Determination of naphthodianthrones in plant extracts from Hypericum perforatum L. by liquid chromatography–electrospray mass spectrometry

Piperopoulos, Georgios; Lotz, Ralf; Wixforth, A.; Schmierer, Thilo; Zeller, Klaus‐Peter

doi:10.1016/s0378-4347(97)00188-6

Cited by 60 publications

(33 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…4 neutral is thought to be favored by the high stability of the ejected neutral, as previously reported. The mechanism proposed in the literature 12 may involve the formation of a five-membered ring.…”

Section: Ms/ms Of the [M-h]mentioning

confidence: 99%

“…The resulting ring-opened structure is thought to be more suited to rationalize the H 2 O moieties than the mechanism associated with the formation of a benzyne-like structure previously proposed. 12 …”

Section: Fragmentation Of Ion a Relative To The [M-h]mentioning

confidence: 99%

“…Nevertheless, isopseudohypericin has never been analyzed by this technique. 12 Hypericin and its analogs cannot be efficiently analyzed by classical electron impact ionization due to the high temperatures required for their vaporization and their thermolability. Hypericin, pseudohypericin, protohypericin and protopseudohypericin were successfully characterized by liquid chromatography/electrospray ionization triple quadrupole mass spectrometry and with collision-induced dissociation MS/MS experiments.…”

mentioning

confidence: 99%

“…Nevertheless, the mass resolution obtained (typically in the unit mass range) was not sufficient to give unambiguous assignments of some of the detected fragment ions. 12 More recently, liquid chromatography/high-resolution mass spectrometry (LC/HRMS) was used to confirm the structure of the compounds produced by an endophytic fungus isolated from Hypericum perforatum stem samples and cultured in rich mycological medium. 13 HRMS experiments were conducted with a LTQ-orbitrap mass spectrometer, which allowed mass resolution around 60 000 and mass measurement accuracy close to 2 ppm to be achieved.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Study of active naphtodianthrone St John's Wort compounds by electrospray ionization Fourier transform ion cyclotron resonance and multi‐stage mass spectrometry in sustained off‐resonance irradiation collision‐induced dissociation and infrared multiphoton dissociation modes

Hecka¹,

Maunit²,

Aubriet³

et al. 2009

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Five well-known active naphtodianthrone constituents of Hypericum perforatum (St John's Wort) extracts have been investigated by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI-FTICRMS) and ESI-FTICRMSn. The studied compounds were hypericin, pseudohypericin, protohypericin, protopseudohypericin (biosynthetic precursors of the two former compounds, respectively) and isopseudohypericin (alkaline degradation product of pseudohypericin). Dissociation mass spectrometry measurements performed on the [M-H]- ion presented a variable efficiency as a function of the used activation mode. Sustained off-resonance irradiation collision-induced dissociation (SORI-CID) only led to a restricted number of fragment ions. In contrast, IRMPD ensured the detection of numerous product ions. Ions detected in ESI-FTICRMS and ESI-FTICRMSn experiments were measured with a very high mass accuracy (typically mass error is lower than 0.5 mDa at m/z close to 500) that allowed unambiguous formulae to be assigned to each signal observed in a mass spectrum. In spite of similar structures, specific fragmentation patterns were observed for the different compounds investigated. This study may be useful in the future to characterize in natural extracts these compounds (or derivatives of these compounds) by liquid chromatography/tandem mass spectrometry (LC/MS/MS) experiments by considering the MS/MS transitions highlighted in this paper.

show abstract

Section: Ms/ms Of the [M-h]mentioning

confidence: 99%

Section: Fragmentation Of Ion a Relative To The [M-h]mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Study of active naphtodianthrone St John's Wort compounds by electrospray ionization Fourier transform ion cyclotron resonance and multi‐stage mass spectrometry in sustained off‐resonance irradiation collision‐induced dissociation and infrared multiphoton dissociation modes

Hecka¹,

Maunit²,

Aubriet³

et al. 2009

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…perforatum constituents using HPLC with diode array detection (DAD) [16], HPLC coupled simultaneously to mass spectrometry (MS) with electrospray ionization (ESI) [3], combined HPLC-DAD-HPLC-thermospray MS (TSP-MS)-HPLC-ESI-MS [4], HPLC coupled on-line with UV-NMR-MS and MS-MS [5] or HPLC coupled simultaneously to DAD and ESI-MS [6]. In most published procedures, the identification of the peaks was confirmed by ESI-MS in the negative ion mode using neutral solvent systems [3,5,6], except for reference [4], where the positive ion mode was applied for TSP-MS using an acidic eluent system.…”

Section: Hypericum Perforatum L (H Perforatum)mentioning

confidence: 99%

Determination of hypericin and pseudohypericin in extracts fromHypericum Perforatum L. and pharmaceutical preparations by liquid chromatography-fluorescence detection

Zotou

Loukou

2001

Chromatographia

View full text Add to dashboard Cite

SummaryAn isocratic reversed-phase liquid chromatographic method for the simultaneous determination of hypericin and pseudohypericin, l',,vo of the main constituents of Hypericum Perforatum L., has been developed. The compounds were eluted from an Inertsil ODS-3, column by triethylammonium acetate-methanol-acetonirile (5:15:80) eluent and detected fluorimetrically, excitation 478, emission 598 nm. Hypericin and pseudohypericin were extracted from flowering tops by Soxhlet and pseudohypericin was isolated from the extract by collecting its chromatographic peak from the eluent flow. Identification of peaks was by HPLC coupled to a diode array detector and electrospray MS. The method was applied to the determination of hypericin and pseudohypericin in plant extract and in pharmaceutical tablets. For the latter a solidphase extraction procedure was adopted. Riboflavin (0.1 ng.l-tL 1.) was used as internal standard. The linear working range of the method is 0.025-4ng.l-tL 1. and limit of detection 0.2 ng injected on-colu mn. A comparative SPE study for hypericin is presented.

show abstract

High performance liquid chromatography/electrospray mass spectrometry ofHypericum perforatum extracts

Mauri

Pietta

2000

Rapid Commun. Mass Spectrom.

View full text Add to dashboard Cite

Hypericum perforatum L. (St. John's Wort) is a widely distributed herbaceous perennial plant which has been well known as a medicinal plant since antiquity. In recent years, H. perforatum has received increasing attention for the treatment of depression and other neuralgic disorders. The main constituents of H. perforatum extract include flavonoids, naphthodianthrones, phloroglucinols, essential oils and xanthones. The present work reports the analysis of naphthodianthrones and phloroglucinols in H. perforatum extracts by means of high performance liquid chromatography (HPLC) coupled simultaneously to a diode array detector (DAD) and electrospray mass spectrometry (ESI-MS). Hypericin, pseudohypericin, hyperforin and adhyperforin were separated and identified on the base of their on-line UV and mass spectra. Quantitative analysis of hypericin derivatives in different extracts of H. perforatum using DAD and MS detectors was performed. In addition, direct infusion ESI-MS of H. perforatum extracts was applied to obtain rapid mass fingerprints of constituents present in the sample.

show abstract

Determination of naphthodianthrones in plant extracts from Hypericum perforatum L. by liquid chromatography–electrospray mass spectrometry

Cited by 60 publications

References 13 publications

Study of active naphtodianthrone St John's Wort compounds by electrospray ionization Fourier transform ion cyclotron resonance and multi‐stage mass spectrometry in sustained off‐resonance irradiation collision‐induced dissociation and infrared multiphoton dissociation modes

Study of active naphtodianthrone St John's Wort compounds by electrospray ionization Fourier transform ion cyclotron resonance and multi‐stage mass spectrometry in sustained off‐resonance irradiation collision‐induced dissociation and infrared multiphoton dissociation modes

Determination of hypericin and pseudohypericin in extracts fromHypericum Perforatum L. and pharmaceutical preparations by liquid chromatography-fluorescence detection

High performance liquid chromatography/electrospray mass spectrometry ofHypericum perforatum extracts

Contact Info

Product

Resources

About