Crystal Structures of Ecdysteroids: The Role of Solvent Molecules in Hydrogen Bonding and Isostructurality
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.
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20-HE was isolated from the ethyl acetate fraction (EFAD) of A. dimorphostegia and identified as a white crystalline solid (55 mg, mp 237.5-239.5 °C).
“Phytochemical investigation of the EFAD led to the isolation and identification of 20-HE as a white crystalline solid (Figure 1) (55 mg, mp. 237.5–239.5 °C) [34].”
From Phytoecdysteroids and Anabolic Effect of Atriplex dimorphostegia: UPLC-PDA-MS/MS Profiling, In Silico and In Vivo Models (2023) · cites this paper as [34]
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Zaghloul, E., Handousa, H., Singab, A. N. B., Elmazar, M. M., Ayoub, I. M., & Swilam, N. (2023) · Plants · doi:10.3390/plants12010206 · Cited by 11 · see citing works
- Authors
- Fábián, L., Argay, G., Kálmán, A., & Báthori, M.
- Affiliations
- Hungarian Academy of Sciences (HU)
- University of Szeged (HU)
- ORCID
- Fábián, László
- Venue
- Acta Crystallographica Section B Structural Science
- Published
- 2002-07-30
- Volume
- 58
- Issue
- 4
- Pages
- 710-720
- ISSN
- 0108-7681 (ISSN-L)
- OpenAlex
- W2005263296
- Cited by
- 35
- References
- 9
- Citations by year
- 2024: 1 · 2023: 2 · 2021: 1 · 2020: 2 · 2017: 1 · 2016: 2 · 2015: 1 · 2014: 4 · 2013: 1 · 2012: 3
- FWCI
- 0.71
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Acta Crystallographica Section B Structural Science (publishedVersion)
- PubMed (publishedVersion)
- UEA Digital Repository (University of East Anglia) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Inorganic Chemistry › Crystal structures of chemical compounds
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Crystallography and molecular interactions
- Physical Sciences › Materials Science › Materials Chemistry › Crystallization and Solubility Studies
- Keywords
- ecdysteroids, 20-hydroxyecdysone, ecdysone, polypodine B, crystal forms, trihydrate, hydrogen bond network, solvent molecules, isostructurality, unit cell volume
- MeSH terms
- Ecdysterone, Hydrogen Bonding, Models, Molecular, Molecular Conformation, Solvents, Crystallography, X-Ray
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