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Glycinol (pterocarpan)

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Glycinol
Chemical structure of glycinol
Chemical structure of glycinol
Glycinol molecule
Names
Preferred IUPAC name
(6aS,11aS)-6H-[1]Benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C15H12O5/c16-8-1-3-10-12(5-8)19-7-15(18)11-4-2-9(17)6-13(11)20-14(10)15/h1-6,14,16-18H,7H2/t14-,15+/m0/s1 checkY
    Key: QMXOFBXZEKTJIK-LSDHHAIUSA-N checkY
  • O3c1c(ccc(O)c1)[C@@H]4Oc2cc(O)ccc2[C@]4(O)C3
Properties
C15H12O5
Molar mass 272.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (Glycine max) and is biosynthesised from daidzein.

Glycinol has potent phytoestrogenic activity. The so-called osteogenesis that this causes is postulated to be a preventative factor for osteoporosis.[1][2]

Glycinol can be synthethised chemically and possesses two chiral centers.[3] It is a precursor to glyceollins through the action of prenyltransferase enzymes such as trihydroxypterocarpan dimethylallyltransferase.[4]

Biosynthesis

[edit]

In plants such as soybean, glycinol is derived from the daidzein in a sequence of steps. The final hydroxylation reaction is carried out by the enzyme 3,9-dihydroxypterocarpan 6a-monooxygenase, which is a cytochrome P450 protein that uses molecular oxygen to introduce the hydroxy group.[5][6]

2D representation of the chemical structure of daidzein .
daidzein
Multi-step
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27098166.
3,9-dihydroxypterocarpan
Oxgenase
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of glycinol (pterocarpan).
glycinol

References

[edit]
  1. ↑ Boué, Stephen M.; Tilghman, Syreeta L.; Elliott, Steven; Zimmerman, M. Carla; Williams, K. Y.; Payton-Stewart, Florastina; Miraflor, Allen P.; Howell, Melanie H.; Shih, Betty Y.; Carter-Wientjes, Carol H.; Segar, Chris; Beckman, Barbara S.; Wiese, Thomas E.; Cleveland, Thomas E.; McLachlan, John A.; Burow, Matthew E. (2009). "Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)". Endocrinology. 150 (5): 2446–2453. doi:10.1210/en.2008-1235. ISSN 0013-7227. PMC 2671905. PMID 19116342.
  2. ↑ Strong, Amy L; Jones, Robert B; Glowacki, Julie; Boue, Stephen M; Burow, Matthew E; Bunnell, Bruce A (2017). "Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells". Regenerative Medicine. 12 (5): 513–524. doi:10.2217/rme-2016-0148. ISSN 1746-0751. PMID 28718749.
  3. ↑ Luniwal Amarjit; Khupse Rahul S; Reese Michael; Lei Fang; Erhardt Paul W (2009). "Total Syntheses of Racemic and Natural Glycinol". Journal of Natural Products. 72 (11): 2072–2075. doi:10.1021/np900509f. PMID 19943626.
  4. ↑ Leube, Joachim; Grisebach, Hans (1983). "Further Studies on Induction of Enzymes of Phytoalexin Synthesis in Soybean and Cultured Soybean Cells". Zeitschrift für Naturforschung C. 38 (9–10): 730–735. doi:10.1515/znc-1983-9-1011.
  5. ↑ Schopfer, Christel R.; Kochs, Georg; Lottspeich, Friedrich; Ebel, Jürgen (1998). "Molecular characterization and functional expression of dihydroxypterocarpan 6a-hydroxylase, an enzyme specific for pterocarpanoid phytoalexin biosynthesis in soybean ( Glycine max L.)". FEBS Letters. 432 (3): 182–186. doi:10.1016/S0014-5793(98)00866-7. PMID 9720921.
  6. ↑ Liu, Weixin; Feng, Yi; Yu, Suhang; Fan, Zhengqi; Li, Xinlei; Li, Jiyuan; Yin, Hengfu (2021). "The Flavonoid Biosynthesis Network in Plants". International Journal of Molecular Sciences. 22 (23) 12824. doi:10.3390/ijms222312824. PMC 8657439. PMID 34884627.


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