Glyceollin III
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| Preferred IUPAC name
(2S,6aS,11aS)-2-(Prop-1-en-2-yl)-1,2-dihydro-6H-[1]benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11aH)-diol | |
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| C20H18O5 | |
| Molar mass | 338.35 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean (Glycine max).[1] It has an antiestrogenic effect in vivo.[2] In soil, it has an antifungal activity against Aspergillus sojae.[3]
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 steps to the flavanone, liquiritigenin, and then by the action of isoflavonoid synthase (IFS) to the isoflavone, daidzein.[4][5]: Supplement 1
A further sequence of four enzyme-catalysed reactions creates the pterocarpan ring system of the compound glycinol. The prenylation enzyme trihydroxypterocarpan dimethylallyltransferase (G4DT) and then glyceollin synthase (GS) complete the biosynthesis of glyceollin III.[5]
References
- ↑ Banks, Stephen W.; Dewick, Paul M. (1983). "Biosynthesis of glyceollins I, II and III in soybean". Phytochemistry. 22 (12): 2729–2733. doi:10.1016/S0031-9422(00)97682-9.
- ↑ 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.
- ↑ Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; et al. (2010). "Antifungal Activity of Glyceollins Isolated from Soybean Elicited with Aspergillus sojae". Journal of Agricultural and Food Chemistry. 58 (17): 9483–9487. doi:10.1021/jf101694t. PMID 20666365.
- ↑ Lygin, Anatoliy V.; Zernova, Olga V.; Hill, Curtis B.; et al. (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 Khatri, Praveen; Kuflu, Kuflom; McDowell, Tim; et al. (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.
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