D-Psicose (BioDeep_00000015277)

 

Secondary id: BioDeep_00000406169, BioDeep_00001890681

natural product PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


(3R,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one

化学式: C6H12O6 (180.0633852)
中文名称: D-阿洛酮糖, L-塔格糖, Beta-D-呋喃阿洛酮糖
谱图信息: 最多检出来源 Viridiplantae(plant) 0.08%

分子结构信息

SMILES: C(C(C(C(C(=O)CO)O)O)O)O
InChI: InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2

描述信息

The D-enantiomer of psicose.

同义名列表

6 个代谢物同义名

D-Psicose; Sorbose, L-; (3R,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one; DL-Fructose; L-Tagatose; beta-D-Psicofuranose



数据库引用编号

35 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)

5 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

  • Qi-Yang Wang, Hao-Yu Wang, Wei-Guo Zhang, Jian-Zhong Xu. Economical one-pot synthesis of isoquercetin and D-allulose from quercetin and sucrose using whole-cell biocatalyst. Enzyme and microbial technology. 2024 May; 176(?):110412. doi: 10.1016/j.enzmictec.2024.110412. [PMID: 38402828]
  • Maria Sofia Molonia, Federica Lina Salamone, Antonio Speciale, Antonella Saija, Francesco Cimino. D-Allulose Reduces Hypertrophy and Endoplasmic Reticulum Stress Induced by Palmitic Acid in Murine 3T3-L1 Adipocytes. International journal of molecular sciences. 2024 Apr; 25(7):. doi: 10.3390/ijms25074059. [PMID: 38612868]
  • Lukana Preechasuk, Chanoknan Luksameejaroenchai, Watip Tangjittipokin, Tada Kunavisarut. Short-term effects of allulose consumption on glucose homeostasis, metabolic parameters, incretin levels, and inflammatory markers in patients with type 2 diabetes: a double-blind, randomized, controlled crossover clinical trial. European journal of nutrition. 2023 Jul; ?(?):. doi: 10.1007/s00394-023-03205-w. [PMID: 37432472]
  • Shinta Wulansari, Sobroney Heng, Prattana Ketbot, Sirilak Baramee, Rattiya Waeonukul, Patthra Pason, Khanok Ratanakhanokchai, Ayaka Uke, Akihiko Kosugi, Chakrit Tachaapaikoon. A Novel D-Psicose 3-Epimerase from Halophilic, Anaerobic Iocasia fonsfrigidae and Its Application in Coconut Water. International journal of molecular sciences. 2023 Mar; 24(7):. doi: 10.3390/ijms24076394. [PMID: 37047367]
  • Mirai Yamazaki, Misaki Okito, Akio Harada, Keisuke Miyake, Takashi Tamiya, Takehiro Nakamura. d-Allulose Supplementation Prevents Diet-Induced Hepatic Lipid Accumulation via miR-130-Mediated Regulation in C57BL/6 Mice. Molecular nutrition & food research. 2023 02; 67(3):e2200748. doi: 10.1002/mnfr.202200748. [PMID: 36461919]
  • Michael J Haas, Shrina Parekh, Poonam Kalidas, Angela Richter, Firas Warda, Norman C W Wong, Masaaki Tokuda, Arshag D Mooradian. Insulin mimetic effect of D-allulose on apolipoprotein A-I gene. Journal of food biochemistry. 2022 02; 46(2):e14064. doi: 10.1111/jfbc.14064. [PMID: 34984676]
  • Bingyang Liu, Yang Gou, Takamasa Tsuzuki, Takako Yamada, Tetsuo Iida, Sixian Wang, Ryoichi Banno, Yukiyasu Toyoda, Teruhiko Koike. d-Allulose Improves Endurance and Recovery from Exhaustion in Male C57BL/6J Mice. Nutrients. 2022 Jan; 14(3):. doi: 10.3390/nu14030404. [PMID: 35276765]
  • Misato Niibo, Akane Kanasaki, Tetsuo Iida, Keisuke Ohnishi, Taro Ozaki, Kazuya Akimitsu, Tetsuo Minamino. d-allulose protects against diabetic nephropathy progression in Otsuka Long-Evans Tokushima Fatty rats with type 2 diabetes. PloS one. 2022; 17(1):e0263300. doi: 10.1371/journal.pone.0263300. [PMID: 35100325]
  • Yang Gou, Bingyang Liu, Mengyao Cheng, Takako Yamada, Tetsuo Iida, Sixian Wang, Ryoichi Banno, Teruhiko Koike. d-Allulose Ameliorates Skeletal Muscle Insulin Resistance in High-Fat Diet-Fed Rats. Molecules (Basel, Switzerland). 2021 Oct; 26(20):. doi: 10.3390/molecules26206310. [PMID: 34684891]
  • Wanpitak Pongkan, Kewarin Jinawong, Wasana Pratchayasakul, Thidarat Jaiwongkam, Sasiwan Kerdphoo, Masaaki Tokuda, Siriporn C Chattipakorn, Nipon Chattipakorn. D-allulose provides cardioprotective effect by attenuating cardiac mitochondrial dysfunction in obesity-induced insulin-resistant rats. European journal of nutrition. 2021 Jun; 60(4):2047-2061. doi: 10.1007/s00394-020-02394-y. [PMID: 33011844]
  • Akane Kanasaki, Misato Niibo, Tetsuo Iida. Effect of D-allulose feeding on the hepatic metabolomics profile in male Wistar rats. Food & function. 2021 May; 12(9):3931-3938. doi: 10.1039/d0fo03024d. [PMID: 33977954]
  • Satya Narayan Patel, Girija Kaushal, Sudhir P Singh. D-Allulose 3-epimerase of Bacillus sp. origin manifests profuse heat-stability and noteworthy potential of D-fructose epimerization. Microbial cell factories. 2021 Mar; 20(1):60. doi: 10.1186/s12934-021-01550-1. [PMID: 33663507]
  • Francesco Franchi, Dmitry M Yaranov, Fabiana Rollini, Andrea Rivas, Jose Rivas Rios, Latonya Been, Yuma Tani, Masaaki Tokuda, Tetsuo Iida, Noriko Hayashi, Dominick J Angiolillo, Arshag D Mooradian. Effects of D-allulose on glucose tolerance and insulin response to a standard oral sucrose load: results of a prospective, randomized, crossover study. BMJ open diabetes research & care. 2021 02; 9(1):. doi: 10.1136/bmjdrc-2020-001939. [PMID: 33637605]
  • Dayoun Lee, Youngji Han, Eun-Young Kwon, Myung-Sook Choi. d-allulose Ameliorates Metabolic Dysfunction in C57BL/KsJ-db/db Mice. Molecules (Basel, Switzerland). 2020 Aug; 25(16):. doi: 10.3390/molecules25163656. [PMID: 32796637]
  • Youngji Han, Eun-Young Kwon, Myung-Sook Choi. Anti-Diabetic Effects of Allulose in Diet-Induced Obese Mice via Regulation of mRNA Expression and Alteration of the Microbiome Composition. Nutrients. 2020 Jul; 12(7):. doi: 10.3390/nu12072113. [PMID: 32708827]
  • Youngji Han, Haryung Park, Bo-Ra Choi, Yosep Ji, Eun-Young Kwon, Myung-Sook Choi. Alteration of Microbiome Profile by D-Allulose in Amelioration of High-Fat-Diet-Induced Obesity in Mice. Nutrients. 2020 Jan; 12(2):. doi: 10.3390/nu12020352. [PMID: 32013116]
  • Jingjing Chen, Weilai Huang, Tao Zhang, Mei Lu, Bo Jiang. Anti-obesity potential of rare sugar d-psicose by regulating lipid metabolism in rats. Food & function. 2019 May; 10(5):2417-2425. doi: 10.1039/c8fo01089g. [PMID: 30964474]
  • Kunihiro Kishida, Gustavo Martinez, Tetsuo Iida, Takako Yamada, Ronaldo P Ferraris, Yukiyasu Toyoda. d-Allulose is a substrate of glucose transporter type 5 (GLUT5) in the small intestine. Food chemistry. 2019 Mar; 277(?):604-608. doi: 10.1016/j.foodchem.2018.11.003. [PMID: 30502192]
  • Ankita Juneja, Guochang Zhang, Yong-Su Jin, Vijay Singh. Bioprocessing and technoeconomic feasibility analysis of simultaneous production of d-psicose and ethanol using engineered yeast strain KAM-2GD. Bioresource technology. 2019 Mar; 275(?):27-34. doi: 10.1016/j.biortech.2018.12.025. [PMID: 30576911]
  • Bo-Ra Choi, Eun-Young Kwon, Hye-Jin Kim, Myung-Sook Choi. Role of Synbiotics Containing d-Allulose in the Alteration of Body Fat and Hepatic Lipids in Diet-Induced Obese Mice. Nutrients. 2018 Nov; 10(11):. doi: 10.3390/nu10111797. [PMID: 30463250]
  • Jarvis C Noronha, Catherine R Braunstein, Andrea J Glenn, Tauseef A Khan, Effie Viguiliouk, Rebecca Noseworthy, Sonia Blanco Mejia, Cyril W C Kendall, Thomas M S Wolever, Lawrence A Leiter, John L Sievenpiper. The effect of small doses of fructose and allulose on postprandial glucose metabolism in type 2 diabetes: A double-blind, randomized, controlled, acute feeding, equivalence trial. Diabetes, obesity & metabolism. 2018 10; 20(10):2361-2370. doi: 10.1111/dom.13374. [PMID: 29797503]
  • Catherine R Braunstein, Jarvis C Noronha, Andrea J Glenn, Effie Viguiliouk, Rebecca Noseworthy, Tauseef A Khan, Fei Au-Yeung, Sonia Blanco Mejia, Thomas M S Wolever, Robert G Josse, Cyril W C Kendall, John L Sievenpiper. A Double-Blind, Randomized Controlled, Acute Feeding Equivalence Trial of Small, Catalytic Doses of Fructose and Allulose on Postprandial Blood Glucose Metabolism in Healthy Participants: The Fructose and Allulose Catalytic Effects (FACE) Trial. Nutrients. 2018 Jun; 10(6):. doi: 10.3390/nu10060750. [PMID: 29890724]
  • Yasuo Nagata, Narumi Mizuta, Akane Kanasaki, Kazunari Tanaka. Rare sugars, d-allulose, d-tagatose and d-sorbose, differently modulate lipid metabolism in rats. Journal of the science of food and agriculture. 2018 Mar; 98(5):2020-2026. doi: 10.1002/jsfa.8687. [PMID: 28940418]
  • Anjaritha A R Parijadi, Sastia P Putri, Sobir Ridwani, Fenny M Dwivany, Eiichiro Fukusaki. Metabolic profiling of Garcinia mangostana (mangosteen) based on ripening stages. Journal of bioscience and bioengineering. 2018 Feb; 125(2):238-244. doi: 10.1016/j.jbiosc.2017.08.013. [PMID: 28970109]
  • Youngji Han, Eun-Young Kwon, Mi Kyeong Yu, Seon Jeong Lee, Hye-Jin Kim, Seong-Bo Kim, Yang Hee Kim, Myung-Sook Choi. A Preliminary Study for Evaluating the Dose-Dependent Effect of d-Allulose for Fat Mass Reduction in Adult Humans: A Randomized, Double-Blind, Placebo-Controlled Trial. Nutrients. 2018 Jan; 10(2):. doi: 10.3390/nu10020160. [PMID: 29385054]
  • Naohito Nishii, Satoshi Takashima, Yui Kobatake, Masaaki Tokuda, Hitoshi Kitagawa. The long-term safety of D-allulose administration in healthy dogs. The Journal of veterinary medical science. 2017 Nov; 79(11):1780-1784. doi: 10.1292/jvms.17-0367. [PMID: 28924091]
  • Tomonori Kimura, Akane Kanasaki, Noriko Hayashi, Takako Yamada, Tetsuo Iida, Yasuo Nagata, Kazuhiro Okuma. d-Allulose enhances postprandial fat oxidation in healthy humans. Nutrition (Burbank, Los Angeles County, Calif.). 2017 Nov; 43-44(?):16-20. doi: 10.1016/j.nut.2017.06.007. [PMID: 28935140]
  • Younho Song, Chihoon Oh, Hyeun-Jong Bae. Simultaneous production of bioethanol and value-added d-psicose from Jerusalem artichoke (Helianthus tuberosus L.) tubers. Bioresource technology. 2017 Nov; 244(Pt 1):1068-1072. doi: 10.1016/j.biortech.2017.08.079. [PMID: 28851162]
  • Masaru Ochiai, Kohei Misaki, Takako Yamada, Tetsuo Iida, Kazuhiro Okuma, Tatsuhiro Matsuo. Comparison of Anti-Obesity Effect between Two Types of Syrup Containing Rare Sugars in Wistar Rats. Journal of nutritional science and vitaminology. 2017; 63(3):208-213. doi: 10.3177/jnsv.63.208. [PMID: 28757536]
  • Naohito Nishii, Toru Nomizo, Satoshi Takashima, Tatsuya Matsubara, Masaaki Tokuda, Hitoshi Kitagawa. Effects of D-allulose on glucose metabolism after the administration of sugar or food in healthy dogs. The Journal of veterinary medical science. 2016 Dec; 78(11):1657-1662. doi: 10.1292/jvms.16-0302. [PMID: 27452736]
  • Naohito Nishii, Toru Nomizo, Satoshi Takashima, Tatsuya Matsubara, Masaaki Tokuda, Hitoshi Kitagawa. Single oral dose safety of D-allulose in dogs. The Journal of veterinary medical science. 2016 Jul; 78(6):1079-83. doi: 10.1292/jvms.15-0676. [PMID: 26972334]
  • Youngji Han, Hye Jin Han, Ae-Hyang Kim, Ji-Young Choi, Su-Jung Cho, Yong Bok Park, Un Ju Jung, Myung-Sook Choi. d-Allulose supplementation normalized the body weight and fat-pad mass in diet-induced obese mice via the regulation of lipid metabolism under isocaloric fed condition. Molecular nutrition & food research. 2016 07; 60(7):1695-706. doi: 10.1002/mnfr.201500771. [PMID: 26920079]
  • Akram Hossain, Fuminori Yamaguchi, Tatsuhiro Matsuo, Ikuko Tsukamoto, Yukiyasu Toyoda, Masahiro Ogawa, Yasuo Nagata, Masaaki Tokuda. Rare sugar D-allulose: Potential role and therapeutic monitoring in maintaining obesity and type 2 diabetes mellitus. Pharmacology & therapeutics. 2015 Nov; 155(?):49-59. doi: 10.1016/j.pharmthera.2015.08.004. [PMID: 26297965]
  • N Wagner, E Håkansson, S Wahler, S Panke, M Bechtold. Multi-objective optimization for the economic production of d-psicose using simulated moving bed chromatography. Journal of chromatography. A. 2015 Jun; 1398(?):47-56. doi: 10.1016/j.chroma.2015.04.008. [PMID: 25943832]
  • Yasuo Nagata, Akane Kanasaki, Shizuka Tamaru, Kazunari Tanaka. D-psicose, an epimer of D-fructose, favorably alters lipid metabolism in Sprague-Dawley rats. Journal of agricultural and food chemistry. 2015 Apr; 63(12):3168-76. doi: 10.1021/jf502535p. [PMID: 25754616]
  • Akram Hossain, Fuminori Yamaguchi, Kayoko Hirose, Toru Matsunaga, Li Sui, Yuko Hirata, Chisato Noguchi, Ayako Katagi, Kazuyo Kamitori, Youyi Dong, Ikuko Tsukamoto, Masaaki Tokuda. Rare sugar D-psicose prevents progression and development of diabetes in T2DM model Otsuka Long-Evans Tokushima Fatty rats. Drug design, development and therapy. 2015; 9(?):525-35. doi: 10.2147/dddt.s71289. [PMID: 25632221]
  • Chih-Wen Tseng, Chien-Yi Liao, Yuanxia Sun, Chi-Chung Peng, Jason T C Tzen, Rey-Ting Guo, Je-Ruei Liu. Immobilization of Clostridium cellulolyticum D-psicose 3-epimerase on artificial oil bodies. Journal of agricultural and food chemistry. 2014 Jul; 62(28):6771-6. doi: 10.1021/jf502022w. [PMID: 24980476]
  • Masaru Ochiai, Kana Onishi, Takako Yamada, Tetsuo Iida, Tatsuhiro Matsuo. D-psicose increases energy expenditure and decreases body fat accumulation in rats fed a high-sucrose diet. International journal of food sciences and nutrition. 2014 Mar; 65(2):245-50. doi: 10.3109/09637486.2013.845653. [PMID: 24144428]
  • Ikuko Tsukamoto, Akram Hossain, Fuminori Yamaguchi, Yuko Hirata, Youyi Dong, Kazuyo Kamitori, Li Sui, Machiko Nonaka, Masaki Ueno, Kazuyuki Nishimoto, Hirofumi Suda, Kenji Morimoto, Tsuyoshi Shimonishi, Madoka Saito, Tao Song, Ryoji Konishi, Masaaki Tokuda. Intestinal absorption, organ distribution, and urinary excretion of the rare sugar D-psicose. Drug design, development and therapy. 2014; 8(?):1955-64. doi: 10.2147/dddt.s60247. [PMID: 25378908]
  • Amelie Rabot, Clemence Henry, Khaoula Ben Baaziz, Eric Mortreau, Wassim Azri, Jeremy Lothier, Latifa Hamama, Rachid Boummaza, Nathalie Leduc, Sandrine Pelleschi-Travier, José Le Gourrierec, Soulaiman Sakr. Insight into the role of sugars in bud burst under light in the rose. Plant & cell physiology. 2012 Jun; 53(6):1068-82. doi: 10.1093/pcp/pcs051. [PMID: 22505690]
  • Young-Mee Chung, Joo Hyun Lee, Deuk Youl Kim, Se-Hee Hwang, Young-Ho Hong, Seong-Bo Kim, Song Jin Lee, Chi Hye Park. Dietary D-psicose reduced visceral fat mass in high-fat diet-induced obese rats. Journal of food science. 2012 Feb; 77(2):H53-8. doi: 10.1111/j.1750-3841.2011.02571.x. [PMID: 22339545]
  • Akihito Kano, Kouji Hosotani, Kenji Gomi, Yumiko Yamasaki-Kokudo, Chikage Shirakawa, Takeshi Fukumoto, Kouhei Ohtani, Shigeyuki Tajima, Ken Izumori, Keiji Tanaka, Yutaka Ishida, Yoko Nishizawa, Kazuya Ichimura, Yasuomi Tada, Kazuya Akimitsu. D-Psicose induces upregulation of defense-related genes and resistance in rice against bacterial blight. Journal of plant physiology. 2011 Oct; 168(15):1852-7. doi: 10.1016/j.jplph.2011.04.003. [PMID: 21601944]
  • Mohammad A Hossain, Shigeru Kitagaki, Daisuke Nakano, Akira Nishiyama, Yasunobu Funamoto, Toru Matsunaga, Ikuko Tsukamoto, Fuminori Yamaguchi, Kazuyo Kamitori, Youyi Dong, Yuko Hirata, Koji Murao, Yukiyasu Toyoda, Masaaki Tokuda. Rare sugar D-psicose improves insulin sensitivity and glucose tolerance in type 2 diabetes Otsuka Long-Evans Tokushima Fatty (OLETF) rats. Biochemical and biophysical research communications. 2011 Feb; 405(1):7-12. doi: 10.1016/j.bbrc.2010.12.091. [PMID: 21187061]
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  • S H Baek, S J Park, H G Lee. D-psicose, a sweet monosaccharide, ameliorate hyperglycemia, and dyslipidemia in C57BL/6J db/db mice. Journal of food science. 2010 Mar; 75(2):H49-53. doi: 10.1111/j.1750-3841.2009.01434.x. [PMID: 20492234]
  • Tetsuo Iida, Noriko Hayashi, Takako Yamada, Yuko Yoshikawa, Shoko Miyazato, Yuka Kishimoto, Kazuhiro Okuma, Masaaki Tokuda, Ken Izumori. Failure of d-psicose absorbed in the small intestine to metabolize into energy and its low large intestinal fermentability in humans. Metabolism: clinical and experimental. 2010 Feb; 59(2):206-14. doi: 10.1016/j.metabol.2009.07.018. [PMID: 19765780]
  • Shigeru Suna, Fuminori Yamaguchi, Shoji Kimura, Masaaki Tokuda, Fumihiko Jitsunari. Preventive effect of D-psicose, one of rare ketohexoses, on di-(2-ethylhexyl) phthalate (DEHP)-induced testicular injury in rat. Toxicology letters. 2007 Sep; 173(2):107-17. doi: 10.1016/j.toxlet.2007.06.015. [PMID: 17698303]
  • Wayoon Poonperm, Goro Takata, Yasuyo Ando, Verasak Sahachaisaree, Pipob Lumyong, Saisamorn Lumyong, Ken Izumori. Efficient conversion of allitol to D-psicose by Bacillus pallidus Y25. Journal of bioscience and bioengineering. 2007 Mar; 103(3):282-5. doi: 10.1263/jbb.103.282. [PMID: 17434433]
  • Tatsuhiro Matsuo, Ken Izumori. Effects of dietary D-psicose on diurnal variation in plasma glucose and insulin concentrations of rats. Bioscience, biotechnology, and biochemistry. 2006 Sep; 70(9):2081-5. doi: 10.1271/bbb.60036. [PMID: 16960391]
  • Tatsuhiro Matsuo, Tomohiro Tanaka, Mineo Hashiguchi, Ken Izumori, Hiroo Suzuki. Metabolic effects of D-psicose in rats: studies on faecal and urinary excretion and caecal fermentation. Asia Pacific journal of clinical nutrition. 2003; 12(2):225-31. doi: NULL. [PMID: 12810416]
  • Tatsuhiro Matsuo, Hiroo Suzuki, Mineo Hashiguchi, Ken Izumori. D-psicose is a rare sugar that provides no energy to growing rats. Journal of nutritional science and vitaminology. 2002 Feb; 48(1):77-80. doi: 10.3177/jnsv.48.77. [PMID: 12026195]
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