Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards

Dhooghe, Liene; Naessens, Tania; Heyerick, Arne; Keukeleire, Denis De; Vlietinck, A. J.; Pieters, Luc; Apers, Sandra

doi:10.1016/j.talanta.2010.09.041

Cited by 25 publications

(24 citation statements)

References 21 publications

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“…Recently, Dhooghe et al proposed a novel approach for quantitation of prenylflavonoids using HPLC-UV [31]. Instead of preparing calibration curves using primary reference standards, these authors used naringenin and quercetin as secondary calibration standards for quantitation of prenylflavanones and XN, respectively.…”

Section: Other Separation Methodsmentioning

confidence: 99%

“…If these issues are not addressed, errors can be introduced into the final analytical results. Furthermore, only a few reports mention water content [31], and we could find no report concerning the content of residual solvents remaining from purification procedures. A recently developed approach of quantitative NMR (qNMR) [37, 38] may be a better alternative to the chromatographic methods in that it provides both the quantitative and qualitative information about impurities [17].…”

Section: Sources and Purity Of Reference Standardsmentioning

confidence: 97%

“…Consequently, various synthetic and semi-synthetic approaches for preparation of prenylated flavanones have been developed. IX is typically prepared by isomerization of XN in basic medium [14, 31]. In this procedure, XN is dissolved in 1% aqueous or 5% ethanolic sodium hydroxide.…”

Section: Sources and Purity Of Reference Standardsmentioning

confidence: 99%

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Analytical Methods for Quantitation of Prenylated Flavonoids from Hops

Nikolić¹,

Breemen²

2013

Current Analytical Chemistry

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The female flowers of hops (Humulus lupulus L.) are used as a flavoring agent in the brewing industry. There is growing interest in possible health benefits of hops, particularly as estrogenic and chemopreventive agents. Among the possible active constituents, most of the attention has focused on prenylated flavonoids, which can chemically be classified as prenylated chalcones and prenylated flavanones. Among chalcones, xanthohumol (XN) and desmethylxanthohumol (DMX) have been the most studied, while among flavanones, 8-prenylnaringenin (8-PN) and 6-prenylnaringenin (6-PN) have received the most attention. Because of the interest in medicinal properties of prenylated flavonoids, there is demand for accurate, reproducible and sensitive analytical methods to quantify these compounds in various matrices. Such methods are needed, for example, for quality control and standardization of hop extracts, measurement of the content of prenylated flavonoids in beer, and to determine pharmacokinetic properties of prenylated flavonoids in animals and humans. This review summarizes currently available analytical methods for quantitative analysis of the major prenylated flavonoids, with an emphasis on the LC-MS and LC-MS-MS methods and their recent applications to biomedical research on hops. This review covers all methods in which prenylated flavonoids have been measured, either as the primary analytes or as a part of a larger group of analytes. The review also discusses methodological issues relating to the quantitative analysis of these compounds regardless of the chosen analytical approach.

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Section: Other Separation Methodsmentioning

confidence: 99%

Section: Sources and Purity Of Reference Standardsmentioning

confidence: 97%

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Analytical Methods for Quantitation of Prenylated Flavonoids from Hops

Nikolić¹,

Breemen²

2013

Current Analytical Chemistry

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“…Major prenylflavonoids are 6‐prenylnaringenin, 6‐geranylnaringenin, 8‐prenylnaringenin and isoxanthohumol, which can all be found in hops and beer (Stevens and Page, ; Dhooghe et al , ). Of the prenylflavonoids, 8‐prenylnaringenin (Figure ) is the most potent phytoestrogen known.…”

Section: Introductionmentioning

confidence: 99%

The potential health effects of dietary phytoestrogens

Rietjens

Louisse

Beekmann

2016

British J Pharmacology

421

246

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Phytoestrogens are plant‐derived dietary compounds with structural similarity to 17‐β‐oestradiol (E2), the primary female sex hormone. This structural similarity to E2 enables phytoestrogens to cause (anti)oestrogenic effects by binding to the oestrogen receptors. The aim of the present review is to present a state‐of‐the‐art overview of the potential health effects of dietary phytoestrogens. Various beneficial health effects have been ascribed to phytoestrogens, such as a lowered risk of menopausal symptoms like hot flushes and osteoporosis, lowered risks of cardiovascular disease, obesity, metabolic syndrome and type 2 diabetes, brain function disorders, breast cancer, prostate cancer, bowel cancer and other cancers. In contrast to these beneficial health claims, the (anti)oestrogenic properties of phytoestrogens have also raised concerns since they might act as endocrine disruptors, indicating a potential to cause adverse health effects. The literature overview presented in this paper illustrates that several potential health benefits of phytoestrogens have been reported but that, given the data on potential adverse health effects, the current evidence on these beneficial health effects is not so obvious that they clearly outweigh the possible health risks. Furthermore, the data currently available are not sufficient to support a more refined (semi) quantitative risk–benefit analysis. This implies that a definite conclusion on possible beneficial health effects of phytoestrogens cannot be made.Linked ArticlesThis article is part of a themed section on Principles of Pharmacological Research of Nutraceuticals. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v174.11/issuetoc

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“…In the assay the approach of determination of the given compounds using secondary standards was applied [4].…”

Section: Experimental Partmentioning

confidence: 99%

The study of dependence of the prenyl flavonoids content in the hop dry extract on temperature parameters of its obtaining

Dobrovolnyi¹

2014

Vìsn. farm.

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When developing the technology of a dry extract of hop cones as an active pharmaceutical ingredient with the estrogen-like action the key factors that can affect the quality of the finished product have been investigated. Taking into account that hop prenyl flavonoids are relatively unstable compounds and under certain thermodynamic conditions are prone to transformation the influence of the temperature parameters such as evaporation and drying of the hop liquid extract on the content of xanthohumol (X), isoxanthohumol (IX), xanthohumol, isoxanthohumol, 8-prenylnaringenin and 6-prenylnaringenin has been determined by HPLC in the samples of liquid and dry extracts. It has been found that sparing conditions of evaporation and drying used has led to decreasing the quantitative content of X, IX, 8-PN and 6-PN in the dry extract compared with the content of these compounds in the water-alcohol liquid extract in the range of 14, 16, 8, 14%, respectively. The use of plants containing phytoestrogens, with its historical length may be compared with the history of medicine in general. One of the most interesting sources of compounds with the estrogen-like action is a hop cones. The results of the pharmacological studies of hop extracts indicate the relationship between estrogenic activity of the objects and the fraction of prenyl flavonoids: xanthohumol (X), desmethylxanthohumol (DMX), isoxanthohumol (IX), 8-prenylnaringenin (8-PN) and 6-prenylnaringenin (6-PN). It has been found that the marked estrogenic activity of the polyphenolic fraction belongs to 8-PN and characterizes this compound as the most powerful pharmacological agent among the known phytoestrogens [7,8,10].The process chain for obtaining APIs of the plant origin consists of different sets of operations performed according to the specific technological modes. Based on thermolabile properties of most substances of the plant origin the development of the technology for obtaining the corresponding APIs requires the study of dependence of the composition at each process stage involving heating of the product.The aim was to study the influence of temperature parameters of evaporation and drying processes of the hop liquid extract on the content of xanthohumol, isoxanthohumol, 8-prenylnaringenin and 6-prenylnaringenin in the dry extract.The results obtained should become an important factor in development of technology for obtaining the hop dry extract enriched in prenyl flavonoids as the promising API. Experimental PartThe starting materials were hop cones of "Xantha" cultivar (the product of the Polissya Institute of Agriculture at the NAASU) harvested in 2012, n-hexane, ethanol and purified water. For cyclization of chalcones X and DMX to the corresponding flavanones IX, 8-PN and 6-PN the hop cones were pretreated by water steam for 1 hour. After thermal pretreatment the remaining moisture was removed from the raw material, and hop cones were extracted in two steps. All extraction steps were performed by the method of filtration extraction at the room ...

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Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards

Cited by 25 publications

References 21 publications

Analytical Methods for Quantitation of Prenylated Flavonoids from Hops

Analytical Methods for Quantitation of Prenylated Flavonoids from Hops

The potential health effects of dietary phytoestrogens

The study of dependence of the prenyl flavonoids content in the hop dry extract on temperature parameters of its obtaining

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