Glycinol (pterocarpan) explained

Glycinol is a pterocarpan, a type of natural phenol. It is a phytoalexin found in the soybean (Glycine max). It is formed by the cyclisation of daidzein.

More recent literature supports that glycinol has potent phytoestrogenic activity.^{[1] [2]}

The so-called osteogenesis that is causes is postulated to be a preventative factor for osteoporosis.

It can be synthethised chemically and possesses two chiral centers.^[3]

Glycinol is the direct precursor of glyceollins through the action of a prenyltransferase.

Experiments show that the 6a oxygen of glycinol is derived from molecular oxygen.^[4]

Notes and References

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.. Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max). Endocrinology. 150. 5. 2009. 2446–2453. 0013-7227. 10.1210/en.2008-1235. 19116342. 2671905. free.
2. Strong. Amy L. Jones. Robert B. Glowacki. Julie. Boue. Stephen M. Burow. Matthew E. Bunnell. Bruce A. Glycinol enhances osteogenic differentiation and attenuates the effects of age on mesenchymal stem cells. Regenerative Medicine. 12. 5. 2017. 513–524. 1746-0751. 10.2217/rme-2016-0148. 28718749.
3. Total Syntheses of Racemic and Natural Glycinol . Luniwal Amarjit . Khupse Rahul S . Reese Michael . Lei Fang . Erhardt Paul W . 2009 . 72 . 11 . 2072–2075 . Journal of Natural Products . 10.1021/np900509f . 19943626.
4. 10.1016/0031-9422(89)85020-4 . The 6a oxygen of the pterocarpan glycinol is derived from molecular oxygen . 1989 . Matthews . David E. . Plattner . Ronald D. . Vanetten . Hans D. . Phytochemistry . 28 . 1 . 113–115. 1989PChem..28..113M . free .