ar-Turmerone (BioDeep_00000396806)
Main id: BioDeep_00000018305
PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C15H20O (216.151407)
中文名称: 芳姜黄酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=CC=C(C=C1)C(C)CC(=O)C=C(C)C
InChI: InChI=1S/C15H20O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-9,13H,10H2,1-4H3/t13-/m0/s1
描述信息
(+)-(S)-ar-turmerone is a sesquiterpenoid that is 2-methylhept-2-en-4-one substituted by a 4-methylphenyl group at position 6. It has been isolated from Peltophorum dasyrachis. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a plant metabolite. It is a sesquiterpenoid and an enone.
ar-Turmerone is a natural product found in Curcuma amada, Curcuma longa, and other organisms with data available.
A sesquiterpenoid that is 2-methylhept-2-en-4-one substituted by a 4-methylphenyl group at position 6. It has been isolated from Peltophorum dasyrachis.
Ar-turmerone, also known as aromatic-turmerone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Ar-turmerone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ar-turmerone can be found in turmeric, which makes ar-turmerone a potential biomarker for the consumption of this food product.
ar-Turmerone ((+)-ar-Turmerone) is a major bioactive compound of the herb Curcuma longa with anti-tumorigenesis and anti-inflammatory activities[1][2][3]. ar-Turmerone activates apoptotic protein in human lymphoma U937 cells[3]. ar-Turmerone exerts positive modulation on murine DCs. ar-Turmerone induces NSC proliferation and constitutes a promising therapeutic agent for various neurologic disorders[4][5].
ar-Turmerone ((+)-ar-Turmerone) is a major bioactive compound of the herb Curcuma longa with anti-tumorigenesis and anti-inflammatory activities[1][2][3]. ar-Turmerone activates apoptotic protein in human lymphoma U937 cells[3]. ar-Turmerone exerts positive modulation on murine DCs. ar-Turmerone induces NSC proliferation and constitutes a promising therapeutic agent for various neurologic disorders[4][5].
同义名列表
13 个代谢物同义名
2-Hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (6S)-; 2-Hepten-4-one, 2-methyl-6-(4-methylphenyl)-, (S)-; (6S)-2-methyl-6-(4-methylphenyl)hept-2-en-4-one; (6S)-2-Methyl-6-(4-methylphenyl)-2-hepten-4-one; (S)-ar-Turmerone, analytical standard; (+)-(S)-ar-turmerone; aromatic-turmerone; AR-TURMERONE [MI]; (+)-ar-Turmerone; ar-(+)-Turmerone; (S)-ar-Turmerone; Turmerone, AR-; ar-Turmerone
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:70159
- PubChem: 160512
- ChEMBL: CHEMBL1668333
- MeSH: ar-turmerone
- ChemIDplus: 0000532650
- foodb: FDB014314
- CAS: 532-65-0
- medchemexpress: HY-N6703
- MetaboLights: MTBLC70159
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
- Chunlian Li, Weicheng Zhang, Xianyi Wu, Qiuyang Cai, Zekai Tan, Zhengyi Hong, Shiyuan Huang, Yanghe Yuan, Lewen Yao, Lanyue Zhang. Aromatic-turmerone ameliorates DSS-induced ulcerative colitis via modulating gut microbiota in mice.
Inflammopharmacology.
2022 Aug; 30(4):1283-1294. doi:
10.1007/s10787-022-01007-w. [PMID: 35794287] - Sen Yang, Jia Liu, Jianxia Jiao, Linjun Jiao. Ar-Turmerone Exerts Anti-proliferative and Anti-inflammatory Activities in HaCaT Keratinocytes by Inactivating Hedgehog Pathway.
Inflammation.
2020 Apr; 43(2):478-486. doi:
10.1007/s10753-019-01131-w. [PMID: 31773440] - Gregorio Peron, Stefania Sut, Simone Dal Ben, Dario Voinovich, Stefano Dall'Acqua. Untargeted UPLC-MS metabolomics reveals multiple changes of urine composition in healthy adult volunteers after consumption of curcuma longa L. extract.
Food research international (Ottawa, Ont.).
2020 01; 127(?):108730. doi:
10.1016/j.foodres.2019.108730. [PMID: 31882111] - In-Cheng Chao, Chun-Ming Wang, Shao-Ping Li, Li-Gen Lin, Wen-Cai Ye, Qing-Wen Zhang. Simultaneous Quantification of Three Curcuminoids and Three Volatile Components of Curcuma longa Using Pressurized Liquid Extraction and High-Performance Liquid Chromatography.
Molecules (Basel, Switzerland).
2018 06; 23(7):. doi:
10.3390/molecules23071568. [PMID: 29958431] - Iveta Bartoňková, Zdeněk Dvořák. Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2018 Jan; 111(?):374-384. doi:
10.1016/j.fct.2017.11.049. [PMID: 29191726] - Ezzat Abdel-Lateef, Faten Mahmoud, Olfat Hammam, Eman El-Ahwany, Eman El-Wakil, Sherihan Kandil, Hoda Abu Taleb, Mortada El-Sayed, Hanaa Hassenein. Bioactive chemical constituents of Curcuma longa L. rhizomes extract inhibit the growth of human hepatoma cell line (HepG2).
Acta pharmaceutica (Zagreb, Croatia).
2016 Sep; 66(3):387-98. doi:
10.1515/acph-2016-0028. [PMID: 27383887] - Yonglu Wang, Liyao Wang, Xinyi Zhu, Dong Wang, Xueming Li. Choleretic Activity of Turmeric and its Active Ingredients.
Journal of food science.
2016 Jul; 81(7):H1800-6. doi:
10.1111/1750-3841.13348. [PMID: 27228476] - Abbas Ali, Yan-Hong Wang, Ikhlas A Khan. Larvicidal and Biting Deterrent Activity of Essential Oils of Curcuma longa, Ar-turmerone, and Curcuminoids Against Aedes aegypti and Anopheles quadrimaculatus (Culicidae: Diptera).
Journal of medical entomology.
2015 Sep; 52(5):979-86. doi:
10.1093/jme/tjv072. [PMID: 26336212] - Nantiya Joycharat, Sonesay Thammavong, Supayang Piyawan Voravuthikunchai, Patimaporn Plodpai, Watcharapong Mitsuwan, Surasak Limsuwan, Sanan Subhadhirasakul. Chemical constituents and antimicrobial properties of the essential oil and ethanol extract from the stem of Aglaia odorata Lour.
Natural product research.
2014; 28(23):2169-72. doi:
10.1080/14786419.2014.924934. [PMID: 24934340] - Ana Claudia F Amaral, Luciana A Gomes, Jefferson Rocha de A Silva, José Luiz P Ferreira, Aline de S Ramos, Maria do Socorro S Rosa, Alane B Vermelho, Igor A Rodrigues. Liposomal formulation of turmerone-rich hexane fractions from Curcuma longa enhances their antileishmanial activity.
BioMed research international.
2014; 2014(?):694934. doi:
10.1155/2014/694934. [PMID: 25045693] - Akira Murakami, Ikuyo Furukawa, Shingo Miyamoto, Takuji Tanaka, Hajime Ohigashi. Curcumin combined with turmerones, essential oil components of turmeric, abolishes inflammation-associated mouse colon carcinogenesis.
BioFactors (Oxford, England).
2013 Mar; 39(2):221-32. doi:
10.1002/biof.1054. [PMID: 23233214] - Sun Young Park, Young Hun Kim, YoungHee Kim, Sang-Joon Lee. Aromatic-turmerone's anti-inflammatory effects in microglial cells are mediated by protein kinase A and heme oxygenase-1 signaling.
Neurochemistry international.
2012 Oct; 61(5):767-77. doi:
10.1016/j.neuint.2012.06.020. [PMID: 22766494] - Sun Young Park, Mei Ling Jin, Young Hun Kim, YoungHee Kim, Sang Joon Lee. Anti-inflammatory effects of aromatic-turmerone through blocking of NF-κB, JNK, and p38 MAPK signaling pathways in amyloid β-stimulated microglia.
International immunopharmacology.
2012 Sep; 14(1):13-20. doi:
10.1016/j.intimp.2012.06.003. [PMID: 22728094] - Grace G L Yue, Sau-Wan Cheng, Hua Yu, Zi-Sheng Xu, Julia K M Lee, Po-Ming Hon, Mavis Y H Lee, Edward J Kennelly, Gary Deng, Simon K Yeung, Barrie R Cassileth, Kwok-Pui Fung, Ping-Chung Leung, Clara B S Lau. The role of turmerones on curcumin transportation and P-glycoprotein activities in intestinal Caco-2 cells.
Journal of medicinal food.
2012 Mar; 15(3):242-52. doi:
10.1089/jmf.2011.1845. [PMID: 22181075] - Kunishige Onuma, Yuka Suenaga, Ryuta Sakaki, Satoshi Yoshitome, Yu Sato, Satomi Ogawara, Saori Suzuki, Yasuhiro Kuramitsu, Hidekatsu Yokoyama, Akira Murakami, Junichi Hamada, Garth L Nicolson, Masanobu Kobayashi, Junichi Fujii, Futoshi Okada. Development of a quantitative bioassay to assess preventive compounds against inflammation-based carcinogenesis.
Nitric oxide : biology and chemistry.
2011 Aug; 25(2):183-94. doi:
10.1016/j.niox.2011.02.003. [PMID: 21345376] - Grace G L Yue, Ben C L Chan, Po-Ming Hon, Mavis Y H Lee, Kwok-Pui Fung, Ping-Chung Leung, Clara B S Lau. Evaluation of in vitro anti-proliferative and immunomodulatory activities of compounds isolated from Curcuma longa.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2010 Aug; 48(8-9):2011-20. doi:
10.1016/j.fct.2010.04.039. [PMID: 20438793] - Yongkyu Lee. Activation of apoptotic protein in U937 cells by a component of turmeric oil.
BMB reports.
2009 Feb; 42(2):96-100. doi:
10.5483/bmbrep.2009.42.2.096. [PMID: 19250610] - N Y Qin, F Q Yang, Y T Wang, S P Li. Quantitative determination of eight components in rhizome (Jianghuang) and tuberous root (Yujin) of Curcuma longa using pressurized liquid extraction and gas chromatography-mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2007 Jan; 43(2):486-92. doi:
10.1016/j.jpba.2006.07.034. [PMID: 16930909] - H S Lee. Antiplatelet property of Curcuma longa L. rhizome-derived ar-turmerone.
Bioresource technology.
2006 Aug; 97(12):1372-6. doi:
10.1016/j.biortech.2005.07.006. [PMID: 16112857] - Tozo Nishiyama, Tatsumasa Mae, Hideyuki Kishida, Misuzu Tsukagawa, Yoshihiro Mimaki, Minpei Kuroda, Yutaka Sashida, Kazuma Takahashi, Teruo Kawada, Kaku Nakagawa, Mikio Kitahara. Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice.
Journal of agricultural and food chemistry.
2005 Feb; 53(4):959-63. doi:
10.1021/jf0483873. [PMID: 15713005] - Mingjie Ji, Jaesue Choi, Jeongnyeo Lee, Yongkyu Lee. Induction of apoptosis by ar-turmerone on various cell lines.
International journal of molecular medicine.
2004 Aug; 14(2):253-6. doi:
10.3892/ijmm.14.2.253. [PMID: 15254774] - Mara E M Braga, Patrícia F Leal, João E Carvalho, M Angela A Meireles. Comparison of yield, composition, and antioxidant activity of turmeric (Curcuma longa L.) extracts obtained using various techniques.
Journal of agricultural and food chemistry.
2003 Oct; 51(22):6604-11. doi:
10.1021/jf0345550. [PMID: 14558784] - Chae Hee Hong, Min Soo Noh, Woo Young Lee, Sang Kook Lee. Inhibitory effects of natural sesquiterpenoids isolated from the rhizomes of Curcuma zedoaria on prostaglandin E2 and nitric oxide production.
Planta medica.
2002 Jun; 68(6):545-7. doi:
10.1055/s-2002-32560. [PMID: 12094302] - C H Hong, Y Kim, S K Lee. Sesquiterpenoids from the rhizome of Curcuma zedoaria.
Archives of pharmacal research.
2001 Oct; 24(5):424-6. doi:
10.1007/bf02975188. [PMID: 11693544] - L A Ferreira, O B Henriques, A A Andreoni, G R Vital, M M Campos, G G Habermehl, V L de Moraes. Antivenom and biological effects of ar-turmerone isolated from Curcuma longa (Zingiberaceae).
Toxicon : official journal of the International Society on Toxinology.
1992 Oct; 30(10):1211-8. doi:
10.1016/0041-0101(92)90437-a. [PMID: 1440627]