Crystal structures of ecdysteroids: The role of solvent molecules in hydrogen bonding and isostructurality

László Fábián, G. Argay, A. Kálmán, M. Báthori

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29 Citations (Scopus)

Abstract

Three crystal forms of the steroid 20-hydroxyecdysone were identified by single-crystal X-ray diffraction analysis: a solvent-free modification, a methanol solvate hydrate and a trihydrate. The structure of a closely related steroid, polypodine B (the 5,20-dihydroxy derivative of ecdysone), was determined in its monohydrate form. Since the unit-cell volume of unsolvated 20-hydroxyecdysone was found to be considerably smaller than that of ecdysone [Huber & Hoppe (1965). Chem. Ber. 98, 2403-2424], a new structure determination of ecdysone was performed, which confirmed the unexpected difference between the unit-cell volumes. The crystals of ecdysone and 20-hydroxyecdysone are isostructural, while the mixed solvate of 20-hydroxyecdysone is homostructural with the hydrate of polypodine B. A detailed analysis of the hydrogen-bond networks in these closely related crystal pairs highlights their packing similarities, demonstrates the role of solvent molecules, and explains the unexpectedly small cell volume of 20-hydroxyecdysone.

Original languageEnglish
Pages (from-to)710-720
Number of pages11
JournalActa Crystallographica Section B
Volume58
Issue number4
DOIs
Publication statusPublished - Aug 2002

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Ecdysterone
Ecdysteroids
Ecdysone
Hydrogen Bonding
Hydrogen bonds
steroids
Crystal structure
hydrates
crystal structure
Molecules
Cell Size
hydrogen
cells
crystals
molecules
Hydrates
hubs
Crystals
Steroids
methyl alcohol

ASJC Scopus subject areas

  • Structural Biology
  • Condensed Matter Physics

Cite this

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AU - Báthori, M.

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AB - Three crystal forms of the steroid 20-hydroxyecdysone were identified by single-crystal X-ray diffraction analysis: a solvent-free modification, a methanol solvate hydrate and a trihydrate. The structure of a closely related steroid, polypodine B (the 5,20-dihydroxy derivative of ecdysone), was determined in its monohydrate form. Since the unit-cell volume of unsolvated 20-hydroxyecdysone was found to be considerably smaller than that of ecdysone [Huber & Hoppe (1965). Chem. Ber. 98, 2403-2424], a new structure determination of ecdysone was performed, which confirmed the unexpected difference between the unit-cell volumes. The crystals of ecdysone and 20-hydroxyecdysone are isostructural, while the mixed solvate of 20-hydroxyecdysone is homostructural with the hydrate of polypodine B. A detailed analysis of the hydrogen-bond networks in these closely related crystal pairs highlights their packing similarities, demonstrates the role of solvent molecules, and explains the unexpectedly small cell volume of 20-hydroxyecdysone.

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