Isolation and identification of galactinol from castor oilseed meal

Kuo, Tsung Min

doi:10.1007/bf02636110

Cited by 11 publications

(9 citation statements)

References 17 publications

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“…Other standards were extracted and purified from natural sources. DGMI (di-galactosyl myo-inositol) was isolated from seeds of Vicia cracca and tentatively identified after its hydrolysis to galactose and myo-inositol according to method described by Kuo (1992). Standards of galactosyl pinitols (galactopinitol A, di-galactopinitol A named ciceritol, and tri-galactopinitol A) were isolated and purified from seeds of Vicia villosa as was described earlier (Szczeciñski et al 2000).…”

Section: Analysis Of Soluble Carbohydratesmentioning

confidence: 99%

Biosynthesis of raffinose family oligosaccharides and galactosyl pinitols in developing and maturing seeds of winter vetch (Vicia vlllosa Roth.)

Lahuta

2011

Acta Soc Bot Pol

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Changes in the accumulation of two types of α-D-galactosides: raffinose family oligosaccharides and galactosyl pinitols were compared with changes in the activities of galactosyltransferases during winter vetch (Vicia villosa Roth.) seed development and maturation. Occurrence of galactinol and raffinose in young seeds and changes in activities of galactinol synthase and raffinose synthase during seed development indicated that formation of raffinose oligosaccharides (RFOs) preceded synthesis of galactopinitols. Although transfer of galactose residues into raffinose oligosaccharides increased as seeds were maturing, at late stages of seed maturation the accumulation of galactopinitols was preferred to that of RFOs. In the present study, activities of enzymes transferring galactose moieties from galactinol to D-pinitol forming galactopinitol A, and further transfer of galactose moieties from galactinol to mono- and di-galactopinitol A were detected throughout seed development and maturation. This is a new observation, indicating biological potential of winter vetch seeds to synthesize mono-, di- and tri-galactosides of D-pinitol in a pathway similar to RFOs. The pattern of changes in activities of stachyose synthase and enzymes synthesizing galactopinitols (named galactopinitol A synthase and ciceritol synthase) suggests that formation of stachyose, mono- and di-galactopinitol A (ciceritol) is catalyzed by one enzyme. High correlation between activities of verbascose synthase and enzyme catalyzing synthesis of tri-galactopinitol A from galactinol and ciceritol (named tri-galactopinitol A synthase) also suggests that biosynthesis of both types of tri-galactosides was catalyzed by one enzyme, but distinct from stachyose synthase. Changes in concentrations of galactosyl acceptors (sucrose and D-pinitol) can be a factor which regulates splitting of galactose moieties between both types of galactosides in winter vetch seeds

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Section: Analysis Of Soluble Carbohydratesmentioning

confidence: 99%

Biosynthesis of raffinose family oligosaccharides and galactosyl pinitols in developing and maturing seeds of winter vetch (Vicia vlllosa Roth.)

Lahuta

2011

Acta Soc Bot Pol

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“…Commercially unavailable standards of galactosyl pinitols (galactopinitol A, di-galactopinitol A and tri-galactopinitol A) were isolated and purified from seeds of Vicia villosa as described earlier (Szczeciñski et al 2000), and galactosyl chiro-inositols (fagopyritol B1, B2 and B3) were obtained from buckwheat seeds (Steadman et al 2001). Standard of di-galactosyl myo-inositol (DGMI) was isolated from seeds of Vicia cracca and identified after its acidic hydrolysis to galactose and myo-inositol according to the method described by Kuo (1992). Carbohydrate content was calculated from the ratio of the area of peak of each measured component to the area of internal standard peak (xylitol, Sigma).…”

Section: Analysis Of Raffinose Family Oligosaccharides (Rfos) and Galmentioning

confidence: 99%

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

Lahuta

Horbowicz²,

Gojlo

et al. 2011

Acta Soc Bot Pol

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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 (Vicia hirsuta [L.] S.F. Gray). Immature seeds during 6-day incubation with D-chiro-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-chiro-inositol, and subsequent slow desiccation process caused accumulation of free cyclitol only, without biosynthesis of its galactosides. Feeding D-chiro-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-chiro-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

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“…Each car bo hy drate was quan ti fied by us ing au thentic stan dards pur chased from Sigma (raffinose, stachyose, myo-inositol, D-pinitol) and Megazyme, Aus tra lia (verbascose). Other stan dards were extracted and pu ri fied from nat u ral sources: galactinol was ob tained from leaves of Me lissa officinalis ac cord ing to method de scribed by Kuo (1992), di-galactosyl myo-inositol (DGMI) from seeds of Vicia cracca by method de scribed pre viously (Szczeciński et al 2000). DGMI was ten tatively iden ti fied af ter its hy dro ly sis to galactose and myo-inositol (2 N trifluoroacetic acid, 80 °C, 2 hours) ac cord ing to method de scribed by Kuo (1992).…”

Section: Anal Y Ses Of Sol U Ble α-Galactosidesmentioning

confidence: 99%

“…Other stan dards were extracted and pu ri fied from nat u ral sources: galactinol was ob tained from leaves of Me lissa officinalis ac cord ing to method de scribed by Kuo (1992), di-galactosyl myo-inositol (DGMI) from seeds of Vicia cracca by method de scribed pre viously (Szczeciński et al 2000). DGMI was ten tatively iden ti fied af ter its hy dro ly sis to galactose and myo-inositol (2 N trifluoroacetic acid, 80 °C, 2 hours) ac cord ing to method de scribed by Kuo (1992). Stan dards of galactosyl pinitols (galactopinitol A, di-galactopinitol A and tri-galactopinitol A) were iso lated from seeds of Vicia villosa and struc ture was de ter mined by us pre vi ously (Szczeciński et al 2000).…”

Section: Anal Y Ses Of Sol U Ble α-Galactosidesmentioning

confidence: 99%

Differences in accumulation of soluble α-galactosides during seed maturation of several Vicia species

et al. 2005

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Ab stractCom po si tion and lev els of sol u ble α-galactosides: raffinose fam ily oli go sac cha rides (RFOs) and galactosyl cyclitols (Gal-C) in de vel op ing seeds were mea sured by high res o lu tion gas chro ma tog ra phy (HRGC) method. The stud ies were performed on ma tur ing seeds of sev eral wild and cul ti vated Vicia spe cies: Vicia angustifolia L. (com mon vetch), Vicia cracca L. (bird vetch), Vicia grandiflora Scop. (large yel low vetch), Vicia hirsuta (L.) S.F.Gray (tiny vetch), Vicia sativa L. (garden vetch, spring-grow ing cultivar Kwarta), and Vicia villosa Roth (win ter vetch).In all Vicia spe cies sim i lar pat terns in the ac cu mu la tion of RFOs were ob served. Galactinol -the do nor of galactosyl moieties in α-galactosides biosynthesis was pres ent in the mid dle stage of seed de vel op ment, be fore ap pear ing mea sur able levels of RFOs. Ac cu mu la tion of RFOs started par al lel with seed des ic ca tion pro cess. At first ac cu mu la tion of the raffinose, then few days later stachyose and fi nally verbascose was noticed. In the fi nal stage of seed mat u ra tion the verbascose was the main sol u ble α-galactoside (up to 3 % of dry weight, V. sativa). Be sides the RFOs seeds of three Vicia spe cies (V. cracca, V. hirsuta, and V. villosa) ac cu mu lated D-pinitol and its α-ga lactosides (Gal-C). Mono-galactosylpinitols (sim i lar to raffi nose) ap peared in these spe cies 2-4 days af ter galactinol, di-galactosyl pinitol A (com mon name: ciceritol) and di-galactosyl myo-inositol were pres ent sev eral days later than raffinose, and ac cu mu la tion of tri-galactosyl pinitol A (TGPA) be gan af ter ac cu mu la tion of stachyose. Ma tured seeds of V. hirsuta con tained much more RFOs than Gal-C, op po site to seeds of V. villosa, and V. cracca where con cen tra tion of Gal-C was 4-8-fold higher than RFOs. In V. cracca seeds RFOs were al most re placed by Gal-C.In seeds of V. cracca and V. villosa the level of D-pinitol was sig nif i cantly higher, than the level of myo-inositol. Con tents of both cyclitols de clined rap idly at the be gin ning of seed des icca tion, when ac cu mu la tion of RFOs and Gal-C quickly increased. We sug gest that α-galactosides of D-pinitol can substi tute raffinose fam ily oli go sac cha rides and play sim i lar role dur ing seed maturation and storage.List of ab bre vi a tions: RFOs = raffinose fam ily oligo sac cha rides; Gal-C = galactosyl cyclitols; DAF = day af ter flow er ing; FW = fresh weight; DW = dry weight In tro duc tionRaffinose fam ily oli go sac cha rides (RFOs) are com mon in the plant king dom, mainly as con stit uents in seeds. To RFOs be longs raffinose (α-1→6-D -ga lactoside of su crose), and its ho mol ogous com pounds: stachyose, verbascose and 163

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Isolation and identification of galactinol from castor oilseed meal

Cited by 11 publications

References 17 publications

Biosynthesis of raffinose family oligosaccharides and galactosyl pinitols in developing and maturing seeds of winter vetch (Vicia vlllosa Roth.)

Biosynthesis of raffinose family oligosaccharides and galactosyl pinitols in developing and maturing seeds of winter vetch (Vicia vlllosa Roth.)

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

Differences in accumulation of soluble α-galactosides during seed maturation of several Vicia species

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