The Healing-Promoting Properties of Selected Cyclitols—A Review

Introduction: Myo-inositol and its derivatives cyclitols play an important role in the processes of cell regulation, signal transduction, osmoregulation, and ion channel physiology, and are a component of the cell membrane. Free cyclitols present in food or released during the degradation of galactosyl cyclitols by bacteria (in digestive tract) show some physiological benefits. Aim: The aim of this paper is to present and analyze the documented data about curative and healing properties of cyclitols. Results and discussion: Cyclitols are well known compounds in the treatment of an accompanied diabetes insulin resistance, and also obesity and polycystic ovarian syndrome. d-chiro-Inositol deficiency exacerbates insulin resistance in the liver, muscles, and fat, while depletion of myo-inositol results in the development of diabetic complications. Cyclitols are successfully applied in treatment of polycystic ovarian syndrome, simultaneous are observed effective reducing of BMI, improving the hormonal profile, and increasing fertility. Moreover, cyclitols have anti-atherogenic, anti-oxidative, anti-inflammatory, and anti-cancer properties. Conclusion: The properties of cyclitols may be a good therapeutic option in the reduction of metabolically induced inflammation. Due to well drugs tolerance and low toxicity of these compounds, cyclitols are recommend for pregnant women and also for children. Another advantage is their widespread presence and easy availability, which encourages their use in medicine.

Cyclitol galactosides in low-raffinose, low-stachyose soybean embryos after feeding d-chiro-inositol, myo-inositol or d-pinitol

Sucrose, raffinose and stachyose accumulate as stored soluble carbohydrates in embryos during soybean [Glycine max L. (Merrill)] seed development and maturation. Raffinose and stachyose in soybean feed products are not digested by humans, chickens or pigs, resulting in flatulence and reduced nutritional value. Soybean lines selected for low raffinose and low stachyose (LRS) or low raffinose, low stachyose and low phytin (LRSP1, LRSP2) concentrations in mature seeds were compared to a CHECK line with normal raffinose, stachyose and phytin. To determine whether increasing the supply of free cyclitols to immature embryos of these lines results in increased accumulation of galactosyl cyclitols, isolated immature embryos free of maternal tissues were fed solutions containing either d-chiro-inositol, myo-inositol or d-pinitol, or a control solution without cyclitols, for 24 h. Embryos were precociously matured by slow drying for 14 d with daily transfers to stepwise lower relative humidities. Soluble carbohydrates were extracted from axis and cotyledon tissues of mature, dry embryos and analysed by high-resolution gas chromatography. Axis and cotyledons from LRS, LRSP1 and LRSP2 embryos had low concentrations of stachyose compared to CHECK embryos after feeding a control solution without cyclitols. Feeding d-chiro-inositol to isolated embryos increased fagopyritol B1 accumulation in embryos of all lines. Feeding myo-inositol increased stachyose accumulation in LRSP1 and LRSP2 cotyledons. Feeding d-pinitol increased free d-pinitol in cotyledons of all lines but increased galactopinitol A and galactopinitol B only in LRS cotyledons. Supplying additional d-chiro-inositol to immature embryos can enhance accumulation of fagopyritol B1 in mature embryos of low-raffinose and low-stachyose or low-raffinose, low-stachyose and low-phytin soybeans.

Soluble carbohydrates in legume seeds

Mature dry legume seeds may contain up to 30 different soluble carbohydrates. Sucrose is a major component of the total soluble carbohydrates; others include the raffinose family oligosaccharides (RFOs; raffinose, stachyose, verbascose) that are mono-, di- and tri-α-galactosyl derivatives of sucrose. Other galactosides may include α-galactosyl derivatives of the cyclitols myo-inositol (galactinol, digalactosyl myo-inositol and trigalactosyl myo-inositol), d-pinitol (galactopinitol A, digalactosyl pinitol A (ciceritol) and trigalactosyl pinitol A; and galactopinitol B; higher galactosyl oligomers of galactopintiol B have rarely been detected), d-chiro-inositol (fagopyritol B1, fagopyritol B2 and fagopyritol B3) and d-ononitol (galactosyl d-ononitol and digalactosyl d-ononitol). Small amounts of myo-inositol, d-pinitol and d-chiro-inositol may also be present. Raffinose, stachyose and verbascose increase late in seed maturation, with 70% of RFOs accumulating after maximum seed dry weight is attained. RFOs are mostly degraded during germination. Sucrose, myo-inositol, d-pinitol and d-chiro-inositol are synthesized in maternal tissues of some legumes and are transported to and unloaded by seed coats into the apoplastic space surrounding developing seed embryos. Free cyclitols may be 60% of total soluble carbohydrates in leaves and 20% in seed coat cup exudates. Increasing the supply of free cyclitols may increase the accumulation of their respective α-galactosides in mature seeds. Seeds with reduced RFO accumulation, but with normal to elevated concentrations of galactosyl cyclitols (including fagopyritols), have normal field emergence and are also tolerant to imbibitional chilling under laboratory conditions. Molecular structures, biosynthetic pathways, accumulation of soluble carbohydrates in response to seed-expressed mutations and the physiological role of galactosides are reviewed.

Carbohydrates in Colobanthus quitensis and Deschampsia antarctica

Eight to nineteen ethanol-soluble carbohydrate components were identified in vegetative tissues of <em>Colobanthus quitensis</em> and <em>Deschampsia antarctica</em>. The analysed carbohydrates included: monosaccharides, cyclitols, galactosyl cyclitols, raffinose family oligosaccharides, lichnose family oligosaccharides, kestose family oligosaccharides. The analysed vegetative tissues accumulated from 447 to 139 mg/g d.m. soluble carbohydrates in <em>Colobanthus quitensis</em>, <em>Deschampsia antarctica</em> respectively. The raffinose family oligosaccharides constituted 53.3% in <em>Colobanthus quitensis</em> of the identified soluble carbohydrate component pool. Vegetative tissues accumulated starch in <em>Colobanthus quitensis</em> 20.6 mg/g d.m. and 261.6 mg/g d.m. in <em>Deschampsia antarctica</em>. Anatomical and ultrastructural observations of vegetative part of <em>Colobanthus quitensis</em> and <em>Deschmpsia antarctica</em> revealed the presence of various ergastic materials in intercellular spaces, cell walls and protoplasts. Various parts of these plants contain insoluble, PAS positive polysaccharides in intercellular spaces and in cell walls. Chloroplasts of analysed tissues contained starch. Less starch was visible in young, growing parts of shoots of <em>Colobanthus quitensis</em> and <em>Deschmpsia antarctica</em>, more starch appears in mature, differentiated parts.

Cyclitols, galactosyl cyclitols and raffinose family oligosaccharides in Mexican wild lupin seeds

Ten to 16 ethanol-soluble carbohydrate components were identified in the seeds of six Mexican wild lupins. The analysed carbohydrates included: monosaccharides, disaccharides, cyclitols, galactosyl cyclitols and raffinose family oligosaccharides. Stachyose and sucrose were the main carbohydrate component in the <em>Lupinus montanus</em>, <em>L. rotundiflorus</em>, <em>L. exaltatus</em>, <em>L. mexicanus </em>and <em>L. elegans</em> seeds. Only trace quantities of verbascose were detected in <em>Lupinus mexicanus </em>seeds. The analysed seeds accumulated 38 to 78 mg/g d.m. carbohydrates. The raffinose family oligosaccharides constituted 41 to 85.2% of the identified carbohydrate component pool. The analysed <em>Lupinus </em>seeds contained 3 to 8 unidentified carbohydrate components.

Different effects of soil drought on soluble carbohydrates of developing Lupinus pilosus and Lupinus luteus embryos

The aim of this study was to compare the accumulation of soluble carbohydrates in embryos of two lupin species: cultivated <em>Lupinus luteus</em> (cv. Juno) and wild <em>L. pilosus</em>, developing on plants grown under normal soil humidity and soil drought. All analysed seeds accumulated soluble carbohydrates, including: monosaccharides, sucrose, cyclitols, galactosyl cyclitols and raffinose family oligosaccharides. Soil drought caused a nearly two-fold increase of soluble carbohydrate contents in both species. <em>L. pilosus</em> embryos however, responded to water deficiency by increasing the accumulation of cyclitols and galactosyl cyclitols, whereas <em>L. luteus</em> embryos enhanced accumulation of cyclitols and raffinose family oligosaccharides.

Effect of exogenous abscisic acid on accumulation of raffinose family oligosaccharides and galactosyl cyclitols in tiny vetch seeds (Vicia hirsuta [L.] S.F. Gray)

The role of the abscisic acid (ABA) in biosynthesis of raffinose family oligosaccharides (RFOs) and galactosyl cyclitols (Gal-C) in tiny vetch (<em>Vicia hirsuta</em> [L.] S.F. Gray) seeds was investigated. The ABA was applied through incubation of seed at various stage of its development. The level of RFOs and Gal-C was determined in seed maturing on plant and in seed maturing in vitro. In early stages of <em>V. hirsuta</em> seed development, the ABA activated the biosynthesis of galactinol, although the level of arisen galactinol quickly declined. In the later stages of <em>V. hirsuta</em> seed development ABA had stimulatory effect of RFOs and Gal-C biosynthesis. Influence of ABA on biosynthesis of a-galactosides in <em>Vicia hirsuta</em> seed seems to be dependent on abscisic acid concentration. Low concentration of ABA had stimulatory effect on a-galactosides biosynthesis, but high concentration of ABA inhibited the process.

Exogenously applied D-pinitol and D-chiro-inositol modifies the accumulation of α-D-galactosides in developing tiny vetch (Vicia hirsuta [L.] S.F. Gray) seeds

In the present study we have investigated the effect of exogenous cyclitols on the accumulation of their galactosides and raffinose family oligosaccharides (RFOs), as well as on some enzymes important for their biosynthesis in seeds of tiny vetch (<em>Vicia hirsuta</em> [L.] S.F. Gray). Immature seeds during 6-day incubation with D-<em>chiro</em>-inositol (naturally does not appear in seeds of tiny vetch) were accumulated cyclitol and its galactosides (fagopyritols: B1 and B2). Short 4-hour incubation with D-<em>chiro</em>-inositol, and subsequent slow desiccation process caused accumulation of free cyclitol only, without biosynthesis of its galactosides. Feeding D-<em>chiro</em>-inositol to pods of tiny vetch induced accumulation of high levels of its galactosides (fagopyritol B1, B2 and B3) in maturing seeds. Similarly, feeding D-pinitol increased accumulation of its mono-, di- and tri-galactosides: GPA, GPB, DGPA and TGPA in tiny vetch seed. Accumulation of both cyclitols and their galactosides drastically reduced accumulation of verbascose. Inhibition of RFOs biosynthesis by elevated levels of free cyclitols suggests some competition between formation of both types of galactosides and similarity of both biosynthetic routes in tiny vetch seeds. Galactinol synthase (GolS) from tiny vetch seeds demonstrated ability to utilize D-<em>chiro</em>-inositol as galactosyl acceptor, instead of myo-inositol. Presence of both cyclitols, as substrates for GolS, caused synthesis of their galactosides: fagopyritol B1 and galactinol. However, formation of galactinol was more efficient than fagopyritol B1. D-chiro-Inositol and D-pinitol at concentrations several-fold higher than myo-inositol had inhibitory effect on GolS. Thus, we suggest that a level of free cyclitols can have an influence on the rate of galactinol biosynthesis and further accumulation of RFOs and galactosyl cyclitols in tiny vetch seeds.

Mutations modulate soluble carbohydrates composition in seeds of Lathyrus sativus L.

Seeds of <em>Lathyrus sativus</em> cv. Derek and Krab were used as biological material for induced mutagenesis. Three mutant lines were obtained from seeds of grass pea cv. Derek and 15 lines from mutagenised seeds of cv. Krab. Twelve ethanol-soluble carbohydrates were identified in the seeds. We have selected grass pea mutant lines with high oligosaccharides content (lines D4, K56, K25, and K7) and lines with low raffinose family oligosaccharides (RFO) content (lines K12, K29 and K13). Mutations changing the levels of RFO have not affected the contents of galactosyl cyclitols.