Ecdysone
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| Surname | Ecdysone | |||||||||||||||
| other names |
(2 S , 3 R , 5 R , 9 R , 10 R , 13 R , 14 S , 17 R ) -17 - [(2 S , 3 R ) -3,6-dihydroxy-6-methylheptan-2-yl ] -2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1 H -cyclopenta [a] phenanthren-6-one |
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| Molecular formula | C 27 H 44 O 6 | |||||||||||||||
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| properties | ||||||||||||||||
| Molar mass | 464.63 g · mol -1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
239-242 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Ecdysone, or more precisely α-ecdysone, is a hormone that can be found in many animals. The ecdysone has to be hydroxylated for activation . A classic representative here is the 20-hydroxyecdysone (ecdysterone) or β-ecdysone. In the case of insects , spiders and some other animal groups, it is responsible for the molting , which is why these groups are also summarized as molting animals .
It belongs to the ecdysteroids and acts similar to the steroid hormones of vertebrates by stimulating the transcription of certain genes through the mediation of intracellular receptors. Insects secrete it with glands ( prothorax gland ) in the first chest ring , which in turn is under the control of the prothoracotropic hormone (PTTH). Ecdysone triggers larval moulting when juvenile hormones are present at the same time, but if juvenile hormones are absent, adult moulting occurs.
It was first presented in pure crystallized form by Adolf Butenandt and Peter Karlson . The constitution was clarified by Hans Hoffmeister. The biogenesis of ecdysone from cholesterol has also been described in Karlson's working group . A review on the chemistry of ecdysone has also been published.
literature
- P. deFur (Ed.): Endocrine Disruption in Invertebrates: Endocrinology, Testing, and Assessment . (= SETAC technical publications series). Setac press, 1999, ISBN 1-880611-27-9 .
Individual evidence
- ↑ a b Data sheet α-Ecdysone from Sigma-Aldrich , accessed on June 16, 2011 ( PDF ).
- ↑ Hans Hoffmeister: Constitution Enlightenment of the Ecdyson , university publication Munich, natural science. F., Diss. V. June 12, 1963, http://d-nb.info/481953256
- ^ P. Karlson, H. Hoffmeister: On the biogenesis of ecdyson. I. Conversion of cholesterol into ecdyson. In: Hoppe Seylers Z Physiol Chem. 331, Mar 1963, pp. 289-300, PMID 13962541 .
- ^ Peter Karlson, Hans Hoffmeister, Walter Hoppe, Robert Huber: Zur Chemie Des Ecdysons. In: Justus Liebig's Annals of Chemistry. 662, 1963, p. 1, doi: 10.1002 / jlac.19636620102 .