2'-Hydroxy-4',6'-dimethoxychalcone (BioDeep_00000017322)

 

Secondary id: BioDeep_00000270222

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-

化学式: C17H16O4 (284.1048536)
中文名称: 卡瓦黄素内酯B,黄卡瓦胡椒素B, 黄卡瓦胡椒素 B, 黄卡瓦胡椒素B
谱图信息: 最多检出来源 Viridiplantae(plant) 3.7%

分子结构信息

SMILES: C1(OC)=CC(OC)=C(C(=O)/C=C/C2C=CC=CC=2)C(O)=C1
InChI: InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+

描述信息

Flavokawain B is a member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2 and methoxy groups at positions 4 and 6. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities. It has a role as a metabolite, an antileishmanial agent, an anti-inflammatory agent, an apoptosis inducer and an antineoplastic agent. It is a member of chalcones, a dimethoxybenzene and a member of phenols. It is functionally related to a trans-chalcone.
Flavokawain b is a natural product found in Alpinia rafflesiana, Bistorta officinalis, and other organisms with data available.
See also: Piper methysticum root (part of).
A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy group at positions 2 and methoxy groups at positions 4 and 6. Isolated from Piper methysticum and Piper rusbyi, it exhibits antileishmanial, anti-inflammatory and antineoplastic activities.
2-Hydroxy-4,6-dimethoxychalcone is found in beverages. 2-Hydroxy-4,6-dimethoxychalcone is found in kava (Piper methysticum), FDA advises against use of kava in food due to potential risk of severe liver damage (2002).
Found in kava (Piper methysticum), FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
Flavokawain B (Flavokavain B) is a chalcone isolated from the root extracts of kava-kava plant and a potent apoptosis inducer for inhibiting the growth of various cancer cell lines. Flavokawain B (Flavokavain B) shows strong antiangiogenic activity. Flavokawain B (Flavokavain B) inhibits human brain endothelial cell (HUVEC) migration and tube formation with very low and non-toxic concentrations[1][2].
Flavokawain B (Flavokavain B) is a chalcone isolated from the root extracts of kava-kava plant and a potent apoptosis inducer for inhibiting the growth of various cancer cell lines. Flavokawain B (Flavokavain B) shows strong antiangiogenic activity. Flavokawain B (Flavokavain B) inhibits human brain endothelial cell (HUVEC) migration and tube formation with very low and non-toxic concentrations[1][2].

同义名列表

26 个代谢物同义名

2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-; 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (E)-; 2-Propen-1-one,1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-, (2E)-; (2E)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-3-PHENYL-2-PROPEN-1-ONE; (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one; (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one; 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenyl-2-propen-1-one; 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one; (E)-2-Hydroxy-4,6-dimethoxychalcone; Chalcone, 2-hydroxy-4,6-dimethoxy-; 4,6-Dimethoxy-2-hydroxychalcone; CHALCONE,2-HYDROXY-4,6-DIMETHYL; 2-Hydroxy-4,6-dimethoxychalcone; QKQLSQLKXBHUSO-CMDGGOBGSA-N; CHALCONE,6-DIMETHYL; Spectrum5_000188; UNII-R9WC6SM4UQ; PERSICOCHALCONE; MEGxp0_001270; Flavokawain B; flavokavain B; flavokavin B; Flavokawin B; Flavokawain; R9WC6SM4UQ; Flavokawain b



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

28 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

  • Paweł Chlipała, Tomasz Tronina, Monika Dymarska, Monika Urbaniak, Ewa Kozłowska, Łukasz Stępień, Edyta Kostrzewa-Susłow, Tomasz Janeczko. Multienzymatic biotransformation of flavokawain B by entomopathogenic filamentous fungi: structural modifications and pharmacological predictions. Microbial cell factories. 2024 Feb; 23(1):65. doi: 10.1186/s12934-024-02338-9. [PMID: 38402203]
  • Antonio Celentano, Callisthenis Yiannis, Rita Paolini, Pangzhen Zhang, Camile S Farah, Nicola Cirillo, Tami Yap, Michael McCullough. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro. Scientific reports. 2020 09; 10(1):15904. doi: 10.1038/s41598-020-73058-4. [PMID: 32985597]
  • A Palko-Łabuz, E Kostrzewa-Susłow, T Janeczko, K Środa-Pomianek, A Poła, A Uryga, K Michalak. Cyclization of flavokawain B reduces its activity against human colon cancer cells. Human & experimental toxicology. 2020 Mar; 39(3):262-275. doi: 10.1177/0960327119882986. [PMID: 31640425]
  • Xueqin Yang, Tao Zan, Huiyu Yan, Baohua Liu. UPLC-MS/MS determination of flavokawain B, a novel anti-tumor chemotherapeutic agent in rat plasma and its application to a pharmacokinetic study in rats. Biomedical chromatography : BMC. 2019 Feb; 33(2):e4391. doi: 10.1002/bmc.4391. [PMID: 30238480]
  • Mariana C Rossette, Débora C Moraes, Erika K Sacramento, Marco Aurélio Romano-Silva, Juliana L Carvalho, Dawidson A Gomes, Hanna Caldas, Eitan Friedman, Luciana Bastos-Rodrigues, Luiz De Marco. The In Vitro and In Vivo Antiangiogenic Effects of Flavokawain B. Phytotherapy research : PTR. 2017 Oct; 31(10):1607-1613. doi: 10.1002/ptr.5891. [PMID: 28816367]
  • Ibrahim Malami, Ahmad Bustamam Abdul, Rasedee Abdullah, Nur Kartinee Bt Kassim, Rozita Rosli, Swee Keong Yeap, Peter Waziri, Imaobong Christopher Etti, Muhammad Bashir Bello. Crude Extracts, Flavokawain B and Alpinetin Compounds from the Rhizome of Alpinia mutica Induce Cell Death via UCK2 Enzyme Inhibition and in Turn Reduce 18S rRNA Biosynthesis in HT-29 Cells. PloS one. 2017; 12(1):e0170233. doi: 10.1371/journal.pone.0170233. [PMID: 28103302]
  • Keanu D Pinner, Christina T K Wales, Rachel A Gristock, Hoa T Vo, Nadine So, Aaron T Jacobs. Flavokawains A and B from kava (Piper methysticum) activate heat shock and antioxidant responses and protect against hydrogen peroxide-induced cell death in HepG2 hepatocytes. Pharmaceutical biology. 2016 Sep; 54(9):1503-12. doi: 10.3109/13880209.2015.1107104. [PMID: 26789234]
  • Nadiah Abu, M Nadeem Akhtar, Swee Keong Yeap, Kian Lam Lim, Wan Yong Ho, Mohd Puad Abdullah, Chai Ling Ho, Abdul Rahman Omar, Jamil Ismail, Noorjahan Banu Alitheen. Flavokawain B induced cytotoxicity in two breast cancer cell lines, MCF-7 and MDA-MB231 and inhibited the metastatic potential of MDA-MB231 via the regulation of several tyrosine kinases In vitro. BMC complementary and alternative medicine. 2016 Feb; 16(?):86. doi: 10.1186/s12906-016-1046-8. [PMID: 26922065]
  • Nadiah Abu, Nurul Elyani Mohameda, Nirosha Tangarajoo, Swee Keong Yeap, M Nadeem Akhtar, Mohd Puad Abdullah, Abdul Rahman Omar, Noorjahan Banu Alitheen. In vitro Toxicity and in vivo Immunomodulatory Effects of Flavokawain A and Flavokawain B in Balb/C Mice. Natural product communications. 2015 Jul; 10(7):1199-202. doi: . [PMID: 26411010]
  • Nadiah Abu, Nurul Elyani Mohamed, Swee Keong Yeap, Kian Lam Lim, M Nadeem Akhtar, Aimi Jamil Zulfadli, Beh Boon Kee, Mohd Puad Abdullah, Abdul Rahman Omar, Noorjahan Banu Alitheen. In vivo antitumor and antimetastatic effects of flavokawain B in 4T1 breast cancer cell-challenged mice. Drug design, development and therapy. 2015; 9(?):1401-17. doi: 10.2147/dddt.s67976. [PMID: 25834398]
  • Tianshun Zhang, Norio Yamamoto, Yoko Yamashita, Hitoshi Ashida. The chalcones cardamonin and flavokawain B inhibit the differentiation of preadipocytes to adipocytes by activating ERK. Archives of biochemistry and biophysics. 2014 Jul; 554(?):44-54. doi: 10.1016/j.abb.2014.05.008. [PMID: 24845100]
  • Tianshun Zhang, Norio Yamamoto, Hitoshi Ashida. Chalcones suppress fatty acid-induced lipid accumulation through a LKB1/AMPK signaling pathway in HepG2 cells. Food & function. 2014 Jun; 5(6):1134-41. doi: 10.1039/c3fo60694e. [PMID: 24722377]
  • V Lebot, T K T Do, L Legendre. Detection of flavokavins (A, B, C) in cultivars of kava (Piper methysticum) using high performance thin layer chromatography (HPTLC). Food chemistry. 2014 May; 151(?):554-60. doi: 10.1016/j.foodchem.2013.11.120. [PMID: 24423570]
  • Ramez N Eskander, Leslie M Randall, Toshinori Sakai, Yi Guo, Bang Hoang, Xiaolin Zi. Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line. The journal of obstetrics and gynaecology research. 2012 Aug; 38(8):1086-94. doi: 10.1111/j.1447-0756.2011.01841.x. [PMID: 22540374]
  • Shevin R Feroz, Saharuddin B Mohamad, Noraini Bujang, Sri N A Malek, Saad Tayyab. Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin. Journal of agricultural and food chemistry. 2012 Jun; 60(23):5899-908. doi: 10.1021/jf301139h. [PMID: 22624666]
  • Rolf Teschke, Samuel X Qiu, Vincent Lebot. Herbal hepatotoxicity by kava: update on pipermethystine, flavokavain B, and mould hepatotoxins as primarily assumed culprits. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver. 2011 Sep; 43(9):676-81. doi: 10.1016/j.dld.2011.01.018. [PMID: 21377431]
  • Ping Zhou, Shimon Gross, Ji-Hua Liu, Bo-Yang Yu, Ling-Ling Feng, Jan Nolta, Vijay Sharma, David Piwnica-Worms, Samuel X Qiu. Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-kappaB and MAPK signaling pathways. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2010 Dec; 24(12):4722-32. doi: 10.1096/fj.10-163311. [PMID: 20696856]
  • A S Mohamad, M N Akhtar, Z A Zakaria, E K Perimal, S Khalid, P A Mohd, M H Khalid, D A Israf, N H Lajis, M R Sulaiman. Antinociceptive activity of a synthetic chalcone, flavokawin B on chemical and thermal models of nociception in mice. European journal of pharmacology. 2010 Nov; 647(1-3):103-9. doi: 10.1016/j.ejphar.2010.08.030. [PMID: 20826146]
  • Yu-Feng Kuo, Ying-Zhen Su, Yen-Hsueh Tseng, Sheng-Yang Wang, Hsi-Ming Wang, Pin Ju Chueh. Flavokawain B, a novel chalcone from Alpinia pricei Hayata with potent apoptotic activity: Involvement of ROS and GADD153 upstream of mitochondria-dependent apoptosis in HCT116 cells. Free radical biology & medicine. 2010 Jul; 49(2):214-26. doi: 10.1016/j.freeradbiomed.2010.04.005. [PMID: 20398749]
  • Chien-Tsong Lin, K Jayabal Senthil Kumar, Yen-Hsueh Tseng, Zi-Jie Wang, Mu-Yun Pan, Jun-Hong Xiao, Shih-Chang Chien, Sheng-Yang Wang. Anti-inflammatory activity of Flavokawain B from Alpinia pricei Hayata. Journal of agricultural and food chemistry. 2009 Jul; 57(14):6060-5. doi: 10.1021/jf900517d. [PMID: 19537711]
  • Young Hoon Kim, Jeongsoo Kim, Haeil Park, Hyun Pyo Kim. Anti-inflammatory activity of the synthetic chalcone derivatives: inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells. Biological & pharmaceutical bulletin. 2007 Aug; 30(8):1450-5. doi: 10.1248/bpb.30.1450. [PMID: 17666802]
  • Jin-Woo Jhoo, James P Freeman, Thomas M Heinze, Joanna D Moody, Laura K Schnackenberg, Richard D Beger, Klaus Dragull, Chung-Shih Tang, Catharina Y W Ang. In vitro cytotoxicity of nonpolar constituents from different parts of kava plant (Piper methysticum). Journal of agricultural and food chemistry. 2006 Apr; 54(8):3157-62. doi: 10.1021/jf051853j. [PMID: 16608246]
  • Xiaolin Zi, Anne R Simoneau. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice. Cancer research. 2005 Apr; 65(8):3479-86. doi: 10.1158/0008-5472.can-04-3803. [PMID: 15833884]
  • Jian-Qiao Gu, Eun Jung Park, Jose Schunke Vigo, James G Graham, Harry H S Fong, John M Pezzuto, A Douglas Kinghorn. Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase. Journal of natural products. 2002 Nov; 65(11):1616-20. doi: 10.1021/np020249p. [PMID: 12444686]
  • Di Wu, Muraleedharan G Nair, David L DeWitt. Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme. Journal of agricultural and food chemistry. 2002 Feb; 50(4):701-5. doi: 10.1021/jf010963x. [PMID: 11829631]