Ecdysone

Last updated
Ecdysone
Ecdysone.svg
Ecdysone 3D ball.png
Names
IUPAC name
(22R)-2β,3β,14α,22,25-Pentahydroxy-5β-cholest-7-en-6-one
Systematic IUPAC name
(1R,3aS,5aR,7R,8S,9aR,9bR,11aR)-1-[(2S,3R)-3,6-Dihydroxy-6-methylheptan-2-yl]-3a,7,8-trihydroxy-9a,11a-dimethyl-1,2,3,3a,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-5H-cyclopenta[a]phenanthren-5-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.692 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1 Yes check.svgY
    Key: UPEZCKBFRMILAV-JMZLNJERSA-N Yes check.svgY
  • InChI=1/C27H44O6/c1-15(20(28)8-9-24(2,3)32)16-7-11-27(33)18-12-21(29)19-13-22(30)23(31)14-25(19,4)17(18)6-10-26(16,27)5/h12,15-17,19-20,22-23,28,30-33H,6-11,13-14H2,1-5H3/t15-,16+,17-,19-,20+,22+,23-,25+,26+,27+/m0/s1
    Key: UPEZCKBFRMILAV-JMZLNJERBR
  • O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@H](C)[C@H](O)CCC(O)(C)C)C
Properties
C27H44O6
Molar mass 464.63 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ecdysone is a[ clarification needed ] prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdysteroids act as moulting hormones of arthropods but also occur in other related phyla where they can play different roles. [1] [2] In Drosophila melanogaster , an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires. It causes chromosome puffs (sites of high expression) to form in polytene chromosomes. Recent findings in the laboratory of Chris Q. Doe have found a novel role of this hormone in regulating temporal gene transitions within neural stem cells of the fruit fly. [3]

Contents

Ecdysone and other ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. [4] These phytoecdysteroids have been reputed to have medicinal value. They are part of herbal adaptogenic remedies like Cordyceps, yet an ecdysteroid precursor in plants has been shown to have cytotoxic properties [5] as well as antioxidant properties on lipid peroxidation. [6]

Tebufenozide, sold under the Bayer trademark MIMIC, [7] has ecdysteroid activity although its chemical structure has little resemblance to the ecdysteroids. [8]

See also

Related Research Articles

Juvenile hormones (JHs) are a group of acyclic sesquiterpenoids that regulate many aspects of insect physiology. The first discovery of a JH was by Vincent Wigglesworth. JHs regulate development, reproduction, diapause, and polyphenisms.

<span class="mw-page-title-main">20-Hydroxyecdysone</span> Chemical compound

20-Hydroxyecdysone is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. It is also a phytoecdysteroid produced by various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides where its purpose is presumably to disrupt the development and reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In humans, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein-coding gene.

<i>Rhaponticum carthamoides</i> Species of flowering plants in the daisy family Asteraceae

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<span class="mw-page-title-main">Nuclear receptor</span> Protein

In the field of molecular biology, nuclear receptors are a class of proteins responsible for sensing steroids, thyroid hormones, vitamins, and certain other molecules. These intracellular receptors work with other proteins to regulate the expression of specific genes, thereby controlling the development, homeostasis, and metabolism of the organism.

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<span class="mw-page-title-main">Cholesterol 7 alpha-hydroxylase</span> Protein-coding gene in the species Homo sapiens

Cholesterol 7 alpha-hydroxylase also known as cholesterol 7-alpha-monooxygenase or cytochrome P450 7A1 (CYP7A1) is an enzyme that in humans is encoded by the CYP7A1 gene which has an important role in cholesterol metabolism. It is a cytochrome P450 enzyme, which belongs to the oxidoreductase class, and converts cholesterol to 7-alpha-hydroxycholesterol, the first and rate limiting step in bile acid synthesis.

<span class="mw-page-title-main">Ecdysteroid</span> Group of steroid hormones

Ecdysteroids are arthropod steroid hormones that are mainly responsible for molting, development and, to a lesser extent, reproduction; examples of ecdysteroids include ecdysone, ecdysterone, turkesterone and 2-deoxyecdysone. These compounds are synthesized in arthropods from dietary cholesterol upon metabolism by the Halloween family of cytochrome P450s. Phytoecdysteroids also appear in many plants mostly as a protection agents against herbivore insects.

Phytoecdysteroids are plant-derived ecdysteroids. Phytoecdysteroids are a class of chemicals that plants synthesize for defense against phytophagous insects. These compounds are mimics of hormones used by arthropods in the molting process known as ecdysis. When insects eat the plants with these chemicals they may prematurely molt, lose weight, or suffer other metabolic damage and die.

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Ecdysone 20-monooxygenase (EC 1.14.99.22) is an enzyme that catalyzes the chemical reaction

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The enzyme juvenile hormone esterase (EC 3.1.1.59, systematic name methyl-(2E,6E,10R)-10,11-epoxy-3,7,11-trimethyltrideca-2,6-dienoate acylhydrolase, JH esterase) catalyzes the hydrolysis of juvenile hormone:

<span class="mw-page-title-main">Ecdysone receptor</span>

The ecdysone receptor is a nuclear receptor found in arthropods, where it controls development and contributes to other processes such as reproduction. The receptor is a non-covalent heterodimer of two proteins, the EcR protein and ultraspiracle protein (USP). It binds to and is activated by ecdysteroids. Insect ecdysone receptors are currently better characterized than those from other arthropods, and mimics of ecdysteroids are used commercially as caterpillar-selective insecticides.

<span class="mw-page-title-main">Halloween genes</span> Set of genes that influence embryonic development

The halloween genes are a set of genes identified in Drosophila melanogaster that influence embryonic development. All of the genes code for cytochrome P450 enzymes in the ecdysteroidogenic pathway (biosynthesis of ecdysone from cholesterol). Ecdysteroids such as 20-hydroxyecdysone and ecdysone influence many of the morphological, physiological, biochemical changes that occur during molting in insects.

The prothoracic glands are either of a pair of endocrine glands located in the prothorax of certain insects that regulate molting. They have an ectodermal origin and secrete ecdysteroids, such as ecdysone and 20-hydroxyecdysone. They usually disappear in adults.

An insect growth regulator (IGR) is a chemical insecticide that kills insects indirectly by disrupting their life cycles. The term was initially proposed to describe the effects of juvenile hormone analogs. Although the term "insect growth disruptor" more accurately describes the actions of IGRs, it did not become widely used. IGRs encompass chemical classes with three modes of action : juvenile hormone analogs, chitin synthesis inhibitors, and ecdysone receptor agonists.

<span class="mw-page-title-main">Tebufenozide</span> Chemical compound

Tebufenozide is an insecticide that acts as a molting hormone. It is an agonist of the ecdysone receptor that causes premature molting in larvae. It is primarily used against caterpillar pests. It belongs to the class of bisacylhydrazines.

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Cytochrome P450, family 305, also known as CYP305, is an animal cytochrome P450 family found in insect genome. The first gene identified in this family is the CYP305A1 from the Drosophila melanogaster.

References

  1. Hoffmeister, Hans; Rufer, Clemens; Ammon, Helmut (February 1, 1965). "Ausscheidung von Ecdyson bei Insekten" [Excretion of Ecdysone by Insects]. Zeitschrift für Naturforschung B. 20 (2): 130–133. doi: 10.1515/znb-1965-0207 . PMID   14345159. S2CID   95079385. Physiologisch-Chemisches Institut der Universität Marburg/Lahn.
  2. Karlson, P; Hoffmeister, H (March, 1963). On the biogenesis of ecdyson. I. Conversion of cholesterol into ecdyson. Hoppe Seylers Z Physiol Chem., 331, 289–300. In German. PMID 1396254
  3. Syed, Mubarak Hussain; Mark, Brandon; Doe, Chris Q. (2017). "Steroid hormone induction of temporal gene expression in Drosophila brain neuroblasts generates neuronal and glial diversity". eLife. 6. doi: 10.7554/eLife.26287 . PMC   5403213 . PMID   28394252.
  4. Dinan L, Savchenko T, Whiting P (2001). "On the distribution of phytoecdysteroids in plants". Cellular and Molecular Life Sciences. 58 (8): 1121–1132. doi:10.1007/PL00000926. PMC   11337386 . PMID   11529504. S2CID   8496934.
  5. Wang YS, Yang JH, Luo SD, Zhang HB, Li L, Molecules. 2007;12(3):536-42
  6. Kuzmenko AI, Niki E, Noguchi N (2001). "New functions of 20-hydroxyecdysone in lipid peroxidation". Journal of Oleo Science. 50 (6): 497–506. doi: 10.5650/jos.50.497 .
  7. apvma.gov.au: "Tebufenozide in the product Mimic 700 WP Insecticide, Mimic 240 SC Insecticide"
  8. Carlson, Glenn R. (2000). "Tebufenozide: A Novel Caterpillar Control Agent with Unusually High Target Selectivity". Green Chemical Syntheses and Processes. ACS Symposium Series. Vol. 767. pp. 8–17. doi:10.1021/bk-2000-0767.ch002. ISBN   978-0-8412-3678-3.