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Glyceollin

From Wikipedia, the free encyclopedia
Group of plant chemicals

Glyceollins are a family of prenylatedpterocarpans found in ineffective types of nodule insoybean 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 :

Effects

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They arephytoalexins[3] with anantiestrogenic activity.[4] Lyginet al. 2013[5] findsantifungal activity againstPhytophthora sojae andMacrophomina phaseolina, and Kimet al. 2010 againstAspergillus sojae.[3] Kaplanet al. 1980 findsnematicidal activity againstMeloidogyne incognita.[3] Parniskeet al. 1991 finds anantibacterial effect.[3] Glyceollin is a vital part ofsoybean immunity.[3]

Metabolism

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Lyginet al. 2013[5] find thatdaidzein is a precursor.[3] Glyceollin is a product of thephenylpropanoid pathway.[3]Glycinol is the direct precursor of glyceollins through the action of aprenyltransferase.Glyceollin synthase then transforms those prenylated precursors into glyceollins.

Inhibitors

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Somepathogens produce inhibitors.[3] Ziegler & Pontzen 1982 findPhytophthora megasperma produces an extracellularinvertase, amannanglycoprotein (aglycoprotein ofmannan), which prevents glyceollin accumulation not by its enzymatic action but due to an effect of itscarbohydrate moiety.[3]

References

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  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.doi:10.1021/op200112g.ISSN 1083-6160.
  3. ^abcdefghiBauters, 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.(LBORCID:0000-0001-5456-9305).
  4. ^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
  5. ^abLygin, 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 AgainstPhytophthora sojae andMacrophomina phaseolina".Phytopathology.103 (10).American Phytopathological Society:984–994.doi:10.1094/phyto-12-12-0328-r.ISSN 0031-949X.PMID 23617338.S2CID 12170923.


Types of pterocarpans
Pterocarpans:
O-methylated
Prenylated
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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