Volemitol
(Synonyms: 庚七醇) 目录号 : GC37919Volemitol (D-Volemitol) 是一种七碳糖醇,源于报春花属, 有重要的生理功能。volemitol 是所有发育阶段叶子中的主要非结构碳水化合物。volemitol 是一种光合产品,韧皮部易位 (韧皮部移动) 和储存碳水化合物。volemitol 生物合成由一种新的 NADPH 依赖性酮糖还原酶进行。
Cas No.:488-38-0
Sample solution is provided at 25 µL, 10mM.
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Volemitol (D-Volemitol) is a seven-carbon sugar alcohol that fulfills several important physiological functions in certain species of the genus Primula. Volemitol is the major nonstructural carbohydrate in leaves of all stages of development. Volemitol functions as a photosynthetic product, phloem translocate (phloem-mobile), and storage carbohydrate.Volemitol biosynthesis proceeds by a novel, NADPH-dependent, ketose reductase (sedoheptulose reductase)[1].
[1]. Hafliger B, et al. Metabolism of D-glycero-D-manno-heptitol, volemitol, in polyanthus. Discovery Of a novel ketose reductase1. Plant Physiol. 1999 Jan;119(1):191-8.
Cas No. | 488-38-0 | SDF | |
别名 | 庚七醇 | ||
Canonical SMILES | OC[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO | ||
分子式 | C7H16O7 | 分子量 | 212.2 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 4.7125 mL | 23.5627 mL | 47.1254 mL |
5 mM | 0.9425 mL | 4.7125 mL | 9.4251 mL |
10 mM | 0.4713 mL | 2.3563 mL | 4.7125 mL |
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Metabolism of D-glycero-D-manno-heptitol, Volemitol, in polyanthus. Discovery Of a novel ketose reductase1
Plant Physiol 1999 Jan;119(1):191-8.PMID:9880360DOI:10.1104/pp.119.1.191.
Volemitol (D-glycero-D-manno-heptitol, alpha-sedoheptitol) is an unusual seven-carbon sugar alcohol that fulfills several important physiological functions in certain species of the genus Primula. Using the horticultural hybrid polyanthus (Primula x polyantha) as our model plant, we found that Volemitol is the major nonstructural carbohydrate in leaves of all stages of development, with concentrations of up to 50 mg/g fresh weight in source leaves (about 25% of the dry weight), followed by sedoheptulose (D-altro-2-heptulose, 36 mg/g fresh weight), and sucrose (4 mg/g fresh weight). Volemitol was shown by the ethylenediaminetetraacetate-exudation technique to be a prominent phloem-mobile carbohydrate. It accounted for about 24% (mol/mol) of the phloem sap carbohydrates, surpassed only by sucrose (63%). Preliminary 14CO2 pulse-chase radiolabeling experiments showed that Volemitol was a major photosynthetic product, preceded by the structurally related ketose sedoheptulose. Finally, we present evidence for a novel NADPH-dependent ketose reductase, tentatively called sedoheptulose reductase, in volemitol-containing Primula species, and propose it as responsible for the biosynthesis of Volemitol in planta. Using enzyme extracts from polyanthus leaves, we determined that sedoheptulose reductase has a pH optimum between 7.0 and 8.0, a very high substrate specificity, and displays saturable concentration dependence for both sedoheptulose (apparent Km = 21 mM) and NADPH (apparent Km = 0.4 mM). Our results suggest that Volemitol is important in certain Primula species as a photosynthetic product, phloem translocate, and storage carbohydrate.
Effect of cultivar on the content of selected phytochemicals in avocado peels
Food Res Int 2021 Feb;140:110024.PMID:33648254DOI:10.1016/j.foodres.2020.110024.
The peels of ripe fruit of 'Hass' and 'Hass' type (HT) avocado cultivars were evaluated for phytochemical composition and other attributes. Peels represented from 8.78 to 14.11% of fruit weight. Their color ranged from homogeneous black to black with very small greenish spots. The oil content in the peels was low. Twelve fatty acids were identified in peel oil and the ratio of unsaturated to saturated fatty acids suggested that peel oil might contribute to human health. The phytochemical composition varied significantly with cultivar. However, many HT peels were superior than 'Hass' peel in their content of α-tocopherol, β-sitosterol, perseitol, and cyanidin-3-glucoside, which was up to 211.67, 45.92, 337.17, and 519.27% higher in HT peels, respectively. The content of some phenolic compounds, especially procyanidin B2 and epicatechin, was significantly lower in 'Hass' than in many HT peels. Few HT peels showed a higher content of carotenoids and chlorophyll than 'Hass' peels. Lutein was the most abundant carotenoid. Chlorophyll a and b were also abundant in peels and low concentrations of chlorophyll derivatives were observed. Avocado peels are an important source of bioactive compounds, including some carotenoids, acids, sterols, and Volemitol, which were observed for the first time.
Theoretical prediction of properties of aliphatic polynitrates
J Phys Chem A 2011 Feb 10;115(5):795-804.PMID:21214268DOI:10.1021/jp1054155.
Aliphatic polynitrates are studied using the density functional theory B3LYP method with basis set 6-31G*. The assigned infrared spectrum is obtained and is used to compute the thermodynamic properties based on the frequencies scaled by 0.96 and the principle of statistic thermodynamics. On comparison of the theoretical densities with the experimental ones, the reliability of this theoretical method is tested. Detonation properties are evaluated using the modified Kamlet-Jacobs equations based on the calculated densities and heats of formation. According to the largest exothermic principle, the relative specific impulse (Is) is investigated by calculating the enthalpy of combustion (ΔH(comb)) and the total heat capacity (C(p,gases)). It is found that the introduction of methylene nitrate group could decrease the specific impulses on whole. Moreover, in combination with the energetic properties, xylitol pentanitrate, mannitol hexanitrate, Volemitol heptanitrate, and 1,2,3,4,5,6,7,8-octanitrate n-octane are potential candidates for high energy density compounds.
Unusual carbohydrates from the lichen, Parmotrema cetratum
Phytochemistry 1993 Oct;34(3):715-7.PMID:7764148DOI:10.1016/0031-9422(93)85345-r.
The lichen Parmotrema cetratum contains traces of the unusual threitol and unexpected Volemitol, along with galactose (2%). Present is a complex containing a lightly branched beta-glucan containing (1-->3) and (1-->4)-linkages in a 25:47 molar ratio chemically linked to a galactomannan with structural features common in other lichens. A glucogalactomannan with a small proportion of Glc rho side chains was also characterized.
Development and validation of HILIC-UHPLC-ELSD methods for determination of sugar alcohols stereoisomers and its application for bioconversion processes of crude glycerin
J Chromatogr A 2019 Mar 29;1589:56-64.PMID:30621908DOI:10.1016/j.chroma.2018.12.044.
The recent increase in the production of crude glycerin through the manufacture of biodiesel has imputed a commercial issue, the excess of this raw material in the market and its constant devaluation, which resulted in the need for new technologies for its use. Crude glycerin can be used in biotechnological processes for the production of high value-added compounds. This study presents novel, simple and fast methods based on ultra-high performance liquid chromatography (UHPLC) using evaporative light scattering detection (ELSD) for simultaneous analysis of ten sugar alcohols with a hydrophilic interaction chromatography (HILIC) column. The selected compounds and their possible stereoisomers have major commercial importance and they can be obtained by biotechnological routes. Under optimized conditions, threitol, erythritol, adonitol, xylitol, arabitol, iditol, sorbitol, mannitol, dulcitol and Volemitol can be analyzed simultaneously within 15.0 min. The use of different column temperatures was a key parameter to reach the selectivity during the separation of some stereoisomers. Regression equations revealed a good linear relationship (R > 0.995) over the range from 50.0 to 800.0 ng. Limits of detection (LOD) and quantification (LOQ) ranged from 30.0 to 45.0 ng and 50.0-75.0 ng, respectively. The HILIC-UHPLC-ELSD methods showed good precision with low coefficient of variation (CV%) for the intra- and inter-assays experiments (≤ 5.1%) and high repeatability in terms of retention times for each analyte (≤ 0.5%). The accuracy was confirmed with an average recovery ranging from 92.3 to 107.3%. The developed methods employ an analytical technique more accessible and suitable for routine analyzes and have shown to be suitable for simultaneous analysis of sugar alcohols present in crude bioconverted glycerin samples using different classes of microorganisms.