Abstract
This article surveys the currently isolated and identified GA conjugates, their synthesis and evaluates modern methods for analysing GA glucose conjugates. The metabolism of applied GAs in higher plant systems leading, in most cases, to GA conjugates is also considered. The enzymology of the formation and hydrolysis of GA glucose conjugates is discussed in connection with their possible physiological function.
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Abbreviations
- API =:
-
atmospheric pressure ionization
- FAB =:
-
fast atom bombardment
- GA-GE =:
-
gibberellin glucosyl ester
- GA-O-G =:
-
gibberellin-O-glucoside
- GC =:
-
gas chromatography
- GC-MS =:
-
combined gas chromatography-mass spectrometry
- HPLC =:
-
high performance liquid chromatography
- LC-MS =:
-
combined high performance liquid chromatography-mass spectrometry
- MS =:
-
mass spectrometry
- NMR =:
-
nuclear magnetic resonance
- PME =:
-
permethyl
- SIM =:
-
selected ion monitoring
- TMS =:
-
trimethylsilyl
References
Asakawa Y, Tamari K, Shoji A and Kaji J (1974) Metabolic products of gibberellin A3 and their interconversion in dwarf kidney bean plants. Agric Biol Chem 38: 719–725
Barendse GWM (1971) Formation of bound gibberellins in Pharbitis nil. Planta 99: 290–301
Barendse GWM (1974) Accumulation and metabolism of radioactive gibberellic acid in seedlings of Pharbitis nil Choisy. In: Tamura S (ed) Plant Growth Substances 1973, pp 332–341. Tokyo: Hirokawa
Barendse GWM (1976) The metabolism of gibberellins in Pharbitis nil. In: Pilet E-P (ed) Abstr. 9th Intern. Conf. Plant Growth Substances, p 24. Lausanne
Barendse GWM and De Klerk GJM (1975) The metabolism of applied gibberellic acid in Pharbitis nil Choisy: tentative identification of its sole metabolite as gibberellic acid gluco-side and some of its properties. Planta 126: 25–35
Barendse GWM, Kende H and Lang A (1968) Fate of radioactive gibberellin A1 in maturing and germinating seeds of peas and Japanese morning glory. Plant Physiol 43: 815–822
Benes I (1983) Studie v rade diterpenu. Thesis, Czechoslovakian Academy of Sciences, Prague
Blechschmidt S, Castel U, Gaskin P, Hedden P, Graebe JE and MacMillan J (1984) GC/MS Analysis of the plant hormones in seeds of Cucurbita maxima. Phytochemistry 23: 553–558
Crozier A, Kuo CC, Durley RC and Pharis RP (1970) The biological activities of 26 gibberellins in nine plant bioassays. Can J Bot 48: 867–877
Crozier A, Turnbull CGN, Malcolm JM and Graebe JE (1991) Gibberellin metabolism in cell-free preparations from Phaseolus coccineus. In: Takahashi N, Phinney BO and MacMillan J (eds) Gibberellins, pp 83–93. New York: Springer
Dathe W, Sembdner G, Kefeli VI and Vlasov PV (1978) Gibberellins, abscisic acid, and related inhibitors in branches and bleeding sap of birch (Betula pubescens Ehrh). Biochem Physiol Pflanzen 173: 238–248
Dathe W, Sembdner G, Yamaguchi I and Takahashi N (1982) Gibberellins and growth inhibitors in spring bleeding sap, roots and branches of Juglans regia L. Plant Cell Physiol 23: 115–123
Davies PJ (ed) (1987) Plant Hormones and their Role in Plant Growth and Development. Dordrecht, Boston, Lancaster: Martinus Nijhoff Publ
Davies PJ, Birnberg PR, Maki SL and Brenner ML (1986) Photoperiod modification of [14C]gibberellin A12 aldehyde metabolism in shoots of pea, line G2. Plant Physiol 81: 991–996
Davies LJ and Rappaport L (1975) Metabolism of tritiated gibberellins in d-5 dwarf maize. I. In excised tissue and intact dwarf and normal plants. Plant Physiol 55: 620–625
Davies LJ and Rappaport L (1975) Metabolism of tritiated gibberellins in d-5 dwarf maize. II. [3H]Gibberellin A1, [3H]gibberellin A3, and related compounds. Plant Physiol 56: 60–66
De Bottini GA, Bottini R, Koshioka M, Pharis RP and Coombe BG (1987) Metabolism of [3H]gibberellin A5 by immature seeds of apricot (Prunus armeniaca L.). Plant Physiol 83: 137–142
Doumas P, Imbault N, Moritz T and Oden PC (1992) Detection and identification of gibberellins in douglas fir (Pseudotsuga menziesii) shoots. Physiol Plant 85: 489–494
Durley RC, Railton ID and Pharis RP (1974) The metabolism of gibberellin A1 and gibberellin A14 in seedlings of dwarf Pisum sativum. In: Tamura S (ed) Plant Growth Substances 1973, pp 285–293. Tokyo: Hirokawa
Esteban Hopp H and Favret EA (1980) Metabolism of [3H]-gibberellin A1 in a gigas mutant of barley. Plant Physiol 65(Suppl. 95)
Fang N and Rappaport L (1990) GAs chromatography/mass spectrometry of permethylated gibberellins. Biomed Environ Mass Spectrom 19: 123–128
Frydman VM and MacMillan J (1975) The metabolism of gibberellins A9, A20, and A29 in immature seeds of Pisum sativum cv. Progress No. 9. Planta 125: 181–195
Garcia-Martinez JL, Ohlrogge JB and Rappaport L (1981) Differential compartmentation of gibberellin A1 and its metabolites in vacuoles of cowpea and barley leaves. Plant Physiol 68: 865–867
Gaskin P and MacMillan J (1991) GC-MS of Gibberellins and Related Compounds: Methodology and a Library of Spectra. Bristol: Cantocks Enterprises
Graebe JE, Großelindemann E, Stöckl D and Zander M (1987) Gibberellin biosynthesis in cell-free systems and germinating seeds. In: Lilov D, Vassilev G, Christov Ch and Andonova T (eds) Plant Growth Regulators, Vol 1, pp 29–38. Sofia: Bulg Acad Sci
Harada H and Yokota T (1970) Isolation of gibberellin A8-glucoside from shoot apices of Althaea rosea. Planta 92: 100–104
Hemphill DD, Baker LR and Sell HM (1973) Isolation of novel conjugated gibberellins from Cucumis sativus seed. Can J Biochem 51: 1647–1653
Heupel RC, Phinney RD, Spray CR, Gaskin P, MacMillan J Hedden P and Graebe JE (1985) Native gibberellins and the metabolism of [14C]gibberellin A53 and of [17-13C,17-3H2]gibberellin A20 in tassels of Zea mays. Phytochemistry 24: 47–53
Hiraga K, Kawabe S, Yokota T, Murofushi N and Takahashi N (1974) Isolation and characterization of plant growth substances in immature seeds and etiolated seedlings of Phaseolus vulgaris. Agric Biol Chem 38: 2521–2527
Hiraga K, Yokota T, Murofushi N and Takahashi N (1972) Isolation and characterization of a free gibberellin and glucosyl esters of gibberellins in mature seeds of Phaseolus vulgaris. Agric Biol Chem 36: 345–347
Hiraga K, Yokota T, Murofushi N and Takahashi N (1974) Isolation and characterization of gibberellins in mature seeds of Phaseolus vulgaris. Agric Biol Chem 38: 2511–2520
Hiraga K, Yokota T and Takahashi N (1974) Biological activity of some synthetic gibberellin glucosyl esters. Phytochemistry 13: 2371–2376
Jensen E, Crozier A and Monteiro AM (1986) Analysis of gibberellins and gibberellin conjugates by ion-suppression reversed-phase high-performance liquid chromatography. J Chromatogr 367: 377–384
Jones DF (1964) Examination of the gibberellins of Zea mays and Phaseolus multiflorus using thin-layer chromatography. Nature 202: 1309–1310
Kamiya JE and Graebe JE (1983) The biosynthesis of all major pea gibberellins in a cell free system from Pisum sativum. Phytochemistry 22: 681–689
Keay PJ, Moffatt JS and Mulholland TPC (1965) Some functional derivatives and transformation products of gibberellic acid. J Chem Soc: 1605–1615
Keith B, Boal R and Srivastava LM (1980) On the uptake, metabolism and retention of [3H]gibberellin A1 by barley aleurone layers at low temperatures. Plant Physiol 66: 956–961
Kende H (1967) Preparation of radioactive gibberellin A1 and its metabolism in dwarf peas. Plant Physiol 42: 1612–1618
Knöfel H-D, Schwarzkopf E, Müller P and Sembdner G (1984) Enzymic glucosylation of gibberellins. Plant Growth Regul 3: 127–140
Koshioka M, Douglas TJ, Ernst D, Huber J and Pharis RP (1983) Metabolism of [3H]gibberellin A4 in somatic suspension cultures of anise. Phytochemistry 22: 1577–1584
Koshioka M, Harada J, Takeno K, Noma M, Sassa T, Ogiyama K, Taylor JS, Rood SB, Legge RL and Pharis RP (1983) Reversed-phase C18 high-performance liquid chromatography of acidic and conjugated gibberellins. J Chromatogr 256: 101–115
Koshioka M, Hisajima S, Pharis RP and Murofushi N (1985) Metabolism of [3H]gibberellin A5 in cell suspension cultures of Pharbitis nil. Agric Biol Chem 49: 2627–2631
Koshioka M, Jones A, Koshioka MN and Pharis RP (1983) Metabolism of [3H]gibberellin A4 in somatic suspension cell cultures of carrot. Phytochemistry 22: 1585–1590
Koshioka M, Jones A and Pharis RP (1988) The potential of cell suspension cultures of Daucus carota L. as a source of isotope labelled gibberellins. I. Metabolism of [3H]GA5. Agric Biol Chem 52: 55–61
Koshioka M, Matsuta N, Mander LN and Pharis RP (1988) Gibberellin A5 metabolism in peach suspension cells. In: Pharis PR and Rood SB (eds) Abstr. 13th Intern Conf Plant Growth Substances, No. 218. Calgary
Koshioka M, Pharis RP, King RW, Murofushi N and Durley RC (1985) Metabolism of [3H]gibberellin A5 in developing Pharbitis nil seeds. Phytochemistry 24: 663–671
Koshioka M, Pharis RP, Matsuta N and Mander LN (1988) Metabolism of [3H]gibberellin A5 and [2H]gibberellin A5 in cell suspension cultures of Prunus persica. Phytochemistry 27: 3799–3805
Koshioka M, Yamada T, Takeno K, Beall FD, Janzen LM, Pharis RP and Mander LN (1988) Gibberellin A4 metabolism in rice plant seedlings. In: Pharis RP and Rood SB (eds) Abstr. 13th Intern Conf Plant Growth Substances, No. 217. Calgary
Larsen K and Rood SB (1988) Gibberellin metabolism in situ in Brassica napus. In: Pharis PR and Rood SB (eds) Abstr. 13th Inter Conf Plant Growth Substances, No. 348. Calgary
Lattke P (1987) Untersuchungen zum Metabolismus von Gibberellin A20 und Gibberellin A20-13-O-glucosid in Vicia faba L. Thesis, Halle
Lattke P and Schneider G (1985) Formation of GA20 glucosyl conjugates in seedlings of Vicia faba. Plant Growth Regul 4: 71–79
Lehmann H and Sembdner G (1986) Plant hormone conjugates. In: Purohit SS (ed) Hormonal Regulation of Plant Growth and Development, Vol 3, pp 245–310. Bikaner: Agro Botanical Publ
Lenton JR and Appleford NEJ (1991) Gibberellin production and action during germination of wheat. In: Takahashi N, Phinney BO and MacMillan J (eds) Gibberellins, pp 125–135. New York: Springer
Lenton JR, Appleford NEJ and Crokers J (1993) Gibberellin-dependent α-amylase production in germinating wheat (Triticum aestivum) grain. In: Frontiers of Gibberellin Research 1993, Abstr., 19. Tokyo Riken
Liebisch HW (1974) Uptake, translocation and metabolism of GA3 glucosyl ester. In: Schreiber K, Schütte and Sembdner G (eds) Biochemistry and Chemistry of Plant Growth Regulators, pp 109–113. Halle: Inst Plant Biochem Acad Sci GDR
Liebisch HW (1980) Vergleichende Untersuchungen über den Stoffwechsel von GA1, GA3 und GA9 in Zellsuspension-skulturen von Lycopersicon esculentum und in verschiedenen intakten Pflanzen. Biochem Physiol Pflanzen 175: 797–805
Liebisch HW (1987) Sub-cellular localization of gibberellins in suspension grown tomato cells. In: Lilov D, Vassilev G, Christov Ch and Andonova T (eds) Plant Growth Regulators Vol 1, pp 39–44. Sofia: Bulg Acad Sci
Lorenzi R, Horgan R and Heald JK (1976) Gibberellin A9 glucosyl ester in needles of Picea sitchensis. Phytochemistry 15: 789–790
MacMillan J and Suter PJ (1958) The occurrence of gibberellin A1 in higher plants: isolation from the seed of runner bean (Phaseolus multiflorus). Naturwiss 45: 46–47
Maki SL and Brenner ML (1991) [14C]GA12-aldehyde, [14C]GA12, and [2H] and [14C]GA53 metabolism by elongating pea pericarp. Plant Physiol 97: 1359–1366
McComb AJ (1961) “Bound” gibberellins in mature runner bean seeds. Nature 192: 575–576
McInnes AG, Smith DG, Durley RC, Pharis RP, Arsenault GP, MacMillan J, Gaskin P and Vining LC (1977) Biosynthesis of gibberellins in Gibberella fujikuroi. Gibberellin A47. Can J Biochem 55: 728–735
Meyer A, Schneider G and Sembdner G (1984) Endogenous gibberellins and inhibitors of the douglas fir. In: Abstr Intern Symp Plant Growth Regul, 51. Liblice
Moritz T (1992) The use of combined capillary liquid chromatography/mass spectrometry for the identification of a gibberellin glucosyl conjugate. Phytochem Anal 3: 32–37
Moritz T, Schneider G and Jensen E (1992) Capillary liquid chromatography/fast atom bombardment mass spectrometry of gibberellin glucosyl conjugates. Biol Mass Spectrom 21: 554–559
Müller P, Knöfel H-D and Sembdner G (1974) Studies on the enzymatical synthesis of gibberellin-O-glucosides. In: Schreiber K, Schütte HR and Sembdner G (eds) Biochemistry and Chemistry of Plant Growth Regulators, pp 115–119. Halle: Inst Plant Biochem Acad Sci GDR
Murakami Y (1961) Formation of gibberellin A3 glucoside in plant tissues. Bot Mag 74: 424–425
Murakami Y (1962) Occurrence of water-soluble gibberellins in higher plants. Bot Mag 75: 451–452
Murakami Y (1985) Distribution of bound gibberellin in higher plants and its hydrolysis by enzymes from different sources. Bull Nat Inst Agric Sci, Ser D No. 36: 69–123
Murofushi N, Nakayama M, Takahashi N, Gaskin P and MacMillan J (1988) 12-Hydroxylation of gibberellins A12 and A14 by prothallia of Lygodium japonicum and identification of a new gibberellin, GA74. Agric Biol Chem 52: 1825–1828
Murofushi N, Yang Y-Y, Yamaguchi I, Schneider G and Kato Y (1992) Liquid chromatography/atmospheric pressure chemical ionization mass spectrometry of gibberellin conjugates. In: Karssen CM, van Loon LC and Vreugdenhil D (eds) Progress in Plant Growth Regulations, pp 900–904. Dordrecht, Boston, London: Kluwer Academic Publishers
Nadeau R and Rappaport L (1972) Metabolism of gibberellin A1 in germinating bean seeds. Phytochemistry 11: 1611–1616
Nadeau R, Rappaport L and Stolp CG (1972) Uptake and metabolism of 3H-gibberellin A1 by barley aleurone layers: response to abscisic acid. Planta 107: 315–324
Nash LJ and Crozier A (1975) Translocation and metabolism of [3H]gibberellins by light-grown Phaseolus coccineus seedlings. Planta 127: 221–231
Noma M, Huber J, Ernst D and Pharis RP (1982) Quantitation of gibberellins and the metabolism of [3H]gibberellin A1 during somatic embryogenesis in carrot and anise cell cultures. Planta 155: 369–376
Pharis RP, Jenkins PA, Aoki H and Sassa T (1981) Hormonal physiology of wood growth in Pinus radiata D. Don: effects of gibberellin A4 and the influence of abscisic acid upon [3H]gibberellin A4 metabolism. Aust J Plant Physiol 8: 559–570
Phinney BO and Schneider G (1987) Metabolism of GA-conjugates in Zea mays. In: Schreiber K, Schütte HR and G Sembdner (eds) Conjugated Plant Hormones. Structures, Metabolism and Function, pp 167–175. Berlin: VEB Deutscher Verlag der Wissenschaften
Radley M (1958) The distribution of substances similar to gibberellic acid in higher plants. Ann Bot 22: 297–307
Rappaport L, Davies L, Lavee S, Nadeau R, Patterson R and Stolp CF (1974) Significance of metabolism of [3H]GA1 for plant regulation. In: Tamura S (ed) Plant Growth Substances 1973, pp 314–324. Tokyo: Hirokawa
Rivier L, Gaskin P, Albone K-YS and MacMillan J (1981) GC-MS Identification of endogenous gibberellins and gibberellin conjugates as their permethylated derivatives. Phytochemistry 20: 687–692
Rood SB (1986) Heterosis and the metabolism of [3H]gibberellin A1 in maize. Can J Bot 64: 2160–2164
Rood SB (1993) Genetic and environmental control of gibberellin physiology in Brassica. In: Frontiers of Gibberellin Research 1993, Abstr., 38. Tokyo Riken
Rood SB, Beall FD and Pharis RP (1986) Photocontrol of gibberellin metabolism in situ in maize. Plant Physiol 80: 448–453
Rood SB and Junttila O (1989) Lack of influence of photoperiod on the metabolism of gibberellin A20 in Salix pentandra. Physiol Plant 75: 506–510
Rood SB, Kaufman PB, Abe H and Pharis RP (1987) Gibberellins and gravitropism in maize shoots. Endogenous gibberellin-like substances and movement and metabolism of [3H]gibberellin A20. Plant Physiol 83: 645–651
Rood SB, Koshioka M, Douglas TJ and Pharis RP (1982) Metabolism of tritiated gibberellin A20 in maize. Plant Physiol 70: 1614–1618
Rood SB and Pharis RP (1987) Evidence for reversible conjugation of gibberellins in higher plants. In: Schreiber K, Schütte HR and Sembdner G (eds) Conjugated Plant Hormones. Structure, Metabolism and Function, pp 183–190. Berlin: VEB Deutscher Verlag der Wissenschaften
Rood SB, Pharis RP and Koshioka M (1983) Reversible conjugation of gibberellins in situ in maize. Plant Physiol 73: 340–346
Sato Y, Yamane H, Kobayashi M, Yamaguchi I and Takahashi N (1985) Metabolism of GA9 methyl ester in a culture of prothallia of Lygodium japonicum. Agric Biol Chem 49: 255–258
Schliemann W (1984) Hydrolysis of conjugated gibberellins by β-glucosidases of dwarf rice (Oryza sativa L. cv. “Tan-ginbozu”). J Plant Physiol 116: 123–132
Schliemann W (1987) Enzymic hydrolysis of gibberellin conjugates. In: Schreiber K, Schütte HR and Sembdner G (eds) Conjugated Plant Hormones. Structure, Metabolism and Function, pp 191–198. Berlin: VEB Deutscher Verlag der Wissenschaften
Schliemann W (1987) Partial characterization of butanolinsoluble metabolites of [3H]GA1 in maturing fruits of Phaseolus coccineus L. Biochem Physiol Pflanzen 182: 153–163
Schliemann W (1988) β-Glucosidase with gibberellin A8-2-O-glucoside hydrolysing activity from pods of runner beans. Phytochemistry 27: 689–692
Schliemann W (1991) Zum Konzept der reversiblen Konjugation bei Phytohormonen. Naturwiss 78: 392–401
Schliemann W, Schaller B, Jensen E and Schneider G (1994) Native gibberellin-O-glucosides from mature seeds of Phaseolus coccineus. Phytochemistry 35: 35–38
Schliemann W and Schneider G (1989) Metabolic formation and occurrence of gibberellin A1-3-O-β-D-glucopyranoside in immature fruits of Phaseolus coccineus L. Plant Growth Regul 8: 85–90
Schmidt J, Schneider G and Jensen E (1988) Capillary gas chromatography/mass spectrometry of permethylated gibberellin glucosides. Biomed Environ Mass Spectrom 17: 7–13
Schneider G (1981) Synthese von Gibberellinglucosiden. Thesis, Halle
Schneider G (1981) Über strukturelle Einflüsse bei der Glucosylierung von Gibberellinen. Tetrahedron 37: 545–549
Schneider G (1983) Gibberellin conjugates. In: Crozier A (ed) The Biochemistry and Physiology of Gibberellins, Vol 1, pp 389–456. New York: Praeger Publishers
Schneider G (1987) Gibberellin conjugation. In: Schreiber K, Schütte HR and Sembdner G (eds) Conjugated Plant Hormones. Structure, Metabolism and Function, pp 158–166. Berlin: VEB Deutscher Verlag der Wissenschaften
Schneider G (1987) Gaschromatographie von Gibberellinen. In: Sembdner G, Schneider G and Schreiber K (eds) Methoden zur Pflanzenhormonanalyse, pp 127–132. Berlin, Heidelberg, New York: Springer
Schneider G, Jensen E, Spray CR and Phinney BO (1992) Hydrolysis and reconjugation of gibberellin A20 glucosyl ester by seedlings of Zea mays L. Proc Natl Acad Sci USA 89: 8045–8048
Schneider G, Miersch O and Liebisch HW (1977) Synthesis von O-β-D-Glucopyranosyl-Gibberellin-O-β-D-glucopyranosylestern. Tetrahedron Lett: 405–406
Schneider G and Moritz T (1993) Synthesis and analysis of gibberellin glycosyl esters. In: Frontiers of gibberellin research 1993, Abstr., 64. Tokyo Riken
Schneider G, Schaller B and Jensen R (1993) Reverse phase high pressure chromatographic separation of permethylated free and glucosylated gibberellins — a method for the analysis of gibberellin metabolites. Phytochem Anal 5: 111–115
Schneider G and Schliemann W (1993) The occurrence of gibberellin-O-glucosides in mature seeds of Gramineae and Leguminosae. XVth Intern Bot Congress Yokohama 1993, Abstr. 4160
Schneider G, Schliemann W, Schaller B and Jensen E (1992) Identification of native gibberellin-O-glucosides in Zea mays L. and Hordeum vulgare L. In: Karssen CM, van Loon LC and Vreugdenhil D (eds) Progress in Plant Growth Regulation, pp 566–570. Dordrecht, Boston, London: Kluwer Academic Publishers
Schneider G and Schmidt J (1990) Conjugation of gibberellins in Zea mays. In: Pharis RP and Rood SB (eds) Plant Growth Substances 1988, pp 300–306. Berlin, Heidelberg: Springer
Schneider G and Schmidt J (1994) Synthesis of 13-O-β-D-glucopyranosylgibberellin A5 β-D-glucopyranosyl ester. Liebigs Ann Chem (submitted)
Schneider G, Schmidt J and Phinney BO (1987) GC-MS Identification of GA20-13-O-glucoside formed from GA20 in normal plants and dwarf-1 mutants of Zea mays L. Plant Growth Regul 5: 217–223
Schneider G, Schreiber K, Jensen E and Phinney BO (1990) Synthesis of gibberellin A29 β-D-glucosides and β-D-glucosyl derivatives of [17-13C, T2]gibberellin A5, A20, and A29. Liebigs Ann Chem 1990: 491–494
Schneider G, Sembdner G, Jensen E, Bernhard U and Wagenbreth D (1992) GC-MS Identification of native gibberellin-O-glucosides in pea seeds. Plant Growth Regul 11: 15–18
Schneider G, Sembdner G and Schreiber K (1974) Zur Synthese von Gibberellin-A3-β-D-glucopyranosiden. Z Chem 14: 474–475
Schneider G, Sembdner G and Schreiber K (1977) Synthese von O(3)- und O(13)-glucosylierten Gibberellinen. Tetrahedron 33: 1391–1397
Schneider G, Sembdner G and Phinney BO (1984) Synthesis of GA20 glucosyl derivatives and the biological activity of some gibberellin conjugates. J Plant Growth Regul 3: 207–215
Schneider G, Sembdner G, Schreiber K and Phinney BO (1989) Partial synthesis of some physiologically relevant gibberellin glucosyl conjugates. Tetrahedron 45: 1355–1364
Schreiber K, Schneider G, Sembdner G and Focke I (1966) Isolierung von O(2)-Acetyl-Gibberellinsäure als Stoffwech-selprodukt von Fusarium moniliforme Sheld. Phytochemistry 5: 1221–1225
Schreiber K, Weiland J and Sembdner G (1967) Isolierung und Struktur eines Gibberellinglucosides. Tetrahedron Lett: 4285–4288
Schreiber K, Weiland J and Sembdner G (1969) Synthese von O(2)-β-D-Glucopyranosylgibberellin-A3-methylester. Tetrahedron 25: 5541–5545
Schreiber K, Weiland J and Sembdner G (1970) Isolierung von Gibberellin-A8-O(3)-β-D-glucopyranosid aus Früchten von Phaseolus coccineus. Phytochemistry 9: 189–198
Sembdner G (1974) Conjugates of plant hormones. In: Schreiber K, Schütte HR and Sembdner G (eds) Biochemistry and Chemistry of Plant Growth Regulators, pp 283–302. Halle: Inst Plant Biochem Acad Sci GDR
Sembdner G, Borgmann E, Schneider G, Liebisch HW, Miersch O, Adam G, Lischewski M and Schreiber K (1976) Biological activity of some conjugated gibberellins. Planta 132: 249–257
Sembdner G, Grß D, Liebisch H-W and Schneider G (1980) Biosynthesis and metabolism of plant hormones. In: MacMillan J (ed) Encyclopedia of Plant Physiology, New Series, Vol 9, pp 281–444. Berlin, Heidelberg, New York: Springer
Sembdner G, Knöfel H-D, Schwarzkopf E and Liebisch HW (1985) In vitro glucosylation of gibberellins. Biol Plant 27: 231–236
Sembdner G, Schliemann W and Schneider G (1991) Biochemical and physiological aspects of gibberellin conjugation. In: Takahashi N, Phinney BO and MacMillan J (eds) Gibberellins, pp 249–263. New York: Springer
Sembdner G and Schneider G (1990) Gibberellin conjugation — a physiologically relevant process in hormone metabolism of plants. In: Kutacek M, Elliott MC and Machackova I (eds) Molecular Aspects of Hormonal Regulation of Plant Development, Proc 14th Biochemical Congress Prague 1988, pp 151–173. The Hague: SPB Academic Publishing bv
Sembdner G, Schneider G, Weiland J and Schreiber K (1964) Über ein gebundenes Gibberellin aus Phaseolus coccineus L. Experientia 20: 89–90
Sembdner G, Weiland J, Aurich O and Schreiber K (1968) Isolation, structure and metabolism of a gibberellin glucoside. In: Plant Growth Regulators, S.C.I. Monograph No. 31, pp 70–86. London
Sembdner G, Weiland J, Schneider G, Schreiber K and Focke I (1972) Recent advances in the metabolism of gibberellins. In: Carr DJ (ed) Plant Growth Substances 1970, pp 145–150. Berlin, Heidelberg, New York: Springer
Sponsel VM and MacMillan J (1977) Further studies on the metabolism of gibberellins (GAs) A9, A20 and A29 in immature seeds of Pisum sativum cv. Progress No. 9. Planta 135: 129–136
Sponsel VM and MacMillan J (1978) Metabolism of gibberellin A29 in seeds of Pisum sativum cv. Progress No. 9. Use of [2H] and [3H]GAs, and the identification of a new GA catabolite. Planta 144: 69–78
Stoddart JL (1984) Growth and gibberellin-A1 metabolism in normal and gibberellin-insensitive (Rht3) wheat (Triticum aestivium L.) seedlings. Planta 161: 432–438
Stoddart JL and Foster CA (1976) ‘Bakanae barley — a new mutant of Hordeum vulgare L. with an accelerated growth rate. In: Pilet E-P (ed) Abstr. 9th Intern. Conf. Plant Growth Substances, pp 374–375. Lausanne
Stoddart JL and Jones RL (1977) Gibberellin metabolism in excised lettuce hypocotyls: evidence for the formation of gibberellin A1 glucosyl conjugates. Planta 136: 261–269
Stoddart JL and Venis MA (1980) Molecular and subcellular aspects of hormone action. In: MacMillan J (ed) Encyclopedia of Plant Physiology, New Series, Vol 9, pp 445–510. Berlin, Heidelberg, New York: Springer
Turnbull CGN and Crozier A (1989) Metabolism of [1,2-3H]gibberellin A4 by epicotyls and cell-free preparations from Phaseolus coccineus L. seedlings. Planta 178: 267–274
Turnbull CGN, Crozier A and Schneider G (1986) HPLC-Based methods for the identification of gibberellin conjugates: metabolism of [3H]gibberellin A4 in seedlings of Phaseolus coccineus. Phytochemistry 25: 1823–1828
Wample RL, Durley RC and Pharis RP (1975) Metabolism of gibberellin A4 by vegetative shoots of douglas fir at three stages of ontogeny. Physiol Plant 35: 273–278
Yamaguchi I, Kobayashi M and Takahashi N (1980) Isolation and characterization of glucosyl esters of gibberellin A5 and A44 from immature seeds of Pharbitis purpurea. Agric Biol Chem 44: 1975–1977
Yamaguchi I, Yokei M, Nishizawa M, Yang YY, Chinio M and Murofushi N (1993) Immunological technique in the research of gibberellins. XVth Intern Bot Congress Yokohama 1993, Abstr. 4.3.1.3
Yamaguchi I, Yokota T, Yoshida S and Takahashi N (1979) High pressure liquid chromatography of conjugated gibberellins. Phytochemistry 18: 1699–1702
Yamane H (1993) Antheridiogens and gibberellins in schizaeaceous ferns. XVth Intern Bot Congress Yokohama 1993, Abstr. 4.3.2.3
Yamane H, Murofushi N, Osada H and Takahashi N (1977) Metabolism of gibberellins in early immature bean seeds. Phytochemistry 16: 831–835
Yamane H, Murofushi N and Takahashi N (1975) Metabolism of gibberellins in maturing and germinating bean seeds. Phytochemistry 14: 1195–1200
Yamane H, Sato Y, Nohara K, Nakayama M, Murofushi N, Takahashi N, Takeno K, Furuya M, Furber M and Mander LN (1988) The methyl ester of a new gibberellin, GA73: the principal antheridiogen in Lygodium japonicum. Tetrahedron Lett 29: 3959–3962
Yamane H, Takahashi N, Takeno K and Furuya M (1979) Identification of gibberellin A9 methyl ester as a natural substance regulating formation of reproductive organs in Lygodium japonicum. Planta 147: 251–256
Yamane H, Yamaguchi I, Kobayashi M, Takahashi M, Sato Y, Takahashi N, Iwatsuki K, Phinney BO, Spray CR, Gaskin P and MacMillan J (1985) Identification of ten gibberellins from sporophytes of the tree fern, Cyathea australis. Plant Physiol 78: 899–903
Yamane H, Yamaguchi I, Murofushi N and Takahashi N (1971) Isolation and structure of gibberellin A35 and its glucoside from immature seed of Cytisus scoparius. Agric Biol Chem 35: 1144–1146
Yamane H, Yamaguchi I, Murofushi N and Takahashi N (1974) Isolation and structures of gibberellin A35 and its glucoside from immature seed of Cytisus scoparius. Agric Biol Chem 38: 649–655
Yokota T, Hiraga K, Yamane H and Takahashi N (1975) Mass spectrometry of trimethylsilyl derivatives of gibberellin glucosides and glucosyl esters. Phytochemistry 14: 1569–1574
Yokota T, Kobayashi S, Yamane H and Takahashi N (1978) Isolation of a novel gibberellin glucoside, 3-O-β-D-glucopyranosylgibberellin A1 from Dolichos lablab seed. Agric Biol Chem 42: 1811–1812
Yokota T, Murofushi N and Takahashi N (1970) Structure of new gibberellin glucoside in immature seeds of Pharbitis nil. Tetahedron Lett 1970: 1489–1491
Yokota T, Murofushi N, Takahashi N and Katsumi M (1971) Biological activities of gibberellins and their glucosides in Pharbitis nil. Phytochemistry 10: 2943–2949
Yokota T, Murofushi N, Takahashi N and Tamura S (1971) Gibberellins in immature seeds of Pharbitis nil. III. Isolation and structures of gibberellin glucosides. Agric Biol Chem 35: 583–595
Yokota T, Takahashi N, Murofushi N and Tamura S (1969) Isolation of gibberellins A26 and A27 and their glucosides from immature seeds of Pharbitis nil. Planta 87: 180–184
Yokota T, Takahashi N, Murofushi N and Tamura S (1969) Structures of new gibberellin glucosides in immature seeds of Pharbitis nil. Tetrahedron Lett 1969: 2081–2084
Yokota T, Yamazaki S, Takahashi N and Iitaka Y (1974) Structure of pharbitic acid, a gibberellin-related diterpenoid. Tetrahedron Lett 1974: 2957–2960
Zhu Y-X, Davies PJ and Halinska A (1991) Metabolism of gibberellin A12 and A12-aldehyde in developing seeds of Pisum sativum L. Plant Physiol 97: 26–33
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Schneider, G., Schliemann, W. Gibberellin conjugates: an overview. Plant Growth Regul 15, 247–260 (1994). https://doi.org/10.1007/BF00029898
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DOI: https://doi.org/10.1007/BF00029898