HPLC−CD On-Line Coupling in Combination with HPLC−NMR and HPLC−MS/MS for the Determination of the Full Absolute Stereostructure of New Metabolites in Plant Extracts

Bringmann, Gerhard; Messer, Kim; Wohlfarth, Michael; Kraus, Jürgen; Dumbuya, and Karifala; Rückert, Markus

doi:10.1021/ac990001d

Cited by 92 publications

(61 citation statements)

References 24 publications

(45 reference statements)

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“…Fifteen micrograms (∼52 nmol) of oxypeucedanin (22 μg of oxypeucedanin hydrate, ∼72 nmol) in the 1.5 μL detection cell were sufficient to obtain an unambiguous 1 H NMR spectrum in about 2 min 20 s. This technique reduces the required sample quantity by a factor of up to 15 in comparison to a 5 mm tube in a conventional commercial probe. It is for this reason that the microcoil 1 H NMR technique proves useful with mass-limited samples and as a detector in capillary separations, as often demonstrated by our group [27][28][29][30] and several other very active European groups [31][32][33][34][35][36]. Moreover, our results confirmed that disk diffusion is a reliable, easy and inexpensive semi-quantitative susceptibility testing method that is sufficiently sensitive and ideally suited for preliminary investigations on the nano-to microscale.…”

Section: Resultssupporting

confidence: 80%

An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae

et al. 2010

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Using Radix imperatoriae (the root of masterwort) as an example, we describe an efficient approach for the isolation, identification and evaluation of bioactive plant components on an analytical scale. The extraction of Radix imperatoriae with ethyl acetate was enhanced by the application of ultrasound oscillations. This rhizome extract was applied to three pathogenic bacteria (Bacillus cereus, Escherichia coli, and Staphylococcus aureus) to determine its antimicrobial activity. Disk diffusion was utilized to determine susceptibility. The extract components were separated using a series of chromatography approaches (semi-preparative RP-HPLC, or RP-HPLC on an analytical scale), followed by testing. All fractions were analyzed by LC-UV-ESI-MS and 600 MHz microcoil 1 H NMR spectroscopy. Among other findings, in the fraction with the highest antibacterial activity we were able to identify oxypeucedanin and oxypeucedanin hydrate. Subsequent analysis revealed that only oxypeucedanin hydrate had antibacterial activity, whereas oxypeucedanin itself was inactive at the concentrations applied. Furthermore, oxypeucedanin hydrate appears to be largely, or exclusively, a by-product of sample preparation, since it is either not synthesized by the plant as a second metabolite or is produced by it in only very small quantities.

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Section: Resultssupporting

confidence: 80%

An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae

et al. 2010

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“…HPLC chromatographic fingerprints can be then applied for documentation of complete herbal extracts with more information and on-line qualitative analysis becomes possible. Several valuable review articles dealing with LC-MS and its application in the analysis of botanical extracts have been published [128][129][130][131][132][133][134][135], In last decades, the increasing usage of LC-MS and HPLC-DAD in the analysis of herbal medicines is quite obvious [136][137][138][139][140][141][142][143][144][145][146]. Several good reviews have been published for the analysis of the bioactive chemical compounds in plants and herbal medicines, in which the technique used most is HPLC, especially the hyphenated HPLC techniques [147,148] Moreover, combined HPLC-DAD-MS techniques take advantage of chromatography as a separation method and both DAD and MS as an identification method.…”

Section: Hplc-dad Hplc-ms and Othersmentioning

confidence: 99%

Quality control of herbal medicines

Liang¹,

Xie²,

Chan³

2004

Journal of Chromatography B

495

401

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Different chromatographic and electrophoretic techniques commonly used in the instrumental inspection of herbal medicines (HM) are first comprehensively reviewed. Chemical fingerprints obtained by chromatographic and electrophoretic techniques, especially by hyphenated chromatographies, are strongly recommended for the purpose of quality control of herbal medicines, since they might represent appropriately the "chemical integrities" of the herbal medicines and therefore be used for authentication and identification of the herbal products. Based on the conception of phytoequivalence, the chromatographic fingerprints of herbal medicines could be utilized for addressing the problem of quality control of herbal medicines. Several novel chemometric methods for evaluating the fingerprints of herbal products, such as the method based on information theory, similarity estimation, chemical pattern recognition, spectral correlative chromatogram (SCC), multivariate resolution, etc. are discussed in detail with examples, which showed that the combination of chromatographic fingerprints of herbal medicines and the chemometric evaluation might be a powerful tool for quality control of herbal products.

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“…Assignment of the absolute configuration of the respective enantiomers was attained by hyphenation of the above mentioned chiral HPLC analysis with circular dichroism (CD) spectroscopy. This HPLC-CD coupling, which has recently been introduced into phytochemical analysis (Bringmann et al, 1999), permitted measurement of the full CD spectra of all four isomers in the stop-flow mode without prior isolation. The on-line CD spectra of PPB 1 methyl esters were interpreted by comparison with that of authentic 15(S)-prostaglandin B 1 methyl ester, which has a similar chromophore (Fig.…”

Section: Resolution Of Ppb 1 Enantiomersmentioning

confidence: 99%

B1-Phytoprostanes Trigger Plant Defense and Detoxification Responses

et al. 2005

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Phytoprostanes are prostaglandin/jasmonate-like products of nonenzymatic lipid peroxidation that not only occur ubiquitously in healthy plants but also increase in response to oxidative stress. In this work, we show that the two naturally occurring B 1 -phytoprostanes (PPB 1 ) regioisomers I and II (each comprising two enantiomers) are short-lived stress metabolites that display a broad spectrum of biological activities. Gene expression analysis of Arabidopsis (Arabidopsis thaliana) cell cultures treated with PPB 1 -I or -II revealed that both regioisomers triggered a massive detoxification and defense response. Interestingly, expression of several glutathione S-transferases, glycosyl transferases, and putative ATP-binding cassette transporters was found to be increased by one or both PPB 1 regioisomers, and hence, may enhance the plant's capacity to inactivate and sequester reactive products of lipid peroxidation. Moreover, pretreatment of tobacco (Nicotiana tabacum) suspension cells with PPB 1 considerably prevented cell death caused by severe CuSO 4 poisoning. Several Arabidopsis genes induced by PPB 1 , such as those coding for adenylylsulfate reductase, tryptophan synthase b-chain, and PAD3 pointed to an activation of the camalexin biosynthesis pathway that indeed led to the accumulation of camalexin in PPB 1 treated leaves of Arabidopsis. Stimulation of secondary metabolism appears to be a common plant reaction in response to PPB 1 . In three different plant species, PPB 1 -II induced a concentration dependent accumulation of phytoalexins that was comparable to that induced by methyl jasmonate. PPB 1 -I was much weaker active or almost inactive. No differences were found between the enantiomers of each regioisomer. Thus, results suggest that PPB 1 represent stress signals that improve plants capacity to cope better with a variety of stresses.Phytoprostanes belong to a novel family of plant effectors that are formed nonenzymatically by a free radical catalyzed biochemical mechanism from a-linolenic acid. Via an identical nonenzymatic mechanism, isoprostanes (isomers of prostaglandins) are formed in animals from arachidonic acid. Nomenclature used to name different phytoprostane classes conforms with the general isoprostane/prostaglandin terminology . Due to the nonenzymatic formation of phytoprostanes, two racemic regioisomers (type I and II) of each class can be generated. One pathway leads to the formation of B 1 -phytoprostanes (PPB 1 ; Fig. 1) that are chemically stable end products of lipid peroxidation. In animals, isoprostanes are not only extremely reliable markers of oxidative stress but also display potent (prostaglandin-) receptor-mediated biological activities in the nanomolar concentration range (Cracowski et al., 2002). Therefore, it is postulated that isoprostanes represent mediators of oxidant injury in animals.In plants, several classes of phytoprostanes are constitutively present, and, notably, their levels increase in a variety of conditions associated with enhanced free radical generatio...

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HPLC−CD On-Line Coupling in Combination with HPLC−NMR and HPLC−MS/MS for the Determination of the Full Absolute Stereostructure of New Metabolites in Plant Extracts

Cited by 92 publications

References 24 publications

An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae

An efficient approach for the isolation, identification and evaluation of antimicrobial plant components on an analytical scale, demonstrated by the example of Radix imperatoriae

Quality control of herbal medicines

B1-Phytoprostanes Trigger Plant Defense and Detoxification Responses

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