Digalactosyldiacylglycerol (BioDeep_00000185110)

   

human metabolite blood metabolite


代谢物信息卡片


1-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propan-2-yl octadeca-9,12-dienoate

化学式: C49H88O15 (916.6122898)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)OC(=O)CCCCCCCC=CCC=CCCCCC
InChI: InChI=1S/C49H88O15/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-41(52)62-37(34-59-40(51)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-60-48-47(58)45(56)43(54)39(64-48)36-61-49-46(57)44(55)42(53)38(33-50)63-49/h11,13,17-18,37-39,42-50,53-58H,3-10,12,14-16,19-36H2,1-2H3

描述信息

1-16:0-2-18:2-digalactosyldiacylglycerol, also known as digalactosylglycerol or dgdg (diacyl glyceride di gal), is a member of the class of compounds known as glycosyldiacylglycerols. Glycosyldiacylglycerols are diacylglycerols that carry a saccharide moiety linked to the glycerol. 1-16:0-2-18:2-digalactosyldiacylglycerol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1-16:0-2-18:2-digalactosyldiacylglycerol can be found in a number of food items such as sweet basil, abiyuch, cocoa bean, and lotus, which makes 1-16:0-2-18:2-digalactosyldiacylglycerol a potential biomarker for the consumption of these food products.

同义名列表

5 个代谢物同义名

1-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propan-2-yl octadeca-9,12-dienoate; 1-16:0-2-18:2-Digalactosyldiacylglycerol; DGDG (Diacyl glyceride di gal); Digalactosyldiacylglycerol; Digalactosylglycerol



数据库引用编号

3 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

  • Sam Wilson, Charlea D Clarke, M Alejandra Carbajal, Roberto Buccafusca, Roland A Fleck, Vangelis Daskalakis, Alexander V Ruban. Hydrophobic Mismatch in the Thylakoid Membrane Regulates Photosynthetic Light Harvesting. Journal of the American Chemical Society. 2024 May; 146(21):14905-14914. doi: 10.1021/jacs.4c05220. [PMID: 38759103]
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  • Soo Jeong Lee, Yejin Song, Min-Yu Chung, In-Hwan Kim, Byung Hee Kim. Isolation and compositional analysis of galactoglycerolipids from perilla [Perilla frutescens (L.) Britton] leaves and comparison to the galactoglycerolipids from spinach and parsley. Journal of food science. 2020 Dec; 85(12):4271-4280. doi: 10.1111/1750-3841.15521. [PMID: 33174278]
  • Jinlu Li, Lu-Ning Liu, Qingwei Meng, Hai Fan, Na Sui. The roles of chloroplast membrane lipids in abiotic stress responses. Plant signaling & behavior. 2020 11; 15(11):1807152. doi: 10.1080/15592324.2020.1807152. [PMID: 32815751]
  • Chunjuan Liu, Yijian Liu, Shiwen Wang, Qingbo Ke, Lina Yin, Xiping Deng, Baili Feng. Arabidopsis mgd mutants with reduced monogalactosyldiacylglycerol contents are hypersensitive to aluminium stress. Ecotoxicology and environmental safety. 2020 Oct; 203(?):110999. doi: 10.1016/j.ecoenv.2020.110999. [PMID: 32888604]
  • Egi Tritya Apdila, Shukumi Inoue, Mie Shimojima, Koichiro Awai. Complete Replacement of the Galactolipid Biosynthesis Pathway with a Plant-Type Pathway in the Cyanobacterium Synechococcus elongatus PCC 7942. Plant & cell physiology. 2020 Sep; 61(9):1661-1668. doi: 10.1093/pcp/pcaa090. [PMID: 32645152]
  • Miao Yang, Fantao Kong, Xi Xie, Peichun Wu, Yadong Chu, Xupeng Cao, Song Xue. Galactolipid DGDG and Betaine Lipid DGTS Direct De Novo Synthesized Linolenate into Triacylglycerol in a Stress-Induced Starchless Mutant of Chlamydomonas reinhardtii. Plant & cell physiology. 2020 Apr; 61(4):851-862. doi: 10.1093/pcp/pcaa012. [PMID: 32061132]
  • Zhou Peng, Lei Feng, Xiaoxue Wang, Xiaoling Miao. Adaptation of Synechococcus sp. PCC 7942 to phosphate starvation by glycolipid accumulation and membrane lipid remodeling. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2019 12; 1864(12):158522. doi: 10.1016/j.bbalip.2019.158522. [PMID: 31487556]
  • Radosław Mazur, Agnieszka Mostowska, Joanna Szach, Katarzyna Gieczewska, Joanna Wójtowicz, Katarzyna Bednarska, Maciej Garstka, Łucja Kowalewska. Galactolipid deficiency disturbs spatial arrangement of the thylakoid network in Arabidopsis thaliana plants. Journal of experimental botany. 2019 09; 70(18):4689-4704. doi: 10.1093/jxb/erz219. [PMID: 31087066]
  • Masato Murakawa, Hiroyuki Ohta, Mie Shimojima. Lipid remodeling under acidic conditions and its interplay with low Pi stress in Arabidopsis. Plant molecular biology. 2019 Sep; 101(1-2):81-93. doi: 10.1007/s11103-019-00891-1. [PMID: 31201686]
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  • Inès Belhaj, Sawsan Amara, Goetz Parsiegla, Priscila Sutto-Ortiz, Moulay Sahaka, Hafedh Belghith, Audric Rousset, Dominique Lafont, Frédéric Carrière. Galactolipase activity of Talaromyces thermophilus lipase on galactolipid micelles, monomolecular films and UV-absorbing surface-coated substrate. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 09; 1863(9):1006-1015. doi: 10.1016/j.bbalip.2018.05.016. [PMID: 29859246]
  • Sho Fujii, Koichi Kobayashi, Noriko Nagata, Tatsuru Masuda, Hajime Wada. Digalactosyldiacylglycerol Is Essential for Organization of the Membrane Structure in Etioplasts. Plant physiology. 2018 08; 177(4):1487-1497. doi: 10.1104/pp.18.00227. [PMID: 29946018]
  • Hsou-Min Li, Chun-Wei Yu. Chloroplast Galactolipids: The Link Between Photosynthesis, Chloroplast Shape, Jasmonates, Phosphate Starvation and Freezing Tolerance. Plant & cell physiology. 2018 Jun; 59(6):1128-1134. doi: 10.1093/pcp/pcy088. [PMID: 29727004]
  • Susann Schaller-Laudel, Dariusz Latowski, Małgorzata Jemioła-Rzemińska, Kazimierz Strzałka, Sebastian Daum, Kirsten Bacia, Christian Wilhelm, Reimund Goss. Influence of thylakoid membrane lipids on the structure of aggregated light-harvesting complexes of the diatom Thalassiosira pseudonana and the green alga Mantoniella squamata. Physiologia plantarum. 2017 Jul; 160(3):339-358. doi: 10.1111/ppl.12565. [PMID: 28317130]
  • Matej Kanduč, Alexander Schlaich, Alex H de Vries, Juliette Jouhet, Eric Maréchal, Bruno Demé, Roland R Netz, Emanuel Schneck. Tight cohesion between glycolipid membranes results from balanced water-headgroup interactions. Nature communications. 2017 04; 8(?):14899. doi: 10.1038/ncomms14899. [PMID: 28367975]
  • Joanna Skupień, Joanna Wójtowicz, Łucja Kowalewska, Radosław Mazur, Maciej Garstka, Katarzyna Gieczewska, Agnieszka Mostowska. Dark-chilling induces substantial structural changes and modifies galactolipid and carotenoid composition during chloroplast biogenesis in cucumber (Cucumis sativus L.) cotyledons. Plant physiology and biochemistry : PPB. 2017 Feb; 111(?):107-118. doi: 10.1016/j.plaphy.2016.11.022. [PMID: 27915172]
  • Qing Liu, Qigao Guo, Sehrish Akbar, Yao Zhi, Anna El Tahchy, Madeline Mitchell, Zhongyi Li, Pushkar Shrestha, Thomas Vanhercke, Jean-Philippe Ral, Guolu Liang, Ming-Bo Wang, Rosemary White, Philip Larkin, Surinder Singh, James Petrie. Genetic enhancement of oil content in potato tuber (Solanum tuberosum L.) through an integrated metabolic engineering strategy. Plant biotechnology journal. 2017 01; 15(1):56-67. doi: 10.1111/pbi.12590. [PMID: 27307093]
  • Oliver Gräb, Maryna Abacilar, Fabian Daus, Armin Geyer, Claudia Steinem. 3D-Membrane Stacks on Supported Membranes Composed of Diatom Lipids Induced by Long-Chain Polyamines. Langmuir : the ACS journal of surfaces and colloids. 2016 10; 32(39):10144-10152. doi: 10.1021/acs.langmuir.6b02575. [PMID: 27603681]
  • Javier Hoyo, Ester Guaus, Juan Torrent-Burgués. Influence of membrane galactolipids and surface pressure on plastoquinone behaviour. Bioelectrochemistry (Amsterdam, Netherlands). 2016 Oct; 111(?):123-30. doi: 10.1016/j.bioelechem.2016.06.002. [PMID: 27317998]
  • Amélie A Kelly, Barbara Kalisch, Georg Hölzl, Sandra Schulze, Juliane Thiele, Michael Melzer, Rebecca L Roston, Christoph Benning, Peter Dörmann. Synthesis and transfer of galactolipids in the chloroplast envelope membranes of Arabidopsis thaliana. Proceedings of the National Academy of Sciences of the United States of America. 2016 09; 113(38):10714-9. doi: 10.1073/pnas.1609184113. [PMID: 27601658]
  • Eri Maida, Koichiro Awai. Digalactosyldiacylglycerol is essential in Synechococcus elongatus PCC 7942, but its function does not depend on its biosynthetic pathway. Biochimica et biophysica acta. 2016 09; 1861(9 Pt B):1309-1314. doi: 10.1016/j.bbalip.2016.03.011. [PMID: 26979760]
  • Koichi Hori, Takashi Nobusawa, Tei Watanabe, Yuka Madoka, Hideyuki Suzuki, Daisuke Shibata, Mie Shimojima, Hiroyuki Ohta. Tangled evolutionary processes with commonality and diversity in plastidial glycolipid synthesis in photosynthetic organisms. Biochimica et biophysica acta. 2016 09; 1861(9 Pt B):1294-1308. doi: 10.1016/j.bbalip.2016.04.015. [PMID: 27108062]
  • Fatma Bejaoui, Joaquín J Salas, Issam Nouairi, Abderrazak Smaoui, Chedly Abdelly, Enrique Martínez-Force, Nabil Ben Youssef. Changes in chloroplast lipid contents and chloroplast ultrastructure in Sulla carnosa and Sulla coronaria leaves under salt stress. Journal of plant physiology. 2016 Jul; 198(?):32-8. doi: 10.1016/j.jplph.2016.03.018. [PMID: 27131842]
  • Eiji Omoto, Yugo Iwasaki, Hiroshi Miyake, Mitsutaka Taniguchi. Salinity induces membrane structure and lipid changes in maize mesophyll and bundle sheath chloroplasts. Physiologia plantarum. 2016 May; 157(1):13-23. doi: 10.1111/ppl.12404. [PMID: 26555406]
  • Joana Rocha, Joe Sarkis, Aline Thomas, Laurence Pitou, Jens Radzimanowski, Magali Audry, Valérie Chazalet, Daniele de Sanctis, Monica M Palcic, Maryse A Block, Agnès Girard-Egrot, Eric Maréchal, Christelle Breton. Structural insights and membrane binding properties of MGD1, the major galactolipid synthase in plants. The Plant journal : for cell and molecular biology. 2016 Mar; 85(5):622-33. doi: 10.1111/tpj.13129. [PMID: 26935252]
  • Yang-Tsung Lin, Lih-Jen Chen, Cornelia Herrfurth, Ivo Feussner, Hsou-Min Li. Reduced Biosynthesis of Digalactosyldiacylglycerol, a Major Chloroplast Membrane Lipid, Leads to Oxylipin Overproduction and Phloem Cap Lignification in Arabidopsis. The Plant cell. 2016 Jan; 28(1):219-32. doi: 10.1105/tpc.15.01002. [PMID: 26721860]
  • Barbara Kalisch, Peter Dörmann, Georg Hölzl. DGDG and Glycolipids in Plants and Algae. Sub-cellular biochemistry. 2016; 86(?):51-83. doi: 10.1007/978-3-319-25979-6_3. [PMID: 27023231]
  • Irene González-Thuillier, Louise Salt, Gemma Chope, Simon Penson, Peter Skeggs, Paola Tosi, Stephen J Powers, Jane L Ward, Peter Wilde, Peter R Shewry, Richard P Haslam. Distribution of Lipids in the Grain of Wheat (cv. Hereward) Determined by Lipidomic Analysis of Milling and Pearling Fractions. Journal of agricultural and food chemistry. 2015 Dec; 63(49):10705-16. doi: 10.1021/acs.jafc.5b05289. [PMID: 26582143]
  • Wenqiang Yang, Tyler M Wittkopp, Xiaobo Li, Jaruswan Warakanont, Alexandra Dubini, Claudia Catalanotti, Rick G Kim, Eva C M Nowack, Luke C M Mackinder, Munevver Aksoy, Mark Dudley Page, Sarah D'Adamo, Shai Saroussi, Mark Heinnickel, Xenie Johnson, Pierre Richaud, Jean Alric, Marko Boehm, Martin C Jonikas, Christoph Benning, Sabeeha S Merchant, Matthew C Posewitz, Arthur R Grossman. Critical role of Chlamydomonas reinhardtii ferredoxin-5 in maintaining membrane structure and dark metabolism. Proceedings of the National Academy of Sciences of the United States of America. 2015 Dec; 112(48):14978-83. doi: 10.1073/pnas.1515240112. [PMID: 26627249]
  • Blaženka Gašparović, Snježana P Kazazić, Ana Cvitešić, Abra Penezić, Sanja Frka. Improved separation and analysis of glycolipids by Iatroscan thin-layer chromatography-flame ionization detection. Journal of chromatography. A. 2015 Aug; 1409(?):259-67. doi: 10.1016/j.chroma.2015.07.047. [PMID: 26209191]
  • Javier Hoyo, Ester Guaus, Juan Torrent-Burgués, Fausto Sanz. Biomimetic monolayer films of digalactosyldiacylglycerol incorporating plastoquinone. Biochimica et biophysica acta. 2015 Jun; 1848(6):1341-51. doi: 10.1016/j.bbamem.2015.03.003. [PMID: 25771450]
  • Raida Jallouli, Houcemeddine Othman, Sawsan Amara, Goetz Parsiegla, Frédéric Carriere, Najet Srairi-Abid, Youssef Gargouri, Sofiane Bezzine. The galactolipase activity of Fusarium solani (phospho)lipase. Biochimica et biophysica acta. 2015 Mar; 1851(3):282-9. doi: 10.1016/j.bbalip.2014.12.010. [PMID: 25529980]
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  • Aïcha Belkadhi, Antonio De Haro, Sara Obregon, Wided Chaïbi, Wahbi Djebali. Positive effects of salicylic acid pretreatment on the composition of flax plastidial membrane lipids under cadmium stress. Environmental science and pollution research international. 2015 Jan; 22(2):1457-67. doi: 10.1007/s11356-014-3475-6. [PMID: 25163565]
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