Stereoisomers of eudesmane sesquiterpene From Cleome droserifolia
Stereoisomers of eudesmane sesquiterpene From Cleome droserifolia
The present study reports the chemical investigation on the aerial parts of Cleome droserifolia yielding the related eudesmane sesquiterpene solyraterpenoid A (1) and the novel cledrone A (2) from the acetonitrile fraction of the dichloromethane extract. These compounds were separated by column chromatography, centrifugal thin layer chromatography (CTLC) followed by semipreparative reversed-phase high performance liquid chromatography (RP-HPLC). The chemical structure of these compounds was determined by mono and bidimensional NMR techniques, IR spectroscopy, and HRESIMS, while the absolute configuration was established by computational analysis of ECD spectra. Furthermore, the structure and absolute configuration of both 1 and 2 were unambiguously confirmed via single crystal X-ray diffraction (scXRD). Both compounds showed antibacterial activity against Escherichia coli and Pseudomonas aeruginosa strains, with compound 2 being more active.
chromatographic techniques, Cleome droserifolia, ECD calculations, eudesmane sesquiterpene, single crystal X-ray diffraction, stereoisomers
Ahmed, Sarfaraz
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Nur-e-Alam, Mohammad
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Calice, Umberto
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Scafato, Patrizia
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Orton, James B.
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Bonomo, Maria Grazia
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Alharbi, Hattan A.
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Fantoukh, Omer I.
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Superchi, Stefano
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Al-Rehaily, Adnan J.
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2 June 2025
Ahmed, Sarfaraz
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Nur-e-Alam, Mohammad
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Calice, Umberto
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Scafato, Patrizia
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Orton, James B.
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Bonomo, Maria Grazia
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Alharbi, Hattan A.
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Fantoukh, Omer I.
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Superchi, Stefano
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Al-Rehaily, Adnan J.
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Ahmed, Sarfaraz, Nur-e-Alam, Mohammad, Calice, Umberto, Scafato, Patrizia, Orton, James B., Bonomo, Maria Grazia, Alharbi, Hattan A., Fantoukh, Omer I., Superchi, Stefano and Al-Rehaily, Adnan J.
(2025)
Stereoisomers of eudesmane sesquiterpene From Cleome droserifolia.
Chirality, 37 (6), [e70038].
(doi:10.1002/chir.70038).
Abstract
The present study reports the chemical investigation on the aerial parts of Cleome droserifolia yielding the related eudesmane sesquiterpene solyraterpenoid A (1) and the novel cledrone A (2) from the acetonitrile fraction of the dichloromethane extract. These compounds were separated by column chromatography, centrifugal thin layer chromatography (CTLC) followed by semipreparative reversed-phase high performance liquid chromatography (RP-HPLC). The chemical structure of these compounds was determined by mono and bidimensional NMR techniques, IR spectroscopy, and HRESIMS, while the absolute configuration was established by computational analysis of ECD spectra. Furthermore, the structure and absolute configuration of both 1 and 2 were unambiguously confirmed via single crystal X-ray diffraction (scXRD). Both compounds showed antibacterial activity against Escherichia coli and Pseudomonas aeruginosa strains, with compound 2 being more active.
Text
Chirality Revised Manuscript
- Accepted Manuscript
More information
Accepted/In Press date: 19 May 2025
e-pub ahead of print date: 2 June 2025
Published date: 2 June 2025
Keywords:
chromatographic techniques, Cleome droserifolia, ECD calculations, eudesmane sesquiterpene, single crystal X-ray diffraction, stereoisomers
Identifiers
Local EPrints ID: 503773
URI: http://eprints.soton.ac.uk/id/eprint/503773
ISSN: 0899-0042
PURE UUID: 87e161f1-cde8-40c2-ab3f-8a01765712fb
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Date deposited: 12 Aug 2025 17:14
Last modified: 12 Aug 2025 17:14
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Contributors
Author:
Sarfaraz Ahmed
Author:
Mohammad Nur-e-Alam
Author:
Umberto Calice
Author:
Patrizia Scafato
Author:
James B. Orton
Author:
Maria Grazia Bonomo
Author:
Hattan A. Alharbi
Author:
Omer I. Fantoukh
Author:
Stefano Superchi
Author:
Adnan J. Al-Rehaily
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