5‐O‐Caffeoylshikimic acid from Solanum somalense leaves: Advantage of centrifugal partition chromatography over conventional column chromatography

Solanum somalense leaves, used in Djibouti for their medicinal properties, were extracted by MeOH. Because of the high polyphenol and flavonoid contents of the extract, respectively, determined at 80.80 ± 2.13 mg gallic acid equivalent/g dry weight and 24.4 ± 1.01 mg quercetin equivalent/g dry weigh...

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Bibliographic Details
Published in:Journal of separation science 2014-09, Vol.37 (17), p.2331-2339
Main Authors: Chideh, Saïda, Pilard, Serge, Attoumbré, Jacques, Saguez, Robert, Hassan‐Abdallah, Alshaimaa, Cailleu, Dominique, Wadouachi, Anne, Baltora‐Rosset, Sylvie
Format: Article
Language:English
Subjects:
Bioautography
Biological and medical sciences
Caffeoylshikimic acids
Chemical Sciences
Chromatography
Chromatography - instrumentation
Chromatography - methods
Column chromatography
Dactylifric acid
Drying
Enrichment
Equivalence
gallic acid
General pharmacology
Herbal medicine
leaves
Mass Spectrometry
Medical sciences
medicinal plants
medicinal properties
Metabolites
Molecular Structure
nuclear magnetic resonance spectroscopy
Partitions
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Plant Leaves - chemistry
Polyphenols
Purification
quercetin
secondary metabolites
Shikimic Acid - analogs & derivatives
Shikimic Acid - chemistry
Shikimic Acid - isolation & purification
silica gel
Solanum
Solanum - chemistry
Solanum somalense
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Summary:Solanum somalense leaves, used in Djibouti for their medicinal properties, were extracted by MeOH. Because of the high polyphenol and flavonoid contents of the extract, respectively, determined at 80.80 ± 2.13 mg gallic acid equivalent/g dry weight and 24.4 ± 1.01 mg quercetin equivalent/g dry weight, the isolation and purification of the main polyphenols were carried out by silica gel column chromatography and centrifugal partition chromatography. Column chromatography led to 11 enriched fractions requiring further purification, while centrifugal partition chromatography allowed the easy recovery of the main compound of the extract. In a solvent system composed of CHCl₃/MeOH/H₂O (9.5:10:5), 21.8 mg of this compound at 97% purity was obtained leading to a yield of 2.63%. Its structure was established as 5‐O‐caffeoylshikimic acid by mass spectrometry and NMR spectroscopy. This work shows that S. somalense leaves contain very high level of 5‐O‐caffeoylshikimic acid (0.74% dry weight), making it a potential source of production of this secondary metabolite that is not commonly found in nature but could be partly responsible of the medicinal properties of S. somalense leaves.
ISSN:1615-9306
1615-9314
DOI:10.1002/jssc.201400226