A Regioselective Synthesis of E-Guggulsterone

Abstract

We have successfully prepared E-guggulsterone from 16,17-epoxy-pregnenolone in 84% yield over two steps via a hydrazine reduction and Oppenhauer oxidation. Additionally, isomerization was induced by heat, light (hν) and acid catalysis to convert E- guggulsterone into the corresponding Z isomer.

Therapeutic use of Guggulsterone in COVID-19 induced obesity (COVIBESITY) and significant role in immunomodulatory effect

“…The presence of Ketone group in 17 th position increases the lipid lowering activity by inhibiting the Farnesoid X receptor. Z-guggulusterone is 16,17-epoxypregnenolone where there is replacement of methyl and hydrogen group vice versa in the position of E-guggulusterone, which is to reduce the toxicity( Ham, Chin, & Kang, 2011 ). It has also shown its effectiveness in regulating appetite and thus reducing weight which can be used as a swift and effective management for Covibesity.…”

Beyond Bile Acids: Targeting Farnesoid X Receptor (FXR) with Natural and Synthetic Ligands

“…2) are considered as the key active ingredients responsible for the therapeutic effects of the gum resin. The readily availability of guggulsterones by synthetic approaches has allowed to better define the biological mechanisms and clinical significance of this class of compounds [31,32]. At this regard, while some studies showed that the biological activity of guggulsterones is at least partly due to their action as gene selective FXR modulators, others have indicated that additional pathways are involved in the pharmacological action of guggulsterones [33][34][35].…”

Guggulsterone – a potent bioactive phytosteroid: synthesis, structural modification, and its improved bioactivities

“…Ham and co-workers 77 described a regioselective synthesis of GS using 98% pure hydrazine monohydrate (Fig. 6).…”