meso-Zeaxanthin (BioDeep_00000015328)

   


代谢物信息卡片


(3R,3S)-beta,beta-Carotene-3,3-diol

化学式: C40H56O2 (568.4280076)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 2.27%

分子结构信息

SMILES: C1C(C)(C)C(/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2=C(C)C[C@H](O)CC2(C)C)=C(C)C[C@H]1O
InChI: InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+

描述信息

A carotenol that is beta,beta-carotene carrying two hydroxy substituents at positions 3 and 3 (the 3R,3S-diastereomer). It is rarely found in diet and is believed to be formed at the macula by metabolic transformations of ingested carotenoids.
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

3 个代谢物同义名

meso-Zeaxanthin; (3R,3S)-beta,beta-Carotene-3,3-diol; (3R,3S)-Zeaxanthin



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Rebecca Power, John M Nolan, Alfonso Prado-Cabrero, Warren Roche, Robert Coen, Tommy Power, Ríona Mulcahy. Omega-3 fatty acid, carotenoid and vitamin E supplementation improves working memory in older adults: A randomised clinical trial. Clinical nutrition (Edinburgh, Scotland). 2022 02; 41(2):405-414. doi: 10.1016/j.clnu.2021.12.004. [PMID: 34999335]
  • Richard A Bone, Pinakin Gunvant Davey, Betzabe O Roman, David W Evans. Efficacy of Commercially Available Nutritional Supplements: Analysis of Serum Uptake, Macular Pigment Optical Density and Visual Functional Response. Nutrients. 2020 May; 12(5):. doi: 10.3390/nu12051321. [PMID: 32384663]
  • Nicole T Stringham, Philip V Holmes, James M Stringham. Effects of macular xanthophyll supplementation on brain-derived neurotrophic factor, pro-inflammatory cytokines, and cognitive performance. Physiology & behavior. 2019 11; 211(?):112650. doi: 10.1016/j.physbeh.2019.112650. [PMID: 31425700]
  • Nicole Tressa Stringham, Philip V Holmes, James M Stringham. Supplementation with macular carotenoids reduces psychological stress, serum cortisol, and sub-optimal symptoms of physical and emotional health in young adults. Nutritional neuroscience. 2018 May; 21(4):286-296. doi: 10.1080/1028415x.2017.1286445. [PMID: 28198205]
  • Rebecca Power, Robert F Coen, Stephen Beatty, Riona Mulcahy, Rachel Moran, Jim Stack, Alan N Howard, John M Nolan. Supplemental Retinal Carotenoids Enhance Memory in Healthy Individuals with Low Levels of Macular Pigment in A Randomized, Double-Blind, Placebo-Controlled Clinical Trial. Journal of Alzheimer's disease : JAD. 2018; 61(3):947-961. doi: 10.3233/jad-170713. [PMID: 29332050]
  • Rajalekshmy Shyam, Aruna Gorusupudi, Kelly Nelson, Martin P Horvath, Paul S Bernstein. RPE65 has an additional function as the lutein to meso-zeaxanthin isomerase in the vertebrate eye. Proceedings of the National Academy of Sciences of the United States of America. 2017 10; 114(41):10882-10887. doi: 10.1073/pnas.1706332114. [PMID: 28874556]
  • O S Ademowo, H K I Dias, I Milic, A Devitt, R Moran, R Mulcahy, A N Howard, J M Nolan, H R Griffiths. Phospholipid oxidation and carotenoid supplementation in Alzheimer's disease patients. Free radical biology & medicine. 2017 07; 108(?):77-85. doi: 10.1016/j.freeradbiomed.2017.03.008. [PMID: 28315450]
  • Martin P Horvath, Evan W George, Quang T Tran, Kody Baumgardner, Gabe Zharov, Sarah Lee, Hassan Sharifzadeh, Saeed Shihab, Ty Mattinson, Binxing Li, Paul S Bernstein. Structure of the lutein-binding domain of human StARD3 at 1.74 Å resolution and model of a complex with lutein. Acta crystallographica. Section F, Structural biology communications. 2016 08; 72(Pt 8):609-18. doi: 10.1107/s2053230x16010694. [PMID: 27487925]
  • John M Nolan, Rebecca Power, Jim Stringham, Jessica Dennison, Jim Stack, David Kelly, Rachel Moran, Kwadwo O Akuffo, Laura Corcoran, Stephen Beatty. Enrichment of Macular Pigment Enhances Contrast Sensitivity in Subjects Free of Retinal Disease: Central Retinal Enrichment Supplementation Trials - Report 1. Investigative ophthalmology & visual science. 2016 Jun; 57(7):3429-39. doi: 10.1167/iovs.16-19520. [PMID: 27367585]
  • Aruna Gorusupudi, Rajalekshmy Shyam, Binxing Li, Preejith Vachali, Yumna K Subhani, Kelly Nelson, Paul S Bernstein. Developmentally Regulated Production of meso-Zeaxanthin in Chicken Retinal Pigment Epithelium/Choroid and Retina. Investigative ophthalmology & visual science. 2016 Apr; 57(4):1853-61. doi: 10.1167/iovs.16-19111. [PMID: 27082300]
  • Rohini Vishwanathan, Wolfgang Schalch, Elizabeth J Johnson. Macular pigment carotenoids in the retina and occipital cortex are related in humans. Nutritional neuroscience. 2016; 19(3):95-101. doi: 10.1179/1476830514y.0000000141. [PMID: 25752849]
  • David I Thurnham, John M Nolan, Alan N Howard, Stephen Beatty. Macular response to supplementation with differing xanthophyll formulations in subjects with and without age-related macular degeneration. Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie. 2015 Aug; 253(8):1231-43. doi: 10.1007/s00417-014-2811-3. [PMID: 25311651]
  • Norihiro Nagai, Kanako Izumi-Nagai, Misa Suzuki, Hajime Shinoda, Takashi Koto, Atsuro Uchida, Hiroshi Mochimaru, Yohei Tomita, Seiji Miyake, Saori Kobayashi, Mariko Sasaki, Kazuo Tsubota, Yoko Ozawa. Association of macular pigment optical density with serum concentration of oxidized low-density lipoprotein in healthy adults. Retina (Philadelphia, Pa.). 2015 Apr; 35(4):820-6. doi: 10.1097/iae.0000000000000382. [PMID: 25473786]
  • Katherine A Meagher, David I Thurnham, Stephen Beatty, Alan N Howard, Eithne Connolly, Wayne Cummins, John M Nolan. Serum response to supplemental macular carotenoids in subjects with and without age-related macular degeneration. The British journal of nutrition. 2013 Jul; 110(2):289-300. doi: 10.1017/s0007114512004837. [PMID: 23211762]
  • Alikkunjhi P Firdous, Edakkadath R Sindhu, Viswanathan Ramnath, Ramadasan Kuttan. Amelioration of radiation-induced damages in mice by carotenoid meso-zeaxanthin. International journal of radiation biology. 2013 Mar; 89(3):171-81. doi: 10.3109/09553002.2013.741283. [PMID: 23078295]
  • A P Firdous, Ramadasan Kuttan. Amelioration of cisplatin-induced toxicity in mice by carotenoid meso-zeaxanthin. Human & experimental toxicology. 2012 Jul; 31(7):710-7. doi: 10.1177/0960327111431707. [PMID: 22241628]
  • Preejith Vachali, Binxing Li, Kelly Nelson, Paul S Bernstein. Surface plasmon resonance (SPR) studies on the interactions of carotenoids and their binding proteins. Archives of biochemistry and biophysics. 2012 Mar; 519(1):32-7. doi: 10.1016/j.abb.2012.01.006. [PMID: 22286029]
  • Alikunjhi P Firdous, Ramadasan Kuttan. Chemo protective activity of carotenoid meso-zeaxanthin against doxorubicin-induced cardio toxicity. Journal of experimental therapeutics & oncology. 2012; 10(2):101-6. doi: ". [PMID: 23350349]
  • Eithne E Connolly, Stephen Beatty, James Loughman, Alan N Howard, Michael S Louw, John M Nolan. Supplementation with all three macular carotenoids: response, stability, and safety. Investigative ophthalmology & visual science. 2011 Nov; 52(12):9207-17. doi: 10.1167/iovs.11-8025. [PMID: 21979997]
  • Alikunjhi P Firdous, Edakkadath R Sindhu, Ramadasan Kuttan. Hepato-protective potential of carotenoid meso-zeaxanthin against paracetamol, CCl4 and ethanol induced toxicity. Indian journal of experimental biology. 2011 Jan; 49(1):44-9. doi: . [PMID: 21365995]
  • Eithne E Connolly, Stephen Beatty, David I Thurnham, James Loughman, Alan N Howard, Jim Stack, John M Nolan. Augmentation of macular pigment following supplementation with all three macular carotenoids: an exploratory study. Current eye research. 2010 Apr; 35(4):335-51. doi: 10.3109/02713680903521951. [PMID: 20373901]
  • David I Thurnham, Aurélie Trémel, Alan N Howard. A supplementation study in human subjects with a combination of meso-zeaxanthin, (3R,3'R)-zeaxanthin and (3R,3'R,6'R)-lutein. The British journal of nutrition. 2008 Dec; 100(6):1307-14. doi: 10.1017/s0007114508971336. [PMID: 18405400]
  • Prakash Bhosale, Bogdan Serban, Da You Zhao, Paul S Bernstein. Identification and metabolic transformations of carotenoids in ocular tissues of the Japanese quail Coturnix japonica. Biochemistry. 2007 Aug; 46(31):9050-7. doi: 10.1021/bi700558f. [PMID: 17630780]
  • Yingming Wang, Sonja L Connor, Wei Wang, Elizabeth J Johnson, William E Connor. The selective retention of lutein, meso-zeaxanthin and zeaxanthin in the retina of chicks fed a xanthophyll-free diet. Experimental eye research. 2007 Mar; 84(3):591-8. doi: 10.1016/j.exer.2006.11.013. [PMID: 17227674]
  • Jörg Schlatterer, Svenja Maurer, Dietmar E Breithaupt. Quantification of 3R,3'R-zeaxanthin in plant derived food by a diastereomeric dilution assay applying chiral high-performance liquid chromatography. Journal of chromatography. A. 2006 Dec; 1137(2):216-22. doi: 10.1016/j.chroma.2006.10.027. [PMID: 17070819]
  • Prakash Bhosale, Paul S Bernstein. Synergistic effects of zeaxanthin and its binding protein in the prevention of lipid membrane oxidation. Biochimica et biophysica acta. 2005 May; 1740(2):116-21. doi: 10.1016/j.bbadis.2005.02.002. [PMID: 15949677]
  • Shazia S Ahmed, McGregor N Lott, Dennis M Marcus. The macular xanthophylls. Survey of ophthalmology. 2005 Mar; 50(2):183-93. doi: 10.1016/j.survophthal.2004.12.009. [PMID: 15749308]
  • Dietmar E Breithaupt, Philipp Weller, Maike Wolters, Andreas Hahn. Comparison of plasma responses in human subjects after the ingestion of 3R,3R'-zeaxanthin dipalmitate from wolfberry (Lycium barbarum) and non-esterified 3R,3R'-zeaxanthin using chiral high-performance liquid chromatography. The British journal of nutrition. 2004 May; 91(5):707-13. doi: 10.1079/bjn20041105. [PMID: 15137922]
  • Frederick Khachik, Fabiana F de Moura, Da-You Zhao, Claude-Pierre Aebischer, Paul S Bernstein. Transformations of selected carotenoids in plasma, liver, and ocular tissues of humans and in nonprimate animal models. Investigative ophthalmology & visual science. 2002 Nov; 43(11):3383-92. doi: NULL. [PMID: 12407147]
  • J T Landrum, R A Bone. Lutein, zeaxanthin, and the macular pigment. Archives of biochemistry and biophysics. 2001 Jan; 385(1):28-40. doi: 10.1006/abbi.2000.2171. [PMID: 11361022]
  • R A Bone, J T Landrum, L M Friedes, C M Gomez, M D Kilburn, E Menendez, I Vidal, W Wang. Distribution of lutein and zeaxanthin stereoisomers in the human retina. Experimental eye research. 1997 Feb; 64(2):211-8. doi: 10.1006/exer.1996.0210. [PMID: 9176055]
  • R A Bone, J T Landrum, G W Hime, A Cains, J Zamor. Stereochemistry of the human macular carotenoids. Investigative ophthalmology & visual science. 1993 May; 34(6):2033-40. doi: NULL. [PMID: 8491553]