Evidence of two-step deprotonation of d-mannitol in aqueous solution

Gaidamauskas, Ernestas; Norkus, Eugenijus; Vaičiūnienė, Jūratė; Crans, Debbie C.; Vuorinen, Tapani; Jačiauskienė, Janė; Baltrūnas, G.

doi:10.1016/j.carres.2005.03.006

Cited by 15 publications

(11 citation statements)

References 37 publications

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“…An anomeric doublet at δ H 4.742 (J= 8.0 Hz), characteristic of a β-ᴅ-glucosyl unit, correlated in the HMBC spectrum to C-1, as in most iridoid glucosides [6]. Its 13 C NMR spectrum confirmed the presence of these functionalities and was in accordance with the apodanthoside structural pattern [6], except for the presence of an additional methoxy group at C-10. The stereochemistry of compound 1 was determined on the basis of ROESY experiment, which showed diagnostic cross peaks between H-1/H-1', H-5/H-9 and H-8/H-1, and confirmed by ECD analysis.…”

supporting

confidence: 53%

“…3), in addition to agreement of sugar signals with those of xyloside, except for the downfield shift of C-5' due to glycosylation [8]. The stereochemistry of compound 2 was established by comparison of its 1 H and 13 C NMR data with those previously reported for analogues [7]. Therefore, compound 2 was identified as (3S,6S)-cis linalool-3,7-oxide β-ᴅ-glucopyranosyl-(1''→5')-β-ᴅ-xylofuranoside.…”

mentioning

confidence: 98%

“…Other compounds isolated from the flowers were identified as the monoterpene, 6,7- dihydroxy linalool ( 5 ) [11], β-sitosterol glucoside ( 6 ) [12], the monoterpene glycosides: (3 S ,6 R )- cis -linalool-3,6-oxide β-D-glucopyranoside ( 7 ) [7], and (3 S , 6 R ) cis -linalool 3,6 oxide, O -β-D-xylopyranosyl-(1″→6′)-β-D-glucopyranoside ( 9 ) [7], D-mannitol ( 10 ) [13], p -hydroxy benzoic acid ( 11 ) [14], chlorogenic acid methyl ester ( 12 ) [15], quercetin 3- O -rutinoside-7- O -rhamnoside ( 13 ) [16], kaempferol-7- O - α -L-rhamnopyranoside ( 14 ) [17], quercetin-7- O - α -L-rhamnopyranoside ( 15 ) [16], and quercetin ( 16 ) [17]. From the leaves, 6 compounds were isolated and identified as scandoside methyl ester ( 17 ) [9], syringaresinol-4′- O -β-D-monoglucopyranoside ( 18 ) [18], kaempferol-3- O -rutinoside-7- O -rhamnoside ( 19 ) [19] and 4,5-dicaffeoyl quinic acid methyl ester ( 20 ) [20] in addition to compounds 12 and 14 .…”

mentioning

confidence: 99%

“…F3a-1 (476 mg) was purified by Sephadex LH-20 (50 g) CC, eluting with DCM-MeOH (1:1) to afford 1 (20 mg). F3a-3 (263.5 mg) was subjected to Sephadex LH-20 (30.0 g) CC to afford 3 sub-fractions (1-9),(10)(11)(12)(13)(14)(15)(16) and(17- 23).Further purification of F3a-3-(17-23) (40.0 mg) using SPE-C18 (2 g) eluted with H 2 O then a H 2 O-MeOH gradient afforded 3 (8.6 mg). F3a-4 (223 mg) was subjected to Sephadex LH-20 (30.0 g) CC eluted with MeOH to afford 3 sub-fractions (1-5), (6-10) and (11-14).…”

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confidence: 99%

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New Glycosides and Trypanocidal Metabolites from Vangueria edulis

Mohamed

Elokely

Bachkeet

et al. 2015

Natural Product Communications

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A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1″→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively.

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supporting

confidence: 53%

mentioning

confidence: 98%

mentioning

confidence: 99%

mentioning

confidence: 99%

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New Glycosides and Trypanocidal Metabolites from Vangueria edulis

Mohamed

Elokely

Bachkeet

et al. 2015

Natural Product Communications

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“…The acid–base properties of erythritol ( Ery ) have been studied by experimental potentiometric measurements, while, in the case of the sorbitol ( Sorb ), − maltol ( Malt ), and ethylmaltol ( EMalt ), literature data have been considered. The hydrolytic constants of the metal cations, Ca 2+ , Zn 2+ , Sn 2+ , and in the last case also the solubility product of the sparingly soluble species Sn(OH) 2(s) , have been taken into account in the elaboration of the complex formation constants. , The conversion from the molar to the molal concentration scale of the constants was carried out by using the appropriate density values…”

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confidence: 99%

Thermodynamic Behavior of Polyalcohols and Speciation Studies in the Presence of Divalent Metal Cations

et al. 2020

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The acid−base properties and complexing ability of some biologically relevant polyalcohols (erythritol, sorbitol, maltol, and ethylmaltol) toward bivalent metal cations have been determined by potentiometric measurements with an ISE-H + glass electrode in NaNO 3 aqueous solutions at I = 0.151 mol•kg −1 and T = 298.15 K. For the erythritol system, the investigations have been carried out in the ionic strength range 0.1 ≤ I/mol•kg −1 ≤ 1.0, and the dependence on the ionic strength of the protonation and stability constants has been modeled by the specific ion interaction theory (SIT). The sequestering ability of the different ligands toward the considered metal cations (Ca 2+ , Zn 2+ , and Sn 2+ ) has been evaluated by the pL 0.5 parameter. For example, for M 2+ /maltol systems, at T = 298.15 K in NaNO 3(aq) , I = 0.151 mol•kg −1 , and pH 7.4, the sequestering ability toward Zn 2+ (pL 0.5 = 4.60) is higher than that toward Sn 2+ (pL 0.5 = 3.94) and Ca 2+ (pL 0.5 = 1.27).

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Chiral Mesostructured BiOBr Films with Circularly Polarized Colour Response

Ding

Deng

et al. 2021

Angewandte Chemie

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Achieving strong and broadband circularly polarized colour responses in chiral inorganic materials is challenging. Here, we fabricated chiral mesostructured bismuth oxybromide (BiOBr) films (CMBFs) via hydrothermal growth using chiral sugar alcohols as symmetry‐breaking agents. The layered slabs of BiOBr crystals with weak van‐der‐Waals interactions are prone to mismatching due to the chiral driving force, resulting in hierarchically chiral arrangements of fine size. Three levels of chirality exist in the CMBFs: primary, helical distortion crystal lattices of a nanoflake, secondary, helical stacking of nanoflakes to form nanoplates, and tertiary, chiral vortexes arranged by nanoplates. The CMBFs displayed optical activities (OAs) over a wide wavelength range of 350–2500 nm with an anisotropic factor of up to 0.99, which led to a significant chirality‐dependent colour response to circularly polarized light. The high selectivity can be considered as the result of enhanced resonance due to structural‐handedness matching and the synergistic effect of multiple OAs.

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Evidence of two-step deprotonation of d-mannitol in aqueous solution

Cited by 15 publications

References 37 publications

New Glycosides and Trypanocidal Metabolites from Vangueria edulis

New Glycosides and Trypanocidal Metabolites from Vangueria edulis

Thermodynamic Behavior of Polyalcohols and Speciation Studies in the Presence of Divalent Metal Cations

Chiral Mesostructured BiOBr Films with Circularly Polarized Colour Response

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