal activity against Phytophthora sojae and Macrophomina phaseolina, and Kim et al. 2010 against Aspergillus sojae.[3] Kaplan et al. 1980 finds nematicidal activity against Meloidogyne incognita.[3] Parniske et al. 1991 finds an antibacterial effect.[3] Glyceollin is a vital part of soybean immunity.[3]
Metabolism
Lygin et al. 2013[5] find that daidzein is a precursor.[3] Glyceollin is a product of the phenylpropanoid pathway.[3] 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.[3] 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.[3]
References
- ^ 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.
- ^ 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. doi:10.1021/op200112g. ISSN 1083-6160.
- ^ a b c d e f g h i Bauters, Lander; Stojilković, Boris; Gheysen, Godelieve (2021-08-19). "Pathogens pulling the strings: Effectors manipulating salicylic acid and phenylpropanoid biosynthesis in plants". Molecular Plant Pathology. 22 (11). British Society for Plant Pathology (W-B): 1436–1448. doi:10.1111/mpp.13123. ISSN 1464-6722. PMC 8518561. PMID 34414650. (LB ORCID: 0000-0001-5456-9305).
- ^ 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, doi:10.4255/mcpharmacol.10.21
- ^ a b Lygin, Anatoliy V.; Zernova, Olga V.; Hill, Curtis B.; Kholina, Nadegda A.; Widholm, Jack M.; Hartman, Glen L.; Lozovaya, Vera V. (2013). "Glyceollin is an Important Component of Soybean Plant Defense Against Phytophthora sojae and Macrophomina phaseolina". Phytopathology. 103 (10). American Phytopathological Society: 984–994. doi:10.1094/phyto-12-12-0328-r. ISSN 0031-949X. PMID 23617338. S2CID 12170923.
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Types of pterocarpans
- Erybraedin C
- Erythrabyssin II
- Folitenol
- Glycinol
- Maackiain
- Orientanol A, B and C
- Pisatin
- Sophorol
- Trifolirhizin
- Bitucarpin A and B
- Glyceollidin I and II
- Glyceollins (Glyceollin I, II, III and IV)
- Glycyrrhizol A
- Morisianine
- Phaseolin
- Striatine
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