Selective 1D-TOCSY and chemometrics to evaluate authenticity of Turnera diffusa and related botanical extracts

Lucio‐Gutiérrez, J. Ricardo; Delgado-Montemayor, Cecilia; Coello, J.; Waksman, Noemí; Saucedo, Alma L.

doi:10.1016/j.phytol.2019.01.011

Cited by 11 publications

(6 citation statements)

References 27 publications

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“…As is evident, the complexity of the spectrum is significantly reduced because only the signals of the hydrogens coupled in the spin system of the irradiated nucleus are observed. In the selective 1D-TOCSY spectrum, the six signals of the spin system conforming the hepatodamianol rhamnopyranoside moiety are clearly identified (CH-1‴, δ H 4.60 ppm; CH-2‴, δ H 3.65 ppm; CH-3‴, δ H 3.00 ppm; CH-4‴, δ H 2.94 ppm; CH-5‴, δ H 2.12 ppm; and CH 3 -6‴, δ H 0.51 ppm), and the chemical shift values agree with those previously reported for this molecule [ 8 ]. This evidence indicates that the signal at 0.515 ppm corresponds unequivocally to hepatodamianol:CH 3 -6‴.…”

Section: Resultssupporting

confidence: 88%

“…In traditional medicine, it has been used for the relief of colds and coughs, among other conditions [ 1 ]. T. diffusa is considered the most important species of the turneraceae; evidence of this is the growing number of scientific publications focused on the study of its therapeutic effects as well as in the quality control of herbal products [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Numerous research groups have reported its biological activities, including its use as an aphrodisiac [ 10 ], antidiabetic [ 11 ], antioxidant [ 5 ], amidst others.…”

Section: Introductionmentioning

confidence: 99%

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Two Ways to Achieve the Same Goal—Two Validated Quantitative NMR Strategies for a Low-Abundance Natural Product in Standardized Extracts: The Case of Hepatodamianol in Turnera diffusa

et al. 2022

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The quantification of low-abundance secondary metabolites in plant extracts is an analytical problem that can be addressed by different analytical platforms, the most common being those based on chromatographic methods coupled to a high-sensitivity detection system. However, in recent years nuclear magnetic resonance (NMR) has become an analytical tool of primary choice for this type of problem because of its reliability, inherent simplicity in sample preparation, reduced analysis time, and low solvent consumption. The versatility of strategies based on quantitative NMR (qNMR), such as internal and external standards and electronic references, among others, and the need to develop validated analytical methods make it essential to compare procedures that must rigorously satisfy the analytical well-established acceptance criteria for method validation. In this work, two qNMR methods were developed for the quantification of hepatodamianol, a bioactive component of T. diffusa. The first method was based on a conventional external standard calibration, and the second one was based on the pulse length-based concentration determination (PULCON) method using the ERETIC2 module as a quantitation tool available in TopSpin software. The results show that both procedures allow the content of the analyte of interest in a complex matrix to be determined in a satisfactory way, under strict analytical criteria. In addition, ERETIC2 offers additional advantages such as a reduction in experimental time, reagent consumption, and waste generated.

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Section: Resultssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Two Ways to Achieve the Same Goal—Two Validated Quantitative NMR Strategies for a Low-Abundance Natural Product in Standardized Extracts: The Case of Hepatodamianol in Turnera diffusa

et al. 2022

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“…The 1D TOCSY was first shown to be useful in a metabolomics setting with the analysis of low-concentration metabolites in honey samples where carbohydrate signals were extremely strong and dominated the NMR spectra [91]. Selective excitation TOCSY experiments are another variant of the TOCSY experiment that can be used to resolve the spectral overlapping problem and to aid in metabolite identification [90,142,143]…”

Section: Two-dimensional (2d) Nmr Spectroscopymentioning

confidence: 99%

NMR Spectroscopy for Metabolomics Research

et al. 2019

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Over the past two decades, nuclear magnetic resonance (NMR) has emerged as one of the three principal analytical techniques used in metabolomics (the other two being gas chromatography coupled to mass spectrometry (GC-MS) and liquid chromatography coupled with single-stage mass spectrometry (LC-MS)). The relative ease of sample preparation, the ability to quantify metabolite levels, the high level of experimental reproducibility, and the inherently nondestructive nature of NMR spectroscopy have made it the preferred platform for long-term or large-scale clinical metabolomic studies. These advantages, however, are often outweighed by the fact that most other analytical techniques, including both LC-MS and GC-MS, are inherently more sensitive than NMR, with lower limits of detection typically being 10 to 100 times better. This review is intended to introduce readers to the field of NMR-based metabolomics and to highlight both the advantages and disadvantages of NMR spectroscopy for metabolomic studies. It will also explore some of the unique strengths of NMR-based metabolomics, particularly with regard to isotope selection/detection, mixture deconvolution via 2D spectroscopy, automation, and the ability to noninvasively analyze native tissue specimens. Finally, this review will highlight a number of emerging NMR techniques and technologies that are being used to strengthen its utility and overcome its inherent limitations in metabolomic applications.

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“…Papaemmanouil et al [ 26 ] introduced the term “NMR spin-chromatography” to emphasize the advantages of the selective 1D-TOCSY experiment in the analysis of complex mixtures through the selective excitation of nuclei, without the necessity of previous isolation steps. Recently, we reported applying the selective 1D-TOCSY experiment for the unambiguous identification of hepatodamianol in crude extracts of T. diffusa as a strategy to verify the authenticity of T. diffuse botanical material in combination with chemometrics methods [ 20 ]. The selective 1D-TOCSY experiments of the rhamnopyranosyl and xylo-hexopyranos-3-uloside moieties were obtained by specific irradiation on the resonance frequencies of 6´´ and 6´´´ methyl groups at 0.512 and 1.401 ppm, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Finally, 600 μ L of the supernatant was transferred to standard 5 mm NMR tubes. 1 H-NMR spectra were recorded using a 30° pulse experiment, under the following acquisition parameters: 16 and 128 scans with a fixed receiver gain value of 32, the spectral width of 20.0 ppm, 65,536 points in the time domain, and acquisition time 4.0 s. Selective total correlation spectroscopy spectrum (1D-TOCSY) was used to identify hepatodamianol in each sample, as previously described by Lucio-Gutiérrez et al [ 20 ]. 1D-TOCSY lselmlpg pulse sequence was used.…”

Section: Methodsmentioning

confidence: 99%

Development of a Hepatoprotective Herbal Drug from Turnera diffusa

Delgado-Montemayor

Cordero-Pérez

Torres-González

et al. 2022

Evidence-Based Complementary and Alternative Medicine

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The incidence of liver diseases, such as nonalcoholic fatty liver disease and drug-induced liver injury, continues to rise and is one of the leading causes of acute hepatitis. Current trends suggest that these types of conditions will increase in the coming years. There are few drugs available for the prevention or treatment of hepatic diseases, and there is a growing need for the development of safe hepatoprotective agents. The medicinal plant, Turnera diffusa, has many ethnopharmacological uses, one of which is the production of a flavonoid named hepatodamianol, which is the principal component responsible for this plant’s hepatoprotective properties. In the present study, we describe the development and standardization of an active extract obtained from T. diffusa. We conducted nuclear magnetic resonance spectroscopy to identify hepatodamianol unambiguously in each sample. Using this extract, hepatoprotection could be demonstrated in vivo for the first time. The hepatoprotective effect did not display a significant difference in vivo when compared with silymarin used as a positive control at the same doses. Implementation of quality criteria used for standardization, such as flavonoid and hepatodamianol content, hepatoprotective activity, and absence of residual solvents, will allow future preclinical trials with this herbal drug.

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Selective 1D-TOCSY and chemometrics to evaluate authenticity of Turnera diffusa and related botanical extracts

Cited by 11 publications

References 27 publications

Two Ways to Achieve the Same Goal—Two Validated Quantitative NMR Strategies for a Low-Abundance Natural Product in Standardized Extracts: The Case of Hepatodamianol in Turnera diffusa

Two Ways to Achieve the Same Goal—Two Validated Quantitative NMR Strategies for a Low-Abundance Natural Product in Standardized Extracts: The Case of Hepatodamianol in Turnera diffusa

NMR Spectroscopy for Metabolomics Research

Development of a Hepatoprotective Herbal Drug from Turnera diffusa

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