Preferences help
enabled [disable] Abstract
Number of results
2008 | 55 | 1 | 135-140
Article title

Metabolism of conjugated sterols in eggplant. Part 2. Phospholipid : steryl glucoside acyltransferase

Title variants
Languages of publication
A membrane-bound phospholipid : steryl glucoside acyltransferase from Solanum melongena leaves was partially purified and its specificity and molecular as well as kinetic properties were defined. Among the steryl glycosides tested (e.g. typical plant steryl glucosides, steryl galactosides and cholesteryl xyloside) the highest activity was found with cholesteryl glucoside, but some structurally related compounds such as sito- and stigmasteryl glucoside or galactoside as well as cholesteryl galactoside were also acylated, albeit at lower rates. The investigated enzyme was able to use all classes of phosphoglycerolipids (phosphatidylethanolamine, phosphatidylcholine, phosphatidylserine, phosphatidylinositol, phosphatidylglycerol) as an acyl source for biosynthesis of acylated steryl glucoside. Among them 1,2-dimirystoylphosphatidylic acid appeared to be the best acyl donor. Apart from phosphoglycerolipids, 1,2-diacylglycerols were also used as acyl donor for steryl glucoside acylation, although at a distinctly lower rate. The acyl moiety was transferred from the C-1 position of phospholipid molecule. The investigated acyltrasferase activity was stimulated by 2-mercaptoethanol, Triton X-100, 1-monoacylglycerols and inhibited in the presence of divalent cations such as Ca2+, Mn2+, Zn2+ or Co2+, some lipids (MDGD, ceramide), detergents (Tween 20, 40, 60 and 80, Tyloxapol, sodium deoxycholate) and high ionic strength.
Physical description
  • Institute of Biochemistry, Warsaw University, Warszawa, Poland
  • Institute of Biochemistry, Warsaw University, Warszawa, Poland
  • Baisted DJ (1978) Steryl glucoside and acyl glucoside biosynthesis in maturing pea seeds. Phytochemistry 17: 435-438.
  • Catz DS, Tandecarz JS, Cardini CE (1985) UDP-glucose: sterol glucosyltransferase and a steryl glucoside acyltransferase activity in amyloplast membranes from potato tubers. J Exp Bot 36: 602-609.
  • Chaudhuri PS, Chaudhuri D, Nanda DK, Achari B, Bhattacharaya D, Saha C (1996) Chemical nature of earthworm repellent factor in the plant (polygonum hydropiper l.) extract. Indian J Exp Biol 34: 277-278.
  • Eichenberger W, Siegrist HP (1975) Steryl glycoside acyltransferase from carrots. FEBS Lett 52: 153-156.
  • Forsee WT, Valkovich G, Elbein AD (1976) Acylation of steryl glucosides by phospholipids. solubilization and properties of the acyl transferase. Arch Biochem Biophys 172: 410-418.
  • Galliard T (1968) Aspects of lipid metabolism in higher plants. i. identification and quantitative determination of the lipids in potato tubers. Phytochemistry 7: 1907-1914.
  • Guevara A, Lim-Sylianco C, Dayrit F, Finch P (1990) Antimutagens from Momordica charantia. Mutat Res 230: 121-126.
  • Heinz E, Dieler HP, Rullköter J (1975) Enzymatic acylation of steryl glucoside. Z Pflanzenphysiol 75: 78-87.
  • Janiszowska W, Wiłkomirski B, Kasprzyk Z (1980) Synthesis of oleanolic acid 3-O-monoglucoside. Pol J Chem 54: 2147-2152.
  • Kalinowska M, Wojciechowski ZA (1986) Enzymatic synthesis of nuatigenin 3β-d-glucoside in oat (avena sativa l.) leaves. Phytochemistry 25: 2525-2529.
  • Khan RA, Singh AK, Agrawal PK (1997) Sitosterol sucroside from the suckers of Mentha arvensis. Phytochemistry 45: 1295-1296.
  • Kintia PK, Wojciechowski ZA (1974) Free and bound sterols in seedlings of Cucumis sativus. Phytochemistry 13: 2235-2238.
  • Kiriakidis S, Stathi S, Jha HC, Hartmann R, Egge H (1997) Fatty acid esters of sitosterol-3-β-glucoside from soybeans and tempe (fermented soybeans) as antiproliferative substances. J Clin Biochem Nutr 22: 139-147.
  • Kiribuchi T, Yasimatsu N, Funahashi S (1967) Synthesis of 6-O-palmitoyl-β-d-glucosyl-β-sitosterol. Agric Biol Chem 31: 1244-1246.
  • Kojima M, Ohnishi M, Ito S, Fujino Y (1989) Characterization of acylmono-, mono-, di-, tri- and tetraglycosylsterol and saponin in adzuki bean (Vigna angularis) seeds. Lipids 24: 849-856.
  • Lepage M (1964) Isolation and characterization of an esterified form of steryl glucoside. J Lipid Res 5: 587-592.
  • McDonald RE, Miller WR, McCollum TG (2000) Canopy position and heat treatments influence gamma-irradiation-induced changes in phenylpropanoid metabolism in grapefruit. J Am Soc Hort Sci 125: 364-369.
  • Misiak M, Kalinowska M, Wojciechowski ZA (1991) Characterization of acyllipid: sterol glucoside acyltransferase from oat (Avena sativa L.) seedlings. Acta Biochim Polon 38: 43-45.
  • Moreau RA, Powell MJ, Whitaker BD, Bailey BA, Anderson JD (1994) Xylanase treatment of plant cell induces glycosylation and fatty acylation of phytosterols. Physiol Plant 91: 575-580.
  • Palta JP, Whitaker BD, Weiss LS (1993) Plasma membrane lipids associated with genetic variability in freezing tolerance and cold acclimation of Solanum species. Plant Physiol 103: 793-803.
  • Peaud-Lenoel C (1972) d-Glucosylation des phytosterols et acylation des steryl-d-glucosides en presence d'enzymes de plantes. Carbohydr Res 24: 247-262.
  • Picchioni GA, Watada AE, Whitaker BD, Reyes A (1996) Calcium delays senescence-related membrane lipid changes and increases net synthesis of membrane lipid components in shredded carrots. Postharvest Biol Technol 9: 235-245.
  • Picchioni GA, Watada AE, Conway WS, Whitaker BD, Sams CE (1998) Postharvest calcium infiltration delays membrane lipid catabolism in apple fruit. J Agric Food Chem 46: 2452-2457.
  • Potocka A, Zimowski J (2008) Metabolism of conjugated sterols in eggplant. Part 1. UDP-glucose : sterol glucosyltransferase. Acta Biochim Polon 55: 127-134.
  • Quartacci MF, Cosi E, Navari-Izzo F (2001) Lipids and nadph-dependent superoxide production in plasma membrane vesicles from roots of wheat grown under copper deficiency or excess. J Exp Bot 52: 77-84.
  • Staphylakis K, Gegiou D (1985) Free, esterified and glucosidic sterols in cocoa butter. Lipids 20: 723-728.
  • Whitaker BD, Lee EH, Rowland RA (1990) EDU and ozone protection: foliar glycerolipids and steryl lipids in snapbean exposed to O3. Physiol Plant 80: 286-293.
  • Wojciechowski ZA (1991) Biochemistry of phytosterols conjugates. In Physiology and Biochemistry of Sterols. Patterson GW, Nes WD, eds, pp 361-393, AOCS, Champaign, Il.
  • Wojciechowski ZA, Zimowski J (1975) Acyl composition and biosynthesis of acylated steryl glucosides in Calendula officinalis. Biochim Biophys Acta 398: 111-117.
  • Yamaguchi M, Kasamo K (2001) Modulation in the activity of purified tonoplast H+-ATP-ase by tonoplast glycolipids prepared from cultured rice (Oryza sativa L. var. Boro) cells. Plant Cell Physiol 42: 516-523.
  • Zimowski J (1991) The occurrence of a glucosyltransferase specific for solanidine in potato plants. Phytochemistry 30: 1187-1193.
  • Zimowski JG, Wojciechowski ZA (1983) Enzymatic synthesis of steryl 6'-O-acyl-β-d-glucosides in Sinapis alba and some others plants. Phytochemistry 22: 2175-2178.
  • Żelazny AM, Shaish A, Pick U (1995) Plasma membrane sterols are essential for sensing osmotic changes in halotolerant alga Dunaliella. Plant Physiol 109: 1395-1403.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.