Structure–activity analysis on ecdysteroids: A structural and quantum chemical approach based on two biological systems

Cellular stress response mechanisms as therapeutic targets of ginsenosides

“…In addition, numerous PPT‐type ginsenosides, such as Rg1, and several metabolites of PPDs, such as compound K, show a structural similarity with ecdysteroids, which also process a steroid backbone with a C‐20 sugar side chain and a C‐3 hydroxyl group . Such similarity contributes the binding activity of ginsenosides to the ecdysteroid receptor, which may interrupt the life cycle of insects . Moreover, the difference in the C‐6 position between ecdysteroids, which are occupied by an oxygen group, and ginsenosides, which possess a hydrogen or hydroxyl group plays minor or nonsignificant role in the ecdysteroid receptor binding affinity as evaluated by biochemical analysis …”

“…40 Ginsenosides may also interrupt the life cycle of insects by binding to the ecdysteroid receptor due to the structural similarities between ginsenosides and ecdysteroids, which are the insect molting and metamorphosis hormones. 41,42…”

Investigation of plants containing unusual ecdysteroids with ring in their side-chain

“…Previous ecdysteroid structure-activity concepts were based on essential or nonessential functional groups, 12 but recent studies have revealed that no single feature is essential for activity, and not all functional groups are equally important for the display of biological activity (Figure 7). 15,113 Both activities measured in the BII assay and predictions for hypothetical steroids indicate that a cis-A/B-ring junction is not essential for activity. Although the 7-en-6-one moiety is not essential, the absence of both the double bond and the keto group seems to be accompanied by a decreased activity.…”

“…A 14-hydroxy group could facilitate the intermolecular connection between the side-chain and ring A. 113 The research carried out by…”

“…The ligand, a steroid molecule with plane restriction will not need more than two main points to reach sufficient associated bond energy, once in contact with the receptor. Ferro et al 113 therefore consider that the 22-hydroxy group should be involved in a direct reaction to induce intermolecular forces, while the other functional groups of the side-chain are contributors to the molecular properties, and modulate the biological activity.…”