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Ecdysone (Molecule of the Month for October 2008)

20-hydroxyecdysone



Ecdysone is a steroidal prohormone of the major insect molting hormone 20-hydroxyecdysone, which is secreted from the prothoracic glands. 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.

In fruit flys (Drosophila melanogaster), an increase in ecdysone concentration induces the expression of genes coding for proteins that the larva requires, and it causes chromosome puffs (sites of high expression) to form.

Ecdysteroids also appear in many plants mostly as a protection agent (toxins or antifeedants) against herbivorous insects. These phytoecdysteroids have medicinal value and are part of herbal adaptogenic remedies like Cordyceps.

Formal Chemical Name (IUPAC)
(2S,3R,5R,9R,10R,13R,14S,17R)-17-((2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl)-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one

References

http://en.wikipedia.org/wiki/Ecdysone

Picture of Ecdysone 3D model

click on the picture of  Ecdysone above to interact
with the 3D model of the
Ecdysone structure
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Picture of Ecdysone

C27 H44 O6



Update by Karl Harrison
(Molecule of the Month for October 2008 )

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