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antheraxanthin

natural substances and extractives
2D:
3D:
CAS Number: 640-03-9
FDA UNII: 0306J2L3DV
Category: natural substances and extractives
IUPAC Name: antheraxanthin
InChI : InChI=1/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
Std.InChI: InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
InChIKey : OFNSUWBAQRCHAV-OYQUVCAXBE
Std.InChIKey: OFNSUWBAQRCHAV-OYQUVCAXSA-N
SMILES : CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@]23[C@](O2)(C[C@H](CC3(C)C)O)C)/C)/C
Molar Refractivity : 188.97 ± 0.3 cm3 (est)
Parachor : 1433.2 ± 6.0 cm3 (est)
Index of Refraction : 1.597 ± 0.02 (est)
Surface Tension : 44.7 ± 3.0 dyne/cm (est)
Density : 1.055 ± 0.06 g/cm3 (est)
Polarizability : 74.91 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

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Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
water, 6.407e-010 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

BOC Sciences
For experimental / research use only.
ANTHERAXANTHIN(SH)

Safety Information:

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for antheraxanthin usage levels up to:
not for fragrance use.
Recommendation for antheraxanthin flavor usage levels up to:
not for flavor use.

Safety References:

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281223
National Institute of Allergy and Infectious Diseases:Data
(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Chemidplus:0000640039

References:

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281223
Pubchem (cas):640-03-9

Other Information:

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C08579
HMDB (The Human Metabolome Database):Search
FooDB:FDB014193
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

bean black bean root
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cabbage leaf
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capsicum annuum
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carrot leaf
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cayenne fruit
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corn leaf
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grape fruit
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orange fruit
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orange tissue culture
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papaya
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papaya fruit
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passion fruit
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pepper bell pepper fruit
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rice plant
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rose hips
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soybean leaf
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Synonyms:

beta,beta-carotene-3,3'-diol, 5,6-epoxy-5,6-dihydro- (VAN)
5,6-epoxy-5,6-dihydro-beta,beta-carotene-3,3'-diol
(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

Articles:

PubMed:Characterization of carotenoid profile of Spanish Sanguinos and Verdal prickly pear (Opuntia ficus-indica, spp.) tissues.
PubMed:Photosynthetic parameters and redox homeostasis of Artemisia santonica L. under conditions of Elton region.
PubMed:Response of the seagrass Halophila ovalis to altered light quality in a simulated dredge plume.
PubMed:Seagrass ecophysiological performance under ocean warming and acidification.
PubMed:The green microalga Tetraselmis suecica reduces oxidative stress and induces repairing mechanisms in human cells.
PubMed:Composition by LC-MS/MS of New Carotenoid Esters in Mango and Citrus.
PubMed:Carotenogenesis diversification in phylogenetic lineages of Rhodophyta.
PubMed:Molecular studies on structural changes and oligomerisation of violaxanthin de-epoxidase associated with the pH-dependent activation.
PubMed:Carotenoid metabolism during bilberry (Vaccinium myrtillus L.) fruit development under different light conditions is regulated by biosynthesis and degradation.
PubMed:Photosynthetic pigments of oceanic Chlorophyta belonging to prasinophytes clade VII.
PubMed:Functional and structural characterization of domain truncated violaxanthin de-epoxidase.
PubMed:Carotenoid composition of strawberry tree (Arbutus unedo L.) fruits.
PubMed:Carotenoid profile and retention in yellow-, purple- and red-fleshed potatoes after thermal processing.
PubMed:Photosynthetic Pigments in Diatoms.
PubMed:Photoprotection related to xanthophyll cycle pigments in epiphytic orchids acclimated at different light microenvironments in two tropical dry forests of the Yucatan Peninsula, Mexico.
PubMed:Explaining the variability of the photochemical reflectance index (PRI) at the canopy-scale: Disentangling the effects of phenological and physiological changes.
PubMed:Carotenoid composition of the flowers of Mimulus lewisii and related species: Implications regarding the prevalence and origin of two unique, allenic pigments.
PubMed:Biosynthetic routes of hydroxylated carotenoids (xanthophylls) in Marchantia polymorpha, and production of novel and rare xanthophylls through pathway engineering in Escherichia coli.
PubMed:Positive feedback regulation of a Lycium chinense-derived VDE gene by drought-induced endogenous ABA, and over-expression of this VDE gene improve drought-induced photo-damage in Arabidopsis.
PubMed:Canopy light heterogeneity drives leaf anatomical, eco-physiological, and photosynthetic changes in olive trees grown in a high-density plantation.
PubMed:Colour and carotenoid changes of pasteurised orange juice during storage.
PubMed:Photosynthesis in extreme environments: responses to different light regimes in the Antarctic alga Koliella antarctica.
PubMed:Psidium cattleianum fruit extracts are efficient in vitro scavengers of physiologically relevant reactive oxygen and nitrogen species.
PubMed:Tocopherol-deficient rice plants display increased sensitivity to photooxidative stress.
PubMed:Xanthophyll cycle pool size and composition in several Cosmarium strains (Zygnematophyceae, Streptophyta) are related to their geographic distribution patterns.
PubMed:Putrescine, a fast-acting switch for tolerance against osmotic stress.
PubMed:Erythronium dens-canis L. (Liliaceae): an unusual case of change of leaf mottling.
PubMed:Carotenoid analysis of a liverwort Marchantia polymorpha and functional identification of its lycopene β- and ε-cyclase genes.
PubMed:Alternative electron transports participate in the maintenance of violaxanthin De-epoxidase activity of Ulva sp. under low irradiance.
PubMed:Lupinus albus plants acquire mercury tolerance when inoculated with an Hg-resistant Bradyrhizobium strain.
PubMed:Desiccation induces accumulations of antheraxanthin and zeaxanthin in intertidal macro-alga Ulva pertusa (Chlorophyta).
PubMed:Assessing leaf photoprotective mechanisms using terrestrial LiDAR: towards mapping canopy photosynthetic performance in three dimensions.
PubMed:Comparison of different cells of Haematococcus pluvialis reveals an extensive acclimation mechanism during its aging process: from a perspective of photosynthesis.
PubMed:Or mutation leads to photo-oxidative stress responses in cauliflower (Brassica oleracea) seedlings during de-etiolation.
PubMed:Carotenoid profiling in tubers of different potato (Solanum sp) cultivars: accumulation of carotenoids mediated by xanthophyll esterification.
PubMed:In vitro investigation of the bioaccessibility of carotenoids from raw, frozen and boiled red chili peppers (Capsicum annuum).
PubMed:Occurrence of the PsbS and LhcSR products in the green alga Ulva linza and their correlation with excitation pressure.
PubMed:Degradation of carotenoids in apricot (Prunus armeniaca L.) during drying process.
PubMed:Increase in β-ionone, a carotenoid-derived volatile in zeaxanthin-biofortified sweet corn.
PubMed:Molecular cloning and characterization of violaxanthin de-epoxidase (CsVDE) in cucumber.
PubMed:Characterization of 12 Capsicum varieties by evaluation of their carotenoid profile and pungency determination.
PubMed:Molecular characterization and primary functional analysis of PeVDE, a violaxanthin de-epoxidase gene from bamboo (Phyllostachys edulis).
PubMed:UV-B radiation impacts shoot tissue pigment composition in Allium fistulosum L. cultigens.
PubMed:Cis carotenoids: colorful molecules and free radical quenchers.
PubMed:Thermal degradation kinetics of xanthophylls from blood orange in model and real food systems.
PubMed:Three pools of zeaxanthin in Quercus coccifera leaves during light transitions with different roles in rapidly reversible photoprotective energy dissipation and photoprotection.
PubMed:Antagonist effect between violaxanthin and de-epoxidated pigments in nonphotochemical quenching induction in the qE deficient brown alga Macrocystis pyrifera.
PubMed:Cashew apple (Anacardium occidentale L.) extract from by-product of juice processing: a focus on carotenoids.
PubMed:Independent fluctuations of malate and citrate in the CAM species Clusia hilariana Schltdl. under low light and high light in relation to photoprotection.
PubMed:Decreased photochemical efficiency of photosystem II following sunlight exposure of shade-grown leaves of avocado: because of, or in spite of, two kinetically distinct xanthophyll cycles?
PubMed:Effect of heat processing on the profile of pigments and antioxidant capacity of green and red jalapeño peppers.
PubMed:Cloning and functional characterization of a gene for capsanthin-capsorubin synthase from tiger lily (Lilium lancifolium Thunb. 'Splendens').
PubMed:Effect of microfluidization on bioaccessibility of carotenoids from Chlorella ellipsoidea during simulated digestion.
PubMed:Identification and quantitative analysis of carotenoids and their esters from sarsaparilla (Smilax aspera L.) berries.
PubMed:Violaxanthin de-epoxidase is rate-limiting for non-photochemical quenching under subsaturating light or during chilling in Arabidopsis.
PubMed:Acclimatory responses of Arabidopsis to fluctuating light environment: comparison of different sunfleck regimes and accessions.
PubMed:Identification and quantification, by HPLC-DAD-MS/MS, of carotenoids and phenolic compounds from the Amazonian fruit Caryocar villosum.
PubMed:Thermal degradation kinetics of neoxanthin, violaxanthin, and antheraxanthin in virgin olive oils.
PubMed:Determination of carotenoids in Taraxacum formosanum by HPLC-DAD-APCI-MS and preparation by column chromatography.
PubMed:Violaxanthin and diadinoxanthin de-epoxidation in various model lipid systems.
PubMed:Seasonal changes of violaxanthin cycle pigment de-epoxidation in wintergreen and evergreen plants.
PubMed:UVR defense mechanisms in eurytopic and invasive Gracilaria vermiculophylla (Gracilariales, Rhodophyta).
PubMed:Activation of violaxanthin cycle in darkness is a common response to different abiotic stresses: a case study in Pelvetia canaliculata.
PubMed:Effects of cadmium on cork oak (Quercus suber L.) plants grown in hydroponics.
PubMed:The xanthophyll cycle and antioxidative defense system are enhanced in the wheat hybrid subjected to high light stress.
PubMed:Photoprotection in the brown alga Macrocystis pyrifera: evolutionary implications.
PubMed:Non-photochemical fluorescence quenching in Chromera velia is enabled by fast violaxanthin de-epoxidation.
PubMed:Carotenoid composition and vitamin A value in ají (Capsicum baccatum L.) and rocoto (C. pubescens R. & P.), 2 pepper species from the Andean region.
PubMed:A model for describing the light response of the nonphotochemical quenching of chlorophyll fluorescence.
PubMed:Lutein from deepoxidation of lutein epoxide replaces zeaxanthin to sustain an enhanced capacity for nonphotochemical chlorophyll fluorescence quenching in avocado shade leaves in the dark.
PubMed:Determination of carotenoids by liquid chromatography/mass spectrometry: effect of several dopants.
PubMed:Relationship between xanthophyll cycle and non-photochemical quenching in rice (Oryza sativa L.) plants in response to light stress.
PubMed:Photosystem II fluorescence lifetime imaging in avocado leaves: contributions of the lutein-epoxide and violaxanthin cycles to fluorescence quenching.
PubMed:Origin of absorption changes associated with photoprotective energy dissipation in the absence of zeaxanthin.
PubMed:Chemistry and biotechnology of carotenoids.
PubMed:Reversal of multidrug resitance by natural substances from plants.
PubMed:Photosynthesis and photoprotection in coffee leaves is affected by nitrogen and light availabilities in winter conditions.
PubMed:Light stress is not effective to enhanced crassulacean acid metabolism.
PubMed:Regulation and function of xanthophyll cycle-dependent photoprotection in algae.
PubMed:Photosynthetic response of pepper plants to wilt induced by Verticillium dahliae and soil water deficit.
PubMed:A large scale method for preparation of plant thylakoids for use in body weight regulation.
PubMed:Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS.
PubMed:Adaptation of the obligate CAM plant Clusia alata to light stress: Metabolic responses.
PubMed:Carotenoids with anti-Helicobacter pylori activity from Golden delicious apple.
PubMed:Lutein accumulation in the absence of zeaxanthin restores nonphotochemical quenching in the Arabidopsis thaliana npq1 mutant.
PubMed:Increase in nutritionally important sweet corn kernel carotenoids following Mesotrione and atrazine applications.
PubMed:The metabolomics of carotenoids in engineered cell factory.
PubMed:Water deficit alters differentially metabolic pathways affecting important flavor and quality traits in grape berries of Cabernet Sauvignon and Chardonnay.
PubMed:Highly sensitive and accurate profiling of carotenoids by supercritical fluid chromatography coupled with mass spectrometry.
PubMed:Physiological, biochemical, and ultrastructural responses of the green macroalga Urospora penicilliformis from Arctic Spitsbergen to UV radiation.
PubMed:New transgenic line of Arabidopsis thaliana with partly disabled zeaxanthin epoxidase activity displays changed carotenoid composition, xanthophyll cycle activity and non-photochemical quenching kinetics.
PubMed:Seasonal changes in abundance and phosphorylation status of photosynthetic proteins in eastern white pine and balsam fir.
PubMed:Photosynthesis, non-photochemical pathways and activities of antioxidant enzymes in a resilient evergreen oak under different climatic conditions from a valley-savanna in Southwest China.
PubMed:Pharmacognostic research on Viola tricolor L. (Violaceae).
PubMed:Does variability in carotenoid composition and concentration in tissues of the breast and reproductive tract in women depend on type of lesion?
PubMed:De novo synthesis and degradation of Lx and V cycle pigments during shade and sun acclimation in avocado leaves.
PubMed:PHOTOINHIBITION IN RED ALGAL SPECIES WITH DIFFERENT CAROTENOID PROFILES(1).
PubMed:Photosynthesis, chloroplast pigments, and antioxidants in Pinus canariensis under free-air ozone fumigation.
PubMed:Mechanism and regulation of the violaxanthin cycle: the role of antenna proteins and membrane lipids.
PubMed:Antiproliferative effects of carotenoids extracted from Chlorella ellipsoidea and Chlorella vulgaris on human colon cancer cells.
PubMed:HPLC-DAD-MS(n) characterisation of carotenoids from apricots and pumpkins for the evaluation of fruit product authenticity.
PubMed:Analysis of native carotenoid composition in orange juice using C30 columns in tandem.
PubMed:Overexpression of 1-Deoxy-D-xylulose-5-phosphate reductoisomerase gene in chloroplast contributes to increment of isoprenoid production.
PubMed:The role of lutein in the acclimation of higher plant chloroplast membranes to suboptimal conditions.
PubMed:Application of comprehensive two-dimensional liquid chromatography to elucidate the native carotenoid composition in red orange essential oil.
PubMed:Fast and reversible response of thylakoid-associated polyamines during and after UV-B stress: a comparative study of the wild type and a mutant lacking chlorophyll b of unicellular green alga Scenedesmus obliquus.
PubMed:Short- and long-term modulation of the lutein epoxide and violaxanthin cycles in two species of the Lauraceae: sweet bay laurel (Laurus nobilis L.) and avocado (Persea americana Mill.).
PubMed:A pronounced light-induced zeaxanthin formation accompanied by an unusually slight increase in non-photochemical quenching: a study with barley leaves treated with methyl viologen at moderate light.
PubMed:Pittosporumxanthins, cycloaddition products of carotenoids with alpha-tocopherol from seeds of Pittosporum tobira.
PubMed:Occurrence of neoxanthin and lutein epoxide cycle in parasitic Cuscuta species.
PubMed:The ABA1 gene and carotenoid biosynthesis are required for late skotomorphogenic growth in Arabidopsis thaliana.
PubMed:Nicotiana glauca engineered for the production of ketocarotenoids in flowers and leaves by expressing the cyanobacterial crtO ketolase gene.
PubMed:Fast, sensitive, and inexpensive alternative to analytical pigment HPLC: quantification of chlorophylls and carotenoids in crude extracts by fitting with Gauss peak spectra.
PubMed:Enhanced carnosic acid levels in two rosemary accessions exposed to cold stress conditions.
PubMed:Photoinhibition, carotenoid composition and the co-regulation of photochemical and non-photochemical quenching in neotropical savanna trees.
PubMed:Carotenoids, color, and ascorbic acid content of a novel frozen-marketed orange juice.
PubMed:Lutein is needed for efficient chlorophyll triplet quenching in the major LHCII antenna complex of higher plants and effective photoprotection in vivo under strong light.
PubMed:Pigments in avocado tissue and oil.
PubMed:Winter acclimation of PsbS and related proteins in the evergreen Arctostaphylos uva-ursi as influenced by altitude and light environment.
PubMed:Winter down-regulation of intrinsic photosynthetic capacity coupled with up-regulation of Elip-like proteins and persistent energy dissipation in a subalpine forest.
PubMed:Carotenoid profile modification during refrigerated storage in untreated and pasteurized orange juice and orange juice treated with high-intensity pulsed electric fields.
PubMed:The roles of specific xanthophylls in light utilization.
PubMed:[The current concepts of functional role of carotenoids in the eukaryotic chloroplasts].
PubMed:Metabolic engineering of potato tuber carotenoids through tuber-specific silencing of lycopene epsilon cyclase.
PubMed:Leaf angle responds to nitrogen supply in eucalypt seedlings. Is it a photoprotective mechanism?
PubMed:Evidence for a rebinding of antheraxanthin to the light-harvesting complex during the epoxidation reaction of the violaxanthin cycle.
PubMed:Quantitative variations of individual carotenoids in relationship with the leaflet development of six species of the genus Ceratozamia (Cycads).
PubMed:Metabolic responses to water deficit in two Eucalyptus globulus clones with contrasting drought sensitivity.
PubMed:Isolation and characterization of a xanthophyll-rich fraction from the thylakoid membrane of Dunaliella salina(green algae).
PubMed:Identification of isolutein (lutein epoxide) as cis-antheraxanthin in orange juice.
PubMed:Photosystem II efficiency and mechanisms of energy dissipation in iron-deficient, field-grown pear trees (Pyrus communis L.).
PubMed:Characterization of acclimation of Hordeum vulgare to high irradiation based on different responses of photosynthetic activity and pigment composition.
PubMed:Influence of Ca(2+) on the thylakoid lumen violaxanthin de-epoxidase activity through Ca(2+) gating of H(+) flux at the CF(o) H(+) channel.
PubMed:The inhibited xanthophyll cycle is responsible for the increase in sensitivity to low temperature photoinhibition in rice leaves fed with glutathione.
PubMed:Antisense suppression of violaxanthin de-epoxidase in tobacco does not affect plant performance in controlled growth conditions.
PubMed:Fe Resupply to Fe-deficient Sugar Beet Plants Leads to Rapid Changes in the Violaxanthin Cycle and other Photosynthetic Characteristics without Significant de novo Chlorophyll Synthesis.
PubMed:Xanthophyll cycle-dependent nonphotochemical quenching in Photosystem II: Mechanistic insights gained from Arabidopsis thaliana L. mutants that lack violaxanthin deepoxidase activity and/or lutein.
PubMed:Dependence of photosynthesis and energy dissipation activity upon growth form and light environment during the winter.
PubMed:Suppression of zeaxanthin formation does not reduce photosynthesis and growth of transgenic tobacco under field conditions.
PubMed:Transgenic tobacco with suppressed zeaxanthin formation is susceptible to stress-induced photoinhibition.
PubMed:Non-photochemical chlorophyll fluorescence quenching and structural rearrangements induced by low pH in intact cells of Chlorella fusca (Chlorophyceae) and Mantoniella squamata (Prasinophyceae).
PubMed:Identification of carotenoids in ovarian tissue in women.
PubMed:Tissue specific protochlorophyll(ide) forms in dark-forced shoots of grapevine (Vitis viniferaL.).
PubMed:A mutational analysis of the ABA1 gene of Arabidopsis thaliana highlights the involvement of ABA in vegetative development.
PubMed:Towards elucidating the energy of the first excited singlet state of xanthophyll cycle pigments by X-ray absorption spectroscopy.
PubMed:Balance of xanthophylls molecular and protonated molecular ions in electrospray ionization.
PubMed:Herbicidal and antioxidant responses of transgenic rice overexpressing Myxococcus xanthus protoporphyrinogen oxidase.
PubMed:Effects of aluminum on light energy utilization and photoprotective systems in citrus leaves.
PubMed:Seasonal changes in photosynthesis and photoprotection in a Quercus ilex subsp. ballota woodland located in its upper altitudinal extreme in the Iberian Peninsula.
PubMed:Photosynthetic acclimation to dynamic changes in environmental conditions associated with deciduous overstory p
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