**14. References**


Extraction and Analysis of Inositols and Other Carbohydrates from Soybean Plant Tissues 437

Decker, P. & Schweer, H. (1982). Gas-liquid chromatography on OV-225 of tetroses and

Denison, R.F.; Hunt, S. & Layzell D.B. (1992). Nitrogenase activity, nodule respiration and

Dmitriev, B.A.; Backinowsky, L.V.; Chizhov, O.S.; Zolotzrev, B.M. & Kochetkow, N.K.

Dogruel, D. & Williams, P. (1995). Detection of human IgM at m/z 1 MDa. Rapid Comm

Eagle, H.; Oyama, V.I.; Levy, M. & Freeman, A.E. (1957) . myo-Inositol as an essential

Ensminger A.; Ensminger, M.; Konlande, J. & Robson J. (Ed.). (1995). *The Concise Encyclopedia Of Foods & Nutrition,* Boca Raton, London, Tokyo: CRC Press, pp.580-581. Evershed, R.P. (1993). Advances in Silylation. In: *Handbook of derivatives for chromatography*,

Farquhar, G.D. & Sharkey, T.D. (1982). Stomatal conductance and photosynthesis. Annu.

Fontes, C.M.G.A. &. Gilbert, H.J. (2010). Cellulosomes:Highly efficient nanomachines

Fougere, F.; LeRudulier, D. & Streeter, J.G. (1991). Effects of salt stress on amino acid,

Fountain, K.J.; Hudalla, C.; Grumbach, E.S. & McCabe, D. (2009). Analysis of carbohydrates

Fugimoto, T.; Sakari, S.; Tsutsuri, A.; Furihata, K.; Machinami, T. & Tashiro, M. (2005).

Fux, M.; Levine, J.; Aviv, A. & Belmaker, R.H. (1996). Inositol treatment of obsessivecompulsive disorder. American Journal of Psychiatry, 153:1219-1221. Garland, S.; S. Goheen, S.; Donald, P.; McDonald, L & Campbell, J. (2009). Application of

Gaskell, S. (1997). Electrospray: Principles and Practices. *Journal of Mass Spectrometry*, 32:677-

Gee, M. & Walker H.G. (1962). Gas-liquid chromatography of some methylated mono-, di-,

quantitation of pinitol in plant roots. Anal. Letters 42:2096-2105.

designed to deconstruct plant cell wall complex carbohydrates. Annual Review

organic acid, and carbohydrate composition of roots, bacteroids, and cytosol of

by ultraperformance liquid chromatography and mass spectrometry. LCGC, ASIA

Observation of 1,6-anhdro-beta-maltose and 1,6-anhdro-beta-D-glucopyranose complexed with rubidium by NMR spectroscopy and electrospray ionization mass

derivatization gas chromatography/mass spectrometry for the identification and

K. Blau & J.M. Halket, (Ed.), Chichester, U.K.: Wiley, p.53, p.59.

alfalfa (*medicago sativa L.).* Plant Physiol. 96: 1228-1236.

373.

98:894-900.

266: 191-205

Mass Spectrom. 9:625

Rev. Plant Physiol. 33:317-345.

Biochem. 79:655-681.

Pacific, Volume 12, issue 4.

688.

spectrometry. Anal. Sci., 21: 1245-1247.

and trisaccharides. Anal. Chem. 34:650-653.

aldopentoses as their O-methoxime and O-n-butoxime pertrifluoroacetyl derivatives and of C3-C6 alditol pertrifluoroacetates*. J. of Chromatography*, 236:369-

O2 permeability following detopping of alfalfa and birdsfoot trefoil*. Plant Physiol*.

(1971). Gas-liquid chromatography and mass spectrometry of aldononitrile acetates and partially methylated aldononitrile acetates. Carbohydrate Research 19:432-435.

growth factor for normal and malignant human cells in tissue culture. *J. Biol. Chem.*


Asp, N-G. (1993). Nutritional importance and classification of food carbohydrates , In: *Plant* 

Benjamin, J.; Levine, J.; Fux, M.; Aviv, A. & Belmaker, R.H. (1995). Double-blind, placebo-

Berridge, M.J.; Helsop J.P.; Irvine, R.F. & Brown K.D. (1984). Inositol trisphosphate

Binder, R. G. & Haddon, W. F. (1984). *Analysis of O-methylinositols by gas-liquid* 

Bisho , C.T. (1964). *Gas-Liquid chromatography of carbohydrate derivatives*. Advances in

Bishop, C.T. & Cooper, F.P. (1960). Separation of carbohydrate derivatives by gas-liquid

Blakeney , A.B.; Harris, P.J.; Henry, J. & Stone, B.A. (1983). A simple and rapid preparation

Bohnert, H.J.; Nelson, D.E. & Jensenay, R.G. (1995). The Plant Cell, *Adaptations to* 

Brockwell, J.; Bottomley, P.J. & Thies, J.E. (1995). Manipulation of rhizobia microflora for

Campbell, J. A.; Hess, W.P.; Lohman, J.R. & Goheen, S.C. ( 2001). Analysis of Hanford-

Chiera, J.M.; Streeter, J.G. & Finer, J.J. (2006). Ononitol and pinitol production in transgenic

Churms, S.C. (1990). Recent developments in the chromatographic analysis of

Churms, S.C. (1996). Recent progress in carbohydrate separation by high-performance liquid

Clements, R.S., Jr. & Darnell, R. (1980).myo-Inositol content of common foods: development

Colowick, S.P. & Kaplan, N.O. (1951). Carbohydrate metabolism. *Annual Review of* 

Corey, E. J. & Chaykovsky, M. (1962). Methylsulfinylcarbanion. *J. Am. Chem. Soc.* 84: 866-867. Cote, G.G. & Crain, R.C. (1993). Biochemistry of phosphoinositides. *Annual Review of Plant* 

Daughaday, W.H.; Larner, J. & Hartnett, C, (1955). The synthesis of inositol in the immature

mass spectrometry. J. Radioanalytical and Nucl. Chem., 250: 247-253. Campling, J.D. & Nixon, D.A. (1954). The inositol content of foetal blood and foetal fluids. J.

of alditol acetates for monosaccharide analysis. Carbohydrate Research, 113:291-

improving legume productivity and soil fertility: a critical assessment. *Plant Soil*.

related organics using matrix-assisted laser desorption ionization time-of-flight

soybean containing the inositol methyl transferase gene from *Mesembryanthemum*

chromatography based on size exclusion. *Journal of Chromatography*, A., 720:151-166.

Chem., Cambridge, U.K., pp. 121-126.

Carbohydrate Chemistry 19:95-147.

*Environmental Stresses,* Vol. 7, 1099-1111.

299.

174: 143-180.

Physiol. (I954). I26, 7I-80

*Biochemistr,* 20:513-558.

*Physiology.* 44:333-356.

*crystallinum*. Plant Sci. 171: 647-654.

carbohydrates. *Journal of Chromatography.* 500:555-583.

of a high-*myo*-inositol diet. *J.Am. Clin. Nutr.* 33:1954-1967.

rat and chick embryo. *J. Biol. Chem.* 212:869-875.

derived growth factor. *Biochem. J*. 222: 195-201.

*chromatography-mass spectrometry Carbohydr.* Res.129:21-32.

partition chromatography. Candian J. Chem., 38:388-398.

*of Psychiatry*. 152: 1084-1086.

*Polymeric Carbohydrates*, Meuser, F., Manners, D.J., & Seibel, (Ed.), W. Royal Soc.

controlled, crossover trial of inositol treatment for panic disorder. *American Journal* 

formation and calcium mobilization in Swiss 3T3 cells in response to platelet-


Extraction and Analysis of Inositols and Other Carbohydrates from Soybean Plant Tissues 439

Hansen, B. & Ortmeyer, H. (1996). Inositols-Potential roles for insulin action in diabetes:

Harvey, D.J. (1999). Matrix-assisted laser desorption/ionization mass spectrometry of

Harvey, D.J. (2010). Analysis of carbohydrates and glycoconjugates by matrix-assisted laser

Hasegawa, P.M.; Bressan, R.A.; Zhu, J.K. & Bohnert, H.J. (2000). Plant cellular and molecular responses to high salinity, Annu. Rev. Plant Physiol. Plant Mol. Biol. 51:463–99. Henderson, J.W., Jr.; & Berry, J. (2007). Isocratic Stevia seetner analysis using selective

Henry, E.W. (1976). Determination of inositol in inbred and hybrid corn (*Zea mays*)

Hillenkamp, F.; Karas, M.; Beavis, R.C. & Chait, B.T. (1991). Matrix-assisted laser

Hoffmann-Ostenhof, O. & Pittner, F. (1982). The biosynthesis of myo-inositol and its

Holm, P.J.; Booth, M.H.; Schmidt, T.; Greve, H. & Callesen, H. (1999). Theriogenology 52:

Holub, B. J. (1986). Metabolism and function of myo-inositol phospholipids. Ann. Rev. Nutr.

Honda, S.; Kakehi, K. & Okada, K. (1979). A convenient method for the gas chromatographic

Horecker, B.L. & Mehler, A.H. (1955). Carbohydrate metabolism. Annual Review of

Irvine, R.F., & Schell, M.J. (2001). Back in the water: the return of the inositol phosphates.

Ismail, M.N.; Stone, E.L.; Panico, M.; Lee, S.H.; Luu, Y.; Ramirez, K.; Ho, S.B.; Minory M.;

Jaindl, M. & Popp, M. (2006). Cyclitols protect glutamine synthetase and malate

Jiao, J,; Zhang, H. & Reinhold, V. (2010). High Performance IT-MS" Sequencing of Glycans.

Johansen, S. L.; A. Sivasothy, A.; Dowd, M.K.; Reilly, P.J. & Hammond, E.G. (1996). Low-

soapstocks. Journal of the American Oil Chemists' Society 73:1275-1286.

Biochem and Biophysical Research Communications 345:761-765.

683-700. "High bovine blastocyst development in a static in vitro production system using sofaa medium supplemented with sodium citrate and myo-inositol

analysis of hexosamines in the presence of neutral monosaccharides and uronic

Haslam J.D.; Stuart, M. & Dell, A. (2010). High Sensitivity *O-glycomic Analysis of Mice Deficient in* Core 2131,6-N-*acetylglucosaminyl* transferases. Glycobiology. 21:82-

dehydrogenase against the induced deactivation and thermal denaturation.

molecular weight organic compositions of acid waters from vegetable oil

desorption/ionization of biopolymers. *Anal. Chem*. 63:1193A-1203A

Diabetes U. Ed. E. Shafrie, pp. 333-348.

Rev. 28:273-361.

carbohydrates. Mass Spectrom. Rev. 18:349-450.

ZORBAX columns. Agilent Application Note. Food.

seedlings*. Journal of Experimental Botany* 27:259-262.

acids. Journal of Chromatography. 176:367-273.

isomers. Can. J. Chem*.*60:1863-1871.

with or without serum-proteins"

Biochemistry 24:207-274.

Mol. Cell. Biol. 2:327-338.

Int. J. Mass Spectrometry. 303:109-117.

6: 563-597.

98.

Evidence form insulin-resistant nonhuman primates. Lessons from Animal

desorption/ionization mass spectrometry: an update for 2003-2004. Mass Spectrom.


Geethan, P.K. & Prince, P.S. (2008). Antihyperlipidemic effect of D-pinitol on streptozotocin-

George, T.S.; Richardson, A.E.; Hadobas, P. & Simpson R.J. (2004). Characterization of

George, T.S.; Simpson, R.J.; Hadobas, P.A. & Richardson, A.E. (2005). Expression of a fungal

Gerli, S.; Mignosa, M. & Di Renzo, G.C. (2003). Effects of inositol on ovarian function and

Gerli, S.; Papaleo, E.; Ferrari, A. & Di Renzo, G.C. (2007). Randomized, double blind

Goheen, S. C.; Wahl, K.L.; Campbell, J.A. & Hess, W.P.(1997). Mass spectrometry of low

Gomes, C. I.; Obendorf, R.L. & Horbowicz, M. (2005). myo-Inositol, D-chiro-Inositol, and D-

Gregersen, G.; Bersting, H.; Theil, P & Servo, C. (1978). Myoinositol and function of peripheral nerves in human diabetes. Acta Neurol. Scand. 58:241-248. Gregersen, G.; Bartelsen, B. & Harbo, H. (1983). Oral supplementation of myo-Inositol:

Guo, C. & Oosterhuis, D.M. (1997). Effect of water-deficit stress and genotypes on pinitol

Hakomori, S. (1964). A rapid permethylation of glycolipid, and polysaccharide catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide. J. Biochem 55:205-208. Halket, J.M. (1993). Derivatives for GC-MS. In: Handbook of derivatives for chromatography, ed. K. Blau and J.M. Halket, Chichester, U.K., Wiley, 304. Halford, N.G.; Curtis, T.Y.; Muttucumaru, N.; Postles, J. & Mottran, D.S. (2010). Sugars in

Hall, M.B. (2003). Challenges with nonfiber carbohydrate methods. J. Anim. Sci. 81:3226-

Halliday, J.W. & Anderson, L. (1955). The synthesis of myo-inositol in the rat. Journal of

Hanneman, A. R.; Cesar, J.; Ashline, D. E. & Reinhold, V. N. (2006) Isomer and Glycomer

Complexities of Core GlcNAcs in *Caenorhabditis e/egans.*Glycobiology, 16: 874 - 890.

occurrence in soybean plants. Environ. Exper. Bot. 37:147-152.

transgenic *Trifolium subterraneum* L. which expresses *phyA* and releases extracellular phytase: growth and P nutrition in laboratory media and soil. Plant Cell Environ.

phytase gene in *Nicotiana tabacum* improves phosphorus nutrition of plants grown

metabolic factors in women with PCOS: a randomized double blind placebocontrolled trial. European Review for Medical and Pharmacological Sciences. 7:151-

placebo-controlled trial: effects of Myo-inositol on ovarian function and metabolic factors in women with PCOS. European Review for Medical and Pharmacological

molecular mass solids by matrix-assisted laser desorption/ionization. J. Mass

Pinitol synthesis, transport, and galactoside formation in soybean explants. Crop

effects of peripheral nerves in human diabetics and on the concentration in plasma, erythrocytes, urine, and muscle tissue in human diabetics and normals. Acta

induced diabetic Wistar rats, J. Biochem. Mol. Toxicol. 22:220-224.

in amended soils. Plant Biotechnol. J. 3:129-140.

27:1351-1361.

Sciences, 11(5):347-354.

Spectr. 32: 820-828.

Sci. 45:1312-1319.

3232

Neurol. Scand. 67:164-172.

crop plants. Ann Appl Biol 158:1-25.

biological chemistry 217:797-802.

159.


Extraction and Analysis of Inositols and Other Carbohydrates from Soybean Plant Tissues 441

LaFosse, M. & Herbreteau, B. (2002). In: *Carbohydrate Analysis by Modern chromatography and* 

Larson, S & Raboy, V. (1999). Linkage mapping of maize and barley *myo*-inositol phosphate

Lau, K.; Partridge; E. A.; Grigorian, A.; Silvescu, C. I.; Reinhold, V. N.; Demetriou;Michael;

Layzell, D.B., Hunt, S.; Moloney, A.H.M.; Fernando, S.M. & Diaz del Castillo. L. (1990).

Lee, L.S. & Morris, N.J. (1963). Isolation and identification of pinitol from peanut flour, *Agr.* 

Lee, Y.C. (1996). Carbohydrate analyses with high-performance anion-exchange

Lehrfield, J. (1981). Differential gas-liquid chromatography for the determination of uronic

Levine J.; Barak, Y,; Kofman, O.; & Belmaker, R.H. (1995). Follow-up and relapse analysis of

Li, B.W.; Schuhmann, P.J.;. &. Holden, J.M.( 1983). Determination of sugars in yoghurt by

Lind, Y.; Engman, J.; L. Jorhem, L. & Wicklund, G.A. (1988). Accumulation of cadmium from

Logemann, E.; Wu, S.; Schröder, J.; Schmelzer, E.;. Somssich, I.E. & K. Hahlbrock, K. (1995).

Loewus, F.A. & Murthy, P.P.N. (2000). *myo*-Inositol metabolism in plants. *Plant Science* 150:1-

Long, A.R. & Chism III, G.W. (1987). A rapid direct extraction-derivatization method for

McInnes, A.G.; Ball, D.H.; Cooper, F.P. & Bishop, C.T. (1958). Separation of carbohydrate derivatives by gas-liquid partition chromatography. *J. of Chromatog* 1:556-557. Manchanda, G. & Garg, N. (2008). Salinity and its effects on the functional biology of

Maniatis, S.; Hui, Z. & Reinhold, V. N. (2010). Rapid De-O-Glycosylation Concomitant with

Peptide Labeling Using Microwave Radiation and anAlkyl Amine Base. Anal.

determining sugars in fruit tissue. *Journal of Food Science* 52:150-154.

an inositol study of depression. *The Israel Journal of Psychiatry and Related Sciences.*

gas-liquid chromatography. Journal of Agricultural and Food Chemistry.l 31:985-

wheat bran, sugar-beet fibre, carrots and cadmium chloride in the liver and kidneys

Gene activation by UV light, fungal elicitor or fungal infection in *Petroselinum crispum* is correlated with repression of cell cycle-related genes. Plant J. 8:865-876. Loewus, M. W.; Bedgar, D.L. & Loewus, F.A. (1984.) 1-L-*myo*-Inositol 1-phosphate synthase

glycan multiplicityand Golgi processing. Cell, 129: 123-134.

Achievements and objectives. Chapman and Hall, New York.

acids in carbohydrate mixtures. *Anal. Biochem*. 115:410-418.

from pollen of *Lilium longifolium*. *J Biol Chem* 259: 7644-7647.

chromatography. *J. Chromatogr A.* 720:137-149.

of mice. *British Journal of Nutrition* 80:205-211.

legumes. Acta Physiol. Plant*.* 30:595-618.

Chem.,82(7):2421-2425.

Chapter 30, 1101-1134.

*Food Chem.* 11: 321-322

32: 14-21.

989.

19.

*Theoretical Applied Genetics* 99:27-36

*electrophoresis, J. of Chromatography Library*, Z. El Rossi (Ed.), Elesevier Science,

synthase DNA sequences: Correspondence with a low phytic acid mutation.

Dennis.James W. (2007). Conditional interpretation of extracellular cues by N-

Physiological, metabolic and developmental implications of O2 regulations in legume nodule. Pp 21-32. In: ? P.M. Gresshoff, (Ed.), Nitrogen fixation:


Johnson, D.C.; Dobberpuhl, D.; Roberts, R. & Vandeberg, P. (1993). Pulsed amperometric

Johnson, M. D., & I. M. Sussex, I.M. (1995). 1-L-*myo*-inosital 1-phosphate synthase from

Johnson, M.D. & Wang, X. (1996). Differentially expressed forms of 1-L-*myo*-inosital 1 phosphate synthase (EC) in *Phaseolus vulgaris*. *J Biol Chem* 271:17215-17218. Karlsson, G.; Winge, S, & Sandberg, H. (2005). Separation of monosaccharides by

Keski-Hynnila, H.; Kurkela, M.; Elovarra, E.; Antonio, L.; Magdalou, J.; Luukanen, L,;

Kim, J.I.; Kim, J.C.; Kang, M.J.; Lee, M.S.; Kim, J.J. & and Cha, I.J. (2005). Effects of pinitol

Kim, T.; Mullaney, E.J.; Porres, J.M.; Roneker, K.R.; Crowe, S.; Rice, S.; Ko, T.; Ullah, A.H.J.;

Kircher, H. W. (1960). Gas-liquid partition chromatography of methylated sugars. *Anal.* 

Klink, V.P., Hosseini, P.; Matsye, P.; Alkharouf, N.W. & B.F. Matthews, B.F. (2009). A gene

Knapp, D.R. (1979). Carbohydrates In: *Handbook of Analytical Derivatization Reations*. John Wiley and Sons, New York, New York, 1979, Chapter 13, pages 539-598. Kostianinen, R.; Kotiaho, T.; Kuuranne, T. & Auriola, S. (2003). Liquid

Korak, D.A. (1984). Novel biosynthesis of D-pinitol in *Simmondsia chinensis*."*Phytochemistry*

Kumaguai, H. (2001). Application of liquid chromatography/mass spectrometry to the

Lambers, H., Stulen, I. & Van Der Werf, A. (1996). Carbon use in root respiration as affected

by elevated atmospheric CO2. *Plant and Soil*. 187:251-263.

feed additive. *Applied and Environmental Microbiology*. 72:4397-4403.

current state of research. *J. of Chromatography* 640:79-96

*Arabidopsis thaliana*. Plant Physio 107:613-619.

detection. *J. of Chromatogr*. A, 1092:246-249.

biological samples. *Anal. Chem*. 74:3449.

metabolism*. J. Mass Spectrometry* 38:357-372.

*J. Clin Nutrition* 59: 456-458.

*Chem*. 32: 1103-1106.

71:525-567.

23: 65-66. "

Technolgies.

detection of carbohydrates, amines, and sufur species in ion chromatography-the

hydrophilic interaction chromatography with evaporative light scattering

Taskinen, J. & Kostianen, R. Comparison of electrospray, atmospheric pressure chemical ionization, and atomospheric pressure photoionization in the identification of apormophine, dobutamide, and entacapone phase II metabolites in

isolated from soybeans on glycaemic control and cardiovascular risk factors in Korean patients with type II diabetes mellitus: a randomized controlled study.*Eur.* 

Caly, C.G.; Welch, R & Lei, X.G. (2006). Shifting the pH profile of *Aspergillus niger* PhyA phytase to match the stomach pH enhances its effectiveness as an animal

expression analysis of synctia laser microdissected from the roots of the *Glycine max* (soybean) genotype PI 548402 (Peking) undergoing a resistant reaction after infection by *Heterodera glycines* (soybean cyst nematode). *Plant Molecular Biology*

chromatography/atmospheric pressure-ionization- mass spectrometry in drug

analysis of sugars and sugar-alcohol. Application note. 5988-4236EN. Agilent


Extraction and Analysis of Inositols and Other Carbohydrates from Soybean Plant Tissues 443

Phillips, D.V. & A. Smith, A. (1974). Soluble carbohydrates in soybean. Canadian Journal of

Phillips, D.V.; Dougherty, D.E. & Smith, A.E. (1982). Cyclitols in soybean. Journal of

Phillips, D.V. & Smith, A. (1974) Influence of sequential prolonged periods of dark and light on pinitol concentration in clover and soybean tissue. Physiol. Plant. 54: 31-33. Raboy, V. (2007). Seed phosphorus and the development of low-phytate crops. In: Turner,

Reinhold, V.N.; Ashline, D.J.; Zhang, H. (2010).Unravellng the Structural Details of the

Richmond, M.L.;. Barfuss, D.L.; Harte, B.R.; Gray, J.I. & Stine, C.M. (1982). Separation of

Romano, J. (2007). Carbohydrate analysis: column chemistries and detection. Presented at

Ruiz-Matute, A.I.; Hernandez-Hernandez, O.; Rodriguez-Sanchez, S.; Sanz, M.L. &

Sartini, C.M.; Spinabelli U.; C. Riponi, C. & Galassi, S. (2001). Determination of carboxylic

Sanz, M.L., Villamiel, M. & Martinez-Castro, I. (2004). Inositols and carbohydrates in

Sasaki, K. & Taylor, I.F.P. (1986). *myo*-Inositol synthesis from [1-3H]Glucose in *Phaseolus vulgaris* L. during early stages of germination. Plant Physiology 81:493-496. Savidge, R. A. & Forster, H. (2001). Coniferyl alcohol metabolism in conifers II. Coniferyl alcohol and dihydroconiferyl alcohol biosynthesis. Phytochem. 57: 1095-1103. Scheller, H.V. & Ulvskov, P. (2010). Hemicelluloses. Annual Review of Plant Biol. 61:263-

Schiller, M. H.; von der Heydt; Marz, F. & Schmidt, P.C. (2002). Quantification of sugars and

Schlichtherle-Cerny, H.; Affolter, M. & Cerny, C. (2003). Hydrophilic interaction liquid

organic acids in hygroscopic pharmaceutical herbal dry extracts. J. of Chrom A.,

chromatography coupled to electrospray mass spectrometry of small polar

different fresh fruit juices. Food Chemistry 87: 325-328.

compounds in food analysis. Anal. Chem. , 75:2349-2354.

Scott, R.P.W. (2011). Liquid Chromatography, Chrom Ed. Series,

analyses. J. of Chromatography B Available online 8 December 2010 Saghai Maroof, M.A.; Glover, N.M.; Biyashev, R.M.; Buss, G.R. &. Grabau, E.A. (2009).

and John F.J. Todd.Chapter 23,706-736. CCR Press, Boca Raton, FL.

B.L., Richardson, A.E., Mullaney, E.J. (Eds.)., Inositol phosphates linking

Glycoproteome by Ion Trap Mass Spectrometry, *in Practical Aspects of Trapped Ion Mass Spectrometry. Vol.* 4: *Theory and Instrumentation.* Edited by Raymond E. March

carbohydrates in dairy products by high performance liquid chromatography. J.

the Carbohydrates in Feeds Methodology Forum, AOAC 2007 Annual Meeting,

Martinez-Castro, I. (2010). Derivatization of carbohydrates for GC and GC-MS

Genetic basis of the low-phytate trait in the soybean line CX1834. Crop Sci: 49: 69-

acids, carbohydrates, glycerol, ethanol, and 5-HMF in beer by high-performance liquid chromatography and UV-refractive index double detection. J. Chromatogr.

Botany 52:2447-2452.

Dairy Sci. 65:1394-1400.

Sci., June, 39(6):235-238.

76.

289.

968: 101-111.

Anaheim, CA, September 18, 2007.

Agricultural & Food Chemistry 30:456-458.

agriculture and the environment. CABI, Oxfordshire.


March, R.E. & Todd, J.F.J. (2005a). A historical review of the development of the quadrupole

March, R.E. & Todd, J.F.J. (2005b). Linear quadrupole ion trap mass spectrometer. In:

Martens, D.A. & Frankenberger, W.T. (1990). Determination of saccharides by high

Masle, J.; Farquhar, G.D. & Gifford, R.M. (1990). Growth and carbon economy of wheat

Mauri, P.; Minoggio, M.; Somonetti, P.; Gardana, C. & Pietta, P. (2002). Analysis of

Munnik, T.; Irvine, R.F. & Musgrave, A. (1998). Phospholipid signalling in plants, Biochim.

Murphy, A.M.; Otto, B.; Brearley, C.A.; Carr, J.P. & Hanke, D.E. (2008). A role for inositol

Nachtmann, F. & Budna, K.W. (1977). Sensitive determination of derivatized carbohydrates by high-performance liquid chromatography. J. Chromatography 136:279-287. Nachtmann, F. (1976). Some properties of 4-nitrobenzoates of saccharides and glycosides; application to high-pressure liquid chromatography. Z. Anal. Chem.282:209-213. Narayanan, C. (1987). Pinitol-A new anti-diabetic compound from the leaves of

Nelson, R.W.; Meulenkijk, J.A.P. & Underberg, W.J.W. (1990). Ultraviolet-Visible

Nordin, P. (1984). Preferential leaching of pinitol from soybeans during imbibition. Plant

Ochoa, S. & Stern, J.R. (1952). Carbohydrate metabolism. Annual Review of Biochemistry

Ogunyemi, O.; Pittner, F., & Hoffmann-Ostenhof, O. (1978). Studies on the biosynthesis of

Perera, I. Y.; I. Heilmann, &. Boss, W.F. (1999). Transient and sustained increases in inositol

Pessarakli, M. (2005). Handbook of photosynthesis M. Pressarakli ed, 2nd edition. Taylor &

maize pulvini. Proc. Natl. Acad. Sci. USA 96:5838-5843.

Francis Group, CRC, Boca Raton, FL.

Derivatization. In: *Detection –Oriented Derivatization Techniques in Liquid Chromatography*, H. Lingeman & W.J.M. Underberg, (Ed.), Marcel Dekker, Inc, New

cyclitols. XXXVI. Purification of *myo*-inositol-I-phosphate synthase of the duckweed *Lemna gibba* to homogeneity by affinity chromatography on NAD Sepharose. Molecular and catalytic properties of the enzyme. Hoppe-Seyler's Z Physiol Chem

1,4,5-trisphosphate precede the differential growth response in gravistimulated

Sons, Inc., Hoboken, N.J., Chapter 1.

detection. *Chromatographia* 29:7-12.

of CO2. Aust. J. Plant Physiol. 17:465-487.

Rapid Commun. Mass Spectrom., 16:743-748

*Bouganivillea*. Current Science, 56:139-141.

York, New York, pp. 268-270.

Physiol 76:313-315.

21:547-602.

359: 613-616.

Hoboken, N.J., Chapter 5.

Biophys. Acta 1389 222–272.

Journal 56:638-652.

ion trap. In: *Quadrupole Ion Trap Mass Spectrometry*, 2nd edition, John Wiley and

*Quadrupole Ion Trap Mass Spectrometry*, 2nd edition, John Wiley and Sons, Inc,

performance anion-exchange chromatography with pulsed amperometric

seedlings as affected by soil resistance to penetration and ambient partial pressure

saccharides in beer samples by flow injection with electrospray mass spectrometry.

hexakisphosphate in the maintenance of basal resistance to plant pathogens. Plant


Extraction and Analysis of Inositols and Other Carbohydrates from Soybean Plant Tissues 445

Taylor, V.F.; March, R.E.; Longerich, H.P. & Stadey, C.J. (2005). A mass spectrometric study

Thibault, P. & Honda, S. (Eds.). (2003). *Capillary electrophoresis of carbohydrates. Methods in* 

Togami, D.W.; Poulsen,B.J.; Batalao, C.W. & Rolls, W.A. (1991). Separation of carbohydrates

Twilly , J.W. ( 1984). The analysis of exudate glant gums In their artistic applications: An

Udvardi, M.K. & Day, D.A. (1997). Metabolite transport across symbiotic membranes of

Vallance, S.L.; Singer, B.W.; Hitchen, S.M. & Townsend, J.H. (1998). The development and

Vernon, D. M. & Bohnert, H.J. (1992). A nove1 methyl transferase induced by osmotic stress

Vessey, J.K.; Walsh, K.B. & Layzell, D.B.(1988a). Oxygen limitation of N2 fixation in stem

Vessey, J.K.; Walsh, K.B. & Layzell, D.B. (1988b). Can a limitation in phloem supply to

Walker, W. H.(2010). Is the "comb over" dying? A mouse model for male patter baldness

Walker, H. G.; Gee, M. & McCready, R.M. (1962). Complete methylation of reducing

Wei, Y. & Ding, M. (2000). Analysis of carbohydrates in drinks by high-performance liquid

Weisshaupl, V.; Scheiner, O.; Dworsky, P.; Hoffmann-Ostenhof, O. & Allgem, Z. (1976).

Wilcox, M.; Hefley, J.R. & Walsh, J.W. (2001). HPLC determination of carbohydrates: A

Carbohydrate Session 59A, 2001 IFT Annual Meeting,. New Orleans, La. Williams, J.H.H. & Farrar, J.F. (1990). Control of barley root respiration. Physiolo. Plant.

Wilson, R.F. (2004). Seed composition Pp 621-677. In H.R. Boerma and J. E. Specht, co-

media. *Journal of American Institute for Conservation*. 37:294-311.

girdled and nitrate-treated soybean. Physiol Plant. 73:113-121.

(Androgenic Alopecia). Endocrinology 151: 1981-1983.

scattering detection. J. of Chromatography A. 904:113-117.

electrospray ionization. Int*. J. Mass Spectrom*., 243:71-84.

*Molecular Biology*. Humana Press, Totowa, N.J., 318 pages.

Biotechniques 10(5):650-655.

48:493-523.

2085.

American Chemical Society. 357-394.

soybean? Physiol. Plant. 74:137-146.

Mikrobiol. 16: 81-86.

79:259-266.

carbohydrates. J. Org. Chem. 27: 2100-2102.

of glucose, sucrose, and fructose using an inductively coupled plasma and

and carbohydrate derivatives with cation-exchange columns at high pH.

interim report. Archaeological Chemistry, Vol. 3, J.Lambert, (Ed.), American Chemical Society, Advances in Chemistry series, no. 205, Washington, D.C.,

legume nodules. Annual Review of Plant Physiology and Plant Molecular Biology

initial application of a gas chromatographic method for the characterization of gum

in the facultative halophyte *Mesembuyanthemum crystalliunum*. EMBO J 11:2077-

nodules account for the inhibitory effect of nitrate on nitrogenase activity in

chromatography with a dynamically modified amino column and evaporative light

comparison of six different columns with ELS detection. Presented at the

editors, Soybeans: Improvement, production and uses. Third Edition Number 16 Agronomy Monograph. American Society of Agronomy, Inc., Crop Science Society of America, Inc., and Soil Science Society of America, Inc.. Madison, WI, USA.

 http://www.chromatography-online.org/HPLC/Refractive-Index/rs33.html, accessed March 8, 2011.).


Shah, M.M., Clauss, T.R.; Clauss, S.C.; Campbell, J.A.; Goheen, S.C. & Bennett, K.A. (1998).

Sharp, R.E. & Davies, W.J. (1979). Solute regulation and growth by roots and shoots of

Sheveleva, E.; Chmara, W.; Bohnert, H.J. & Jensen, R.G. (1997). Increased salt and drought

Shigaki, T. & Bhattacharyya, M.K. (2000). Decreased inositol 1,4,5-trisphosphate content in

Smith, D. (1973). The nonstructural carbohydrates. In: Chemistry and Biochemistry of herbage, Vol. 1, eds. G.W. Butler, R.W. Bailey, Academic Press, London. Somerville, C. (2006). Cellulose synthesis in higher plants. Annual Review of Cell and

Stieglitz, K.A.; Yang, H.; Roberts, M.F. & B. Stec, B. (2005). Reaching for mechanistic

Streeter, J. G. (1980). Carbohydrates in soybean nodules.II. Distribution of compounds in seedlings during the onset of nitrogen fixation. *Plant Physiology*. 66:471-476. Streeter, J.G. & Strimbu, C. (1998). Simjultaneous extraction and derivatization of

Streeter, J. G.; Lohnes, D.G. &. Fioritto, R.J. (2001). Patterns of pinitol accumulation in

Stumpo, K.A.R.& Reinhold, V. (2010). The N-Glycome of Human Plasma. *Journal of Proteome* 

Sullivan, J.E. & Schewe, L.R. (1977). Pareparation and gas chromatography of highly volatile

Sweeley, C.C.; R. Bentley, R.; Makita, M. & Wells, W.W. (1963). Gas-liquid chromtograpy of

Taormina, C.R.; Baca, J.T.; Asher, S.A.; Grabowski, J.J. & Finegold, D.N. (2007). Analysis of

Tate, R.L. (1995). Soil microbiology (symbiotic nitrogen fixation), pp. 307-333. John Wiley

concensus across life kingdoms: Structure and insights into catalysis of the *myo*inositol-1-phosphate synthase (mIPS) from Archaeoglobus fulgidus. *Biochemistry*

carbohydrates from green plant tissues for analysis by gas-liquid chromatograpy.

soybean plants and relationships to drought tolerance. *Plant, Cell and Environment*

trifluoroacetylated carbohydrates using N-methylbis[trifluoroacetamide]. *J. of* 

trimethylsilyl derivatives of sugars and related substances. J. of Am. Chem. Soc.

tear glucose concentration with electrospray ionization mass spectrometry. *J. Am.* 

Determination of Molecular Weight Distribution of Insoluble Carbohydrates from corn fiber using HPLC and Light Scattering Detector. Presented at the Corn

tolerance by D-ononitol production in transgenic *Nicotiana tabacum* L. Plant Physiol.

http://www.chromatography-online.org/HPLC/Refractive-Index/rs33.html,

Utilization Conference, June 1-3, 1998, St. Louis, Mo.

pathogen-challenged soybean cells. MPMI 13:563-567.

water-stressed maize plants. Planta 147:43-49.

Developmental Biology. 22:53-78.

Anal. Biochem. 259:253-257..E,. Strimbu

accessed March 8, 2011.).

115:1211-1219.

44: 213-224.

24:429-438.

85:2497-2507.

*Research*, 9(8):4823-4830.

*Chromatographic Science* 15:196-197.

*Soc. Mass Spectrom*., 18:32-336.

and Sons, Inc., New York, N.Y.


**21** 

*Madrid Spain* 

**Extraction and Enzymatic Modification of** 

*Instituto de Investigación en Ciencias de la Alimentación (CIAL), CSIC-UAM* 

Crude vegetable oils contain triacylglycerols as major component and various minor components such as diacylglycerols, monoacylglycerols, free fatty acids, phospholipids, tocopherols, sterols, squalene, color pigments, waxes, aldehydes, ketones, triterpene alcohols and metals that may affect the quality of the final product. The minor components are removed partially or entirely by either physical or chemical refining in order to make the vegetable oils suitable for human consumption. Deodorization is the last major processing step in the refining of edible oils. It has the responsibility for removing both the undesirable ingredients occurring in natural fats and oils and those which may be imparted by prior unit processes such as caustic refining, bleaching, hydrogenation, or even storage conditions. It is this unit process that finally establishes the oil characteristics of "flavor and odor," which are

Deodorizer distillate is a by-product of deodorization, which is the last major step in vegetable oil refining process. It is a complex mixture of free fatty acids, mono-, di- and triacyglycerols, sterols and their esters, tocopherols, hydrocarbons, pesticides, and breakdown products of fatty acids, aldehydes, ketones and acylglycerol species (Ramamurthi & McCurdy, 1993). Deodorizer distillate is an excellent source of valuable compounds such as phytosterols, tocopherols and squalene, which can be recovered and further used as food additives, in pharmaceutical industry and cosmetics. Their commercial value however, is mainly dependent on their tocopherol content (Fernandes & Cabral, 2007). Although in recent years, efforts from industry resulted in a significant number of reports, describing better and improved methods for phytosterol recovery and purification. Such surge is closely related to growing market for phytosterols, particularly given the

Numerous procedures have been described to isolate bioactive compounds from soybean oil deodorizer distillate to improve the value and the quality of this by-product. All these procedures can be grouped in three generic categories: crystallization and precipitation,

One important bioactive compound concentrated in intermediate byproducts and waste streams during the refining of soybean oil is squalene. Recently, steroidal hydrocarbons and

those most readily recognized by the consumer (Gavin, 1978).

widespread dissemination of functional foods (Fernandes & Cabral, 2007).

chemical and enzymatic modification, and extraction and fractionation.

**1. Introduction** 

**Functional Lipids from Soybean** 

Carlos F. Torres, Guzmán Torrelo and Guillermo Reglero *Departamento de Producción y Caracterización de Nuevos Alimentos* 

**Oil Deodorizer Distillate** 

