The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review

Abstract

The phytoecdysteroids (PEs) comprise a large group of biologically-active plant steroids, which have structures similar to those of insect-molting hormones. PEs are distributed in plants as secondary metabolites that offer protection against phytophagus (plant-eating) insects. When insects consume the plants containing these chemicals, they promptly molt and undergo metabolic destruction; the insects eventually die. Chemically, ecdysteroids are a group of polyhydroxylated ketosteroids that are structurally similar to androgens. The carbon skeleton of ecdysteroids is termed as cyclopentanoperhydro-phenanthrene with a β -side chain at carbon-17. The essential characteristics of ecdysteroids are a cis -(5 β -H) junction of rings A and B, a 7-en-6-one chromophore, and a trans -(14 α -OH) junction of rings C and D. Plants only synthesize PEs from mevalonic acid in the mevalonate pathway of the plant cell using acetyl-CoA as a precursor; the most common PE is 20-hydroxyecdysone. So far, over 400 PEs have been identified and reported, and a compilation of 166 PEs originating from 1998 has been previously reviewed. In the present review, we have summarized 212 new PEs reported between 1999 and 2019. We have also critically analyzed the biological, pharmacological, and medicinal properties of PEs to understand the full impact of these phytoconstituents in health and disease.

Functional Components and Anti-Nutritional Factors in Gluten-Free Grains: A Focus on Quinoa Seeds

“…Phytoecdysteroids (PE) are a wide group of plant steroids whose structure is characterized by a steroid skeleton 5β-cholestanol containing a 6-ketone ring B and a hydroxyl group in position C-14α [63]. They occur as polar and non-polar conjugates, including esters of aliphatic and phenolic acids, sulfate and phosphate, ethers, and glycosides.…”

“…They occur as polar and non-polar conjugates, including esters of aliphatic and phenolic acids, sulfate and phosphate, ethers, and glycosides. Despite being widespread, a small percentage of plants contain detectable levels of PE [63]. The compound 20-Hydroxyecdysone (20 HE) is the most common phytoecdysteroid.…”

“…Based on in-vitro and in-vivo studies, they are considered to play important activities in the human body. They act as anabolic, growth-promoting, antidiabetic, immunomodulatory, hepatoprotective, neuroprotective, hypocholesterolemic, wound healing, antidepressive and antioxidant agents [63].…”

Two Ecdysteroids Isolated from Micropropagated Lychnis flos-cuculi and the Biological Activity of Plant Material

“…Although the absolute stereochemistry of compounds 1 and 2 , which can be crucial for the biological activity, was not determined, it is assumed that they are 2 S ,3 R ,14 S ,20 R ,22 R ,25-hexahydroxy-5 S -cholest-7-en-6-one (2β,3β,14α,20 R ,22 R ,25-hexahydroxy-5β-cholest-7-en-6-one) and 2 S ,3 R ,5 S, 14 S ,20 R ,22 R ,25-heptahydroxy-5 S -cholest-7-en-6-one (2β,3β,5β,14α,20 R ,22 R ,25-heptahydroxy-5β-cholest-7-en-6-one), respectively, as established by X-ray crystallographic studies [ 28 ], which confirmed an earlier established structure of an ecdysone skeleton [ 29 ]. Additionally, one general route of ecdysone biosynthesis in plants has been established without variability in the stereochemistry, except for the trans or cis junction of A/B rings [ 10 , 30 ]. Moreover, any epimeric form would be recognized by an apparent change in the multiplicity and magnitude of coupling constants of a methine 1 H NMR signal at a chiral center, and a chemical 13 C NMR shift of the vicinal carbon signal, as exemplified by 22 R and 22 S epimers of 20-hydroxyecdysone [ 31 ].…”

“…Both are dominant ecdysteroids in L. flos-cuculi [ 6 ]. The adaptogenic, anabolic, and neuroprotective properties of ecdysteroids have been widely reported and reviewed [ 8 , 9 , 10 ]. Their multidirectional activity also includes an antimicrobial effect, which, according to some studies, is especially attributed to less polar derivatives [ 11 ].…”