GA20, Me-TMS

• Formula: C₂₃H₃₄O₅Si
• Molecular weight: 418.5986
• IUPAC Standard InChI: InChI=1S/C23H34O5Si/c1-14-12-21-13-22(14,28-29(4,5)6)11-8-15(21)23-10-7-9-20(2,19(25)27-23)17(23)16(21)18(24)26-3/h15-17H,1,7-13H2,2-6H3/t15?,16-,17?,20-,21+,22+,23-/m0/s1 Copy

  
• IUPAC Standard InChIKey: ZXVZVLFTWHDLQN-LYIOEFPQSA-N Copy
• Chemical structure:
  This structure is also available as a 2d Mol file
• Stereoisomers:
  • [2H2]GA20, MeTMSi
• Other names: GA20 methyl ester TMS ether; Gibberellin GA20, methyl ester trimethylsilyl ether; Gibberelline GA20, methyl ester TMS ether
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas Chromatography
  • References
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Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Schneider, Jensen, et al., 1992
Schneider, G.; Jensen, E.; Spray, C.R.; Phinney, B.O., Hydrolysis and reconjugation of gibberellin A₂₀ glucosyl ester by seedlings of Zea mays L., Proc. Nat. Acad. Sci. U.S.A., 1992, 89, 17, 8045-8048, https://doi.org/10.1073/pnas.89.17.8045 . [all data]

Emery, Pearce, et al., 2001
Emery, R.J.N.; Pearce, D.W.; Pharis, R.P.; Reid, D.M.; Chinnappa, C.C., Stem elongation and gibberellins in alpine and prairie ecotypes of Stellaria longipes, Plant Growth Regul., 2001, 35, 1, 17-29, https://doi.org/10.1023/A:1013823517189 . [all data]

Morvan-Bertrand, Ernstsen, et al., 2001
Morvan-Bertrand, A.; Ernstsen, A.; Lindgård, B.; Koshioka, M.; le Saos, J.; Boucaud, J.; Prud'homme, M.-P.; Junttila, O., Endogenous gibberellins in Lolium perenne and influence of defoliation on their contents in elongating leaf bases and in leaf sheaths, Physiol. Plant., 2001, 111, 2, 225-231, https://doi.org/10.1034/j.1399-3054.2001.1110214.x . [all data]

Koshioka, Miyamoto, et al., 1998
Koshioka, M.; Miyamoto, K.; Horio, T.; Namura, S.; Hisamatsu, T.; Kubota, S.; Ernstsen, A.; Junttila, O.; Mander, L.N., Identification of endogenous gibberellins in stems and leaves in vegetative growth stage of Gentiana triflora, J. Plant Physiol., 1998, 153, 1-2, 230-232, https://doi.org/10.1016/S0176-1617(98)80071-0 . [all data]

Nakayama, Yokota, et al., 1996
Nakayama, M.; Yokota, T.; Sohma, R.; Mander, L.N.; Twitchin, B.; Komatsu, H.; Matsui, H.; Bukovac, M.J., Gibberellins in immature seed of Prunus cerasus: structure determination and synthesis of gibberellin, GA₉₅ (1,2-didehydro-GA₂₀), Phytochemistry, 1996, 42, 4, 913-920, https://doi.org/10.1016/0031-9422(96)00035-0 . [all data]

Toyomasu, Tsuji, et al., 1993
Toyomasu, T.; Tsuji, H.; Yamane, H.; Nakayama, M.; Yamaguchi, I.; Murofushi, N.; Takahashi, N.; Inoue, Y., Light effects on endogenous levels of gibberellins in photoblastic lettuce seeds, J. Plant Growth Regul., 1993, 12, 2, 85-90, https://doi.org/10.1007/BF00193238 . [all data]

Tanno, Yokota, et al., 1992
Tanno, N.; Yokota, T.; Abe, M.; Okagami, N., Identification of endogenous gibberellins in dormant bulbils of Chinese yam, Dioscorea opposita, Plant Physiol., 1992, 100, 4, 1823-1826, https://doi.org/10.1104/pp.100.4.1823 . [all data]

Poling, 1991
Poling, S.M., Identification of endogenous gibberellins in immature navel orange fruit, J. Agric. Food Chem., 1991, 39, 4, 677-680, https://doi.org/10.1021/jf00004a010 . [all data]

Talón, Hedden, et al., 1990
Talón, M.; Hedden, P.; Primo-Millo, E., Gibberellins in Citrus sinensis: a comparison between seeded and seedless varieties, J. Plant Growth Regul., 1990, 9, 4, 201-206, https://doi.org/10.1007/BF02041963 . [all data]

Talon, Koornneef, et al., 1990
Talon, M.; Koornneef, M.; Zeevaart, J.A.D., Endogenous gibberellins in Arabidopsis thaliana and possible steps blocked in the biosynthetic pathways of the semidwarf ga4 and ga5 mutants, Proc. Nat. Acad. Sci. U.S.A., 1990, 87, 20, 7983-7987, https://doi.org/10.1073/pnas.87.20.7983 . [all data]

Talon and Zeevaart, 1990
Talon, M.; Zeevaart, J.A.D., Gibberellins and stem growth as related to photoperiod in Silene armeria L., Plant Physiol., 1990, 92, 4, 1094-1100, https://doi.org/10.1104/pp.92.4.1094 . [all data]

Hedden, Croker, et al., 1989
Hedden, P.; Croker, S.J.; Rademacher, W.; Jung, J., Effects of the triazole plant growth retardant BAS 111..W on gibberellin levels in oilseed rape, Brassica napus, Physiol. Plant., 1989, 75, 4, 445-451, https://doi.org/10.1111/j.1399-3054.1989.tb05607.x . [all data]

Kim, Lee, et al., 2003
Kim, S.-K.; Lee, S.-C.; Shin, D.-H.; Jang, S.-W.; Nam, J.-W.; Park, T.-S.; Lee, I.-J., Quantification of endogenous gibberellins in leaves and tubers of Chinese yam, Dioscorea opposita Thunb. cv. Tsukune during tuber enlargement, Plant Growth Regul., 2003, 39, 2, 125-130, https://doi.org/10.1023/A:1022569506883 . [all data]

Pearce, Hutt, et al., 2002
Pearce, D.W.; Hutt, O.E.; Rood, S.B.; Mander, L.N., Gibberellins in shoots and developing capsules of Populus species, Phytochemistry, 2002, 59, 6, 679-687, https://doi.org/10.1016/S0031-9422(02)00009-2 . [all data]

Gutiérrez-Mañero, Ramos-Solano, et al., 2001
Gutiérrez-Mañero, F.J.; Ramos-Solano, B.; Probanza, A.; Mehouachi, J.; Tadeo, R.; Talon, M., The plant-growth-promoting rhizobacteria Bacillus pumilus and Baillus licheniformis produce high amounts of physiologically active gibberellins, Physiol. Plant., 2001, 111, 2, 206-211, https://doi.org/10.1034/j.1399-3054.2001.1110211.x . [all data]

Kobayashi, MacMillan, et al., 2000
Kobayashi, M.; MacMillan, J.; Phinney, B.; Gaskin, P.; Spray, C.R.; Hedden, P., Gibberellin biosynthesis: metabolic evidence for three steps in the early 13-hydroxylation pathway of rice, Phytochemistry, 2000, 55, 4, 317-321, https://doi.org/10.1016/S0031-9422(00)00265-X . [all data]

Taylor, Blake, et al., 2000
Taylor, D.R.; Blake, P.S.; Crisp, C.M., Identification of gibberellins in leaf tissues of day-neutral strawberry (Fragaria × ananassa Duch.) cultivars, Plant Growth Regul., 2000, 30, 1, 5-7, https://doi.org/10.1023/A:1006275024517 . [all data]

Davis, Kobayashi, et al., 1999
Davis, G.; Kobayashi, M.; Phinney, B.O.; Lange, T.; Croker, S.J.; Gaskin, P.; MacMillan, J., Gibberellin biosynthesis in maize. Metabolic studies with GA₁₅, GA₂₄, GA₂₅, GA₇, and 2,3-dehydro-GA₉, Plant Physiol., 1999, 121, 3, 1037-1045, https://doi.org/10.1104/pp.121.3.1037 . [all data]

Roberts, Blake, et al., 1999
Roberts, A.V.; Blake, P.S.; Lewis, R.; Taylor, J.M.; Dunstan, D.I., The effect of gibberellins on flowering in roses, J. Plant Growth Regul., 1999, 18, 3, 113-119, https://doi.org/10.1007/PL00007058 . [all data]

Davis, Kobayashi, et al., 1998
Davis, G.; Kobayashi, M.; Phinney, B.O.; MacMillan, J.; Gaskin, P., The Metabolism of GA₉ in maize (ZEA mays), Phytochemistry, 1998, 47, 4, 635-639, https://doi.org/10.1016/S0031-9422(97)87974-5 . [all data]

Hisamatsu, Koshioka, et al., 1998
Hisamatsu, T.; Koshioka, M.; Kubota, S.; Nishijima, T.; Yamane, H.; King, R.W.; Mander, L.N., Isolation and identification of GA₁₁₂ (12β-hydroxy-GA₁₂) in Matthiola incana, Phytochemistry, 1998, 47, 1, 3-6, https://doi.org/10.1016/S0031-9422(97)00543-8 . [all data]

Webb, Appleford, et al., 1998
Webb, S.E.; Appleford, N.E.J.; Gaskin, P.; Lenton, J.R., Gibberellins in internodes and ears of wheat containing different dwarfing alleles, Phytochemistry, 1998, 47, 5, 671-677, https://doi.org/10.1016/S0031-9422(97)00684-5 . [all data]

Grünzweig, Rabinowitch, et al., 1997
Grünzweig, J.M.; Rabinowitch, H.D.; Katan, J.; Wodner, M.; Ben-Tal, Y., Endogenous gibberellins in foliage of tomato (Lycopersicon esculentum), Phytochemistry, 1997, 46, 5, 811-815, https://doi.org/10.1016/S0031-9422(97)00383-X . [all data]

Kappers, Jordi, et al., 1997
Kappers, I.F.; Jordi, W.; Maas, F.M.; van der Plas, L.H.W., Gibberellins in leaves of Alstroemeria hybrida: identification and quantification in relation to leaf age, J. Plant Growth Regul., 1997, 16, 4, 219-225, https://doi.org/10.1007/PL00007000 . [all data]

Rijnders, Yang, et al., 1997
Rijnders, J.G.H.M.; Yang, Y.-Y.; Kamiya, Y.; Takahashi, N.; Barendse, G.W.M.; Blom, C.W.P.M.; Voesenek, L.A.C.J., Ethylene enhances gibberellin levels and petiole sensitivity in flooding-tolerant Rumex palustris but not in flooding-intolerant R. acetosa, Planta, 1997, 203, 1, 20-25, https://doi.org/10.1007/s00050160 . [all data]

Kobayashi, Spray, et al., 1996
Kobayashi, M.; Spray, C.R.; Phinney, B.O.; Gaskin, P.; MacMillan, J., Gibberellin metabolism in maize. The stepwise conversion of gibberellin A₁₂-aldehyde to gibberellin A₂₀, Plant Physiol., 1996, 110, 413-418. [all data]

Ridoutt, Pharis, et al., 1995
Ridoutt, B.G.; Pharis, R.P.; Sands, R., Identification and quantification of cambial region hormones of Eucalyptus globulus, Plant Cell Physiol., 1995, 36, 6, 1143-1147. [all data]

Santes, Hedden, et al., 1995
Santes, C.M.; Hedden, P.; Gaskin, P.; Garcia-Martinez, J.L., Gibberellins and related compounds in young fruits of pea and their relationship to fruit-set, Phytochemistry, 1995, 40, 5, 1347-1355, https://doi.org/10.1016/0031-9422(95)00489-T . [all data]

Talo, Spray, et al., 1995
Talo, A.; Spray, C.R.; Somers, D.A.; Donovan, C.M.; Gaskin, P.; Macmillian, J.; Phinney, B.O., Endogenous gibberellins from callus cultures of maize, Phytochemistry, 1995, 40, 1, 11-15, https://doi.org/10.1016/0031-9422(95)00000-W . [all data]

Blake and Browning, 1994
Blake, P.S.; Browning, G., Gibberellins in developing fruits of Prunus avium, Phytochemistry, 1994, 35, 6, 1383-1386, https://doi.org/10.1016/S0031-9422(00)86860-0 . [all data]

Hasan, Ridoutt, et al., 1994
Hasan, O.; Ridoutt, B.G.; Ross, J.J.; Davies, N.W.; Reid, J.B., Identification and quantification of endogenous gibberellins in apical buds and the cambial region of Eucalyptus, Physiol. Plant., 1994, 90, 3, 475-480, https://doi.org/10.1111/j.1399-3054.1994.tb08804.x . [all data]

Kobayashi, Gaskin, et al., 1994
Kobayashi, M.; Gaskin, P.; Spray, C.R.; Phinney, B.O.; MacMillan, J., The metabolism of gibberellin A₂₀ to gibberellin A₁ by tall and dwarf mutants of Oryza sativa and Arabidopsis thaliana, Plant Physiol., 1994, 106, 1367-1372. [all data]

Pearce, Koshioka, et al., 1994
Pearce, D.W.; Koshioka, M.; Pharis, R.P., Chromatography of gibberellins, J. Chromatogr. A, 1994, 658, 1, 91-122, https://doi.org/10.1016/0021-9673(94)85210-3 . [all data]

Taylor, Blake, et al., 1994
Taylor, D.R.; Blake, P.S.; Browning, G., Identification of gibberellins in leaf tissues of strawberry (Fragaria × ananassa Duch.) grown under different photoperiods, Plant Growth Regul., 1994, 15, 3, 235-240, https://doi.org/10.1007/BF00029896 . [all data]

Hedden, Hoad, et al., 1993
Hedden, P.; Hoad, G.V.; Gaskin, P.; Lewis, M.J.; Green, J.R.; Furber, M.; Mander, L.N., Kaurenoids and gibberellins, including the newly characterized gibberellin A₈₈, in developing apple seeds, Phytochemistry, 1993, 32, 2, 231-237, https://doi.org/10.1016/S0031-9422(00)94973-2 . [all data]

Waycott, Smith, et al., 1991
Waycott, W.; Smith, V.A.; Gaskin, P.; MacMillan, J.; Taiz, L., The endogenous gibberellins of dwarf mutants of lettuce, Plant Physiol., 1991, 95, 4, 1169-1173, https://doi.org/10.1104/pp.95.4.1169 . [all data]

Poling and Maier, 1988
Poling, S.M.; Maier, V.P., Identification of endogenous gibberellins in navel orange shoots, Plant Physiol., 1988, 88, 3, 639-642, https://doi.org/10.1104/pp.88.3.639 . [all data]

Gaskin, Gilmour, et al., 1984
Gaskin, P.; Gilmour, S.J.; Lenton, J.R.; MacMillan, J.; Sponsel, V.M., Endogenous gibberellins and kauranoids identified from developing and germinating barley grain, J. Plant Growth Regul., 1984, 2, 1-4, 229-242, https://doi.org/10.1007/BF02042252 . [all data]

Oyama, Yamauchi, et al., 1996
Oyama, N.; Yamauchi, T.; Yamane, H.; Yamaguchi, I.; Schraudolf, H.; Mander, L.N.; Murofushi, N., Gibberellins and antheridiogens in prothallia and sporophytes of Anemia phyllitidis, Biosci. Biotechnol. Biochem., 1996, 60, 2, 301-304, https://doi.org/10.1271/bbb.60.301 . [all data]

Oyama, Yamauchi, et al., 1996, 2
Oyama, N.; Yamauchi, T.; Yamane, H.; Murofushi, N.; Agatsuma, M.; Pour, M.; Mander, L.N., Identification of gibberellins and 9,15-cyclogibberellins in developing apple seeds, Biosci. Biotechnol. Biochem., 1996, 60, 2, 305-308, https://doi.org/10.1271/bbb.60.305 . [all data]

Fujioka, Yamane, et al., 1988
Fujioka, S.; Yamane, H.; Spray, C.R.; Gaskin, P.; Macmillan, J.; Phinney, B.O.; Takahashi, N., Qualitative and quantitative analyses of gibberellins in vegetative shoots of normal, dwarf-1, dwarf-2, dwarf-3, and dwarf-5 seedlings of Zea mays L., Plant Physiol., 1988, 88, 4, 1367-1372, https://doi.org/10.1104/pp.88.4.1367 . [all data]

Lange, Kappler, et al., 2005
Lange, T.; Kappler, J.; Fischer, A.; Frisse, A.; Padeffke, T.; Schmidtke, S.; Lange, M.J.P., Gibberellin biosynthesis in developing pumpkin seedlings, Plant Physiol., 2005, 139, 1, 213-223, https://doi.org/10.1104/pp.105.064162 . [all data]

Chung, Kuo, et al., 2003
Chung, J.-D.; Kuo, S.-R.; Chien, C.-T., Identification and quantification of gibberellin transformation and dosage changes in good and poor flowering clones of Calocedrus formosana grafts, Taiwan J. For. Sci., 2003, 18, 4, 387-400. [all data]

Yamazaki, Nishijima, et al., 2002
Yamazaki, H.; Nishijima, T.; Koshioka, M.; Miura, H., Gibberellins do no act against abscisic acid in the regulation of bulb dormancy of Allium wakegi Araki, Plant Growth Regul., 2002, 36, 3, 223-229, https://doi.org/10.1023/A:1016577529378 . [all data]

Chang, Chen, et al., 2001
Chang, S.-T.; Chen, W.-S.; Koshioka, M.; Mander, L.N.; Huang, K.-L.; Du, B.-S., Gibberellins in relation to flowering in Polianthes tuberosa, Physiol. Plant., 2001, 112, 3, 429-432, https://doi.org/10.1034/j.1399-3054.2001.1120317.x . [all data]

Fos, Nuez, et al., 2000
Fos, M.; Nuez, F.; Garcia-Martinez, J.L., The gene pat-2, which induces natural partenocarpy, alters the gibberellin content in unpollinated tomato ovaries, Plant Physiol., 2000, 122, 2, 471-479, https://doi.org/10.1104/pp.122.2.471 . [all data]

Martínez-García, Santes, et al., 2000
Martínez-García, J.F.; Santes, C.M.; García-Martínez, J.L., The end-of-day far-red irradiation increases gibberellin A₁ content in cowpea (Vigna sinensis) epicotyls by reducing its inactivation, Physiol. Plant., 2000, 108, 4, 426-434, https://doi.org/10.1034/j.1399-3054.2000.t01-1-100413.x . [all data]

Pérez, Viani, et al., 2000
Pérez, F.J.; Viani, C.; Retamales, J., Bioactive gibberellins in seeded and seedless grapes: identification and changes in content during berry development, Am. J. Enol. Vitic, 2000, 51, 4, 315-318. [all data]

Ross, MacKenzie-Hose, et al., 1999
Ross, J.J.; MacKenzie-Hose, A.K.; Davies, P.J.; Lester, D.R.; Twitchin, B.; Reid, J.B., Further evidence for feedback regulation of gibberellin biosynthesis in pea, Physiol. Plant., 1999, 105, 3, 532-538, https://doi.org/10.1034/j.1399-3054.1999.105319.x . [all data]

Wang, Little, et al., 1996
Wang, Q.; Little, C.H.A.; Moritz, T.; Odén, P.C., Identification of endogenous gibberellins, and metabolism of tritiated and deuterated GA₄, GA₉, and GA₂₀, in Scots pine (Pinus sylvestris) shoots, Physiol. Plant., 1996, 97, 4, 764-771, https://doi.org/10.1111/j.1399-3054.1996.tb00542.x . [all data]

van Huizen, Ozga, et al., 1995
van Huizen, R.; Ozga, J.A.; Reinecke, D.M.; Twitchin, B.; Mander, L.N., Seed and 4-chloroindole-3-acetic acid regulation of gibberellin metabolism in pea pericarp, Plant Physiol., 1995, 109, 4, 1213-1217, https://doi.org/10.1104/pp.109.4.1213 . [all data]

Kawaide, Sassa, et al., 1995
Kawaide, H.; Sassa, T.; Kamiya, Y., Plant-like biosynthesis of gibberellin A₁ in the fungus Phaeosphaeria Sp. L487, Phytochemistry, 1995, 39, 2, 305-310, https://doi.org/10.1016/0031-9422(95)00006-S . [all data]

Koshioka, Nishijama, et al., 1995
Koshioka, M.; Nishijama, T.; Mander, L.N., Gibberellin metabolism in suspension cultured cells of Raphanus Sativus, Phytochemistry, 1995, 38, 2, 359-363, https://doi.org/10.1016/0031-9422(94)00624-3 . [all data]

Lange, Hedden, et al., 1993
Lange, T.; Hedden, P.; Graebe, J.E., Biosynthesis of 12α- and 13-hydroxylated gibberellins in a cell-free system from Cucurbita maxima endosperm and the identification of new endogenous gibberellins, Planta, 1993, 189, 3, 340-349, https://doi.org/10.1007/BF00194430 . [all data]

Nishijima, Murakami, et al., 1993
Nishijima, T.; Murakami, F.; Koshioka, M.; Yamazaki, H., Endogenous gibberellins in Aralia cordata, Japan Society for Biosci. Biotechnol. Agrochem., 1993, 57, 1, 1953-1954, https://doi.org/10.1271/bbb.57.1953 . [all data]

Talon, Zacarias, et al., 1992
Talon, M.; Zacarias, L.; PRimo-Millo, E., Gibberellins and Partenocarpic ability in developing ovaries of seedless mandarins, Plant Physiol., 1992, 99, 4, 1575-1581, https://doi.org/10.1104/pp.99.4.1575 . [all data]

Beall, Morgan, et al., 1991
Beall, F.D.; Morgan, P.W.; Mander, L.N.; Miller, F.R.; Babb, K.H., Genetic regulation of development in Sorghum bicolor. V. The ma₃^R allele results in gibberellin enrichment, Plant Physiol., 1991, 95, 1, 116-125, https://doi.org/10.1104/pp.95.1.116 . [all data]

Garcia-Martinez, Santes, et al., 1991
Garcia-Martinez, J.L.; Santes, C.; Croker, S.J.; Hedden, P., Identification, quantitation and distribution of gibberellins in fruits of Pisum sativum L. cv. Alaska during pod development, Planta, 1991, 184, 1, 53-60, https://doi.org/10.1007/BF00208236 . [all data]

Matheussen, Morgan, et al., 1991
Matheussen, A.-M.; Morgan, P.W.; Frederiksen, R.A., Implication of gibberellins in head smut (Sporisorium reilianum) of Sorghum bicolor, Plant Physiol., 1991, 96, 2, 537-544, https://doi.org/10.1104/pp.96.2.537 . [all data]

Talon, Zeevaart, et al., 1991
Talon, M.; Zeevaart, J.A.D.; Gage, D.A., Identification of gibberellins in spinach and effects of light and darkness on their levels, Plant Physiol., 1991, 97, 4, 1521-1526, https://doi.org/10.1104/pp.97.4.1521 . [all data]

Nakayama, Yamane, et al., 1990
Nakayama, M.; Yamane, H.; Yokota, T.; Yamaguchi, I.; Murofushi, N.; Takahashi, N.; Nishijima, T.; Katsura, N.; Nonaka, M.; Gaskin, P.; MacMillan, J.; Mander, L.N.; Chu, A., Endogenous gibberellins in mature seed of Raphanus sativus L. cv. Taibyo-sobutori, Agric. Biol. Chem., 1990, 54, 3, 837-840, https://doi.org/10.1271/bbb1961.54.837 . [all data]

Yamane, Fujioka, et al., 1988
Yamane, H.; Fujioka, S.; Spray, C.R.; Phinney, B.O.; MacMillan, J.; Gaskin, P.; Takahashi, N., Endogenous Gibberellines from Sporophytes of Two Tree Ferns, Cibotium glaucum and Dicksonia antarctica, Plant Phisiol., 1988, 86, 3, 857-862, https://doi.org/10.1104/pp.86.3.857 . [all data]

Notes

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