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Synthesis and Biological functions of 20-hydroxyecdysone

Jun 20，2022

20-hydroxyecdysone (20E) is a steroid hormone conserved among arthropods. 20-hydroxyecdysone induces the transcription of many ecdysone responsive genes via a nuclear receptor ecdysone receptor (EcR). It mainly functions to trigger molting and metamorphosis. 20E signaling also contributes to embryogenesis, reproduction, and diapause.

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Structure

20E is a 6-oxo steroid that is 5β-cholest-7-en-6-one substituted by hydroxy groups at positions 2, 3, 14, 20, 22, and 25 (the 2β, 3β, 14α, 20R, and 22R stereoisomer). 20E is biosynthesized by hydroxylating the precursor ecdysone at position 20.

Properties

Molecular weight is 480.06 g/mol. Soluble in water, acetic acid, ethanol, methanol, or DMSO.

Synthesis

20-hydroxyecdysone is biosynthesized from dietary sterols such as cholesterol. NPC1a and Noppera-bo (Nobo) contribute to the cholesterol incorporation in ecdysteroidogenic tissues.Ecdysone biosynthesis is catalyzed by several enzymes, including Neverland (Nvd), CYP307A1/Spook (Spo), CYP307A2/Spookier (Spok), CYP6T3, Shroud (Sro)/ nonmolting glossy (Nm-g), CYP306A1/Phantom (Phm), CYP302A1/Disembodied (Dib), and CYP315A1/ Shadow (Sad).

The intermediate conversion step from 7-dehydrocholesterol to 5β-ketodiol has not been fully elucidated. For this reason, this step is often called the “black box.” Ecdysone is finally converted to the biologically active 20E by CYP314A1/Shade (Shd)5. Genes encoding the ecdysteroidogenic enzymes are called “Halloween genes.” 20E is inactivated by several enzymes, including Ecdysone oxidase6 and CYP18A1.

Biological functions

Target cells/tissues and functions

20-hydroxyecdysone is the most common biologically active form of ecdysteroids in arthropods. 20E regulates a wide range of developmental and cellular processes such as cell polarity, cell cycle, cell migration, cell proliferation, differentiation, histolysis, and apoptosis. In the adults, 20E regulates courtship behavior, vitellogenesis, germline stem cell self-renewal, reproductive diapause, innate immunity, sleep, circadian rhythm, stress resistance, and lifespan.

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