Abscisic aldehyde

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Abscisic aldehyde
Abscisic aldehyde.png
Abscisic aldehyde-3D-balls.png
Names
Preferred IUPAC name
(2Z,4E)-5-[(1S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienal
Other names
Abscisyl aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C15H20O3/c1-11(6-8-16)5-7-15(18)12(2)9-13(17)10-14(15,3)4/h5-9, 18H,10H2,1-4H3/b7-5+,11-6-/t15-/m1/s1
    Key: RIKWDZWVHUIUAM-KICRZJJPSA-N
  • CC1=CC(=O)CC([C@]1(/C=C/C(=C\C=O)/C)O)(C)C
Properties
C15H20O3
Molar mass 248.322 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Abscisic aldehyde is an intermediate in the biosynthesis of the plant hormone abscisic acid. [1] [2] It is produced by the dehydrogenation of xanthoxin by xanthoxin dehydrogenases, which is an NAD+ dependent short-chain dehydrogenase, [3] followed by selective oxidation by abscisic aldehyde oxygenase. [4]

Xanthtoaba.svg

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In enzymology, a xanthoxin dehydrogenase (EC 1.1.1.288) is an enzyme that catalyzes the chemical reaction

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Neoxanthin Chemical compound

Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is often present in two forms: all-trans and 9-cis isomers. It is produced from violaxanthin, but a suspected neoxanthin synthase is still to be confirmed. Two different genes were confirmed to be implied in violaxanthin conversion to neoxanthin in Arabidopsis and tomato. It has a specific role in protection against photooxidative stress. It is a major xanthophyll found in green leafy vegetables such as spinach.

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Xanthoxin is an intermediate in the biosynthesis of the plant hormone abscisic acid.

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References

  1. Ram K. Sindhu, David H. Griffin and Daniel C. Walton (1990). "Abscisic Aldehyde Is an Intermediate in the Enzymatic Conversion of Xanthoxin to Abscisic Acid in Phaseolus vulgaris L. Leaves". Plant Physiology . 93 (2): 689–694. doi:10.1104/pp.93.2.689. PMC   1062571 . PMID   16667524.
  2. Seo, M; Koshiba, T (2002). "Complex regulation of ABA biosynthesis in plants". Trends in Plant Science . 7 (1): 41–8. doi:10.1016/S1360-1385(01)02187-2. PMID   11804826.
  3. Gonzalez-Guzman, M. (25 July 2002). "The Short-Chain Alcohol Dehydrogenase ABA2 Catalyzes the Conversion of Xanthoxin to Abscisic Aldehyde". The Plant Cell Online. 14 (8): 1833–1846. doi:10.1105/tpc.002477. PMC   151468 . PMID   12172025.
  4. Seo, Mitsunori; Koiwai, Hanae; Akaba, Shuichi; Komano, Teruya; Oritani, Takayuki; Kamiya, Yuji; Koshiba, Tomokazu (August 2000). "Abscisic aldehyde oxidase in leaves of Arabidopsis thaliana". The Plant Journal. 23 (4): 481–488. doi: 10.1046/j.1365-313x.2000.00812.x . PMID   10972874.