Stingless bee honey, a novel source of trehalulose: a biologically active disaccharide with health benefits

Fletcher, Mary T.; Hungerford, Natasha L.; Webber, Dennis; Jesus, Matheus Carpinelli de; Zhang, Jiali; Stone, Isobella S. J.; Blanchfield, Joanne T.; Zawawi, Norhasnida

doi:10.1038/s41598-020-68940-0

Cited by 70 publications

(83 citation statements)

References 28 publications

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“…Trehalulose structure was first reported by Cookson et al with 13 C NMR [12] and confirmed later with additional 1 H NMR studies [1,4,26], These results have shown the existence of two major tautomers in water, α-Dglucopyranosyl-1,1-β-D-fructopyranose (major form) and α-D-glucopyranosyl-1,1-β-D-fructofuranose, designated as A and B, respectively, in Figure S5. The existence of α-Dglucopyranosyl-1,1-α-D-fructofuranose, designated as C in Figure S5, was only reported by Bates et al [27], in which the 13 C NMR data of fructose carbon 1 were lost.…”

Section: 5supporting

confidence: 58%

“…The sweetness of trehalulose is approximately 60% that of sucrose. Owing to its non-cariogenic property and slow release rate of monosaccharides into the blood, trehalulose has become a promising sucrose substitute for potential applications in the food and pharmaceutical industries to prevent dental cavities, mitigate diabetes mellitus, and maintain body weight [1][2][3]. However, the natural amount of trehalulose in honey is low, and the chemical synthesis of this sucrose isomer is difficult.…”

Section: Introductionmentioning

confidence: 99%

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Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography

Xue

Zhang

et al. 2021

J of Separation Science

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A simple and efficient method was developed for the preparation of high-purity trehalulose from the waste syrup of isomaltulose production. The waste syrup was pre-treated with C18 solid-phase extraction, where 98% decolorization and 97% reducing sugar recovery were obtained, followed by hydrophilic interaction liquid chromatography separation on a cysteine-bonded zwitterionic column. Under optimized conditions, trehalulose was separated from isomaltulose isomer and prepared on a semi-preparative scale with >99% purity. The structure of the prepared trehalulose was subsequently confirmed by nuclear magnetic resonance, and three tautomers of trehalulose (α-D-glucosylpyranosyl-1,1-β-D-fructopyranose, α-D-glucosylpyranosyl-1,1-β-D-fructofuranose, and α-D-glucosylpyranosyl-1,1-α-D-fructofuranose) were detected and completely characterized by 13 C NMR spectroscopy for the first time in this study. The tautomerization of α-D and β-D type transition was observed by hydrophilic interaction liquid chromatography on an AdvanceBio Glycan Mapping column, with smaller particle size (2.7 μm). Furthermore, the prepared trehalulose was applied as a standard for trehalulose quantification during the sucrose conversion by Klebsiella sp. LX3. The combination of solid-phase extraction and hydrophilic interaction liquid chromatography offers a new avenue for the preparation of sugar isomers from complex natural or fermentation products.

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Section: 5supporting

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography

Xue

Zhang

et al. 2021

J of Separation Science

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“…Trehalulose was an unusual α-(1 → 1) glucose-fructose isomer of sucrose with known acariogenic [ 28 ] and low glycemic index properties [ 29 ]. This disaccharide was recently detected for the first time in Meliponini honeys from different locations (Australia, Malaysia, and Brazil), and five different bee species were detected by Fletcher et al [ 30 ], who suggested that trehalulose could be a marker for the authenticity of pot-honey. Its presence in the studied African stingless bee honey confirmed that it could be a biomarker for stingless bee honey.…”

Section: Discussionmentioning

confidence: 99%

A Preliminary Study of Chemical Profiles of Honey, Cerumen, and Propolis of the African Stingless Bee Meliponula ferruginea

Popova

Gerginova

Trusheva

et al. 2021

Foods

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Recently, the honey and propolis of stingless bees have been attracting growing attention because of their health-promoting properties. However, studies on these products of African Meliponini are still very scarce. In this preliminary study, we analyzed the chemical composition of honey, two cerumen, and two resin deposits (propolis) samples of Meliponula ferruginea from Tanzania. The honey of M. ferruginea was profiled by NMR and indicated different long-term stability from Apis mellifera European (Bulgarian) honey. It differed significantly in sugar and organic acids content and had a very high amount of the disaccharide trehalulose, known for its bioactivities. We suggested trehalulose to be a potential marker for African stingless bee honey analogously to the recent proposal for Meliponini honey from Asia, South America, and Australia and demonstrated its easy discrimination by 13C NMR. Propolis and cerumen were studied by GC-MS (gas chromatography-mass spectometry). The samples contained mainly terpenoids (di-and triterpenes) but demonstrated qualitative and quantitative differences. This fact was an indication that possibly M. ferruginea has no strict preferences for resins used to construct and protect their nests. The antimicrobial and anti-quorum sensing properties of the two materials were also tested. These first results demonstrated that the honey, cerumen, and propolis of African stingless bees were rich in biologically active substances and deserved further research.

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“…Another characteristic of this honey is its resistance to form hydroxymethylfurfural (HMF) when subjected to high temperatures (Biluca et al, 2014), which is an added value for its use in pharmaceutical and food industries where the negative effects associated with excess HMF should be avoided (Shapla, Solayman, Alam, Khalil, & Gan, 2018). A more recent study revealed that SBH is the only natural product known to be enriched with a biologically active sugar (trehalulose), which has both antidiabetic and acariogenic properties (Fletcher et al, 2020). These recent findings among others suggest that current and future research into the chemical properties of SBH, offers opportunities to better characterize these under-investigated natural product (and for some, non-timber forest products), while discovering novel molecules relevant to human.…”

Section: Introductionmentioning

confidence: 99%

Characterization of honeys produced by sympatric species of Afrotropical stingless bees (Hymenoptera, Meliponini)

et al. 2022

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We investigated the effect of bee species identity and harvesting methods on the chemical composition and antiradical activity of 53 honey samples, produced by six stingless bee species in western Kenya (Kakamega forest). Our results illustrate that none of the assayed parameters significantly varied between the honey samples harvested by "punching holes" (n = 25) and "squeezing" (n = 28) methods. By contrast, species identity drove significant differences in the assayed parameters. Positive correlations between the antiradical activity and the phytochemicals (phenols and flavonoids) were observed, and honeys from Liotrigona sp. exhibited the highest amounts of phenols (214 mg GAE/100 g), flavonoids (73.0 mg QE/100 g) and antiradical activity (76.2%). The physicochemical analyses confirm the need to establish separate stingless bee honey standards for moisture, free acidity, invertase, electrical conductivity, and HMF, as these parameters significantly diverged from the set limits for Apis mellifera honey.

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Stingless bee honey, a novel source of trehalulose: a biologically active disaccharide with health benefits

Abstract: also known to be acariogenic 10,11 , and a highly active antioxidant 12 , and these properties may in no small way contribute to the reported beneficial health properties of stingless bee honey.

Cited by 70 publications

References 28 publications

Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography

Simple and efficient preparation of high‐purity trehalulose from the waste syrup of isomaltulose production using solid‐phase extraction followed by hydrophilic interaction chromatography

A Preliminary Study of Chemical Profiles of Honey, Cerumen, and Propolis of the African Stingless Bee Meliponula ferruginea

Characterization of honeys produced by sympatric species of Afrotropical stingless bees (Hymenoptera, Meliponini)

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