mollugin (BioDeep_00000229881)

   

PANOMIX_OTCML-2023


代谢物信息卡片


2H-Naphtho(1,2-b)pyran-5-carboxylic acid, 6-hydroxy-2,2-dimethyl-, methyl ester

化学式: C17H16O4 (284.1048536)
中文名称: 大叶茜草素, 大叶茜草素
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 50%

分子结构信息

SMILES: CC1(C=CC2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)C
InChI: InChI=1S/C17H16O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-9,18H,1-3H3

描述信息

Rubimaillin is a benzochromene that is 2H-benzo[h]chromene which is substituted by two methyl groups at position 2, a methoxycarbonyl group at position 5, and a hydroxy group at position 6. Found in the Chinese medical plant Rubia cordifola, It has an anti-cancer effect by inhibition of TNF-alpha-induced NF-kappaB activation. It is also a dual inhibitor of acyl-CoA:cholesterol acyltransferase 1 and 2 (ACAT1 and ACAT2), but is more selective for the ACAT2 isozyme. It has a role as a plant metabolite, an acyl-CoA:cholesterol acyltransferase 2 inhibitor, a NF-kappaB inhibitor, an antineoplastic agent, an apoptosis inducer, a neuroprotective agent and an anti-inflammatory agent. It is a benzochromene, a methyl ester and a member of phenols.
Mollugin is a natural product found in Rubia alata, Rubia argyi, and other organisms with data available.
Mollugin is an orally active and potent NF-κB inhibitor. Mollugin induces S-phase arrest of HepG2 cells, and increased intracellular reactive oxygen species (ROS) levels. Mollugin induces DNA damage in HepG2 cells, as well as an increase in the expression of p-H2AX. Mollugin shows anti-cancer effect by inhibiting TNF-α-induced NF-κB activation. Mollugin enhances the osteogenic action of BMP-2 (bone morphogenetic protein 2) via the p38-Smad signaling pathway[1][2][3].
Mollugin is an orally active and potent NF-κB inhibitor. Mollugin induces S-phase arrest of HepG2 cells, and increased intracellular reactive oxygen species (ROS) levels. Mollugin induces DNA damage in HepG2 cells, as well as an increase in the expression of p-H2AX. Mollugin shows anti-cancer effect by inhibiting TNF-α-induced NF-κB activation. Mollugin enhances the osteogenic action of BMP-2 (bone morphogenetic protein 2) via the p38-Smad signaling pathway[1][2][3].
Mollugin is an orally active and potent NF-κB inhibitor. Mollugin induces S-phase arrest of HepG2 cells, and increased intracellular reactive oxygen species (ROS) levels. Mollugin induces DNA damage in HepG2 cells, as well as an increase in the expression of p-H2AX. Mollugin shows anti-cancer effect by inhibiting TNF-α-induced NF-κB activation. Mollugin enhances the osteogenic action of BMP-2 (bone morphogenetic protein 2) via the p38-Smad signaling pathway[1][2][3].

同义名列表

21 个代谢物同义名

2H-Naphtho(1,2-b)pyran-5-carboxylic acid, 6-hydroxy-2,2-dimethyl-, methyl ester; 2H-Naphtho[1,2-b]pyran-5-carboxylate, 2,2-dimethyl-6-hydroxy-, methyl ester; methyl 6-hydroxy-2,2-dimethyl-2h-benzeno[h]chromene-5-carboxylate; Methyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate #; Methyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate; methyl 6-hydroxy-2,2-dimethyl-benzo[h]chromene-5-carboxylate; methyl 6-hydroxy-2,2-dimethylbenzo[h]chromene-5-carboxylate; 3-carbomethoxy-4-hydroxy-6,6-dimethylnaphtho(1,2-2,3)pyran; VLGATXOTCNBWIT-UHFFFAOYSA-N; Mollugin, >=98\\% (HPLC); UNII-M98N6A8Z2F; Mollugin,(S); rubimaillin; M98N6A8Z2F; Rubimailin; C17H16O4; mollugin; 6-hydroxy-2,2-dimethyl-benzo[h]chromene-5-carboxylic acid methyl ester; 6-hydroxy-2,2-dimethyl-5-benzo[h]chromenecarboxylic acid methyl ester; CCRIS 6432; 55481-88-4



数据库引用编号

9 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)

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

  • Xiaojun Liu, Xiaofei Shen, Han Wang, Jiayi Wang, Yanlin Ren, Min Zhang, Sixu Li, Lijuan Guo, Jingyu Li, Yi Wang. Mollugin prevents CLP-induced sepsis in mice by inhibiting TAK1-NF-κB/MAPKs pathways and activating Keap1-Nrf2 pathway in macrophages. International immunopharmacology. 2023 Dec; 125(Pt A):111079. doi: 10.1016/j.intimp.2023.111079. [PMID: 38149576]
  • Wei Wang, Lijiang Zhou, Xinyu Zhang, Zheng Li. Mollugin suppresses proliferation and drives ferroptosis of colorectal cancer cells through inhibition of insulin-like growth factor 2 mRNA binding protein 3/glutathione peroxidase 4 axis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Oct; 166(?):115427. doi: 10.1016/j.biopha.2023.115427. [PMID: 37677963]
  • Zhuanzhuan Wang, Xin Cui, Wenhui Yan, Na Liu, Jia Shang, Xinyao Yi, Tingli Guo, Xiaotong Wei, Yuzhuo Sun, Hao Hu, Weina Ma, Wei Cui, Lina Chen. Mollugin activates GLP-1R to improve cognitive dysfunction in type 2 diabetic mice. Life sciences. 2023 Aug; 331(?):122026. doi: 10.1016/j.lfs.2023.122026. [PMID: 37607641]
  • Xin-Ge Ke, Yi-Yi Xiong, Bing Yu, Chong Yuan, Peng-Yu Chen, Yan-Fang Yang, He-Zhen Wu. Mollugin induced oxidative DNA damage via up-regulating ROS that caused cell cycle arrest in hepatoma cells. Chemico-biological interactions. 2022 Feb; 353(?):109805. doi: 10.1016/j.cbi.2022.109805. [PMID: 35007525]
  • Han Luo, Yong-Feng Lv, Hong Zhang, Jiang-Miao Hu, Hong-Mei Li, Shou-Jin Liu. Synthesis and Antitumor Activity of 1-Substituted 1,2,3-Triazole-Mollugin Derivatives. Molecules (Basel, Switzerland). 2021 May; 26(11):. doi: 10.3390/molecules26113249. [PMID: 34071319]
  • Liping Zeng, Tianyi Xu, Jie Meng, Dingfang Wu, Shihua Wu. H2O-Induced Hydrophobic Interactions in MS-Guided Counter-Current Chromatography Separation of Anti-Cancer Mollugin from Rubia cordifolia. Molecules (Basel, Switzerland). 2021 Feb; 26(3):. doi: 10.3390/molecules26030751. [PMID: 33540504]
  • Juan Li, Jin-Ling Zhang, Xue-Peng Gong, Meng Xiao, Yuan-Yuan Song, Hui-Fang Pi, Guang Du. Anti-inflammatory Activity of Mollugin on DSS-induced Colitis in Mice. Current medical science. 2020 Oct; 40(5):910-916. doi: 10.1007/s11596-020-2262-5. [PMID: 33123905]
  • Wanli Yan, Zhonglei Jiang, Fengyun Fan. Analgesic action of Rubimaillin in vitro and in vivo. Cellular and molecular biology (Noisy-le-Grand, France). 2020 Jun; 66(3):171-175. doi: . [PMID: 32538766]
  • Zhang Siwei, Wu Zhen, Zhou Zhi, Hu Xuguang, Li Yousheng. Rubimaillin decreases the viability of human ovarian cancer cells via mitochondria-dependent apoptosis. Cellular and molecular biology (Noisy-le-Grand, France). 2019 Sep; 65(7):72-76. doi: 10.14715/cmb/2019.65.7.13. [PMID: 31880521]
  • Ki Bum Hong, Darong Kim, Bo-Kyung Kim, Seo Yeon Woo, Ji Hoon Lee, Seung-Hee Han, Gyu-Un Bae, Soosung Kang. CF₃-Substituted Mollugin 2-(4-Morpholinyl)-ethyl ester as a Potential Anti-inflammatory Agent with Improved Aqueous Solubility and Metabolic Stability. Molecules (Basel, Switzerland). 2018 Aug; 23(8):. doi: 10.3390/molecules23082030. [PMID: 30110934]
  • Mingjie Gao, Jing Yang, Zhibin Wang, Bingyou Yang, Haixue Kuang, Lu Liu, Liqian Wang, Chunjuan Yang. Simultaneous Determination of Purpurin, Munjistin and Mollugin in Rat Plasma by Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry: Application to a Pharmacokinetic Study after Oral Administration of Rubia cordifolia L. Extract. Molecules (Basel, Switzerland). 2016 Jun; 21(6):. doi: 10.3390/molecules21060717. [PMID: 27258244]
  • Hong-shuai Yang, Ju Wang, Cui Guo, Wei Liu, Yuan-yuan Chen, Jin-feng Wei, Wen-yi Kang. Simultaneous determination of alizarin and rubimaillin in Rubia cordifolia by ultrasound-assisted ionic liquid-reversed phase liquid chromatography. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2015 Jul; 40(13):2617-23. doi: ". [PMID: 26697688]
  • Si-Meng Zhao, Zhe Wang, Guang-Zhi Zeng, Wei-Wu Song, Xiao-Qiang Chen, Xiao-Nian Li, Ning-Hua Tan. New cytotoxic naphthohydroquinone dimers from Rubia alata. Organic letters. 2014 Nov; 16(21):5576-9. doi: 10.1021/ol502603f. [PMID: 25310176]
  • Do Youn Jun, Cho Rong Han, Myung Sook Choi, Myung Ae Bae, Mi Hee Woo, Young Ho Kim. Effect of mollugin on apoptosis and adipogenesis of 3T3-L1 preadipocytes. Phytotherapy research : PTR. 2011 May; 25(5):724-31. doi: 10.1002/ptr.3329. [PMID: 21077262]
  • Sun Mi Kim, Hae Sun Park, Do Youn Jun, Hyun Ju Woo, Mi Hee Woo, Chae Ha Yang, Young Ho Kim. Mollugin induces apoptosis in human Jurkat T cells through endoplasmic reticulum stress-mediated activation of JNK and caspase-12 and subsequent activation of mitochondria-dependent caspase cascade regulated by Bcl-xL. Toxicology and applied pharmacology. 2009 Dec; 241(2):210-20. doi: 10.1016/j.taap.2009.08.024. [PMID: 19716835]
  • Kyoung-Jin Kim, Jong Suk Lee, Mi-Kyoung Kwak, Han Gon Choi, Chul Soon Yong, Jung-Ae Kim, Yong Rok Lee, Won Seok Lyoo, Young-Joon Park. Anti-inflammatory action of mollugin and its synthetic derivatives in HT-29 human colonic epithelial cells is mediated through inhibition of NF-kappaB activation. European journal of pharmacology. 2009 Nov; 622(1-3):52-7. doi: 10.1016/j.ejphar.2009.09.008. [PMID: 19765578]
  • Daisuke Matsuda, Taichi Ohshiro, Mio Ohba, Wei Jiang, Bin Hong, Shuyi Si, Hiroshi Tomoda. The molecular target of rubimaillin in the inhibition of lipid droplet accumulation in macrophages. Biological & pharmaceutical bulletin. 2009 Aug; 32(8):1317-20. doi: 10.1248/bpb.32.1317. [PMID: 19652367]
  • Wai-Pui Tse, Christopher H K Cheng, Chun-Tao Che, Ming Zhao, Zhi-Xiu Lin. Induction of apoptosis underlies the Radix Rubiae-mediated anti-proliferative action on human epidermal keratinocytes: implications for psoriasis treatment. International journal of molecular medicine. 2007 Nov; 20(5):663-72. doi: 10.3892/ijmm.20.5.663. [PMID: 17912459]
  • Yanbin Lu, Rui Liu, Cuirong Sun, Yuanjiang Pan. An effective high-speed countercurrent chromatographic method for preparative isolation and purification of mollugin directly from the ethanol extract of the Chinese medicinal plant Rubia cordifolia. Journal of separation science. 2007 Jun; 30(9):1313-7. doi: 10.1002/jssc.200600440. [PMID: 17623473]
  • Samir El-Hady, Jacques Bukuru, Bart Kesteleyn, Luc Van Puyvelde, Tuyen Nguyen Van, Norbert De Kimpe. New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora. Journal of natural products. 2002 Sep; 65(9):1377-9. doi: 10.1021/np020110e. [PMID: 12350172]
  • F Marec, I Kollárová, A Jegorov. Mutagenicity of natural anthraquinones from Rubia tinctorum in the Drosophila wing spot test. Planta medica. 2001 Mar; 67(2):127-31. doi: 10.1055/s-2001-11498. [PMID: 11301857]
  • Y L Liu, Y L Bai. [Studies on the chemical constituents of Rubia schumanniana Pritz]. Yao xue xue bao = Acta pharmaceutica Sinica. 1985 Jan; 20(1):53-8. doi: ". [PMID: 3839622]
  • J M Relton, N S Gee, R Matsas, A J Turner, A J Kenny. Purification of endopeptidase-24.11 ('enkephalinase') from pig brain by immunoadsorbent chromatography. The Biochemical journal. 1983 Dec; 215(3):519-23. doi: 10.1042/bj2150519. [PMID: 6419725]