Neoxanthin

Last updated
Neoxanthin
Neoxanthin2.svg
Names
IUPAC name
(1R,3S)-6-((R,3E,5E,7E,9E,11E,13E,15Z,17E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene)-1,5,5-trimethylcyclohexane-1,3-diol
Other names
Foliaxanthin; Neoxanthine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22-,33-,34-,38+,39+,40-/m0/s1
  • CC(/C=C/[C@@]12[C@@](O2)(C)C[C@@H](O)CC1(C)C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C([H])=[C@@]=C3C(C)(C)C[C@H](O)C[C@]3(O)C
Properties
C40H56O4
Molar mass 600.884 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
all-trans Neoxanthin Neoxanthin.svg
all-trans Neoxanthin

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 [1] is still to be confirmed. Two different genes were confirmed to be implied in violaxanthin conversion to neoxanthin in Arabidopsis and tomato. [2] [3] It has a specific role in protection against photooxidative stress. [4] It is a major xanthophyll found in green leafy vegetables such as spinach.

Related Research Articles

<span class="mw-page-title-main">Plant hormone</span> Chemical compounds that regulate plant growth and development

Plant hormones are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of organ size, pathogen defense, stress tolerance and reproductive development. Unlike in animals each plant cell is capable of producing hormones. Went and Thimann coined the term "phytohormone" and used it in the title of their 1937 book.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

Gibberellins (GAs) are plant hormones that regulate various developmental processes, including stem elongation, germination, dormancy, flowering, flower development, and leaf and fruit senescence. GAs are one of the longest-known classes of plant hormone. It is thought that the selective breeding of crop strains that were deficient in GA synthesis was one of the key drivers of the "green revolution" in the 1960s, a revolution that is credited to have saved over a billion lives worldwide.

<span class="mw-page-title-main">Chromoplast</span> Pigment-bearing organelle in plant cells

Chromoplasts are plastids, heterogeneous organelles responsible for pigment synthesis and storage in specific photosynthetic eukaryotes. It is thought that like all other plastids including chloroplasts and leucoplasts they are descended from symbiotic prokaryotes.

<span class="mw-page-title-main">Jasmonate</span> Lipid-based plant hormones

Jasmonate (JA) and its derivatives are lipid-based plant hormones that regulate a wide range of processes in plants, ranging from growth and photosynthesis to reproductive development. In particular, JAs are critical for plant defense against herbivory and plant responses to poor environmental conditions and other kinds of abiotic and biotic challenges. Some JAs can also be released as volatile organic compounds (VOCs) to permit communication between plants in anticipation of mutual dangers.

<span class="mw-page-title-main">Abscisic acid</span> Plant hormone

Abscisic acid is a plant hormone. ABA functions in many plant developmental processes, including seed and bud dormancy, the control of organ size and stomatal closure. It is especially important for plants in the response to environmental stresses, including drought, soil salinity, cold tolerance, freezing tolerance, heat stress and heavy metal ion tolerance.

<span class="mw-page-title-main">Hydrotropism</span>

Hydrotropism is a plant's growth response in which the direction of growth is determined by a stimulus or gradient in water concentration. A common example is a plant root growing in humid air bending toward a higher relative humidity level.

<span class="mw-page-title-main">Plant senescence</span> Process of aging in plants

Plant senescence is the process of aging in plants. Plants have both stress-induced and age-related developmental aging. Chlorophyll degradation during leaf senescence reveals the carotenoids, such as anthocyanin and xanthophylls, which are the cause of autumn leaf color in deciduous trees. Leaf senescence has the important function of recycling nutrients, mostly nitrogen, to growing and storage organs of the plant. Unlike animals, plants continually form new organs and older organs undergo a highly regulated senescence program to maximize nutrient export.

CRT is the gene cluster responsible for the biosynthesis of carotenoids. Those genes are found in eubacteria, in algae and are cryptic in Streptomyces griseus.

<span class="mw-page-title-main">Acetolactate synthase</span> Class of enzymes

The acetolactate synthase (ALS) enzyme is a protein found in plants and micro-organisms. ALS catalyzes the first step in the synthesis of the branched-chain amino acids.

Drought tolerance is the ability by which a plant maintains its biomass production during arid or drought conditions. Some plants are naturally adapted to dry conditions, surviving with protection mechanisms such as desiccation tolerance, detoxification, or repair of xylem embolism. Other plants, specifically crops like corn, wheat, and rice, have become increasingly tolerant to drought with new varieties created via genetic engineering. From an evolutionary perspective, the type of mycorrhizal associations formed in the roots of plants can determine how fast plants can adapt to drought.

In enzymology, an abscisic-aldehyde oxidase (EC 1.2.3.14) is an enzyme that catalyzes the chemical reaction

In enzymology, a neoxanthin synthase is an enzyme that catalyzes the chemical reaction:

Dehydrin (DHN) is a multi-family of proteins present in plants that is produced in response to cold and drought stress. DHNs are hydrophilic, reliably thermostable, and disordered. They are stress proteins with a high number of charged amino acids that belong to the Group II Late Embryogenesis Abundant (LEA) family. DHNs are primarily found in the cytoplasm and nucleus but more recently, they have been found in other organelles, like mitochondria and chloroplasts.

<span class="mw-page-title-main">Phaseic acid</span> Chemical compound

Phaseic acid is a terpenoid catabolite of abscisic acid. Like abscisic acid, it is a plant hormone associated with photosynthesis arrest and abscission.

<span class="mw-page-title-main">9-cis-epoxycarotenoid dioxygenase</span> Class of enzymes

9-cis-epoxycarotenoid dioxygenase (EC 1.13.11.51, nine-cis-epoxycarotenoid dioxygenase, NCED, AtNCED3, PvNCED1, VP14) is an enzyme in the biosynthesis of abscisic acid (ABA), with systematic name 9-cis-epoxycarotenoid 11,12-dioxygenase. This enzyme catalyses the following chemical reaction

Zeaxanthin epoxidase (EC 1.14.13.90, Zea-epoxidase) is an enzyme with systematic name zeaxanthin,NAD(P)H:oxygen oxidoreductase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Strigolactone</span> Group of chemical compounds

Strigolactones are a group of chemical compounds produced by roots of plants. Due to their mechanism of action, these molecules have been classified as plant hormones or phytohormones. So far, strigolactones have been identified to be responsible for three different physiological processes: First, they promote the germination of parasitic organisms that grow in the host plant's roots, such as Strigalutea and other plants of the genus Striga. Second, strigolactones are fundamental for the recognition of the plant by symbiotic fungi, especially arbuscular mycorrhizal fungi, because they establish a mutualistic association with these plants, and provide phosphate and other soil nutrients. Third, strigolactones have been identified as branching inhibition hormones in plants; when present, these compounds prevent excess bud growing in stem terminals, stopping the branching mechanism in plants.

Jian-Kang Zhu is a plant scientist, researcher and academic. He is a Senior Principal Investigator in the Shanghai Center for Plant Stress Biology, Chinese Academy of Sciences (CAS). He is also the Academic Director of CAS Center of Excellence in Plant Sciences.

Hydraulic signals in plants are detected as changes in the organism's water potential that are caused by environmental stress like drought or wounding. The cohesion and tension properties of water allow for these water potential changes to be transmitted throughout the plant.

References

  1. Bouvier, Florence; D'harlingue, Alain; Backhaus, Ralph A.; Kumagai, Monto H.; Camara, Bilal (2000). "Identification of neoxanthin synthase as a carotenoid cyclase paralog". European Journal of Biochemistry. 267 (21): 6346–6352. doi: 10.1046/j.1432-1327.2000.01722.x . PMID   11029576.
  2. North, Helen M.; de Almeida, Aurélie; Boutin, Jean-Pierre; Frey, Anne; To, Alexandra; Botran, Lucy; Sotta, Bruno; Marion-Poll, Annie (2007). "The Arabidopsis ABA-deficient mutant aba4 demonstrates that the major route for stress-induced ABA accumulation is via neoxanthin isomers". Plant Journal. 50 (5): 810–824. doi: 10.1111/j.1365-313X.2007.03094.x . PMID   17470058.
  3. Neuman, Hadar; Galpaz, Navot; Cunningham Jr, Francis X.; Zamir, Dani; Hirschberg, Joseph (2014). "The tomato mutation nxd1 reveals a gene necessary for neoxanthin biosynthesis and demonstrates that violaxanthin is a sufficient precursor for abscisic acid biosynthesis". Plant Journal. 78 (1): 80–93. doi:10.1111/tpj.12451. PMID   24506237.
  4. Dall'osto, Luca; Cazzaniga, Stefano; North, Helen; Marion-Poll, Annie; Bassi, Roberto (2007). "The Arabidopsis aba4-1 mutant reveals a specific function for neoxanthin in protection against photooxidative stress". Plant Cell. 19 (3): 1048–1064. doi:10.1105/tpc.106.049114. PMC   1867355 . PMID   17351115.