Synthesis, Racemic X‑ray Crystallographic,
and Permeability Studies of Bioactive Orbitides from Jatropha Species
Posted on 2018-10-19 - 23:53
Orbitides are small cyclic peptides
with a diverse range of therapeutic
bioactivities. They are produced by many plant species, including
those of the Jatropha genus. Here, the objective
was to provide new structural information on orbitides to complement
the growing knowledge base on orbitide sequences and activities by
focusing on three Jatropha orbitides: ribifolin (1), pohlianin C (7), and jatrophidin (12). To determine three-dimensional structures, racemic crystallography,
an emerging structural technique that enables rapid crystallization
of biomolecules by combining equal amounts of the two enantiomers,
was used. The high-resolution structure of ribifolin (0.99 Å)
was elucidated from its racemate and showed it was identical to the
structure crystallized from its l-enantiomer only (1.35 Å).
Racemic crystallography was also used to elucidate high-resolution
structures of pohlianin C (1.20 Å) and jatrophidin (1.03 Å),
for which there was difficulty forming crystals without using racemic
mixtures. The structures were used to interpret membrane permeability
data in PAMPA and a Caco-2 cell assay, showing they had poor permeability.
Overall, the results show racemic crystallography can be used to obtain
high-resolution structures of orbitides and is useful when enantiopure
samples are difficult to crystallize or solution structures from NMR
are of low resolution.
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Ramalho, Suelem
D.; Wang, Conan K.; J. King, Gordon; Byriel, Karl A.; Huang, Yen-Hua; Bolzani, Vanderlan S.; et al. (2018). Synthesis, Racemic X‑ray Crystallographic,
and Permeability Studies of Bioactive Orbitides from Jatropha Species. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.8b00447
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AUTHORS (7)
SR
Suelem
D. Ramalho
CW
Conan K. Wang
GJ
Gordon J. King
KB
Karl A. Byriel
YH
Yen-Hua Huang
VB
Vanderlan S. Bolzani
DC
David J. Craik
KEYWORDS
results show racemic crystallographyPAMPAracemic mixturessolution structuresJatropha Species Orbitidesmembrane permeability dataBioactive OrbitidesJatropha orbitidescyclic peptidesenantiopure samplesracemic crystallographyNMRPermeability Studiesplant speciesknowledge baseorbitide sequencesJatropha genusCaco -2 cell assay