Study on 20-hydroxyprogesterone: Chiral resolution, Content determination and Progesterone-like activity.

20-hydroxyprogesterone (20-DHP) is a natural metabolite of progesterone which occurs with two diastereoisomers: 20α-DHP and 20β-DHP. They have drawn attention for their progesterone-like activity since the middle of the 20th century. However, the literature from that era bears witness to a lack of consensus regarding their specific effects. Considered that their stereoisomerism differences, it is essential to investigate their biological activities in vivo separately. In this study, we presented a chemical synthesis technique that yielded highly pure samples of 20α-DHP and 20β-DHP, and performed simultaneous content analysis. Subsequently, we examined and contrasted the progesterone-like properties of 20α-DHP, 20β-DHP, and a 1:1 mixture of 20α-DHP and 20β-DHP. The Morphological observations of the endometrium were conducted via Haematoxylin-eosin staining. Serum hormone levels were measured using enzyme-linked immunosorbent assays. Furthermore, real-time fluorescence quantitative polymerase chain reaction and immunohistochemistry were employed to analyse the relevant mRNA and protein expression, respectively. Our comparison revealed that 20α-DHP and P4 share identical progesterone-like actions, while 20β-DHP exhibits partial similarity. The progesterone activity varied when the two were combined in a 1:1 ratio.

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Declaration of Competing Interest The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed. No writing assistance was utilized in the production of this manuscript.