34W9GO6B2Z (BioDeep_00000396642)

   

PANOMIX_OTCML-2023


代谢物信息卡片


2H-Pyran-2-one, 5,6-dihydro-6-[(E)-2-phenylethenyl]-, (6R)-

化学式: C13H12O2 (200.0837252)
中文名称: (6R)-(+)-5,6-二氢-6-苯乙烯基-2-吡喃酮, GONIOTHALAMIN
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 37.29%

分子结构信息

SMILES: C1C=CC(=O)OC1C=CC2=CC=CC=C2
InChI: InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1

描述信息

Goniothalamin is a natural product found in Cryptocarya latifolia, Cryptocarya wyliei, and other organisms with data available.

同义名列表

15 个代谢物同义名

2H-Pyran-2-one, 5,6-dihydro-6-[(E)-2-phenylethenyl]-, (6R)-; 2H-Pyran-2-one, 5,6-dihydro-6-(2-phenylethenyl)-, (S-(E))-; (6R)-6-[(1E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one; (6R)-6.ALPHA.-((E)-STYRYL)-5,6-DIHYDRO-2H-PYRAN-2-ONE; (2R)-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one; 2H-Pyran-2-one, 5,6-dihydro-6-styryl-, (5S)-(+)-; (2R)-2-[(E)-styryl]-2,3-dihydropyran-6-one; (6R)-(+)-Goniothalamin; (R)-(+)-Goniothalamin; STYRYLDIHYDROPYRAN; (R)-goniothalamin; UNII-34W9GO6B2Z; Goniothalamine; Goniothalamin; 34W9GO6B2Z



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)

0 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

  • Vino Palani, Santhosh Chinnaraj, Murugesh Shanmugasundaram, Arunkumar Malaisamy, Viji Maluventhen, Vijaya Anand Arumugam, Kannan R R Rengasamy, Balamuralikrishnan Balasubramanian, Wen-Chao Liu, Maruthupandian Arumugam. Derivation, Functionalization of (S)-Goniothalamin from Goniothalamus wightii and Their Derivative Targets SARS-CoV-2 MPro, SPro, and RdRp: A Pharmacological Perspective. Molecules (Basel, Switzerland). 2022 Oct; 27(20):. doi: 10.3390/molecules27206962. [PMID: 36296552]
  • H M P Dilrukshi Herath, Sarah Preston, Abdul Jabbar, Jose Garcia-Bustos, Russell S Addison, Sasha Hayes, Topul Rali, Tao Wang, Anson V Koehler, Bill C H Chang, Andreas Hofmann, Rohan A Davis, Robin B Gasser. Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro. International journal for parasitology. Drugs and drug resistance. 2019 04; 9(?):72-79. doi: 10.1016/j.ijpddr.2018.12.006. [PMID: 30739078]
  • Surendra R Punganuru, Hanumantha Rao Madala, Viswanath Arutla, Kalkunte S Srivenugopal. Selective killing of human breast cancer cells by the styryl lactone (R)-goniothalamin is mediated by glutathione conjugation, induction of oxidative stress and marked reactivation of the R175H mutant p53 protein. Carcinogenesis. 2018 12; 39(11):1399-1410. doi: 10.1093/carcin/bgy093. [PMID: 30010803]
  • Nittaya Boonmuen, Natthakan Thongon, Arthit Chairoungdua, Kanoknetr Suksen, Wilart Pompimon, Patoomratana Tuchinda, Vichai Reutrakul, Pawinee Piyachaturawat. 5-Acetyl goniothalamin suppresses proliferation of breast cancer cells via Wnt/β-catenin signaling. European journal of pharmacology. 2016 Nov; 791(?):455-464. doi: 10.1016/j.ejphar.2016.09.024. [PMID: 27640746]
  • Débora Barbosa Vendramini-Costa, Antonio Alcaide, Karin Juliane Pelizzaro-Rocha, Elena Talero, Javier Ávila-Román, Sofia Garcia-Mauriño, Ronaldo Aloise Pilli, João Ernesto de Carvalho, Virginia Motilva. Goniothalamin prevents the development of chemically induced and spontaneous colitis in rodents and induces apoptosis in the HT-29 human colon tumor cell line. Toxicology and applied pharmacology. 2016 06; 300(?):1-12. doi: 10.1016/j.taap.2016.03.009. [PMID: 27016270]
  • Sukanda Innajak, Wilawan Mahabusrakum, Ramida Watanapokasin. Goniothalamin induces apoptosis associated with autophagy activation through MAPK signaling in SK-BR-3 cells. Oncology reports. 2016 May; 35(5):2851-8. doi: 10.3892/or.2016.4655. [PMID: 26987063]
  • Thanet Sophonnithiprasert, Sirinun Nilwarangkoon, Yukio Nakamura, Ramida Watanapokasin. Goniothalamin enhances TRAIL-induced apoptosis in colorectal cancer cells through DR5 upregulation and cFLIP downregulation. International journal of oncology. 2015 Dec; 47(6):2188-96. doi: 10.3892/ijo.2015.3204. [PMID: 26499766]
  • Naoya Wasano, Tomoko Takemura, Raihan Ismil, Baki Bakar, Yoshiharu Fujii. Transcriptomic evaluation of plant growth inhibitory activity of goniothalamin from the Malaysian medicinal plant Goniothalamus andersonii. Natural product communications. 2015 May; 10(5):725-7. doi: ". [PMID: 26058144]
  • Mohamed Ali Seyed, Ibrahim Jantan, Syed Nasir Abbas Bukhari. Emerging anticancer potentials of goniothalamin and its molecular mechanisms. BioMed research international. 2014; 2014(?):536508. doi: 10.1155/2014/536508. [PMID: 25247178]
  • Barbora Orlikova, Marc Schumacher, Tom Juncker, Choo Chee Yan, Salmaan H Inayat-Hussain, Shéhérazade Hajjouli, Claudia Cerella, Mario Dicato, Marc Diederich. Styryl-lactone goniothalamin inhibits TNF-α-induced NF-κB activation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Sep; 59(?):572-8. doi: 10.1016/j.fct.2013.06.051. [PMID: 23845509]
  • Aied Mohammed Alabsi, Rola Ali, Abdul Manaf Ali, Hazlan Harun, Sami Abdo Radman Al-Dubai, Kurubaran Ganasegeran, Mustafa Ahmed Alshagga, Sameer Dirhim Salem, Noor Hayaty Binti Abu Kasim. Induction of caspase-9, biochemical assessment and morphological changes caused by apoptosis in cancer cells treated with goniothalamin extracted from Goniothalamus macrophyllus. Asian Pacific journal of cancer prevention : APJCP. 2013; 14(11):6273-80. doi: 10.7314/apjcp.2013.14.11.6273. [PMID: 24377517]
  • Ploingarm Petsophonsakul, Wilart Pompimon, Ratana Banjerdpongchai. Apoptosis induction in human leukemic promyelocytic HL-60 and monocytic U937 cell lines by goniothalamin. Asian Pacific journal of cancer prevention : APJCP. 2013; 14(5):2885-9. doi: 10.7314/apjcp.2013.14.5.2885. [PMID: 23803048]
  • Rosalind Pei Theng Kim, Vicky Bihud, Khalit Bin Mohamad, Kok Hoong Leong, Jamaludin Bin Mohamad, Fasihuddin Bin Ahmad, Hazrina Hazni, Noraini Kasim, Siti Nadiah Abdul Halim, Khalijah Awang. Cytotoxic and antioxidant compounds from the stem bark of Goniothalamus tapisoides Mat Salleh. Molecules (Basel, Switzerland). 2012 Dec; 18(1):128-39. doi: 10.3390/molecules18010128. [PMID: 23344192]
  • Ching-Yu Yen, Chien-Chih Chiu, Rou-Wen Haung, Chi-Chen Yeh, Kuang-Jing Huang, Kuo-Feng Chang, You-Cheng Hseu, Fang-Rong Chang, Hsueh-Wei Chang, Yang-Chang Wu. Antiproliferative effects of goniothalamin on Ca9-22 oral cancer cells through apoptosis, DNA damage and ROS induction. Mutation research. 2012 Sep; 747(2):253-8. doi: 10.1016/j.mrgentox.2012.06.003. [PMID: 22721813]
  • Tomoko Takemura, Tsunashi Kamo, Raihan Ismil, Baki Bakar, Naoya Wasano, Syuntaro Hiradate, Yoshiharu Fujii. Plant growth inhibitor from the Malaysian medicinal plant Goniothalamus andersonii and related species. Natural product communications. 2012 Sep; 7(9):1197-8. doi: ". [PMID: 23074907]
  • Bushra Abdulkarim Moharam, Ibrahim Jantan, Juriyati Jalil, Fasihuddin Ahmad. Inhibitory effect of compounds from Goniothalamus tapis Miq. and Goniothalamus uvaroides King on platelet-activating factor receptor binding. Phytotherapy research : PTR. 2012 May; 26(5):687-91. doi: 10.1002/ptr.3620. [PMID: 22002630]
  • Aied M Alabsi, Rola Ali, Abdul Manaf Ali, Sami Abdo Radman Al-Dubai, Hazlan Harun, Noor H Abu Kasim, Abdulsamad Alsalahi. Apoptosis induction, cell cycle arrest and in vitro anticancer activity of gonothalamin in a cancer cell lines. Asian Pacific journal of cancer prevention : APJCP. 2012; 13(10):5131-6. doi: 10.7314/apjcp.2012.13.10.5131. [PMID: 23244123]
  • Angelo de Fátima, Willian F Zambuzzi, Luzia V Modolo, Christiane A B Tarsitano, Fernanda R Gadelha, Stephen Hyslop, João Ernesto de Carvalho, Ione Salgado, Carmen V Ferreira, Ronaldo A Pilli. Cytotoxicity of goniothalamin enantiomers in renal cancer cells: involvement of nitric oxide, apoptosis and autophagy. Chemico-biological interactions. 2008 Nov; 176(2-3):143-50. doi: 10.1016/j.cbi.2008.08.003. [PMID: 18771661]
  • Sengottayan Senthil-Nathan, Man-Young Choi, Chae-Hoon Paik, Kandaswamy Kalaivani. The toxicity and physiological effect of goniothalamin, a styryl-pyrone, on the generalist herbivore, Spodoptera exigua Hübner. Chemosphere. 2008 Jul; 72(9):1393-400. doi: 10.1016/j.chemosphere.2008.03.037. [PMID: 18499224]
  • Angelo de Fátima, Luciana K Kohn, João Ernesto de Carvalho, Ronaldo A Pilli. Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells. Bioorganic & medicinal chemistry. 2006 Feb; 14(3):622-31. doi: 10.1016/j.bmc.2005.08.036. [PMID: 16202605]
  • M Ashik Mosaddik, M Ekramul Haque. Cytotoxicity and antimicrobial activity of goniothalamin isolated from Bryonopsis laciniosa. Phytotherapy research : PTR. 2003 Dec; 17(10):1155-7. doi: 10.1002/ptr.1303. [PMID: 14669248]
  • S H Inayat-Hussain, B O Annuar, L B Din, A M Ali, D Ross. Loss of mitochondrial transmembrane potential and caspase-9 activation during apoptosis induced by the novel styryl-lactone goniothalamin in HL-60 leukemia cells. Toxicology in vitro : an international journal published in association with BIBRA. 2003 Aug; 17(4):433-9. doi: 10.1016/s0887-2333(03)00051-1. [PMID: 12849726]
  • S Tanaka, S Yoichi, L Ao, M Matumoto, K Morimoto, N Akimoto, G Honda, M Tabata, T Oshima, T Masuda, M Z bin Asmawi, Z Ismail, S M Yusof, L B Din, I M Said. Potential immunosuppressive and antiinflammatory activities of Malaysian medicinal plants characterized by reduced cell surface expression of cell adhesion molecules. Phytotherapy research : PTR. 2001 Dec; 15(8):681-6. doi: 10.1002/ptr.778. [PMID: 11746860]
  • S H Inayat-Hussain, A B Osman, L B Din, A M Ali, R T Snowden, M MacFarlane, K Cain. Caspases-3 and -7 are activated in goniothalamin-induced apoptosis in human Jurkat T-cells. FEBS letters. 1999 Aug; 456(3):379-83. doi: 10.1016/s0014-5793(99)00984-9. [PMID: 10462048]
  • A H Pihie, J Stanslas, L B Din. Non-steroid receptor-mediated antiproliferative activity of styrylpyrone derivative in human breast cancer cell lines. Anticancer research. 1998 May; 18(3A):1739-43. doi: NULL. [PMID: 9673398]
  • S El-Sharkawy, Z Yusuf, A H Pihie, A M Ali. Metabolism of goniothalamin in animal and microbial system. Bollettino chimico farmaceutico. 1996 Jan; 135(1):35-40. doi: NULL. [PMID: 9004738]