UDP-glucuronic acid:soyasapogenol glucuronosyltransferase involved in saponin biosynthesis in germinating soybean seeds

Planta

Volumn 215, Issue 4, 2002, Pages 620-629

  Kurosawa, Yasunori ^a   Takahara, Hidenari ^a   Shiraiwa, Masakazu ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

Germination; Glucurongsyltransferase; Glycine (saponin); Saponin biosynthesis; Sugar chain

Indexed keywords

BIOSYNTHESIS; CHROMATOGRAPHY; DETERGENTS; ENZYMES; GLUCOSE; PLANTS (BOTANY); POSITIVE IONS; PURIFICATION; SUBSTRATES;

MICROSOMAL FRACTION;

SEED;

CARBON RADIOISOTOPES; CATIONS; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, ION EXCHANGE; ENZYME ACTIVATION; GERMINATION; GLUCURONOSYLTRANSFERASE; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNESIUM; MICROSOMES; OLEANOLIC ACID; SAPONINS; SEEDS; SOLUBILITY; SOYBEANS; SUBSTRATE SPECIFICITY; TEMPERATURE; URIDINE DIPHOSPHATE GLUCURONIC ACID;

GLYCINE MAX;

EID: 0036934814     PISSN: 00320935     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00425-002-0781-x     Document Type: Article

References (45)

1. Bock KW, Josting D, Lilienblum W, Pfeil H (1979) Purification of rat-liver microsomal UDP-glucuronyltransferase. Separation of two enzyme forms inducible by 3-methylcholanthrene or phenobarbital. Eur J Biochem 98:19-26
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
3. Burchell B, Hallinan T (1978) Phospholipid content and activity of pure uridine diphosphate-glucuronyltransferase from rat liver. Biochem J 171:821-824
4. Burrows JC, Price KR, Fenwick GR (1987) Soyasaponin IV, an additional monodesmosidic saponin isolated from soybean. Phytochemistry 26:1214-1215
5. Clarke DJ, George SG, Burchell Ḃ (1992) Multiplicity of UDP-glucuronosyltransferases in fish. Purification and characterization of a phenol UDP-glucuronosyltransferase from the liver of a marine teleost, Pleuronectes platessa. Biochem J 284:417-423
6. Elkind Y, Edwards R, Mavandad M, Hendrick SA, Ribak O, Dixon RA, Lamb CJ (1990) Abnormal plant development and down-regulation of phenylpropanoid biosynthesis in transgenic tobacco containing a heterologous phenylalanine ammonialyase gene. Proc Natl Acad Sci USA 87:9057-9061
7. Gorski JP, Kasper CB (1977) Purification and properties of microsomal UDP-glucuronosyltransferase from rat liver. J Biol Chem 252:1336-1343
8. Hayashi H, Hanaoka S, Tanaka S, Fukui H, Tabata M (1993) Glycyrrhetinic acid 24-hydroxylase activity in microsomes of cultured licorice cells. Phytochemistry 34:1303-1307
9. Hayashi K, Hayashi H, Hiraoka N, Ikeshiro Y (1997) Inhibitory activity of soyasaponin II on virus replication in vitro. Planta Med 63:102-105
10. Ishii Y, Tsuruda K, Tanaka M, Oguri K (1994) Purification of a phenobarbital-inducible morphine UDP-glucuronyltransferase isoform, absent from Gunn rat liver. Arch Biochem Biophys 315:345-351
11. Jiang Y, Zhong GG, Qi H, Ma XY (1993) Antioxidative action of soyasaponin monomers I, A1, A2, and their inhibitory effects on action potential and beating of myocardiocytes in culture. Chung-Kuo Yao Li Hsueh Pao 14:269-273
12. Kanehara H, Yokoya H, Sato M, Yuasa A (1992) Purification and properties of 4-hydroxybiphenyl UDP-glucuronosyltransferase from bovine liver microsomes. J Biochem 112:578-582
13. Kimura S (1984) The revelation of toxicity which is caused by some poisonous substances derived from foodstuffs and its modification under nutritional conditions. Yakugaku Zasshi 104:423-439
14. Kinjo J, Imagire M, Udayama M, Arao T, Nohara T (1998) Structure-hepatoprotective relationships study of soyasaponins I-IV having soyasapogenol B as aglycone. Planta Med 64:233-236
15. Kitagawa I, Wang HK, Taniyama T, Yoshikawa M (1988a) Saponin and sapogenol XLI. Reinvestigation of the structures of soyasapogenol A, B, and E, oleanene-sapogenols from soybean. Structures of soyasaponins I, II, and III. Chem Pharm Bull 36:153-161
16. Kitagawa I, Taniyama T, Nagahama Y, Okubo K, Yamauchi F, Yoshikawa M (1988b) Saponin and sapogenol XLII. Structures of acetyl-soyasaponins A1, A2, and A3, astringent partially acetylated bisdesmosides of soyasapogenol A, from american soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 36:2819-2828
17. Konoshima T, Kokumai M, Kozuka M, Tokuda H, Nishino H, Iwashima A (1992) Anti-tumor-promoting activities of afromosin and soyasaponin I isolated from Wistaria brachybotrys. J Nat Prod 55:1776-1778
18. Kubo M, Matsuda H, Tani T, Namba K, Arichi S, Kitagawa I (1984) Effects of soyasaponin on experimental disseminated intravascular coagulation. I. Chem Pharm Bull 32:1467-1471
19. Kudou S, Tsuizaki I, Uchida T, Okubo K (1991) Purification and some properties of soybean saponin hydrolase from Aspergillus oryzae KO-2. Agric Biol Chem 55:31-36
20. Kudou S, Tonomura M, Tsukamoto C, Shimoyamada M, Uchida T, Okubo K (1992) Isolation and structural elucidation of the major genuine soybean saponin. Biosci Biotech Biochem 56:142-143
21. Laemmli UK (1970) Cleavage of structural proteins during he assembly of the head of bacteriophage T4. Nature 227:680-685
22. Marsh CA (1960) Reactions of uridine diphosphate sugars catalyzed by enzymes of French-bean leaves. Biochim Biophys Acta 44:359-361
23. Meer IM, Stam ME, Tunen AJ, Mol JNM, Stuitje AR (1992) Antisense inhibition of flavonoid biosynthesis in Petunia anthers results in male sterility. Plant Cell 4:253-262
24. Miyao H, Arao T, Udayama M, Kinjo J, Nohara T (1998) Kaikasaponin III and soyasaponin I, major triterpene saponins of Abrus cantoniensis, act on GOT and GPT: Influence on transaminase elevation of rat liver cells concomitantly exposed to CC14 for one hour. Planta Med 64:5-7
25. Möhle B, Heller W, Wellmann E (1985) UV-induced biosynthesis of quercetin-3-O-β-D-glucuronide in dill cell cultures. Phytochemistry 24:465-467
26. Nagashima S, Hirotani M, Yoshikawa T (2000) Purification and characterization of UDP-glucuronic acid: Baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. Cell suspension cultures. Phytochemistry 53:533-238
27. Nakashima H, Okubo K, Honda Y, Tamura T, Matsuda S, Yamamoto N (1989) Inhibitory effect of glycosides like saponin from soybean on the infectivity of HIV in vitro. AIDS (London) 3:655-658
28. Ohminami H, Kimura Y, Okuda H, Arichi S (1984) Effects of soyasaponins on liver injury induced by highly peroxidized fat in rats. Planta Med 46:440-441
29. Okubo K, Iijima M, Kobayashi Y, Yoshikoshi M, Uchida T, Kudou S (1992) Components responsible for the undesirable taste of soybean seeds. Biosci Biotech Biochem 56:99-103
30. Ruzicka L (1953) The isoprene rule and the biogenesis of terpenic compounds. Experientia 9:357-367
31. Schulz M, Wessenböck G (1988) Three specific UDP-glucuronate: Flavone-glucuronosyltransferases from primary leaves of Secale cereale. Phytochemistry 27:1261-1267
32. Shiraiwa M, Yamauchi F, Harada K, Okubo, K (1990) Inheritance of "group A saponin" in soybean seed. Agric Biol Chem 54:1347-1352
33. Shiraiwa M, Kudo S, Shimoyamada M, Harada K, Okubo K (1991a) Composition and structure of "group A saponin" in soybean seed. Agric Biol Chem 55:315-322
34. Shiraiwa M, Harada K, Okubo K (1991b) Composition and structure of "group B saponin" in soybean seed. Agric Biol Chem 55:911-917
35. Shiraiwa M, Nakashima H, Yamamoto N, Tamura T, Matsuda S, Okubo K (1991c) Soybean saponin; structure and physiological properties, especially antiviral activity on HIV in vitro. Proceedings of the International Conference of Soybean Processing and Utilization, Gongzhuling, China, pp 95-101
36. Shiraiwa M, Harada K, Okubo, K (1991d) Composition and content of saponin in soybean seed according to variety, annual cultivation and maturity. Agric Biol Chem 55:323-331
37. Tamagnone L, Merida A, Parr A, Mackay S, Culianez-Macia FA, Roberts K, Martin C (1998) The AmMYB308 and AmMYB330 transcription factors from Antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco. Plant Cell 10:135-154
38. Taniyama T, Yoshikawa M, Kitagawa I (1988a) Saponin and sapogenol. XLIV. Soyasaponin composition in soybeans of various origins and soyasaponin content in various organs of soybean. Structure of soyasaponin V from soybean hypocotyl. Yakugaku Zasshi 108:562-571
39. Taniyama T, Nagahama Y, Yoshikawa M, Kitagawa I (1988b) Saponin and sapogenol XLIII. Acetyl-soyasaponins A4, A5, and A6, new astringent bisdesmosides of soyasapogenol A, from japanese soybean, the seeds of Glycine max MERRILL. Chem Pharm Bull 36:2829-2839
40. Van der Krol AR, Lenting P J, Veenstra JG, Van der Meer IM, Koes RE, Gerats AGM, Mol J NM, Stuitje AR (1988) An antisense chalcone synthase gene in transgenic plants inhibits flower pigmentation. Nature 333:866-869
41. Wojciechowski ZA (1975) Biosynthesis of oleanolic acid glycosides by subcellular fractions of Calendula officinalis seedlings. Phytochemistry 14:1749-1753
42. Yokota H, Yuasa A, Sato R (1988) Purification and properties of a form of UDP-glucuronyltransferase from liver microsomes of 3-methylcholanthrene-treated rats. J Biochem 104:531-536
43. Yokota H, Ohgiya N, Ishihara G, Ohta K, Yuasa A (1989) Purification and properties of UDP-glucuronyltransferase from kidney microsomes of beta-naphthoflavone-treated rat. J Biochem 106:248-52
44. Yoshikoshi M, Yoshiki Y, Okubo K, Seto J, Sasaki Y (1996) Prevention of hydrogen peroxide damage by soybean saponins to mouse fibroblasts. Plant Med 62:252-255
45. Zhong R, Morrison III WH, Negrel J, Ye Z-H (1998) Dual methylation pathways in lignin biosynthesis. Plant Cell 10:2033-2045