Dihydroxyacetone in the Floral Nectar of Ericomyrtus serpyllifolia (Turcz.) Rye (Myrtaceae) and Verticordia chrysantha Endl. (Myrtaceae) Demonstrates That This Precursor to Bioactive Honey Is Not Restricted to the Genus Leptospermum (Myrtaceae).

Ma̅nuka honey is known for its strong bioactivity, which arises from the autocatalytic conversion of 1,3-dihydroxyacetone (dihydroxyacetone, DHA) in the floral nectar of Leptospermum scoparium (Myrtaceae) to the non-peroxide antibacterial compound methylglyoxal during honey maturation. DHA is also a minor constituent of the nectar of several other Leptospermum species. This study used high-performance liquid chromatography to test whether DHA was present in the floral nectar of five species in other genera of the family Myrtaceae: Ericomyrtus serpyllifolia (Turcz.) Rye, Chamelaucium sp. Bendering (T.J. Alford 110), Kunzea pulchella (Lindl.) A.S. George, Verticordia chrysantha Endl., and Verticordia picta Endl. DHA was found in the floral nectar of two of the five species: E. serpyllifolia and V. chrysantha. The average amount of DHA detected was 0.08 and 0.64 µg per flower, respectively. These findings suggest that the accumulation of DHA in floral nectar is a shared trait among several genera within the family Myrtaceae. Consequently, non-peroxide-based bioactive honey may be sourced from floral nectar outside the genus Leptospermum.

TiO2 Catalyzed Dihydroxyacetone (DHA) Conversion in Water: Evidence That This Model Reaction Probes Basicity in Addition to Acidity.

In this paper, evidence is provided that the model reaction of aqueous dihydroxyacetone (DHA) conversion is as sensitive to the TiO2 catalysts' basicity as to their acidity. Two parallel pathways transformed DHA: while the pathway catalyzed by Lewis acid sites gave pyruvaldehyde (PA) and lactic acid (LA), the base-catalyzed route afforded fructose. This is demonstrated on a series of six commercial TiO2 samples and further confirmed by using two reference catalysts: niobic acid (NbOH), an acid catalyst, and a hydrotalcite (MgAlO), a basic catalyst. The original acid-base properties of the six commercial TiO2 with variable structure and texture were investigated first by conventional methods in gas phase (FTIR or microcalorimetry of pyridine, NH3 and CO2 adsorption). A linear relationship between the initial rates of DHA condensation into hexoses and the total basic sites densities is highlighted accounting for the water tolerance of the TiO2 basic sites whatever their strength. Rutile TiO2 samples were the most basic ones. Besides, only the strongest TiO2 Lewis acid sites were shown to be water tolerant and efficient for PA and LA formation.

Sugar and dihydroxyacetone ratios in floral nectar suggest continuous exudation and reabsorption in Leptospermum polygalifolium Salisb.

Leptospermum polygalifolium Salisb. can accumulate high concentrations of dihydroxyacetone (DHA), precursor of the antimicrobial compound methylglyoxal found in honey obtained from floral nectar of Leptospermum spp. Floral nectar dynamics over flower lifespan depends on internal and external factors that invariably impact nectar quality. Current models to estimate nectar quality in Leptospermum spp. overlook time of day, daily (24 h), and long-term dynamics of nectar exudation and accumulation over flower lifespan. To explain the dynamics of nectar quality over flower lifespan, accumulated nectar from flowers of different ages was collected from two L. polygalifolium clones, and then re-collected 24 h later from the same flowers. High-Performance Liquid Chromatography was used to quantify DHA amount and total equivalents of glucose + fructose (Tsugar) per flower in the nectar. DHA and Tsugar amount per flower differed with flower age and between clones. In accumulated nectar, the amount of DHA and Tsugar per flower rose to a broad peak post-anthesis before decreasing. Immediately after peaking DHA declined more quickly than Tsugar in accumulated nectar due to a greater decrease in the exudation of DHA than for Tsugar. The DHA : Tsugar ratios in accumulated nectar and in nectar exuded over the next 24 h were similar and decreased with flower age, indicating that exudation and reabsorption occurred concomitantly across flower development. Hence there is a balance between exudation and reabsorption. A quantitative model suggested that flowers have the potential to exude more DHA and Tsugar than actually accumulated.

Chemoselective and Highly Sensitive Quantification of Gut Microbiome and Human Metabolites.

The microbiome has a fundamental impact on the human host's physiology through the production of highly reactive compounds that can lead to disease development. One class of such compounds are carbonyl-containing metabolites, which are involved in diverse biochemical processes. Mass spectrometry is the method of choice for analysis of metabolites but carbonyls are analytically challenging. Herein, we have developed a new chemical biology tool using chemoselective modification to overcome analytical limitations. Two isotopic probes allow for the simultaneous and semi-quantitative analysis at the femtomole level as well as qualitative analysis at attomole quantities that allows for detection of more than 200 metabolites in human fecal, urine and plasma samples. This comprehensive mass spectrometric analysis enhances the scope of metabolomics-driven biomarker discovery. We anticipate that our chemical biology tool will be of general use in metabolomics analysis to obtain a better understanding of microbial interactions with the human host and disease development.

Probing hepatic metabolism of [2-13C]dihydroxyacetone in vivo with 1H-decoupled hyperpolarized 13C-MR.

OBJECTIVES: To enhance detection of the products of hyperpolarized [2-13C]dihydroxyacetone metabolism for assessment of three metabolic pathways in the liver in vivo. Hyperpolarized [2-13C]DHAc emerged as a promising substrate to follow gluconeogenesis, glycolysis and the glycerol pathways. However, the use of [2-13C]DHAc in vivo has not taken off because (i) the chemical shift range of [2-13C]DHAc and its metabolic products span over 144 ppm, and (ii) 1H decoupling is required to increase spectral resolution and sensitivity. While these issues are trivial for high-field vertical-bore NMR spectrometers, horizontal-bore small-animal MR scanners are seldom equipped for such experiments. METHODS: Real-time hepatic metabolism of three fed mice was probed by 1H-decoupled 13C-MR following injection of hyperpolarized [2-13C]DHAc. The spectra of [2-13C]DHAc and its metabolic products were acquired in a 7 T small-animal MR scanner using three purpose-designed spectral-spatial radiofrequency pulses that excited a spatial bandwidth of 8 mm with varying spectral bandwidths and central frequencies (chemical shifts). RESULTS: The metabolic products detected in vivo include glycerol 3-phosphate, glycerol, phosphoenolpyruvate, lactate, alanine, glyceraldehyde 3-phosphate and glucose 6-phosphate. The metabolite-to-substrate ratios were comparable to those reported previously in perfused liver. DISCUSSION: Three metabolic pathways can be probed simultaneously in the mouse liver in vivo, in real time,  using hyperpolarized DHAc.

A colorimetric comparison of sunless with natural skin tan.

The main ingredient of sunless tanning products is dihydroxyacetone (DHA). DHA reacts with the protein and amino acid composition in the surface layers of the skin, producing melanoidins, which changes the skin colour, imitating natural skin tan caused by melanin. The purpose of this study was to characterise DHA-induced skin colour changes and to test whether we can predict the outcome of DHA application on skin tone changes. To assess the DHA-induced skin colour shift quantitatively, colorimetric and spectral measurements of the inner forearm were obtained before, four hours and 24 hours after application of a 7.5% concentration DHA gel in the experimental group (n = 100). In a control group (n = 60), the same measurements were obtained on both the inner forearm (infrequently sun-exposed) and the outer forearm (frequently sun-exposed); the difference between these two areas was defined as the naturally occurring tan. Skin colour shifts caused by DHA tanning and by natural tanning were compared in terms of lightness (L*), redness (a*) and yellowness (b*) in the standard CIELAB colour space. Naturalness of the DHA-induced skin tan was evaluated by comparing the trajectory of the chromaticity distribution in (L*, b*) space with that of naturally occurring tan. Twenty-four hours after DHA application, approximately 20% of the skin colour samples became excessively yellow, with chromaticities outside the natural range in (L*, b*) space. A principal component analysis was used to characterise the tanning pathway. Skin colour shifts induced by DHA were predicted by a multiple regression on the chromaticities and the skin properties. The model explained up to 49% of variance in colorimetric components with a median error of less than 2 ΔE. We conclude that the control of both the magnitude and the direction of the colour shift is a critical factor to achieve a natural appearance.

A hypothesis for examining dihydroxyacetone, the active component in sunless tanning products, as a topical prophylactic against SARS-COV-2 transmission.

This hypothesis raises the interesting prospect that dihydroxyacetone (DHA), the key ingredient in self-tanning creams, when applied daily to the face and hands may have prophylactic action against SARS-COV-2 transmission and infection. The scientific and mechanistic basis for this hypothesis is elaborated based on our understanding of the chemical reactivity of DHA with proteins to afford advanced glycation products. This piece ends with a proposal for doing key experiments that can be run to test this hypothesis. As more than 30 million people have been infected with this disease world-wide, a safe method for stopping spread is worthy of consideration. Publication of this hypothesis would enable the scientific community at large to test this in a clinically meaningful setting to address the potential for DHA-based prophylaxis. Given the calamity of this crisis, it is anticipated that the publication of this hypothesis, which is supported by key studies on protein and nucleoside glycation, can be disseminated to as many researchers as possible.

Dihydroxyacetone of wheat root exudates serves as an attractant for Heterodera avenae.

Heterodera avenae, as an obligate endoparasite, causes severe yield loss in wheat (Triticum aestivum). Investigation on the mechanisms how H. avenae perceives wheat roots is limited. Here, the attractiveness of root exudates from eight plant genotypes to H. avenae were evaluated on agar plates. Results showed that the attraction of H. avenae to the root exudates from the non-host Brachypodium distachyon variety Bd21-3 was the highest, approximately 50 infective second-stage juveniles (J2s) per plate, followed by that from three H. avenae-susceptible wheat varieties, Zhengmai9023, Yanmai84 and Xiangmai25, as well as the resistant one of Xinyuan958, whereas the lowest attractive activity was observed in the two H. avenae-resistant wheat varieties, Xianmai20 (approximately 12 J2s/plate) and Liangxing66 (approximately 11 J2s/plate). Then Bd21-3, Zhengmai9023 and Heng4399 were selected for further assays as their different attractiveness and resistance to H. avenae, and attractants for H. avenae in their root exudates were characterized to be heat-labile and low-molecular compounds (LM) by behavioral bioassay. Based on these properties of the attractants, a principle of identifying attractants for H. avenae was set up. Then LM of six root exudates from the three plants with and without heating were separated and analyzed by HPLC-MS. Finally, dihydroxyacetone (DHA), methylprednisolone succinate, embelin and diethylpropionin in the root exudates were identified to be putative attractants for H. avenae according to the principle, and the attraction of DHA to H. avenae was validated by behavioral bioassay on agar. Our study enhances the recognition to the orientation mechanism of H. avenae towards wheat roots.

Investigation of Temporal Apparent C4 Sugar Change in Manuka Honey.

New Zealand manuka honeys are known for their propensity to increase apparent C4 sugar content during storage. Depending on the particular storage regime and the initial content of dihydroxyacetone (DHA) in honey, the ready-to-market product often fails the C4 sugar test because of the above phenomenon. We have used DHA labeled with a radioactive 14C isotope in a set of honeys subject to an incubation experiment. These honeys were analyzed for DHA, methylglyoxal (MG), hydroxymethylfurfural (HMF), apparent C4 sugars, and 14C scintillation counts over a period of 18 months. The major conclusion of this experiment is that neither DHA nor MG is responsible for the δ13C shift in the honey protein extract. There must be some other yet unknown substance of manuka honey, which binds to the protein and causes negative δ13C shift. One identified candidate for such a binding is carbon dioxide.

Ultrasound-Assisted Osmotic Dehydration of Apples in Polyols and Dihydroxyacetone (DHA) Solutions.

The aim of this work was to analyse the effect of ultrasound-assisted osmotic dehydration of apples v. Elise on mass transfer parameters, water activity, and colour changes. Ultrasound treatment was performed at a frequency of 21 kHz with a temperature of 40 °C for 30-180 min using four osmotic solutions: 30% concentrated syrups of erythritol, xylitol, maltitol, and dihydroxyacetone (DHA). The efficiency of the used solutes from the polyol groups was compared to reference dehydration in 50% concentrated sucrose solution. Peleg's model was used to fit experimental data. Erythritol, xylitol, and DHA solutions showed similar efficiency to sucrose and good water removal properties in compared values of true water loss. The application of ultrasound by two methods was in most cases unnoticeable and weaker than was expected. On the other hand, sonication by the continuous method allowed for a significant reduction in water activity in apple tissue in all tested solutions.

Closure of the Human TKFC Active Site: Comparison of the Apoenzyme and the Complexes Formed with Either Triokinase or FMN Cyclase Substrates.

Human triokinase/flavin mononucleotide (FMN) cyclase (hTKFC) catalyzes the adenosine triphosphate (ATP)-dependent phosphorylation of D-glyceraldehyde and dihydroxyacetone (DHA), and the cyclizing splitting of flavin adenine dinucleotide (FAD). hTKFC structural models are dimers of identical subunits, each with two domains, K and L, with an L2-K1-K2-L1 arrangement. Two active sites lie between L2-K1 and K2-L1, where triose binds K and ATP binds L, although the resulting ATP-to-triose distance is too large (≈14 Å) for phosphoryl transfer. A 75-ns trajectory of molecular dynamics shows considerable, but transient, ATP-to-DHA approximations in the L2-K1 site (4.83 Å or 4.16 Å). To confirm the trend towards site closure, and its relationship to kinase activity, apo-hTKFC, hTKFC:2DHA:2ATP and hTKFC:2FAD models were submitted to normal mode analysis. The trajectory of hTKFC:2DHA:2ATP was extended up to 160 ns, and 120-ns trajectories of apo-hTKFC and hTKFC:2FAD were simulated. The three systems were comparatively analyzed for equal lengths (120 ns) following the principles of essential dynamics, and by estimating site closure by distance measurements. The full trajectory of hTKFC:2DHA:2ATP was searched for in-line orientations and short distances of DHA hydroxymethyl oxygens to ATP γ-phosphorus. Full site closure was reached only in hTKFC:2DHA:2ATP, where conformations compatible with an associative phosphoryl transfer occurred in L2-K1 for significant trajectory time fractions.

Kinetic Analysis of Hepatic Metabolism Using Hyperpolarized Dihydroxyacetone.

Hyperpolarized carbon-13 magnetic resonance (HP-MR) is a new metabolic imaging method the does not use ionizing radiation. Due to the inherent chemical specificity of MR, not only tracer uptake but also downstream metabolism of the agent is detected in a straightforward manner. HP [2-13C] dihydroxyacetone (DHA) is a promising new agent that directly interrogates hepatic glucose metabolism. DHA has three metabolic fates in the liver: glucose production, glycerol production and potential inclusion into triglycerides, and oxidation in the tricarboxylic acid cycle. Each pathway is regulated by flux through multiple enzymes. Using Duhamel's formula, the kinetics of DHA metabolism is modeled, resulting in estimates of specific reaction rate constants. The multiple enzymatic steps that control DHA metabolism make more simplified methods for extracting kinetic data less than satisfactory. The described modeling paradigm effectively identifies changes in metabolism between gluconeogenic and glycogenolytic models of hepatic function.

Hydroxymethanesulfonate from Volcanic Sulfur Dioxide: A "Mineral" Reservoir for Formaldehyde and Other Simple Carbohydrates in Prebiotic Chemistry.

While formaldehyde (HCHO) was likely generated in Earth's prebiotic atmosphere by ultraviolet light, electrical discharge, and/or volcano-created lightning, HCHO could not have accumulated in substantial amounts in prebiotic environments, including those needed for prebiotic processes that generate nucleosidic carbohydrates. HCHO at high concentrations in alkaline solutions self-reacts in the Cannizzaro reaction to give methanol and formate, neither having prebiotic value. Here, we explore the possibility that volcanic sulfur dioxide (SO2) might have generated a reservoir for Hadean HCHO by a reversible reaction with HCHO to give hydroxymethanesulfonate (HMS). We show that salts of HMS are stable as solids at 90°C and do not react with themselves in solution, even at high (>8 M) concentrations. This makes them effective stores of HCHO, since the reverse reaction slowly delivers HCHO back into an environment where it can participate in prebiotically useful reactions. Specifically, we show that in alkaline borate solutions, HCHO derived from HMS allows formation of borate-stabilized carbohydrates as effectively as free HCHO, without losing material to Cannizzaro products. Further, we show that SO2 can perform similar roles for glycolaldehyde and glyceraldehyde, two intrinsically unstable carbohydrates that are needed by various models as precursors for RNA building blocks. Zircons from the Hadean show that the Hadean mantle likely provided volcanic SO2 at rates at least as great as the rates of atmospheric HCHO generation, making the formation of Hadean HMS essentially unavoidable. Thus, hydroxymethylsulfonate adducts of formaldehyde, glycolaldehyde, and glyceraldehyde, including the less soluble barium, strontium, and calcium salts, are likely candidates for prebiotically useful organic minerals on early Earth.

Kinetics of conversion of dihydroxyacetone to methylglyoxal in New Zealand manuka honey: Part V - The rate determining step.

Monomer formation from dimeric DHA has previously been suggested as the rate-determining step in formation of methylglyoxal, the bioactive component in manuka honey. This step was studied by 1H NMR in DMSO­d6. First order reaction rate was 3.31 × 10-3 ±â€¯9.1 × 10-4 min-1. Upon titration with D2O, little change was observed until ∼15 mass% whereupon an exponential increase in rate occurred until indistinguishable from the rate observed in water. Acid or base caused rate accelerations. Theoretical modelling confirmed the existence of acid and base-catalysed mechanisms for dimer decomposition and the structures of two intermediates observed. In honey it is likely the base-catalysed decomposition predominates with water as catalyst but there is little rate acceleration at the levels of water present normally in honey however a small increase in the mass% of water in the honey could cause significant rate acceleration of dimer decomposition and hence formation of methylglyoxal.

Dihydroxyacetone Production in the Nectar of Australian Leptospermum Is Species Dependent.

This study is the first large-scale survey of the presence of dihydroxyacetone (DHA) in the nectar of the Australian Leptospermum tree species. The work undertaken supports the growing global demand for bioactive Leptospermum honey. Leptospermum honey derived from L. scoparium in New Zealand, also referred to as Ma̅nuka honey, has a reputation for wound-healing and antimicrobial properties, which is based on its methylglyoxal (MGO) content. High-DHA nectar correlates to high-MGO honey, but not all Leptospermum species produce DHA in their nectar. This study investigates 55 of the 84 Leptospermum species native to Australia for their DHA-producing capability, with the DHA to total sugar (DHA:Tsugar) ratio of nectar samples determined by HPLC-PDA. DHA:Tsugar ranged from nondetectable in L. laevigatum, L. coriaceum, and L. trinervium to >16 000 mg/kg in L. speciosum and L. whitei. High-DHA Leptospermum species were identified for beekeepers to target for honey production and plantation development.

Reactions between methylglyoxal and its scavengers in-vivo appear to be catalyzed enzymatically.

Methylglyoxal (MGO) is thought to be an important contributor to the development of diabetic complications. In this paper I propose that MGO, not detoxified by the glyoxalase system, is removed from circulation by MGO-scavengers. Furthermore, since intrinsic rates of reactions between MGO and its scavengers are low, I propose that, in-vivo, these reactions are catalyzed enzymatically.

Difference FTIR Studies of Substrate Distribution in Triosephosphate Isomerase.

Triosephosphate isomerase (TIM) catalyzes the interconversion between dihydroxyacetone phosphate (DHAP) and d-glyceraldehyde 3-phosphate (GAP), via an enediol(ate) intermediate. Determination of substrate population distribution in the TIM/substrate reaction mixture at equilibrium and characterization of the substrate-enzyme interactions in the Michaelis complex are ongoing efforts toward the understanding of the TIM reaction mechanism. By using isotope-edited difference Fourier transform infrared studies with unlabeled and 13C-labeled substrates at specific carbon(s), we are able to show that in the reaction mixture at equilibrium the keto DHAP is the dominant species and the populations of aldehyde GAP and enediol(ate) are very low, consistent with the results from previous X-ray structural and 13C NMR studies. Furthermore, within the DHAP side of the Michaelis complex, there is a set of conformational substates that can be characterized by the different C2═O stretch frequencies. The C2═O frequency differences reflect the different degree of the C2═O bond polarization due to hydrogen bonding from active site residues. The C2═O bond polarization has been considered as an important component for substrate activation within the Michaelis complex. We have found that in the enzyme-substrate reaction mixture with TIM from different organisms the number of substates and their population distribution within the DHAP side of the Michaelis complex may be different. These discoveries provide a rare opportunity to probe the interconversion dynamics of these DHAP substates and form the bases for the future studies to determine if the TIM-catalyzed reaction follows a simple linear reaction pathway, as previously believed, or follows parallel reaction pathways, as suggested in another enzyme system that also shows a set of substates in the Michaelis complex.

Manuka honey (Leptospermum scoparium) inhibits jack bean urease activity due to methylglyoxal and dihydroxyacetone.

Manuka honey (Leptospermum scoparium) exerts a strong antibacterial effect. Bacterial enzymes are an important target for antibacterial compounds. The enzyme urease produces ammonia and enables bacteria to adapt to an acidic environment. A new enzymatic assay, based on photometric detection of ammonia with ninhydrin, was developed to study urease activity. Methylglyoxal (MGO) and its precursor dihydroxyacetone (DHA), which are naturally present in manuka honey, were identified as jack bean urease inhibitors with IC50 values of 2.8 and 5.0mM, respectively. Urease inhibition of manuka honey correlates with its MGO and DHA content. Non-manuka honeys, which lack MGO and DHA, showed significantly less urease inhibition. MGO depletion from manuka honey with glyoxalase reduced urease inhibition. Therefore, urease inhibition by manuka honey is mainly due to MGO and DHA. The results obtained with jack bean urease as a model urease, may contribute to the understanding of bacterial inhibition by manuka honey.

Unique Pattern of Protein-Bound Maillard Reaction Products in Manuka (Leptospermum scoparium) Honey.

As a unique feature, honey from the New Zealand manuka tree (Leptospermum scoparium) contains substantial amounts of dihydroxyacetone (DHA) and methylglyoxal (MGO). Although MGO is a reactive intermediate in the Maillard reaction, very little is known about reactions of MGO with honey proteins. We hypothesized that the abundance of MGO should result in a particular pattern of protein-bound Maillard reaction products (MRPs) in manuka honey. A protein-rich high-molecular-weight fraction was isolated from 12 manuka and 8 non-manuka honeys and hydrolyzed enzymatically. By HPLC-MS/MS, 8 MRPs, namely, N-ε-fructosyllysine, N-ε-maltulosyllysine, carboxymethyllysine, carboxyethyllysine (CEL), pyrraline, formyline, maltosine, and methylglyoxal-derived hydroimidazolone 1 (MG-H1), were quantitated. Compared to non-manuka honeys, the manuka honeys were characterized by high concentrations of CEL and MG-H1, whereas the formation of N-ε-fructosyllysine was suppressed, indicating concurrence reactions of glucose and MGO at the ε-amino group of protein-bound lysine. Up to 31% of the lysine and 8% of the arginine residues, respectively, in the manuka honey protein can be modified to CEL and MG-H1, respectively. CEL and MG-H1 concentrations correlated strongly with the MGO concentration of the honeys. Manuka honey possesses a special pattern of protein-bound MRPs, which might be used to prove the reliability of labeled MGO levels in honeys and possibly enable the detection of fraudulent MGO or DHA addition to honey.

Monitoring acute metabolic changes in the liver and kidneys induced by fructose and glucose using hyperpolarized [2-13 C]dihydroxyacetone.

PURPOSE: To investigate acute changes in glucose metabolism in liver and kidneys in vivo after a bolus injection of either fructose or glucose, using hyperpolarized [2-13 C]dihydroxyacetone. METHODS: Spatially registered, dynamic, multislice MR spectroscopy was acquired for the metabolic products of [2-13 C]dihydroxyacetone in liver and kidneys. Metabolism was probed in 13 fasted rats at three time points: 0, 70, and 140 min. At 60 min, rats were injected intravenously with fructose (n = 5) or glucose (n = 4) at 0.8 g/kg to initiate acute response. Controls (n = 4) did not receive a carbohydrate challenge. RESULTS: Ten minutes after fructose infusion, levels of [2-13 C]phosphoenolpyruvate and [2-13 C]glycerol-3-phosphate halved in liver: 51% (P = 0.0010) and 47% (P = 0.0001) of baseline, respectively. Seventy minutes later, levels returned to baseline. The glucose challenge did not alter the signals significantly, nor did repeated administration of the dihydroxyacetone imaging bolus. In kidneys, no statistically significant changes were detected after sugar infusion other than a 20% increase of the glycerol-3-phosphate signal between 10 and 80 min after fructose injection (P = 0.0028). CONCLUSION: Hyperpolarized [2-13 C]dihydroxyacetone detects a real-time, transient metabolic response of the liver to an acute fructose challenge. Observed effects possibly include ATP depletion and changes in the unlabeled pool sizes of glycolytic intermediates. Magn Reson Med 77:65-73, 2017. © 2016 International Society for Magnetic Resonance in Medicine.