From Retrospective Assessment to Prospective Decisions in Natural Product Isolation: HPLC-SPE-NMR Analysis of Carthamus oxyacantha

An extract of Carthamus oxyacantha (wild safflower) was investigated using two approaches: a traditional, nontarget fractionation by VLC and HPLC, and the hyphenated technique HPLC-PDA-HRMS-SPE-NMR followed by targeted isolation of selected constituents for inclusion in a screening library of pure n...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2011-11, Vol.74 (11), p.2454-2461
Main Authors: Johansen, Kenneth T, Wubshet, Sileshi G, Nyberg, Nils T, Jaroszewski, Jerzy W
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
4-Butyrolactone - isolation & purification
Biological and medical sciences
Biological Products - chemistry
Biological Products - isolation & purification
Carthamus - chemistry
Chromatography, High Pressure Liquid - methods
General pharmacology
Glucosides - chemistry
Glucosides - isolation & purification
Iran
Magnetic Resonance Spectroscopy - methods
Medical sciences
Molecular Structure
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plants, Medicinal - chemistry
Spiro Compounds - chemistry
Spiro Compounds - isolation & purification
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Summary:An extract of Carthamus oxyacantha (wild safflower) was investigated using two approaches: a traditional, nontarget fractionation by VLC and HPLC, and the hyphenated technique HPLC-PDA-HRMS-SPE-NMR followed by targeted isolation of selected constituents for inclusion in a screening library of pure natural products. While the nontarget fractionation involved considerable time spent on pursuing fractions containing well-known or undesired compounds, the hyphenated analysis was considerably faster and required less solvent and other consumables. The results were used to design and execute an optimized, HPLC-HRMS-guided, targeted isolation scheme aiming exclusively at a series of identified spiro compounds. Thus, HPLC-PDA-HRMS-SPE-NMR is a dereplication technique of choice, allowing economical acquisition of comprehensive data about compounds in crude extracts, which can be used for rational, prospective decisions about further isolation efforts. A total of 15 compounds were identified in the extract. Six spiro compounds, of which four have not previously been characterized, and tracheloside (a lignin glucoside) are presented with assigned 1H and 13C chemical shifts.
ISSN:0163-3864
1520-6025
DOI:10.1021/np200780m