Determination of ingenol in homoeopathic mother tinctures of Euphorbia species by high-performance liquid chromatography

Girin, M.A.; Paphassarang, S.; David-Eteve, Ch.; Chaboud, Annie; Raynaud, Jean

doi:10.1016/0021-9673(93)83215-e

Cited by 10 publications

(15 citation statements)

References 3 publications

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“…Despite its biomedical (Appendino et al, 1999b) and toxicological relevance, the analysis of ingenol has so far received little attention, being limited to the quantitative determination (by HPLC with ODS as the stationary phase) of this polyol in hydrolysed homeopathic mother tinctures from various spurges (Girin et al, 1993). The high commercial value and the biomedical importance of ingenol, coupled to the potential interest of the macrocyclic L-factors as a scaffold for the induction/modulation of bioactivity prompted us to develop a method for the analysis of these compounds in the diterpenoid fraction of caper spurge oil and its selective hydrolysis products.…”

Section: Introductionmentioning

confidence: 99%

HPLC‐UV and HPLC‐positive‐ESI‐MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil

Bicchi

Appendino

Cordero

et al. 2001

Phytochemical Analysis

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Caper spurge (Euphorbia lathyris L.) seed oil contains a series of diterpenoids known as Euphorbia factors, or L-factors, L1-L9. They are esters of several polyols (lathyrol, epoxylathyrol, hydroxylathyrol and ingenol) and account for about 3-5% of the oil. The percentage of ingenol-based L-factors is very low, less than 5% of the diterpenoid fraction, but some of them (factors L5 and L6) are responsible for the irritant and co-carcinogenic activities of the oil. This paper reports an HPLC-UV and HPLC-positive-ESI-MS analysis of the diterpenoid fraction of caper spurge seed oil before and after selective hydrolysis of ingenol-based L-factors. Separation of lathyrane polyols and esters, and ingenol and its esters was achieved using a chromatographic system consisting of a C18 stationary phase and acetonitrile: water as mobile phase. A new macrocyclic constituent, the deoxy Euphorbia factor L1, was identified in the oil.

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Section: Introductionmentioning

confidence: 99%

HPLC‐UV and HPLC‐positive‐ESI‐MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil

Bicchi

Appendino

Cordero

et al. 2001

Phytochemical Analysis

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“…However, this finding contradicts the results of Girin et al . () and Upadhyay et al . (), who reported that E. palustris contains ingenol.…”

Section: Resultsmentioning

confidence: 88%

“…The occurrence of ingenol was confirmed (but not quantified) in 12 of these species. Girin et al () have developed a high‐performance liquid chromatography (HPLC) method with UV detection to determine the content of hydrolysable ingenol in eight Euphorbia species; the highest concentration was found in E. resinifera . In subsequent work, Vogg et al () developed another LC method for the screening of ingenol esters in E. leuconeura via MS detection.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Analysis of Ingenol in Euphorbia species via Validated Isotope Dilution Ultra‐high Performance Liquid Chromatography Tandem Mass Spectrometry

Béres¹,

Dragull

Pospíšil

et al. 2017

Phytochemical Analysis

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ABSTRACT:Introduction -Various species of the Euphorbia genus contain diterpene ingenol and ingenol mebutate (ingenol-3-angelate), a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. A gel formulation of the drug has been approved by the US Food and Drug Administration (FDA) and the European Medicines Agency (EMA) for the topical treatment of actinic keratosis. Objective -To develop a rapid and reliable method for quantification of ingenol in various plant extracts. Methodology -Methanolic extracts of 38 species of the Euphorbia genus were analysed via ultra-high performance liquid chromatography with tandem mass spectrometry (UHPLC-MS/MS) after methanolysis and solid-phase extraction (SPE) purification. The 18 O-labelled ingenol analogue was prepared and used as an internal standard for ingenol content determination and method validation. Results -The highest ingenol concentration (547 mg/kg of dry weight) was found in the lower leafless stems of E. myrsinites. The screening confirms a substantial amount of ingenol in species studied previously and furthermore, reveals some new promising candidates. Conclusion -The newly established UHPLC-MS/MS method shows to be an appropriate tool for screening of the Euphorbia genus for ingenol content and allows selection of species suitable for raw material production and/or in vitro culture initiation.

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“…Diterpene esters were transformed into their parent alcohols by alkaline hydrolysis (0.5 M methanolic potassium hydroxide, 20 min, 20°C). This method was adopted from Evans and Kinghorn (15) and from Girin et al (16). The samples were subsequently neutralized with 0.5 M methanolic hydrochloric acid and fractionated by thin-layer chromatography (TLC) on silica gel 60 (Merck), using nhexane/propan-2-ol (2:1 ,v/v) as a solvent system.…”

Section: Methodsmentioning

confidence: 99%

Tumor promoters in commercial indoor-plant cultivars of the Euphorbiaceae.

Vogg

Mattes

Polack

et al. 1999

Environ Health Perspect

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Certain decorative indoor-plant cultivars are derived from toxic wild plant species. Native members of the Euphorbiaceae (spurge) contain highly irritating and tumor-promoting diterpene esters. Plant breeders and gardeners are constantly searching for less toxic cultivars of the popular Euphorbiaceae indoor plants. In this investigation, 22 commercial cultivars of Euphorbiaceae indoor plants were examined for tumor promoter contents by high-performance liquid chromatography (HPLC). Cultivars of E. milii (E. lomii hybrids), and in particular E. leuconeura, contained ingenol derivatives, whereas cultivars of E. pulcherrima and Codiaeum variegatum were devoid of these compounds. Tumor-promoting activity was assessed by induction of a luciferase reporter gene, which was placed under the control of an Epstein-Barr virus early antigen promoter. The response was closely correlated with ingenol ester content; the latex of the two E. leuconeura cultivars tested gave the strongest response. The HPLC and bioassay methods used in this study provide a basis for the development of nontoxic indoor-plant cultivars and perhaps for consumer-oriented labeling.ImagesFigure 1Figure 2Figure 3Figure 4

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Determination of ingenol in homoeopathic mother tinctures of Euphorbia species by high-performance liquid chromatography

Cited by 10 publications

References 3 publications

HPLC‐UV and HPLC‐positive‐ESI‐MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil

HPLC‐UV and HPLC‐positive‐ESI‐MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil

Quantitative Analysis of Ingenol in Euphorbia species via Validated Isotope Dilution Ultra‐high Performance Liquid Chromatography Tandem Mass Spectrometry

Tumor promoters in commercial indoor-plant cultivars of the Euphorbiaceae.

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