Rheosmin (BioDeep_00000861302)

Main id: BioDeep_00000017334

 

PANOMIX_OTCML-2023


代谢物信息卡片


4-08-00-00506 (Beilstein Handbook Reference)

化学式: C10H12O2 (164.0837)
中文名称: 4-（4-羟基苯基）-2-丁酮, 4-(4-羟苯基) -2-丁酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)CCC1=CC=C(C=C1)O
InChI: InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3

描述信息

Raspberry ketone is a major aromatic compound of red raspberry, widely used as a fragrance in cosmetics and as a flavoring agent in foodstuff; also shows PPAR-α agonistic activity.
Raspberry ketone is a major aromatic compound of red raspberry, widely used as a fragrance in cosmetics and as a flavoring agent in foodstuff; also shows PPAR-α agonistic activity.
Raspberry ketone is a major aromatic compound of red raspberry, widely used as a fragrance in cosmetics and as a flavoring agent in foodstuff; also shows PPAR-α agonistic activity.

同义名列表

35 个代谢物同义名

4-08-00-00506 (Beilstein Handbook Reference); 4-(p-Hydroxyphenyl)-2-butanone (natural); 2-Butanone, 4-(4-hydroxyphenyl)-; 2-BUTANONE, 4-(p-HYDROXYPHENYL)-; 4-(4-Hydroxyphenyl)butan-2-one; 1-(4-Hydroxyphenyl)-3-butanone; 4-(p-hydroxyphenyl)-2-butanone; 1-(p-Hydroxyphenyl)-3-butanone; 4-(4-Hydroxyphenyl)-2-butanone; Hydroxyphenylbutanone, p-; (p-Hydroxybenzyl)acetone; p-Hydroxybenzyl acetone; 4-(3-Oxobutyl)phenol; EINECS 226-806-4; raspberry ketone; W258814_ALDRICH; AE-473\30684056; W258806_ALDRICH; 178519_ALDRICH; FEMA No. 2588; ZINC00154632; WLN: QR D2V1; 56110_FLUKA; oxyphenalon; BRN 0776080; Frambinone; 5471-51-2; NSC 26515; ST5330630; Rasketone; AI3-31812; NSC26515; Rheosmin; Frambione; 4-(4-Hydroxyphenyl)-2-butanone



数据库引用编号

7 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)

30 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。

亚细胞结构定位 关联基因列表


文献列表

  • Humayra Akter, Benjamin G Fanson, Jess Inskeep, Polychronis Rempoulakis. Raspberry ketone feeding makes Queensland fruit fly, Bactrocera tryoni (Froggatt), more vulnerable to desiccation but not starvation. Pest management science. 2023 Dec; 79(12):4858-4867. doi: 10.1002/ps.7687. [PMID: 37507354]
  • Mervat E Askar, Sousou I Ali, Nahla N Younis, Mohamed A Shaheen, Mahmoud E Zaher. Raspberry ketone ameliorates nonalcoholic fatty liver disease in rats by activating the AMPK pathway. European journal of pharmacology. 2023 Oct; 957(?):176001. doi: 10.1016/j.ejphar.2023.176001. [PMID: 37598925]
  • Xinyan Tao, Yuan Liu, Zhenhua Ding, Shuang Xie, Wenxiong Cao, Xiaohong Li. Injectable cell-targeting fiber rods to promote lipolysis and regulate inflammation for obesity treatment. Biomaterials science. 2023 Aug; 11(16):5663-5673. doi: 10.1039/d3bm00619k. [PMID: 37432672]
  • Saurabh Verma, Umesh K Goand, Shivam Rathaur, Richa Garg, Roshan Katekar, Jiaur R Gayen. The combined effect of Raspberry Ketone with Resveratrol against oxidative stress and steatohepatitis in rats: Pharmacokinetic and pharmacodynamic studies. Journal of biochemical and molecular toxicology. 2023 Apr; ?(?):e23336. doi: 10.1002/jbt.23336. [PMID: 37009719]
  • Naoto Uramaru, Azusa Kawashima, Makoto Osabe, Toshiyuki Higuchi. Rhododendrol, a reductive metabolite of raspberry ketone, suppresses the differentiation of 3T3‑L1 cells into adipocytes. Molecular medicine reports. 2023 Feb; 27(2):. doi: 10.3892/mmr.2023.12938. [PMID: 36633126]
  • Soha M Hamdy, Zakaria El-Khayat, Abdel Razik Farrag, Ola N Sayed, Mervat M El-Sayed, Diaa Massoud. Hepatoprotective effect of Raspberry ketone and white tea against acrylamide-induced toxicity in rats. Drug and chemical toxicology. 2022 Mar; 45(2):722-730. doi: 10.1080/01480545.2020.1772279. [PMID: 32482111]
  • Xiaoping Li, Teng Wei, Min Wu, Fang Chen, Peng Zhang, Ze-Yuan Deng, Ting Luo. Potential metabolic activities of raspberry ketone. Journal of food biochemistry. 2022 01; 46(1):e14018. doi: 10.1111/jfbc.14018. [PMID: 34913499]
  • Bo Yuan, Danyue Zhao, Weiting Lyu, Zhiya Yin, Dushyant Kshatriya, James E Simon, Nicholas T Bello, Qingli Wu. Development and validation of a micro-QuEChERS method with high-throughput enhanced matrix removal followed with UHPLC-QqQ-MS/MS for analysis of raspberry ketone-related phenolic compounds in adipose tissues. Talanta. 2021 Dec; 235(?):122716. doi: 10.1016/j.talanta.2021.122716. [PMID: 34517584]
  • Mohammed Abul Monjur Khan, Nandan P Deshpande, Lucas A Shuttleworth, Terry Osborne, Damian Collins, Marc R Wilkins, Geoff M Gurr, Olivia L Reynolds. Raspberry ketone diet supplement reduces attraction of sterile male Queensland fruit fly to cuelure by altering expression of chemoreceptor genes. Scientific reports. 2021 09; 11(1):17632. doi: 10.1038/s41598-021-96778-7. [PMID: 34480052]
  • Chen Chang, Bo Liu, Yihong Bao, Yong Tao, Weifeng Liu. Efficient bioconversion of raspberry ketone in Escherichia coli using fatty acids feedstocks. Microbial cell factories. 2021 Mar; 20(1):68. doi: 10.1186/s12934-021-01551-0. [PMID: 33706766]
  • Suk-Ling Wee, Anthony R Clarke. Male-lure type, lure dosage, and fly age at feeding all influence male mating success in Jarvis' fruit fly. Scientific reports. 2020 09; 10(1):15004. doi: 10.1038/s41598-020-72209-x. [PMID: 32929156]
  • Bo Yuan, Danyue Zhao, Dushyant Kshatriya, Nicholas T Bello, James E Simon, Qingli Wu. UHPLC-QqQ-MS/MS method development and validation with statistical analysis: Determination of raspberry ketone metabolites in mice plasma and brain. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Jul; 1149(?):122146. doi: 10.1016/j.jchromb.2020.122146. [PMID: 32474352]
  • Danyue Zhao, Bo Yuan, Dushyant Kshatriya, Andrew Polyak, James E Simon, Nicholas T Bello, Qingli Wu. Influence of Diet-Induced Obesity on the Bioavailability and Metabolism of Raspberry Ketone (4-(4-Hydroxyphenyl)-2-Butanone) in Mice. Molecular nutrition & food research. 2020 04; 64(8):e1900907. doi: 10.1002/mnfr.201900907. [PMID: 32052560]
  • Dushyant Kshatriya, Xinyi Li, Gina M Giunta, Bo Yuan, Danyue Zhao, James E Simon, Qingli Wu, Nicholas T Bello. Phenolic-enriched raspberry fruit extract (Rubus idaeus) resulted in lower weight gain, increased ambulatory activity, and elevated hepatic lipoprotein lipase and heme oxygenase-1 expression in male mice fed a high-fat diet. Nutrition research (New York, N.Y.). 2019 08; 68(?):19-33. doi: 10.1016/j.nutres.2019.05.005. [PMID: 31252376]
  • Bo Yuan, Danyue Zhao, Ruoyuan Du, Dushyant Kshatriya, Nicholas T Bello, James E Simon, Qingli Wu. A highly sensitive ultra-high performance liquid chromatography/tandem mass spectrometry method with in-source fragmentation for rapid quantification of raspberry ketone. Journal of food and drug analysis. 2019 07; 27(3):778-785. doi: 10.1016/j.jfda.2018.07.005. [PMID: 31324293]
  • Chengcheng Wang, Pu Zheng, Pengcheng Chen. Construction of synthetic pathways for raspberry ketone production in engineered Escherichia coli. Applied microbiology and biotechnology. 2019 May; 103(9):3715-3725. doi: 10.1007/s00253-019-09748-5. [PMID: 30915501]
  • Reem T Attia, Yousra Abdel-Mottaleb, Dalaal M Abdallah, Hanan S El-Abhar, Nabila N El-Maraghy. Raspberry ketone and Garcinia Cambogia rebalanced disrupted insulin resistance and leptin signaling in rats fed high fat fructose diet. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Feb; 110(?):500-509. doi: 10.1016/j.biopha.2018.11.079. [PMID: 30530230]
  • Vasim Khan, Sumit Sharma, Uma Bhandari, Nishtha Sharma, Vikas Rishi, Syed Ehtaishamul Haque. Suppression of isoproterenol-induced cardiotoxicity in rats by raspberry ketone via activation of peroxisome proliferator activated receptor-α. European journal of pharmacology. 2019 Jan; 842(?):157-166. doi: 10.1016/j.ejphar.2018.10.034. [PMID: 30431010]
  • Hoda E Mohamed, Dina M Abo-ELmatty, Noha M Mesbah, Samy M Saleh, Abdel-Moniem A Ali, Amr T Sakr. Raspberry ketone preserved cholinergic activity and antioxidant defense in obesity induced Alzheimer disease in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Nov; 107(?):1166-1174. doi: 10.1016/j.biopha.2018.08.034. [PMID: 30257330]
  • Suk-Ling Wee, Thelma Peek, Anthony R Clarke. The responsiveness of Bactrocera jarvisi (Diptera: Tephritidae) to two naturally occurring phenylbutaonids, zingerone and raspberry ketone. Journal of insect physiology. 2018 Aug; 109(?):41-46. doi: 10.1016/j.jinsphys.2018.06.004. [PMID: 29890169]
  • Sy-Ying Leu, Yung-Chieh Tsai, Wen-Chi Chen, Chih-Hsiung Hsu, Yen-Mei Lee, Pao-Yun Cheng. Raspberry ketone induces brown-like adipocyte formation through suppression of autophagy in adipocytes and adipose tissue. The Journal of nutritional biochemistry. 2018 06; 56(?):116-125. doi: 10.1016/j.jnutbio.2018.01.017. [PMID: 29525531]
  • Vasim Khan, Sumit Sharma, Uma Bhandari, Syed Mansoor Ali, Syed Ehtaishamul Haque. Raspberry ketone protects against isoproterenol-induced myocardial infarction in rats. Life sciences. 2018 Feb; 194(?):205-212. doi: 10.1016/j.lfs.2017.12.013. [PMID: 29225109]
  • Sy-Ying Leu, Yi-Chen Chen, Yung-Chieh Tsai, Yao-Wen Hung, Chih-Hsiung Hsu, Yen-Mei Lee, Pao-Yun Cheng. Raspberry Ketone Reduced Lipid Accumulation in 3T3-L1 Cells and Ovariectomy-Induced Obesity in Wistar Rats by Regulating Autophagy Mechanisms. Journal of agricultural and food chemistry. 2017 Dec; 65(50):10907-10914. doi: 10.1021/acs.jafc.7b03831. [PMID: 29164883]
  • Yung-Chieh Tsai, Bo-Cheng Yang, Wen-Huang Peng, Yen-Mei Lee, Mao-Hsiung Yen, Pao-Yun Cheng. Heme oxygenase-1 mediates anti-adipogenesis effect of raspberry ketone in 3T3-L1 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Jul; 31(?):11-17. doi: 10.1016/j.phymed.2017.05.005. [PMID: 28606512]
  • Bradley M Cotten, Stephanie A Diamond, Taylor Banh, Yung-Hsuan Hsiao, Rachel M Cole, Jinhui Li, Christopher T Simons, Richard S Bruno, Martha A Belury, Yael Vodovotz. Raspberry ketone fails to reduce adiposity beyond decreasing food intake in C57BL/6 mice fed a high-fat diet. Food & function. 2017 Apr; 8(4):1512-1518. doi: 10.1039/c6fo01831a. [PMID: 28378858]
  • Shosuke Ito, Maki Hinoshita, Erina Suzuki, Makoto Ojika, Kazumasa Wakamatsu. Tyrosinase-Catalyzed Oxidation of the Leukoderma-Inducing Agent Raspberry Ketone Produces (E)-4-(3-Oxo-1-butenyl)-1,2-benzoquinone: Implications for Melanocyte Toxicity. Chemical research in toxicology. 2017 03; 30(3):859-868. doi: 10.1021/acs.chemrestox.7b00006. [PMID: 28219012]
  • Danna Lee, Natoiya D R Lloyd, Isak S Pretorius, Anthony R Borneman. Heterologous production of raspberry ketone in the wine yeast Saccharomyces cerevisiae via pathway engineering and synthetic enzyme fusion. Microbial cell factories. 2016 Mar; 15(?):49. doi: 10.1186/s12934-016-0446-2. [PMID: 26944880]
  • Kyoung Sik Park. Raspberry ketone, a naturally occurring phenolic compound, inhibits adipogenic and lipogenic gene expression in 3T3-L1 adipocytes. Pharmaceutical biology. 2015 Jun; 53(6):870-5. doi: 10.3109/13880209.2014.946059. [PMID: 25429790]
  • Eu Jin Choi, Jung Bae Park, Kee Dong Yoon, Soo Kyung Bae. Evaluation of the in vitro/in vivo potential of five berries (bilberry, blueberry, cranberry, elderberry, and raspberry ketones) commonly used as herbal supplements to inhibit uridine diphospho-glucuronosyltransferase. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Oct; 72(?):13-9. doi: 10.1016/j.fct.2014.06.020. [PMID: 24997313]
  • Nagalingam Kumaran, R Andrew Hayes, Anthony R Clarke. Cuelure but not zingerone make the sex pheromone of male Bactrocera tryoni (Tephritidae: Diptera) more attractive to females. Journal of insect physiology. 2014 Sep; 68(?):36-43. doi: 10.1016/j.jinsphys.2014.06.015. [PMID: 25010549]
  • Tomoyo Takata, Chie Morimoto. Raspberry ketone promotes the differentiation of C3H10T1/2 stem cells into osteoblasts. Journal of medicinal food. 2014 Mar; 17(3):332-8. doi: 10.1089/jmf.2013.2763. [PMID: 24404978]
  • Lili Wang, Xianjun Meng, Fengqing Zhang. Raspberry ketone protects rats fed high-fat diets against nonalcoholic steatohepatitis. Journal of medicinal food. 2012 May; 15(5):495-503. doi: 10.1089/jmf.2011.1717. [PMID: 22551412]
  • Chia-Hsiang Victor Lin, Hsiou-Yu Ding, Shiou-Yi Kuo, Ling-Wei Chin, Jiumn-Yih Wu, Te-Sheng Chang. Evaluation of in vitro and in vivo depigmenting activity of raspberry ketone from Rheum officinale. International journal of molecular sciences. 2011; 12(8):4819-35. doi: 10.3390/ijms12084819. [PMID: 21954327]
  • Kyoung Sik Park. Raspberry ketone increases both lipolysis and fatty acid oxidation in 3T3-L1 adipocytes. Planta medica. 2010 Oct; 76(15):1654-8. doi: 10.1055/s-0030-1249860. [PMID: 20425690]
  • Alapati Kavitha, Peddikotla Prabhakar, Muvva Vijayalakshmi, Yenamandra Venkateswarlu. Purification and biological evaluation of the metabolites produced by Streptomyces sp. TK-VL_333. Research in microbiology. 2010 Jun; 161(5):335-45. doi: 10.1016/j.resmic.2010.03.011. [PMID: 20403429]
  • Yun-Lian Lin, Ching-Fen Wu, Yi-Tsau Huang. Phenols from the roots of Rheum palmatum attenuate chemotaxis in rat hepatic stellate cells. Planta medica. 2008 Aug; 74(10):1246-52. doi: 10.1055/s-2008-1074581. [PMID: 18612943]
  • M Akiyama, K Murakami, Y Hirano, M Ikeda, K Iwatsuki, A Wada, K Tokuno, M Onishi, H Iwabuchi. Characterization of headspace aroma compounds of freshly brewed arabica coffees and studies on a characteristic aroma compound of Ethiopian coffee. Journal of food science. 2008 Jun; 73(5):C335-46. doi: 10.1111/j.1750-3841.2008.00752.x. [PMID: 18576978]
  • Jules Beekwilder, Ingrid M van der Meer, Ole Sibbesen, Mans Broekgaarden, Ingmar Qvist, Joern D Mikkelsen, Robert D Hall. Microbial production of natural raspberry ketone. Biotechnology journal. 2007 Oct; 2(10):1270-9. doi: 10.1002/biot.200700076. [PMID: 17722151]
  • M Akiyama, K Murakami, M Ikeda, K Iwatsuki, A Wada, K Tokuno, M Onishi, H Iwabuchi. Analysis of the headspace volatiles of freshly brewed arabica coffee using solid-phase microextraction. Journal of food science. 2007 Sep; 72(7):C388-96. doi: 10.1111/j.1750-3841.2007.00447.x. [PMID: 17995637]
  • G Hrazdina. Aroma production by tissue cultures. Journal of agricultural and food chemistry. 2006 Feb; 54(4):1116-23. doi: 10.1021/jf053146w. [PMID: 16478225]
  • Chie Morimoto, Yurie Satoh, Mariko Hara, Shintaro Inoue, Takahiro Tsujita, Hiromichi Okuda. Anti-obese action of raspberry ketone. Life sciences. 2005 May; 77(2):194-204. doi: 10.1016/j.lfs.2004.12.029. [PMID: 15862604]
  • Keith Klesk, Michael Qian, Robert R Martin. Aroma extract dilution analysis of cv. Meeker (Rubus idaeus L.) red raspberries from Oregon and Washington. Journal of agricultural and food chemistry. 2004 Aug; 52(16):5155-61. doi: 10.1021/jf0498721. [PMID: 15291490]
  • Sunil K Chattopadhyay, Sachin Srivastava, Koneni V Sashidhara, Arun K Tripathi, Asish K Bhattacharya, Arvind S Negi. Betuligenol derivative with growth inhibition and antifeedant activity. Bioorganic & medicinal chemistry letters. 2004 Apr; 14(7):1729-31. doi: 10.1016/j.bmcl.2004.01.040. [PMID: 15026059]
  • H Zorn, M Fischer-Zorn, R G Berger. A labeling study to elucidate the biosynthesis of 4-(4-hydroxyphenyl)-butan-2-one (raspberry ketone) by Nidula niveo-tomentosa. Applied and environmental microbiology. 2003 Jan; 69(1):367-72. doi: 10.1128/aem.69.1.367-372.2003. [PMID: 12514017]
  • S Pedapudi, C K Chin, H Pedersen. Production and elicitation of benzalacetone and the raspberry ketone in cell suspension cultures of Rubus idaeus. Biotechnology progress. 2000 May; 16(3):346-9. doi: 10.1021/bp000033i. [PMID: 10835233]
  • S Sporstøl, R R Scheline. The metabolism of 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) in rats, guinea-pigs and rabbits. Xenobiotica; the fate of foreign compounds in biological systems. 1982 Apr; 12(4):249-57. doi: 10.3109/00498258209052463. [PMID: 7113261]