Gibberellic acid: Difference between revisions
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{{About|the chemical|its function in plants|Gibberellin}} |
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{{Refimprove|date=November 2012}} |
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{{chembox |
{{chembox |
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| ImageFile = Gibberellic acid.svg |
| ImageFile = Gibberellic acid.svg |
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| ImageSize = 240px |
| ImageSize = 240px |
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| ImageFile1 = Gibberellic-acid-from-xtal-3D-bs-17.png |
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| IUPACName = ( |
| IUPACName = (3''S'',3a''S'',4''S'',4a''S'',7''S'',9a''R'',9b''R'',12''S'')-7,12-Dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-''b'']furan-4-carboxylic acid |
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| OtherNames = |
| OtherNames = |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ⚫ | |||
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| Beilstein = 54346 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7995349 |
| ChemSpiderID = 7995349 |
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| DrugBank = DB07814 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = BU0A7MWB6L |
| UNII = BU0A7MWB6L |
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| ⚫ | |||
| InChI = 1/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1 |
| InChI = 1/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1 |
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| InChIKey = IXORZMNAPKEEDV-SNTJWBGVBW |
| InChIKey = IXORZMNAPKEEDV-SNTJWBGVBW |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IXORZMNAPKEEDV-SNTJWBGVSA-N |
| StdInChIKey = IXORZMNAPKEEDV-SNTJWBGVSA-N |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| C=19 | H=22 | O=6 |
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| Formula = C<sub>19</sub>H<sub>22</sub>O<sub>6</sub> |
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| MolarMass = 346.37 g/mol |
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| Appearance = |
| Appearance = |
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| Density = |
| Density = |
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| MeltingPt_notes = (decomposition) |
| MeltingPt_notes = (decomposition) |
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| BoilingPt = |
| BoilingPt = |
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| Solubility = 5 g/ |
| Solubility = 5 g/L (20 °C) |
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}} |
}} |
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|Section3={{Chembox Hazards |
|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| EUClass = Irritant ('''Xi''') |
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| GHSSignalWord = Warning |
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| RPhrases = {{R36}} |
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| HPhrases = {{H-phrases|319}} |
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| PPhrases = {{P-phrases|264|280|305+351+338|337+313}} |
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| MainHazards = |
| MainHazards = |
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| FlashPt = |
| FlashPt = |
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'''Gibberellic acid''' (also called ''' |
'''Gibberellic acid''' (also called '''gibberellin A3''' or '''GA<sub>3</sub>''') is a [[Plant hormone|hormone]] found in plants and fungi.<ref name="GA3">{{cite journal|vauthors=((Silva ALL)), Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, ((Vandenberghe LPS)), Soccol CR|title=Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro|journal=Pakistan Journal of Botany|date=2013|volume=45|issue=6|pages=2057–2064|url=http://www.pakbs.org/pjbot/PDFs/45(6)/30.pdf|access-date=26 November 2014}}</ref> Its [[chemical formula]] is C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>. When purified, it is a white to pale-yellow solid. |
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. Its [[chemical formula]] is C<sub>19</sub>H<sub>22</sub>O<sub>6</sub>. When purified, it is a white to pale-yellow solid. |
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Plants in their normal state produce |
Plants in their normal state produce large amounts of GA3. It is possible to produce the hormone industrially using microorganisms.<ref name="camara">Camara, M. C. et al (2015) General Aspects and Applications of Gibberelins and Gibberellic Acid in Plants. In: Hardy, J.. (Org.). Gibberellins and Gibberellic Acid: Biosynthesis, Regulation and Physiological Effects. 1ed.Hauppauge: Nova Science Publishers, 2015, v., p. 1-21.</ref> Gibberellic acid is a simple [[gibberellin]], a [[Polycyclic compound|pentacyclic]] [[diterpene]] acid promoting growth and elongation of cells. It affects decomposition of plants and helps plants grow if used in small amounts, but eventually plants develop tolerance to it.{{Citation needed|date=October 2012}} GA stimulates the cells of germinating seeds to produce [[messenger RNA|mRNA]] molecules that code for [[Hydrolase|hydrolytic enzymes]]. Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect.<ref name=riley>{{cite web|last=Riley|first=John M.|title=Gibberellic Acid for Fruit Set and Seed Germination|url=http://www.crfg.org/tidbits/gibberellic.html|access-date=26 Oct 2012|archive-date=3 March 2008|archive-url=https://web.archive.org/web/20080303034828/http://www.crfg.org/tidbits/gibberellic.html|url-status=dead}}</ref> It is usually used in concentrations between 0.01 and 10 mg/L.{{Citation needed|date=March 2019}} |
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is produced by submerse fermentation, but this |
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process presented low yield with high production costs and |
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hence higher sale value. One alternative process to reduce |
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costs of the GA3 production is Solid-State Fermentation |
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(SSF) that allows the use of agro-industrial residues.<ref name="GA3"/> |
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Gibberellic acid is a simple [[gibberellin]], a [[Polycyclic compound|pentacyclic]] [[diterpene]] acid promoting growth and elongation of cells. It affects decomposition of plants and helps plants grow if used in small amounts, but eventually plants develop tolerance to it{{Citation needed|date=October 2012}}. GA stimulates the cells of germinating seeds to produce [[messenger RNA|mRNA]] molecules that code for [[Hydrolase|hydrolytic enzymes]]. Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect.<ref name=riley>{{cite web|last=Riley|first=John M.|title=Gibberellic Acid for Fruit Set and Seed Germination|url=http://www.crfg.org/tidbits/gibberellic.html|accessdate=26 Oct 2012}}</ref> It is usually used in concentrations between 0.01 and 10 mg/L. |
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GA was first identified in Japan in 1926, as a metabolic by-product of the plant pathogen ''[[Gibberella fujikuroi]]'' (thus the name), which afflicts [[rice]] plants |
GA was first identified in Japan in 1926, as a metabolic by-product of the plant pathogen ''[[Gibberella fujikuroi]]'' (thus the name), which afflicts [[rice]] plants. ''Fujikuroi''-infected plants develop ''[[bakanae]]'' ("foolish seedling"), which causes them to rapidly elongate beyond their normal adult height. The plants subsequently [[Lodging (agriculture)|lodge]] due to lack of support, and die.<ref name="camara"/> |
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Gibberellins have a number of effects on plant development. |
Gibberellins have a number of effects on plant development. They can stimulate rapid stem and root growth, induce [[mitotic division]] in the leaves of some plants, and increase seed germination rates.<ref>{{cite journal|last1=Edwards|first1=Miriam|title=Dormancy in Seeds of Charlock (Sinapis arvensis L.)|journal=Plant Physiol.|date=1976|volume=58|issue=5|pages=626–630|doi=10.1104/pp.58.5.626|pmc=542271|pmid=16659732}}</ref> |
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==Uses== |
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Gibberellic acid is sometimes used in laboratory and |
Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger [[germination]] in seeds that would otherwise remain [[Dormancy|dormant]].<ref name=riley /> It is also widely used in the grape-growing industry as a hormone to induce the production of larger bunches and bigger grapes, especially [[Sultana (grape)|Thompson seedless]] grapes. In the [[Okanagan]] and [[Creston Valley|Creston]] valleys, it is also used as a [[plant hormone|growth regulator]] in the cherry industry. It is used on Clementine Mandarin oranges, which may otherwise cross-pollinate with other citrus and produce undesirable seeds. Applied directly on the blossoms as a spray, it allows for Clementines to produce a full crop of seedless fruit. |
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It can be used to extend the shelf life of flowers and cut greens in [[floristry]]. The [[shelf life]] of cut shoots of ''[[Polygonatum multiflorum]]'' 'Variegatum' kept in water is about 7 days. To extend their life after cutting, conditioning with gibberellic acid or [[benzyladenine]] is used. This doubles their possible use.<ref name="AA">{{cite journal | vauthors = Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P | title = The longevity of cut ''Polygonatum multiflorum'' (L.) All. shoots depending on postharvest handling| url = https://www.journalssystem.com/agb/The-longevity-of-cut-Polygonatum-multiflorum-L-All-shoots-depending-on-postharvest,176280,0,2.html | journal = Acta Agrobotanica | volume = 76 | issue = | pages = 1–11 | date = December 2023 | pmid = | doi = 10.5586/aa/176280| publisher = Polish Botanical Society | s2cid = | doi-access = free }}</ref> |
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GA is widely used in the barley [[malting]] industry. A GA solution is sprayed on the barley after the steeping process is completed. This stimulates growth in otherwise partly dormant kernels and produces a uniform and rapid growth. |
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==See also== |
==See also== |
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*[[Plant hormone]] |
*[[Plant hormone]] |
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*[[6-Benzylaminopurine]] |
*[[6-Benzylaminopurine]] |
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*[[Auxin]] |
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==References== |
==References== |
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{{Reflist}} |
{{Reflist}} |
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==External links== |
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{{Authority control}} |
{{Authority control}} |
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[[Category:Plant hormones]] |
[[Category:Plant hormones]] |
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[[Category:Cyclohexenols]] |
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[[Category:Tertiary alcohols]] |
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[[Category:Lactones]] |
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[[Category:Heterocyclic compounds with 5 rings]] |
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[[Category:Vinylidene compounds]] |
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[[Category:Plant growth regulators]] |
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Latest revision as of 08:33, 19 July 2024
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| Names | |
|---|---|
| IUPAC name
(3S,3aS,4S,4aS,7S,9aR,9bR,12S)-7,12-Dihydroxy-3-methyl-6-methylene-2-oxoperhydro-4a,7-methano-9b,3-propenoazuleno[1,2-b]furan-4-carboxylic acid
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| Identifiers | |
3D model (JSmol)
|
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| 54346 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.911 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| |
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| Properties | |
| C19H22O6 | |
| Molar mass | 346.379 g·mol−1 |
| Melting point | 233 to 235 °C (451 to 455 °F; 506 to 508 K) (decomposition) |
| 5 g/L (20 °C) | |
| Hazards | |
| GHS labelling: | |
| |
| Warning | |
| H319 | |
| P264, P280, P305+P351+P338, P337+P313 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Gibberellic acid (also called gibberellin A3 or GA3) is a hormone found in plants and fungi.[1] Its chemical formula is C19H22O6. When purified, it is a white to pale-yellow solid.
Plants in their normal state produce large amounts of GA3. It is possible to produce the hormone industrially using microorganisms.[2] Gibberellic acid is a simple gibberellin, a pentacyclic diterpene acid promoting growth and elongation of cells. It affects decomposition of plants and helps plants grow if used in small amounts, but eventually plants develop tolerance to it.[citation needed] GA stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes. Gibberellic acid is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect.[3] It is usually used in concentrations between 0.01 and 10 mg/L.[citation needed]
GA was first identified in Japan in 1926, as a metabolic by-product of the plant pathogen Gibberella fujikuroi (thus the name), which afflicts rice plants. Fujikuroi-infected plants develop bakanae ("foolish seedling"), which causes them to rapidly elongate beyond their normal adult height. The plants subsequently lodge due to lack of support, and die.[2]
Gibberellins have a number of effects on plant development. They can stimulate rapid stem and root growth, induce mitotic division in the leaves of some plants, and increase seed germination rates.[4]
Uses
[edit]Gibberellic acid is sometimes used in laboratory and greenhouse settings to trigger germination in seeds that would otherwise remain dormant.[3] It is also widely used in the grape-growing industry as a hormone to induce the production of larger bunches and bigger grapes, especially Thompson seedless grapes. In the Okanagan and Creston valleys, it is also used as a growth regulator in the cherry industry. It is used on Clementine Mandarin oranges, which may otherwise cross-pollinate with other citrus and produce undesirable seeds. Applied directly on the blossoms as a spray, it allows for Clementines to produce a full crop of seedless fruit.
It can be used to extend the shelf life of flowers and cut greens in floristry. The shelf life of cut shoots of Polygonatum multiflorum 'Variegatum' kept in water is about 7 days. To extend their life after cutting, conditioning with gibberellic acid or benzyladenine is used. This doubles their possible use.[5]
GA is widely used in the barley malting industry. A GA solution is sprayed on the barley after the steeping process is completed. This stimulates growth in otherwise partly dormant kernels and produces a uniform and rapid growth.
See also
[edit]References
[edit]- ^ Silva ALL, Rodrigues C, Costa JL, Machado MP, Penha RO, Biasi LA, Vandenberghe LPS, Soccol CR (2013). "Gibberellic acid fermented extract obtained by solid-state fermentation using citric pulp by Fusarium moniliforme: Influence on Lavandula angustifolia Mill. cultivated in vitro" (PDF). Pakistan Journal of Botany. 45 (6): 2057–2064. Retrieved 26 November 2014.
- ^ a b Camara, M. C. et al (2015) General Aspects and Applications of Gibberelins and Gibberellic Acid in Plants. In: Hardy, J.. (Org.). Gibberellins and Gibberellic Acid: Biosynthesis, Regulation and Physiological Effects. 1ed.Hauppauge: Nova Science Publishers, 2015, v., p. 1-21.
- ^ a b Riley, John M. "Gibberellic Acid for Fruit Set and Seed Germination". Archived from the original on 3 March 2008. Retrieved 26 Oct 2012.
- ^ Edwards, Miriam (1976). "Dormancy in Seeds of Charlock (Sinapis arvensis L.)". Plant Physiol. 58 (5): 626–630. doi:10.1104/pp.58.5.626. PMC 542271. PMID 16659732.
- ^ Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P (December 2023). "The longevity of cut Polygonatum multiflorum (L.) All. shoots depending on postharvest handling". Acta Agrobotanica. 76. Polish Botanical Society: 1–11. doi:10.5586/aa/176280.