Application of high-performance liquid chromatography for analysis and isolation of sesquiterpene lactones

doi:10.1016/S0021-9673(01)96702-0

Journal of Chromatography A

Volume 265, 1983, Pages 97-104

https://doi.org/10.1016/S0021-9673(01)96702-0 Get rights and content

Abstract

The capacity of a reversed-phase high-performance liquid chromatographic system using Ultrasphere-ODS columns and a gradient of acetonitrile—water to separate sesquiterpene lactones has been studied. Retention times and capacity factors of 33 compounds of the pseudoguaianolide and xanthanolide skeletal types occurring in Parthenium (Asteraceae) are reported. Crude extracts of Parthenium schottii containing a mixture of sesquiterpene lactones have been analyzed and separated using the high-performance liquid chromatographic system.

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Separation of parthenolide from feverfew: Performance of conventional and high-pressure extraction techniques

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In present work the extraction of feverfew flower heads was performed using supercritical carbon dioxide at pressures from 200 to 800 bar and at temperatures of 40, 60 and 80 °C. For comparison, the conventional extractions with organic solvents have been performed. Dry feverfew flower heads were used as starting material. Supercritical fluid extraction (SFE) was performed using a semi continuous flow apparatus in a laboratory and pilot scale. The influence of process parameters on the total yield and amount of parthenolide isolated was investigated. Dynamic behaviour of the extraction runs followed by single-step separation was analysed by a mathematical model for initial constant rate extraction period and the subsequent time-dependant diffusion controlling mass transfer rate period. In order to concentrate the obtained extract in parthenolide, a two-step separation was employed.
Review of the analytical techniques for sesquiterpenes and sesquiterpene lactones

2002, Journal of Chromatography A

In this paper the analytical techniques of about the last 2 decades for sesquiterpenes including their lactones are reviewed. For sesquiterpenes, methods like GC, GC–EI-MS, GC–CI-MS, GC–MS–MS, GC–FT-IR, GC–UV, GC–AES, ¹³C-NMR, PY–GC–MS, HPLC, HPLC–TSP, SFE, SFC, SFC–UV are available, GC combined with MS is the most widespread. Sesquiterpene lactones can be analysed by HPLC, HPLC–TSP, HPLC–APCI, HPLC–ESI, HPLC–PB, HPLC–NMR, SFC, MEKC, GC, GC–MS, TLC and OPLC. Here HPLC is the method of choice. The usefulness of the individual methods are briefly discussed.
Chemotaxonomy based on metabolites from glandular trichomes

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Plant metabolites associated with trichomes were up to now consulted little for the investigation of taxonomic relationships. This is unexpected given the fact that plant trichomes provide a unique means of making biomolecules of specific pathways accessible at the plant surface in a concentrated form. In cases where compounds from glandular trichomes have been investigated, they have proved to be reliable taxonomic characters. In combination with microscopic studies, the presence or absence of metabolites in a plant or in specific organs is often predictable, thus avoiding unnecessary chemical analysis. The high resolution of modern chromatography allows the development of fingerprinting techniques for compound assignment of extracts gained directly from trichomes via microsampling. The previous inability of spectroscopic structure identification with analytical sample amounts is now adays partly compensated. On-line techniques such as GC-MS, LC-MS, CE-MS and LC-NMR require sample amounts adjusted to the concentrations found in trichomes. Trichomes were also shown to be useful tools for recent trends in chemosystematics considering information from biosynthetic pathways in plants. Enzymes extracted from living glandular cells were successfully employed to study the biosynthesis of terpenoids. Considering these circumstances, chemotaxonomy based on metabolites from glandular trichomes could become an interesting section of plant systematics – it just has to be attempted.
Supercritical fluid extraction and gas chromatographic determination of the sesquiterpene lactone parthenolide in the medicinal herb feverfew (Tanacetum parthenium)

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Supercritical carbon dioxide was used to extract the sesquiterpene lactone parthenolide, which is reported to be the active component of the medicinal herb feverfew (Tanacetum parthenium), from dried plant material for gas-liquid chromatographic analysis. The extracts also contained significant amounts of camphor and chrysanthenol acetate. The pressure and densities required for quantitative extraction and the methods of sample collection were studied. The addition of methanol or acetonitrile as modifiers in the carbon dioxide gave higher yields of parthenolide bu the extractions were less selective and considerable amounts of co-extractives were obtained. By employing a trapping column made of cellulose or silica the purity of the extracts could be improved and a practical method for the rapid isolation of parthenolide is described.
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A low-pressure liquid chromatographic method using silica gel 60 with hexane—chloroform—ethyl acetate proportions varying from 80:20:0 to 80:20:6 (v/v/v) as eluent is described as a simple and inexpensive process for the isolation of the γ-lactones parthenolide, marrubiin and artemisinin from the aerial parts of feverfew, white horehound and quinghao, respectively. A selective high-performance liquid chromatographic (HPLC) method using a Superspher Si 60 column with hexane—dioxane (85:15, v/v) for elution of parthenolide and marrubiin and (90:10, v/v) for artemisinin and UV detection at 210 nm for parthenolide and artemisinin and 225 nm for marrubiin is described that allows the determination of these γ-lactones in plants. Compared with the HPLC method, the extraction yield of the large-scale process was calculated to be 72.3, 78.4 and 74.1% of the total amount of parthenolide, marrubiin and artemisinin, respectively, contained in each plant.

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Application of high-performance liquid chromatography for analysis and isolation of sesquiterpene lactones

Abstract

Phytochem.

Phytochem.

Biochem. System. Ecol.

Phytochem.

Biochem. System. Ecol.

J. Chromatogr.

Phytochem.

J. Chromatogr.

Fortschr. Chem. Org. Naturst.

Advan. Pharmacol. Chemother.

J. Med. Chem.

Science

Cancer Res.

Dissert. Pharm.

Rev. Latinoam. Quim.

Experientia