Glyceollin
Glyceollins are a family of prenylated pterocarpans found in soybean whose production is enhanced in response to symbiotic infection and that act as phytoalexins.[1] They are derived from the isoflavone, daidzein.
Biosynthesis
[edit]All the glyceollins are products of a pathway in soybean which starts from the amino acid L-phenylalanine. This is converted in a series of reactions to the flavanone, liquiritigenin and then to the isoflavone, daidzein. A further sequence of four enzyme-catalysed steps creates the pterocarpan ring system of the compound glycinol.[2][3]: Supplement 1
The prenylation enzyme trihydroxypterocarpan dimethylallyltransferase (G4DT) and then glyceollin synthase (GS) complete the biosynthesis of glyceollin I. The enzyme G4DT can add the prenyl group in an alternative position in glycinol, giving glycerocarpin. This forms glyceollin II when aced on by glyceollin synthase:[3]
The synthase enzyme also produces the isomer, glyceollin III, from glyceocarpin:
Glyceocarpin is also the precursor to a methylated derivative called glyceollin IV and other related compounds are known to be produced.[3]
Chemical synthesis
[edit]Glyceollin I has been synthesized in the laboratory at a gram level scale.[4]
Effects
[edit]The glyceollins are phytoalexins which help to protect soybean against infection by pathogens such as the bacteria, Rhizobium japonicum, and the fungii Phytophthora sojae, Macrophomina phaseolina, and Aspergillus sojae.[1][2] They also help defend against the plant parasitic nematode, Meloidogyne incognita.[5] Glyceollins have been shown to exhibit antiestrogenic properties in vitro[6] and in vivo.[7]
Inhibitors of glyceollin production
[edit]Some pathogens produce inhibitors that block the biosynthetic path to glyceollins. For example, Phytophthora megasperma produces an extracellular invertase, a glycoprotein of mannan, which prevents glyceollin accumulation.[5]
References
[edit]- 1 2 Werner, Dietrich; Mellor, Robert B.; Hahn, Michael G.; Grisebach, Hans (1985). "Soybean Root Response to Symbiotic Infection Glyceollin I Accumulation in an Ineffective Type of Soybean Nodules with an Early Loss of the Peribacteroid Membrane". Zeitschrift für Naturforschung C. 40 (3–4): 179–181. doi:10.1515/znc-1985-3-407.
- 1 2 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.
- 1 2 3 Khatri, Praveen; Kuflu, Kuflom; McDowell, Tim; Lin, Jie; Kovinich, Nikola; Dhaubhadel, Sangeeta (2025). "Discovery of three cytochrome P450 monooxygenase prenyl cyclases that catalyze the final step of glyceollin biosynthesis in soybean". Molecular Plant. 18 (5): 721–724. doi:10.1016/j.molp.2025.01.022. PMID 39891385.
- ↑ 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.
- 1 2 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.
- ↑ Payton-Stewart, Florastina; Khupse, Rahul S.; Boué, Stephen M.; et al. (2010). "Glyceollin I enantiomers distinctly regulate ER-mediated gene expression". Steroids. 75 (12): 870–878. doi:10.1016/j.steroids.2010.05.007. hdl:11336/58472. PMID 20493896.
- ↑ Salvo, Virgilo A.; Boué, Stephen M.; Fonseca, Juan P.; et al. (2006). "Antiestrogenic Glyceollins Suppress Human Breast and Ovarian Carcinoma Tumorigenesis". Clinical Cancer Research. 12 (23): 7159–7164. doi:10.1158/1078-0432.CCR-06-1426. PMID 17145841.
Types of pterocarpans | |
|---|---|
| Pterocarpans: | |
| O-methylated | |
| Prenylated |
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