Simultaneous determination of the bilirubin oxidation end products Z-BOX A and Z-BOX B in human serum using liquid chromatography coupled to tandem mass spectrometry

Seidel, Raphael A.; Kahnes, Marcel; Bauer, Michael; Pohnert, Georg

doi:10.1016/j.jchromb.2014.10.027

Cited by 18 publications

(37 citation statements)

References 22 publications

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“…[16][17][18] To enable the systematic assessment of biological fate and function, we recently established syntheses, 19,20 purification, and sensitive analytics of Z-BOX A and B. 21 Given the central role of the liver in heme degradation, we studied pharmacokinetics and -dynamics of Z-BOX A and B and explored their impact on hepatic function.…”

Section: Impact Of Higher-order Heme Degradation Products On Hepatic mentioning

confidence: 99%

“…Simultaneous determination of Z-BOX A and B was achieved via LC-MS/MS. 21 To assess possible differences between Z-BOXes concentrations in serum and plasma preparations human serum and plasma samples were spiked with 80 or 300 nmolÁL À1 of both analytes and analyzed accordingly. Gallstones were extracted using acetonitrile/isopropanol/water (2/1/1, v/v/v; 10 llÁmg À1 concrement).…”

Section: Quantification Of Boxesmentioning

confidence: 99%

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Impact of higher-order heme degradation products on hepatic function and hemodynamics

Seidel

Claudel

Schleser

et al. 2017

Journal of Hepatology

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Degradation of the blood pigment heme yields the bile pigment bilirubin and the oxidation products Z-BOX A and Z-BOX B. Serum concentrations of these bioactive molecules increase in jaundice and can impair liver function and integrity. Amounts of Z-BOX A and Z-BOX B that are observed during liver failure in humans have profound effects on hepatic function when added to cultured liver cells or infused into healthy rats.

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Section: Impact Of Higher-order Heme Degradation Products On Hepatic mentioning

confidence: 99%

Section: Quantification Of Boxesmentioning

confidence: 99%

Impact of higher-order heme degradation products on hepatic function and hemodynamics

Seidel

Claudel

Schleser

et al. 2017

Journal of Hepatology

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“…To identify pyrrolic and dipyrrolic Chl degradation products, we initially performed a model oxidation in vitro. We used a procedure established for the investigation of heme degradation to address the lower molecular weight fraction of Chl degradation products . Chl a , suspended in sodium hydroxide solution, was neutralized with hydrogen chloride before oxidation with hydrogen peroxide.…”

Section: Resultsmentioning

confidence: 99%

“…Oxidative degradation : The oxidative degradation of chlorophyll a was carried out based on published protocols for bilirubin . To optimize the process, small test reactions of chlorophyll a were carried out in 5 m NaOH/H 2 O, in EtOH and in 2 m NaOH/MeOH with different amounts of H 2 O 2 (1–10 %) and monitored by UHPLC‐HRMS.…”

Section: Methodsmentioning

confidence: 99%

Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores

Ritter

Oetama

Schulze

et al. 2020

Chemistry A European J

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The degradation of chlorophyll,t he omnipresent green pigment, has been investigatedi ntensively over the last 30 years resulting in manye lucidated tetrapyrrolic degradationp roducts. With ac omparison to the degradation of the structurally similarh eme, we hereby propose an ovel additionalc hlorophyll degradation mechanism to mono-and dipyrrolic products.T his is the first proof of the occurrence of af amilyo fm ono-and dipyrrols in leaves that are previously only known as heme degradationp roducts.T his prod-uct familyi sa lso found in spit and feces of herbivores with specific metabolomic patterns reflecting the origin of the samples. Based on chromatographica nd mass spectrometric evidencea swell as on mechanistic considerations we also suggest severalt entative new degradation products.O ne of them,d ihydro BOX A, was fully confirmed as an ovel natural product by synthesis andc omparison of its spectroscopic data.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.org/10. Scheme1.Enzymatic chlorophyll degradation in plants.Scheme2.Enzymatic (top) andoxidativeheme degradation by reactive oxygen species (ROS) to PDPs and BOXes.

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“…These metabolites are further oxidatively degraded to dipyrrolic propentdyopent-type species (PDPs) and finally to the monopyrrolic birubin oxidation end products (BOXes) [1][2][3][4][5]. The concentration of the BOXes in human bile depends on the structure and is very low (0.1 μm for BOX C and 0.5 μm for BOXes A and B, Scheme 1) [6,7]. The presence of an isomer of BOX C (BOX D: R 1 = Me, R 2 = CH 2 CH 2 COOH) has not been detected yet in human bile.…”

Section: Introductionmentioning

confidence: 99%

BOX A-type monopyrrolic heterocycles modified via the Suzuki-Miyaura cross-coupling reaction

Schulze

Klopfleisch

Görls

et al. 2019

Zeitschrift Für Naturforschung B

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The in vivo oxidation of heme yields bilirubin which is further degraded to the bilirubin oxidation end products (BOXes) that are biologically highly active. To study the mode of action and fate of (Z)-2-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)acetamide (BOX A), the Suzuki-Miyaura cross-coupling reaction allows to introduce various alkenyl- and aryl-substituents in 3-position of the (Z)-2-(4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)acetamides (BOX A-type monopyrroles). The influence of these groups on structural and NMR-spectroscopic parameters of the central monopyrrolic system is negligible. Special focus has been given to derivatives with 3-positioned aryl substituents carrying trifluoromethyl groups for future in vivo19F NMR studies.

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Simultaneous determination of the bilirubin oxidation end products Z-BOX A and Z-BOX B in human serum using liquid chromatography coupled to tandem mass spectrometry

Cited by 18 publications

References 22 publications

Impact of higher-order heme degradation products on hepatic function and hemodynamics

Impact of higher-order heme degradation products on hepatic function and hemodynamics

Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores

BOX A-type monopyrrolic heterocycles modified via the Suzuki-Miyaura cross-coupling reaction

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