Marmesin (BioDeep_00000000059)

 

Secondary id: BioDeep_00000000470, BioDeep_00000861000

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one

化学式: C14H14O4 (246.0892044)
中文名称: S-(+)-印枳树皮素, S-(+)-印度榀椁素, 马梅辛, 异紫花前胡内酯, 2-（2-羟基丙-2-基）-2,3-二氢呋喃并[3,2-g]苯并吡喃-7-酮, S-(+)-印度枸橘素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.04%

Reviewed

Last reviewed on 2024-09-04.

Cite this Page

Marmesin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/marmesin (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000000059). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
InChI: InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3

描述信息

Marmesin is a member of psoralens and a tertiary alcohol.
2-(2-Hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one is a natural product found in Zanthoxylum beecheyanum, Zanthoxylum arnottianum, and other organisms with data available.
Nodakenetin is found in wild celery. Nodakenetin is a constituent of Angelica species
Constituent of Angelica subspecies Nodakenetin is found in wild celery.
(+)-marmesin is a marmesin. It is an enantiomer of a nodakenetin.
Marmesin is a natural product found in Coronilla scorpioides, Clausena dunniana, and other organisms with data available.
S-(+)-Marmesin is a natural coumarin, exhibiting COX-2/5-LOX dual inhibitory activity.

(+)-Marmesin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=13849-08-6 (retrieved 2024-09-04) (CAS RN: 13849-08-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

62 个代谢物同义名

InChI=1/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H; 7H-Furo[3,2-g][1]benzopyran-7-one,2,3-dihydro-2-(1-hydroxy-1-methylethyl)-; 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7h-furo[3,2-g][1]benzopyran-7-one; 2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one #; 2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one; 2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one; 2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one; 2-(1-Hydroxy-1-methylethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one; 2-(2-Hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one; 2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE; ( inverted exclamation markA)-Marmesin; FWYSBEAFFPBAQU-UHFFFAOYSA-N; (+)-Marmesin;(S)-Marmesin; (+/-)-Marmesin; S-(+)-Marmesin; Oprea1_172287; Oprea1_468691; (+)-Marmesin; (±)-Marmesin; (S)-Marmesin; nodakenetin; Marmesin; 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-; 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-; 7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 2,3-DIHYDRO-2-(1-HYDROXY-1-METHYLETHYL)-, (2S)-; 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (2S)-; 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-; (S)-(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one; 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-; (2S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one; (S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one; (+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one; (2S)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one; (S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one; (2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one; 2-(2-Hydroxy-2-propanyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one; (2S)-2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE; 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-; (S)-2-(2-Hydroxypropan-2-yl)-2H-furo[3,2-g]chromen-7(3H)-one; 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-; 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-; FWYSBEAFFPBAQU-LBPRGKRZSA-N; Marmesin ((+)-Marmesin); marmesin, (R)-isomer; Spectrum2_000737; Spectrum3_001642; Spectrum4_001701; Spectrum5_000402; UNII-H5D33D6K5D; MARMESIN, (+)-; MEGxp0_001933; (7S)-marmesin; DivK1c_007014; S(+)-Marmesin; KBio2_007132; KBio3_002583; KBio1_001958; KBio2_001996; KBio2_004564; H5D33D6K5D; Marmesin; 2-(2-Hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

106 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • linear furanocoumarin biosynthesis: (+)-marmesin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + acetone + an oxidized [NADPH-hemoprotein reductase] + psoralen

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(102)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

325 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

  • Zhaoxin Wang, Ying Zhou, Yuefei Wang, Xiaohui Yan. Reconstitution and Optimization of the Marmesin Biosynthetic Pathway in Yeast. ACS synthetic biology. 2023 Sep; ?(?):. doi: 10.1021/acssynbio.3c00267. [PMID: 37767718]
  • Ifeoma C Ezenyi, Jersley D Chirawurah, Nekpen Erhunse, Prakhar Agrawal, Dinkar Sahal, John O Igoli. Marmesin isolated from Celtis durandii Engl. root bioactive fraction inhibits β-hematin formation and contributes to antiplasmodial activity. Journal of ethnopharmacology. 2023 Jun; 317(?):116804. doi: 10.1016/j.jep.2023.116804. [PMID: 37352945]
  • C Hemakumar, B S Ravindranath, G A Ravishankar, D C Ramirez, S V Kiran. Marmesin and Marmelosin Interact with the Heparan Sulfatase-2 Active Site: Potential Mechanism for Phytochemicals from Bael Fruit Extract as Antitumor Therapeutics. Oxidative medicine and cellular longevity. 2023; 2023(?):9982194. doi: 10.1155/2023/9982194. [PMID: 36644581]
  • Yiqin Lin, Yingle Chen, Jingyang Zeng, Shunyuan Li. Nodakenetin Alleviates Inflammatory Pain Hypersensitivity by Suppressing NF-κB Signal Pathway. Neuroimmunomodulation. 2022; 29(4):486-492. doi: 10.1159/000525690. [PMID: 35995035]
  • Xiangyun Jian, Yucheng Zhao, Ziwen Wang, Shan Li, Li Li, Jun Luo, Lingyi Kong. Two CYP71AJ enzymes function as psoralen synthase and angelicin synthase in the biosynthesis of furanocoumarins in Peucedanum praeruptorum Dunn. Plant molecular biology. 2020 Oct; 104(3):327-337. doi: 10.1007/s11103-020-01045-4. [PMID: 32761540]
  • Ping Lei, Chushu Liao, Jianjun Chen, Ming Zhou. In vitro and in vivo growth inhibition of human leukemia cells by Nodakenetin are mediated via mitochondrial apoptosis, cell cycle arrest and inhibition of cell migration and invasion. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2019 May; 24(3):1219-1224. doi: . [PMID: 31424682]
  • Li-Shian Shi, Sheng-Chu Kuo, Han-Dong Sun, Susan L Morris-Natschke, Kuo-Hsiung Lee, Tian-Shung Wu. Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria. Bioorganic & medicinal chemistry. 2014 Mar; 22(6):1889-98. doi: 10.1016/j.bmc.2014.01.052. [PMID: 24582402]
  • Mahendra Jain, Rakhee Kapadia, Ravirajsinh N Jadeja, Menaka C Thounaojam, Ranjitsinh V Devkar, Shri H Mishra. Hepatoprotective activity of Feronia limonia root. The Journal of pharmacy and pharmacology. 2012 Jun; 64(6):888-96. doi: 10.1111/j.2042-7158.2012.01481.x. [PMID: 22571268]
  • Xian Ding, Bo Yin, Li Qian, Zhirui Zeng, Zeliang Yang, Huixian Li, Yongjun Lu, Shining Zhou. Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm. Journal of medical microbiology. 2011 Dec; 60(Pt 12):1827-1834. doi: 10.1099/jmm.0.024166-0. [PMID: 21852522]
  • Eun Jin Kim, Joseph Kwon, Seong Hwa Park, Chiyoul Park, Young-Bae Seo, Hyun-Kyoo Shin, Ho Kyoung Kim, Kwang-Sik Lee, Sang-Yun Choi, Do Hyun Ryu, Geum-Sook Hwang. Metabolite profiling of Angelica gigas from different geographical origins using 1H NMR and UPLC-MS analyses. Journal of agricultural and food chemistry. 2011 Aug; 59(16):8806-15. doi: 10.1021/jf2016286. [PMID: 21774558]
  • Daya L Chothani, H U Vaghasiya. A review on Balanites aegyptiaca Del (desert date): phytochemical constituents, traditional uses, and pharmacological activity. Pharmacognosy reviews. 2011 Jan; 5(9):55-62. doi: 10.4103/0973-7847.79100. [PMID: 22096319]
  • Peng Zhang, Xiu-Wei Yang. A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP-HPLC method. Biomedical chromatography : BMC. 2010 Feb; 24(2):216-21. doi: 10.1002/bmc.1276. [PMID: 19572262]
  • Wen Li, Shilan Feng, Fangdi Hu, Erlin Chen. [Coumarins from Peucedanum harry-smithii var. subglabrum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 May; 34(10):1231-4. doi: . [PMID: 19673384]
  • Peng Zhang, Xiu-Wei Yang. Biotransformation of nodakenin and simultaneous quantification of nodakenin and its aglycone in incubated system of human intestinal bacteria by HPLC method. Journal of Asian natural products research. 2009; 11(4):371-9. doi: 10.1080/10286020902767716. [PMID: 19431019]
  • Max Chavarría, Victor Castro, Luis Poveda, Murillo Renato. [Four new compounds from the non-polar extract of the plant Amyris brenesii (Rutaceae) from Costa Rica]. Revista de biologia tropical. 2008 Sep; 56(3):1043-51. doi: . [PMID: 19419026]
  • Qian-shun Yan, Sen Zhang, Yan-jun Wang, Wei-lie Xiao, Gao-xiong Rao. [Studies on chemical constituents of Peucedanum delavayi]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Aug; 31(8):1157-9. doi: . [PMID: 19112893]
  • Xi-Fei Ding, Xu Feng, Yun-Fa Dong, Xing-Zeng Zhao, Yu Chen, Ming Wang. [Studies on chemical constituents of the roots of Angelica pubescens]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Apr; 31(4):516-8. doi: . [PMID: 18661821]
  • Mi-Jeong Ahn, Mi Kyeong Lee, Young Choong Kim, Sang Hyun Sung. The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography-diode array detector coupled with electrospray ionization/mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2008 Jan; 46(2):258-66. doi: 10.1016/j.jpba.2007.09.020. [PMID: 17997069]
  • Yan-Yan Jiang, Bin Liu, Ren-Bing Shi, Guang-Zhong Tu. [Isolation and structure identification of chemical constituents from Saposhnikovia divaricata (Turcz.) Schischk]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 May; 42(5):505-10. doi: . [PMID: 17703773]
  • Ju Sun Kim, Jin Cheul Kim, Sang Hee Shim, Eun Ju Lee, WenYi Jin, KiHwan Bae, Kun Ho Son, Hyun Pyo Kim, Sam Sik Kang, Hyeun Wook Chang. Chemical constituents of the root of Dystaenia takeshimana and their anti-inflammatory activity. Archives of pharmacal research. 2006 Aug; 29(8):617-23. doi: 10.1007/bf02968244. [PMID: 16964755]
  • Yuan-yan Luu, Li Li, Cun Zhang, Yong-qing Xiao. [Studies on chemical constituents in roots of Heracleum rapula]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Apr; 31(8):667-8. doi: . [PMID: 16830827]
  • Dae Sik Jang, Eun Jung Park, Young-Hwa Kang, Michael E Hawthorne, Jose Schunke Vigo, James G Graham, Fernando Cabieses, Harry H S Fong, Rajendra G Mehta, John M Pezzuto, A Douglas Kinghorn. Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria. Journal of natural products. 2003 Sep; 66(9):1166-70. doi: 10.1021/np0302100. [PMID: 14510590]
  • Ying Xao, Jian-bei Li, Yi Ding. [Studies on the chemical constituents from the roots and rhizomes of Gerbera piloselloides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Aug; 27(8):594-6. doi: ". [PMID: 12776495]
  • S Y Kang, K Y Lee, S H Sung, M J Park, Y C Kim. Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships. Journal of natural products. 2001 May; 64(5):683-5. doi: 10.1021/np000441w. [PMID: 11374978]
  • Y Q Xiao, L Li, B Yang, L Q Huang. [Studies on chemical constituents from root of Saposhnikovia divaricata (Turcz.) Schischk]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Feb; 26(2):117-9. doi: ". [PMID: 12525107]
  • Y F Sun. [Isolation and identification of chemical constituents from an alcoholic extract of Notopterygium incisium]. Zhong yao tong bao (Beijing, China : 1981). 1985 Mar; 10(3):31-3. doi: ". [PMID: 2931199]
  • G Innocenti, A Bettero, G Caporale. [Determination of the coumarinic constituents of Ficus carica leaves by HPLC]. Il Farmaco; edizione scientifica. 1982 Jul; 37(7):475-85. doi: . [PMID: 7128806]
  • . . . . doi: . [PMID: 17068340]