No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
A Maple Syrup Extract Prevents β-Amyloid Aggregation
... However, despite the wide consumption of maple syrup worldwide, and knowledge that it contains a diverse array of phenolic constituents (over 50 phenolics belonging to lignan, stilbene, flavonoid, coumarin, and phenolic acid sub-classes have been isolated and identified from maple syrup) [17][18][19]22], studies evaluating their health promoting effects are very limited. Moreover, based on our knowledge to date, few studies have been conducted to evaluate the neuroprotective effects of this natural sweetener [20,21]. In one of those studies, a phenolicenriched maple syrup extract (MSX) was shown to decrease oligomerization and aggregation of both amyloid β 1−42 peptide (Aβ 1−42 ) and tau peptides, which are proteins involved in AD pathogenesis [20]. ...
... Moreover, based on our knowledge to date, few studies have been conducted to evaluate the neuroprotective effects of this natural sweetener [20,21]. In one of those studies, a phenolicenriched maple syrup extract (MSX) was shown to decrease oligomerization and aggregation of both amyloid β 1−42 peptide (Aβ 1−42 ) and tau peptides, which are proteins involved in AD pathogenesis [20]. In light of the aforementioned factors, and given the paucity of data on the neuroprotective effects of natural plant-derived sweeteners, including maple syrup, we designed the current study. ...
... Taken together, the biophysical data from the ThT assay, TEM analyses, CD experiment, DLS, and zeta potential measurements suggested that the MSX treatments effectively inhibited Aβ 1−42 structural transformation from soluble non-toxic peptides to insoluble neuro-toxic fibrils. These data are in agreement with the previous report for a MSX [20]. However, to date, no previous studies have been conducted to evaluate the neuroprotective effects of maple syrup in brain cells or in an in vivo AD model; therefore, we proceeded with the following experiments (described below). ...
Published data supports the neuroprotective effects of several phenolic-containing natural products, including certain fruit, berries, spices, nuts, green tea, and olive oil. However, limited data are available for phenolic-containing plant-derived natural sweeteners including maple syrup. Herein, we investigated the neuroprotective effects of a chemically standardized phenolic-enriched maple syrup extract (MSX) using a combination of biophysical, in vitro, and in vivo studies. Based on biophysical data (Thioflavin T assay, transmission electron microscopy, circular dichroism, dynamic light scattering, and zeta potential), MSX reduced amyloid β1−42 peptide (Aβ1−42) fibrillation in a concentration-dependent manner (50–500 μg/mL) with similar effects as the neuroprotective polyphenol, resveratrol, at its highest test concentration (63.5 % at 500 μg/mL vs. 77.3 % at 50 μg/mL, respectively). MSX (100 μg/mL) decreased H2O2-induced oxidative stress (16.1 % decrease in ROS levels compared to control), and down-regulated the production of lipopolysaccharide (LPS)-stimulated inflammatory markers (22.1, 19.9, 74.8, and 87.6 % decrease in NOS, IL-6, PGE2, and TNFα levels, respectively, compared to control) in murine BV-2 microglial cells. Moreover, in a non-contact co-culture cell model, differentiated human SH-SY5Y neuronal cells were exposed to conditioned media from BV-2 cells treated with MSX (100 μg/mL) and LPS or LPS alone. MSX-BV-2 media increased SH-SY5Y cell viability by 13.8 % compared to media collected from LPS-BV-2 treated cells. Also, MSX (10 μg/mL) showed protective effects against Aβ1−42 induced neurotoxicity and paralysis in Caenorhabditis elegans in vivo. These data support the potential neuroprotective effects of MSX warranting further studies on this natural product.
... Several of these compounds have been studied for their potential beneficial effects on health. According to several studies, polyphenols extracted from maple syrup may have anti-inflammatory, antimicrobial, antioxidant, antimutagenic and anti-neurodegenerative properties, as well as other beneficial properties [5][6][7][8][9][10][11][12]. ...
The maple syrup industry generates substandard syrups and sugar sand as by-products, which are underused. In this study, we conducted a comprehensive analysis of the physicochemical composition of these products to assess their potential for valorization. Using HPLC analysis, we measured sugar and organic acid content as well as total polyphenol content using the Folin–Ciocalteu method. Additionally, we evaluated the in vitro digestibility using the TIM-1 model. We showed that the composition of ropy and buddy downgraded syrups is comparable to that of standard maple syrup, whereas sugar sand’s composition is highly variable, with carbohydrate content ranging from 5.01 mg/g to 652.89 mg/g and polyphenol content ranging from 11.30 µg/g to 120.95 µg/g. In vitro bioaccessibility reached 70% of total sugars for all by-products. Organic acid bioaccessibility from sugar sand and syrup reached 76% and 109% relative to standard maple syrup, respectively. Polyphenol bioaccessibility exceeded 100% during digestion. This can be attributed to favorable extraction conditions, the breakdown of complex polyphenol forms and the food matrix. In conclusion, our study demonstrates that sugar sand and downgraded maple syrups exhibit digestibility comparable to that of standard maple syrup. Consequently, they hold potential as a source of polyphenols, sugar or organic acids for applications such as industrial fermentation or livestock feeds.
... cause Alzheimer (Hawco, Wang, Taylor, & Weaver, 2015). Besides that, the acetate-based extracts also exhibit anti-inflammatory effects. ...
Food producers have leaned towards alternative natural and synthetic sweeteners in food formulations to satisfy market demands. Even so, several synthetic sweeteners (e.g., aspartame, saccharin, sucralose) are becoming less popular due to health-related concerns, lower nutritional values, and controversies around their safety. Conversely, natural sweeteners confer favourable customer perceptions due to their association to a healthier lifestyle and higher nutritional values. This article discusses the evidence of natural sweeteners in the available commercial products. A comprehensive review of natural sweeteners is presented, which includes their resources, properties and extraction methods, as well as a discussion on several emerging technologies that offer improvements to the traditional extraction methods. Finally, the progress of natural sweeteners in the food industry is assessed, and the commercial food products containing these natural sweeteners are mentioned.
... Our group has conducted extensive chemical compositional studies on maple syrup, a natural sweetener produced by boiling the sap of sugar maple (Acer saccharum) trees, leading to the identification of over sixty phenolic constituents [10][11][12][13][14][15]. A phenolic-enriched maple syrup extract was reported to decrease oligomerization and aggregation of both Aβ1-42 and tau peptides [16]. In addition, our group reported on the anti-neuroinflammatory effects and anti-AD effects of a phenolicenriched maple syrup extract (MSX) in vitro and in Caenorhabditis elegans [17]. ...
Objectives: Alzheimer's disease (AD) is a growing global health crisis exacerbated by increasing life span and an aging demographic. Convergent lines of evidence, including genome-wide association studies, strongly implicate neuroinflammation in the pathogenesis of AD. Several dietary agents, including phenolic-rich foods, show promise for the prevention and/or management of AD, which in large part, has been attributed to their anti-inflammatory effects. We previously reported that a food-grade phenolic-enriched maple syrup extract (MSX) inhibited neuroinflammation in vitro but whether these effects are translatable in vivo remain unknown. Herein, we assessed MSX's ability to attenuate early neuroinflammation in a transgenic mouse model of AD.
Methods: The effects of MSX on AD-related neuroinflammation was evaluated by orally administering MSX (100 and 200 mg/kg/day for 30 days) to the 3xTg-AD mouse model of AD. The expression of inflammatory markers in mouse brains were analyzed with LC-MS/MS with SWATH acquisition.
Results: 3xTg-AD mice dosed orally with MSX have decreased expression of several inflammatory proteins, including, most notably, the AD risk-associated protein ‘triggering receptor expressed on myeloid cells-2’ (TREM2), and stimulator of interferon genes TMEM173, and suppressor of cytokine signaling-6 (SOCS6). However, this decrease in inflammation did not coincide with a decrease in pathogenic amyloid generation or lipid peroxidation.
Discussion: These data demonstrate that oral administration of this maple syrup derived natural product reduces key neuroinflammatory indices of AD in the 3xTg-AD model of AD. Therefore, further studies to investigate MSX's potential as a dietary intervention strategy for AD prevention and/or management are warranted.
... The sugar maple is distributed throughout North America, and maple trees serve an important role in traditional medicine among Native Americans (19). A number of previous studies have examined the chemical composition and biological properties of maple-derived products, including maple syrup (20)(21)(22)(23)(24)(25)(26). ...
Maple syrup is a natural sweetener that is consumed worldwide. It has been previously reported that dark-colored maple syrup exerts an inhibitory effect on colorectal cancer (CRC) proliferation and invasion. In the present study, the underlying mechanism of CRC cell growth inhibition was examined with dark-colored maple syrup treatment using a shotgun liquid chromatography-tandem mass spectrometry-based global proteomic approach. Applying a semi-quantitative method based on spectral counting, 388 proteins were identified with expression changes of >1.5-fold following dark-colored maple syrup treatment. Gene Ontology analysis revealed that these proteins possessed cell cycle-associated functions. It was also indicated that CRC cells treated with dark-colored maple syrup exhibited decreased proliferating cell nuclear antigen (PCNA) expression and S-phase cell cycle arrest. Dark-colored maple syrup treatment also resulted in altered expression of cell cycle-associated genes, including cyclin-dependent kinase (CDK)4 and CDK6. In conclusion, these data suggested that dark-colored maple syrup induced S-phase cell cycle arrest in CRC cells by reducing the expression of PCNA and regulating cell cycle-associated genes. These findings suggest that dark-colored maple syrup may be a source of compounds for the development of novel drugs for colorectal cancer treatment.
... We have recently reported that components of Canadian maple syrup can reduce the aggregation of amyloidogenic Aβ and tau (Hawco et al., 2016), and we were curious if caffeine or other components found in brewed coffee elicit neuroprotective effects through a similar mechanism. Herein we report our investigation into the effects of coffee on the aggregation of misfolded proteins associated with dementia to determine if inhibition of protein aggregation is a viable mechanism of neuroprotection associated with coffee consumption. ...
Coffee consumption has been correlated with a decreased risk of developing Alzheimer’s disease (AD) and Parkinson’s disease (PD), but the mechanism by which coffee may provide neuroprotection in humans is not fully understood. We hypothesized that compounds found in brewed coffee may elicit neuroprotective effects by inhibiting the aggregation of amyloid-beta (Aβ) and tau (AD) or α-synuclein (PD). Three instant coffee extracts (light roast, dark roast, decaffeinated dark roast) and six coffee components [caffeine (1), chlorogenic acid (2), quinic acid (3), caffeic acid (4), quercetin (5), and phenylindane (6)] were investigated for their ability to inhibit the fibrillization of Aβ and tau proteins using thioflavin T (ThT) and thioflavin S (ThS) fluorescence assays, respectively. Inhibition of Aβ and α-synuclein oligomerization was assessed using ELISA assays. All instant coffee extracts inhibit fibrillization of Aβ and tau, and promote α-synuclein oligomerization at concentrations above 100 μg/mL. Dark roast coffee extracts are more potent inhibitors of Aβ oligomerization (IC50 ca. 10 μg/mL) than light roast coffee extract (IC50 = 40.3 μg/mL), and pure caffeine (1) has no effect on Aβ, tau or α-synuclein aggregation. Coffee components 2, 4, and 5 inhibit the fibrillization of Aβ at 100 μM concentration, yet only 5 inhibits Aβ oligomerization (IC50 = 10.3 μM). 1–5 have no effect on tau fibrillization. Coffee component 6, however, is a potent inhibitor of both Aβ and tau fibrillization, and also inhibits Aβ oligomerization (IC50 = 42.1 μM). Coffee components 4 and 5 promote the aggregation of α-synuclein at concentrations above 100 μM; no other coffee components affect α-synuclein oligomerization. While the neuroprotective effect of coffee consumption is likely due to a combination of factors, our data suggest that inhibition Aβ and tau aggregation by phenylindane 6 (formed during the roasting of coffee beans, higher quantities found in dark roast coffees) is a plausible mechanism by which coffee may provide neuroprotection. The identification of 6 as a dual-inhibitor of both Aβ and tau aggregation is noteworthy, and to our knowledge this is the first report of the aggregation inhibition activity of 6.
... Maple syrup mainly comprises sucrose, but also contains various other components, such as oligosaccharides, polysaccharides, organic acids, amino acids, vitamins and minerals (1,2,(4)(5)(6)(7)(8). Previous studies, some recent, reported that maple syrup also contains several phytochemicals, including phenolic compounds that present hypoglycemic, antioxidant, antimutagenic, anticancer, anti-inflammatory, antibiotic and anti-neurodegenerative effects (9)(10)(11)(12)(13)(14)(15)(16)(17). Moreover, biological effects have been noted following maple syrup consumption. ...
Maple syrup is a natural sweetener that is commonly consumed worldwide. While maple syrup mainly comprises sucrose, it also contains phytochemicals that present various biological effects. Maple syrup is made by boiling down sap, and its color and composition vary in accordance with the sap collection season. Typically, seasonal progression is associated with darker syrup color, and antioxidant activity is proportional to the increasingly dark color. The authors previously reported that maple syrup demonstrated inhibitory effects on colorectal cancer cell growth and invasion, which correlated with darker maple syrup color. In the present study, they examined the effects of two different grades of maple syrup on gastrointestinal cancer cell proliferation, to investigate whether the dark-color maple syrup was suitable as a phytomedicine for gastrointestinal cancer treatment. Administration of dark-color maple syrup significantly inhibited gastrointestinal cancer cell growth as compared to non-treated cancer cells. Moreover, administration of dark-color maple syrup clearly inhibited protein kinase B (AKT) phosphorylation and did not impact mitogen-associated protein kinase phosphorylation. These data suggested that dark-color maple syrup may inhibit cell proliferation through suppression of AKT activation and, thus, may be suitable as a phytomedicine for gastrointestinal cancer treatment.
... 7 This recent diversification in the maple-derived food product portfolio is driven, in part, by several recently published in vitro 6−15 and animal studies 16−20 supporting the potential biological effects of maple phytochemicals against oxidation, inflammation, diabetes, and neurodegenerative diseases. 21,22 Given the premium price and popularity of maple-derived foods, the industry is faced with fake labeling claims and counterfeit products such as artificial maple-flavored and caramel-colored and simulated corn fructose-based sweeteners that falsely claim to contain maple syrup. Consequently, the U.S. Food and Drug Administration (FDA) has recently been petitioned by maple producers in North America regarding fake maple labels on food products, with similar petitions being planned for provincial and federal agencies in Canada. ...
The phenolic contents of plant foods are commonly quantified by the Folin-Ciocalteu assay based on gallic acid equivalents (GAEs). However, this may lead to inaccuracies since gallic acid is not always representative of the structural heterogeneity of plant phenolics. Therefore, product-specific standards have been developed for the phenolic quantification of several foods. Currently, maple-derived foods (syrup, sugar, sap/water, and extracts) are quantified for phenolic contents based on GAEs. Since lignans are the predominant phenolics present in maple, herein, a maple phenolic lignan-enriched standard (MaPLES) was purified (by chromatography) and characterized (by UFLC-MS/MS with lignans previously isolated from maple syrup). Using MaPLES and secoisolariciresinol (a commercially available lignan), the phenolic contents of the maple-derived foods increased threefold compared to GAEs. Therefore, lignan-based standards are more appropriate for phenolic quantification of maple-derived foods vs. GAEs. Also, MaPLES can be utilized for the authentication and detection of fake label claims on maple products.
Maple syrup is a naturally sweet product consumed directly or introduced in the preparation of various maple-derived food products. Several studies have described the chemical isolation and identification of maple syrup compounds, with some presenting pharmacological properties. However, a detailed review on maple syrup nutritional properties has not been undertaken. This review presents detailed information about the nutritional, organoleptic, and pharmacological properties of maple syrup. Studies carried out on animal models and a limited number of human models emphasize the potential benefits of maple syrup as a substitute for refined sugars, indicating that it could contribute to improved metabolic health when used in moderation. However, further medical and nutritional health studies based on human health assessments are needed to better understand the mechanisms of action of the various components of maple syrup and its potential therapeutic properties to demonstrate a stronger justification for its consumption relative to refined sugars. In addition, we compare maple syrup and common sweeteners to provide a further critical perspective on the potential nutritional and health benefits of maple syrup.
Maple sap, collected from the sugar maple (Acer saccharum) tree, is boiled to produce the popular plant-derived sweetener, maple syrup, which can then be further evaporated to yield the traditional North American confectionery, maple sugar. While maple sap and maple syrup have been previously studied, the phytochemical constituents of maple sugar are unknown. Herein, thirty phenolic compounds, 1-30, primarily lignans, were isolated and identified (by HRESIMS and NMR) from maple sugar. The isolates included the phenylpropanoid-based lignan tetramers, (erythro,erythro)-4'',4'''-dihydroxy-3,3',3'',3''',5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8'';4',8'''-bisoxy-8,8'-dineolignan-7'',7''',9'',9'''-tetraol, 29, and (threo,erythro)-4'',4'''-dihydroxy-3,3',3'',3''',5,5'-hexamethoxy-7,9';7',9-diepoxy-4,8'';4',8'''-bisoxy-8,8'-dineolignan-7'',7''',9'',9'''-tetraol, 30, neither of which have been identified from maple sap or maple syrup before. Twenty of the isolates (selected based on sample quantity available) were evaluated for their potential biological effects against lipopolysaccharide-induced inflammation in BV-2 microglia in vitro and juglone-induced oxidative stress in Caenorhabditis elegans in vivo. The current study increases scientific knowledge of possible bioactive compounds present in maple-derived foods including maple sugar.
Oxidative stress and free radical generation accelerate the formation of advanced glycation endproducts (AGEs) which are linked to several chronic diseases. Published data suggest that phenolic-rich plant foods, show promise as natural anti-AGEs agents due to their anti-oxidation capacities. A phenolic-enriched maple syrup extract (MSX) has previously been reported to show anti-inflammatory and neuroprotective effects but its anti-AGE effects remain unknown. Therefore, herein, we investigated the anti-glycation and anti-oxidation effects of MSX using biochemical and biophysical methods. MSX (500 μg mL(-1)) reduced the formation of AGEs by 40% in the bovine serum albumin (BSA)-fructose assay and by 30% in the BSA-methylglyoxal (MGO) assay. MSX also inhibited the formation of crosslinks typically seen in the late stage of glycation. Circular dichroism and differential scanning calorimeter analyses demonstrated that MSX maintained the structure of BSA during glycation. In the anti-oxidant assays, MSX (61.7 μg mL(-1)) scavenged 50% of free radicals (DPPH assay) and reduced free radical generation by 20% during the glycation process (electron paramagnetic resonance time scan). In addition, the intracellular levels of hydrogen peroxide induced reactive oxygen species were reduced by 27-58% with MSX (50-200 μg mL(-1)) in normal/non-tumorigenic human colon CCD-18Co cells. Moreover, in AGEs and MGO challenged CCD-18Co cells, higher cellular viabilities and rapid extracellular signal-regulated kinase (ERK) phosphorylation were observed in MSX treated cells, indicating its protective effects against AGEs-induced cytotoxicity. Overall, this study supports the biological effects of MSX, and warrants further investigation of its potential as a dietary agent against diseases mediated by oxidative stress and inflammation.
Maple syrup is a widely consumed plant-derived natural sweetener produced by concentrating xylem sap collected from certain maple (Acer) species. During thermal evaporation of water, natural phytochemical components are concentrated in maple syrup. The polymeric components from maple syrup were isolated by ethanol precipitation, dialysis, and anion exchange chromatography and structurally characterized by glycosyl composition analysis, glycosyl linkage analysis, and nuclear magnetic resonance spectroscopy. Among the maple syrup polysaccharides, one neutral polysaccharide was characterized as inulin with a broad molecular weight distribution, representing the first isolation of this prebiotic carbohydrate from a xylem sap. In addition, two acidic polysaccharides with structural similarity were identified as arabinogalactans derived from rhamnogalacturonan type I pectic polysaccharides.
The antiproliferative effects of Canadian maple syrup (grades C and D) extracts and fifty-one purified phenolic constituents were evaluated against human tumourigenic (HT-29, HCT-116, and CaCo-2) and non-tumourigenic (CCD-18Co) colon cells. Overall, maple syrup ethyl acetate (MS-EtOAc), butanol (MS-BuOH), and methanol (MS-MeOH) extracts were more active against the tumourigenic versus non-tumourigenic colon cells. At equivalent phenolic levels, the antiproliferative activities of grade D>C maple syrup, and MS-BuOH>MS-MeOH>MS-EtOAc. Among the isolates, gallic acid, catechaldehyde, syringaldehyde, and catechol were most active and their higher levels in grade D MS-BuOH extract could account for the highest observed anticancer effects of that extract. Moreover, the maple syrup extracts did not induce apoptosis of the colon cancer cells but induced cell cycle arrest which was also associated with a decrease in cyclins A and D1 levels. These results suggest that phenolics may impart potential biological effects to maple syrup.
Maple syrup is made by boiling the sap collected from certain maple ( Acer ) species. During this process, phytochemicals naturally present in tree sap are concentrated in maple syrup. Twenty-three phytochemicals from a butanol extract of Canadian maple syrup (MS-BuOH) had previously been reported; this paper reports the isolation and identification of 30 additional compounds (1-30) from its ethyl acetate extract (MS-EtOAc) not previously reported from MS-BuOH. Of these, 4 compounds are new (1-3, 18) and 20 compounds (4-7, 10-12, 14-17, 19, 20, 22-24, 26, and 28-30) are being reported from maple syrup for the first time. The new compounds include 3 lignans and 1 phenylpropanoid: 5-(3″,4″-dimethoxyphenyl)-3-hydroxy-3-(4'-hydroxy-3'-methoxybenzyl)-4-(hydroxymethyl)dihydrofuran-2-one (1), (erythro,erythro)-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3,5-dimethoxyphenyl]-1,2,3-propanetriol (2), (erythro,threo)-1-[4-[2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3,5-dimethoxyphenyl]-1,2,3-propanetriol (3), and 2,3-dihydroxy-1-(3,4- dihydroxyphenyl)-1-propanone (18), respectively. In addition, 25 other phenolic compounds were isolated including (threo,erythro)-1-[4-[(2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol (4), (threo,threo)-1-[4-[(2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethoxy]-3-methoxyphenyl]-1,2,3-propanetriol (5), threo-guaiacylglycerol-β-O-4'-dihydroconiferyl alcohol (6), erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (7), 2-[4-[2,3-dihydro-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2-benzofuranyl]-2,6-dimethoxyphenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (8), acernikol (9), leptolepisol D (10), buddlenol E (11), (1S,2R)-2-[2,6-dimethoxy-4-[(1S,3aR,4S,6aR)-tetrahydro-4-(4-hydroxy-3,5-dimethoxyphenyl)-1H,3H-furo[3,4-c]furan-1-yl]phenoxy]-1-(4-hydroxy-3-methoxyphenyl)-1,3-propanediol (12), syringaresinol (13), isolariciresinol (14), icariside E4 (15), sakuraresinol (16), 1,2-diguaiacyl-1,3-propanediol (17), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (19), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (20), dihydroconiferyl alcohol (21), 4-acetylcatechol (22), 3',4',5'-trihydroxyacetophenone (23), 3,4-dihydroxy-2-methylbenzaldehyde (24), protocatechuic acid (25), 4-(dimethoxymethyl)pyrocatechol (26), tyrosol (27), isofraxidin (28), and 4-hydroxycatechol (29). One sesquiterpene, phaseic acid (30), which is a known metabolite of the phytohormone abscisic acid, was also isolated from MS-EtOAc. The antioxidant activities of MS-EtOAc (IC(50) = 75.5 μg/mL) and the pure isolates (IC(50) ca. 68-3000 μM) were comparable to that of vitamin C (IC(50) = 40 μM) and the synthetic commercial antioxidant butylated hydroxytoluene (IC(50) = 3000 μM), in the diphenylpicrylhydrazyl radical scavenging assay. The current study advances scientific knowledge of maple syrup constituents and suggests that these diverse phytochemicals may impart potential health benefits to this natural sweetener.
Twenty-three phenolic compounds were isolated from a butanol extract of Canadian maple syrup (MS-BuOH) using chromatographic methods. The compounds were identified from their nuclear magnetic resonance and mass spectral data as 7 lignans [lyoniresinol (1), secoisolariciresinol (2), dehydroconiferyl alcohol (3), 5'-methoxy-dehydroconiferyl alcohol (4), erythro-guaiacylglycerol-β-O-4'-coniferyl alcohol (5), erythro-guaiacylglycerol-β-O-4'-dihydroconiferyl alcohol (6), and [3-[4-[(6-deoxy-α-l-mannopyranosyl)oxy]-3-methoxyphenyl]methyl]-5-(3,4-dimethoxyphenyl)dihydro-3-hydroxy-4-(hydroxymethyl)-2(3H)-furanone (7)], 2 coumarins [scopoletin (8) and fraxetin (9)], a stilbene [(E)-3,3'-dimethoxy-4,4'-dihydroxystilbene (10)], and 13 phenolic derivatives [2-hydroxy-3',4'-dihydroxyacetophenone (11), 1-(2,3,4-trihydroxy-5-methylphenyl)ethanone (12), 2,4,5-trihydroxyacetophenone (13), catechaldehyde (14), vanillin (15), syringaldehyde (16), gallic acid (17), trimethyl gallic acid methyl ester (18), syringic acid (19), syringenin (20), (E)-coniferol (21), C-veratroylglycol (22), and catechol (23)]. The antioxidant activities of MS-BuOH (IC50>1000 μg/mL), pure compounds, vitamin C (IC50=58 μM), and a synthetic commercial antioxidant, butylated hydroxytoluene (IC50=2651 μM), were evaluated in the diphenylpicrylhydrazyl (DPPH) radical scavenging assay. Among the isolates, the phenolic derivatives and coumarins showed superior antioxidant activity (IC50<100 μM) compared to the lignans and stilbene (IC50>100 μM). Also, this is the first report of 16 of these 23 phenolics, that is, compounds 1, 2, 4-14, 18, 20, and 22, in maple syrup.
Antioxidant activity, inhibition of nitric oxide (NO) overproduction, and antiproliferative effect of ethyl acetate extracts of maple sap and syrup from 30 producers were evaluated in regard to the period of harvest in three different regions of Québec, Canada. Oxygen radical absorbance capacity (ORAC) values of maple sap and syrup extracts are, respectively, 12 +/- 6 and 15 +/- 5 micromol of Trolox equivalents (TE)/mg. The antioxidant activity was also confirmed by a cell-based assay. The period of harvest has no statistically significant incidence on the antioxidant activity of both extracts. The antioxidant activity of pure maple syrup was also determined using the ORAC assay. Results indicate that the ORAC value of pure maple syrup (8 +/- 2 micromol of TE/mL) is lower than the ORAC value of blueberry juice (24 +/- 1 micromol of TE/mL) but comparable to the ORAC values of strawberry (10.7 +/- 0.4 micromol of TE/mL) and orange (10.8 +/- 0.5 micromol of TE/mL) juices. Maple sap and syrup extracts showed to significantly inhibit lipopolysaccharide-induced NO overproduction in RAW264.7 murine macrophages. Maple syrup extract was significantly more active than maple sap extract, suggesting that the transformation of maple sap into syrup increases NO inhibition activity. The highest NO inhibition induced by the maple syrup extracts was observed at the end of the season. Moreover, darker maple syrup was found to be more active than clear maple syrup, suggesting that some colored oxidized compounds could be responsible in part for the activity. Finally, maple syrup extracts (50% inhibitory concentration = 42 +/- 6 microg/mL) and pure maple syrup possess a selective in vitro antiproliferative activity against cancer cells.
In vitro testing for inhibitors of oligomer formation of pathologically misfolded proteins such as Alzheimer's beta-peptide (Abeta) has been limited by the lack of a suitably sensitive high-throughput method for measuring oligomers. Even with the development of oligomer-specific antibodies and a single-site antibody assay, there are multiple controls required to rule out false positives due to compound interactions with the epitopes on the peptide that are recognized by the antibodies or with the antibodies themselves, and the immunoreagents are expensive. A non-radioactive non-immunological method for the measurement of subnanomolar concentrations of Alzheimer's beta-peptide residues 1-42 [Abeta(1-42)] oligomers incorporating the biotin-avidin interaction that has been a workhorse for screening assays is applied here in a single-site NeutrAvidin capture/labeled streptavidin detection configuration to specifically recognize multimeric (>20kDa) oligomers of N-alpha-biotinyl-Abeta(1-42) (bio-Abeta42) but not monomeric bio-Abeta42. The high affinity and specificity of the biotin interaction with NeutrAvidin and streptavidin obviate interference by non-biotin-containing compounds. The reagents are inexpensive and can be applied to any misfolding/oligomerizing peptide or protein that can be biotinylated at a single site.