LICARIN A (BioDeep_00000008228)

 

Secondary id: BioDeep_00000231956

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol

化学式: C20H22O4 (326.1518)
中文名称: 里卡灵A, 里卡灵 A, 去氢二异丁香酚, 脱氢二异丁香酚, 利卡灵 A, 4-(2,3-二氢-7-甲氧基-3-甲基-5-丙烯基-2-苯并呋喃基)-2-甲氧基苯酚
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 51.37%

分子结构信息

SMILES: C/C=C/c1cc(OC)c2c(c1)[C@H](C)[C@@H](c1ccc(O)c(OC)c1)O2
InChI: InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+

描述信息

(-)-Licarin A is a natural product found in Magnolia dodecapetala, Magnolia kachirachirai, and other organisms with data available.
Dehydrodiisoeugenol is a natural product found in Myristica fragrans with data available.
Dehydrodiisoeugenol is isolated from Myristica fragrans Houtt, shows anti-inflammatory and anti-bacterial actions[1]. Dehydrodiisoeugenol inhibits LPS- stimulated NF-κB activation and cyclooxygenase (COX)-2 gene expression in murine macrophages[2].
Dehydrodiisoeugenol is isolated from Myristica fragrans Houtt, shows anti-inflammatory and anti-bacterial actions[1]. Dehydrodiisoeugenol inhibits LPS- stimulated NF-κB activation and cyclooxygenase (COX)-2 gene expression in murine macrophages[2].
Licarin A ((+)-Licarin A), a neolignan, significantly and dose-dependently reduces TNF-α production (IC50=12.6 μM) in dinitrophenyl-human serum albumin (DNP-HSA)-stimulated RBL-2H3 cells. Anti-allergic effects. Licarin A reduces TNF-α and PGD2 production, and COX-2 expression[1].
Licarin A ((+)-Licarin A), a neolignan, significantly and dose-dependently reduces TNF-α production (IC50=12.6 μM) in dinitrophenyl-human serum albumin (DNP-HSA)-stimulated RBL-2H3 cells. Anti-allergic effects. Licarin A reduces TNF-α and PGD2 production, and COX-2 expression[1].

同义名列表

34 个代谢物同义名

(+)(-)-trans-DehydrodIIsoeugenol; (-)-Licarin A; LICARIN A; 2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol; 2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzofuran-2-yl]phenol; 51020-86-1; C10650; 2-methoxy-4-((2R,3R)-7-methoxy-3-methyl-5-((E)-prop-1-en-1-yl)-2,3-dihydrobenzofuran-2-yl)phenol; Phenol, 4-((2R,3R)-2,3-dihydro-7-methoxy-3-methyl-5-(1E)-1-propenyl-2-benzofuranyl)-2-methoxy-; Phenol,4-[(2R,3R)-2,3-dihydro-7-methoxy-3-methyl-5-(1E)-1-propenyl-2-benzofuranyl]-2-methoxy-; trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofurane; trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran; (invertedexclamationmarkA)-LicarinA; ITDOFWOJEDZPCF-OTBILJLCSA-N; (+)-licarin A; isolicarin A; licarine A; Phenol, 4-[(2S,3S)-2,3-dihydro-7-methoxy-3-methyl-5-(1E)-1-propen-1-yl-2-benzofuranyl]-2-methoxy; 4-[(2R,3R)-2,3-Dihydro-7-methoxy-3-methyl-5-[(E)-1-propenyl]benzofuran-2-yl]-2-methoxyphenol; 2-Methoxy-4-(7-methoxy-3-methyl-5-[(1E)-1-propenyl]-2,3-dihydro-1-benzofuran-2-yl)phenol #; 2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol; 2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydrobenzofuran-2-yl]phenol; 2-Methoxy-4-(7-methoxy-3-methyl-5-(prop-1-en-1-yl)-2,3-dihydrobenzofuran-2-yl)phenol; Phenol, 4-(2,3-dihydro-7-methoxy-3-methyl-5-(1-propenyl)-2-benzofuranyl)-2-methoxy-; Phenol, 4-[2,3-dihydro-7-methoxy-3-methyl-5-(1-propenyl)-2-benzofuranyl]-2-methoxy-; Phenol, 4-(2,3-dihydro-7-methoxy-3-methyl-5-propenyl-2-benzofuranyl)-2-methoxy-; 2-Methoxy-4-(7-methoxy-3-methyl-5-propenyl-2,3-dihydrobenzofuran-2-yl) phenol; ITDOFWOJEDZPCF-AATRIKPKSA-N; Diisoeugenol, dehydro-; Isoeugenol, dehydrodi-; Dehydrodiisoeugenol; DEHRODIISOEUGENOL; AC1NTDZA; Licarin A



数据库引用编号

34 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)

94 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。

亚细胞结构定位 关联基因列表
Cytoplasm 10 BECN1, CASP3, CYP1A1, DCTN4, MAPK14, NFKBIA, PODXL, PRKCA, PRKCB, PTGS2
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 5 BECN1, CYP1A1, PRKCA, PRKCB, PTGS2
Endosome membrane 1 BECN1
Endoplasmic reticulum membrane 4 BECN1, CYP1A1, PTGS2, RRBP1
Mitochondrion membrane 2 BECN1, PRKCA
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 10 BECN1, CASP3, CDX1, DCTN4, JUND, MAPK14, NFKBIA, PARP1, PRKCA, PRKCB
autophagosome 1 BECN1
cytosol 10 BECN1, CASP3, DCTN4, GSR, MAPK14, NFKBIA, PARP1, PRKCA, PRKCB, RPE
dendrite 1 BECN1
mitochondrial membrane 2 BECN1, PRKCA
nuclear body 2 BECN1, PARP1
phagocytic vesicle 1 BECN1
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 1 BECN1
centrosome 2 DCTN4, PRKCB
nucleoplasm 7 CASP3, JUND, MAPK14, NFKBIA, PARP1, PRKCA, PRKCB
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 2 PRKCA, TNF
lamellipodium 1 PODXL
Multi-pass membrane protein 1 UCP1
cell cortex 1 DCTN4
cell surface 1 TNF
glutamatergic synapse 2 CASP3, MAPK14
mitochondrial inner membrane 2 CYP1A1, UCP1
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 1 PARP1
endosome 1 BECN1
plasma membrane 5 NFKBIA, PODXL, PRKCA, PRKCB, TNF
Membrane 5 PARP1, PODXL, PRKCA, PRKCB, RRBP1
apical plasma membrane 1 PODXL
caveola 1 PTGS2
extracellular exosome 5 GSR, PODXL, PRKCA, PRKCB, RPE
endoplasmic reticulum 4 BECN1, PRKCA, PTGS2, RRBP1
extracellular space 4 IL10, IL6, PODXL, TNF
perinuclear region of cytoplasm 1 PRKCA
mitochondrion 6 CYP1A1, GSR, MAPK14, PARP1, PRKCA, UCP1
protein-containing complex 2 PARP1, PTGS2
intracellular membrane-bounded organelle 2 CYP1A1, PODXL
Microsome membrane 2 CYP1A1, PTGS2
filopodium 1 PODXL
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 PODXL
Secreted 2 IL10, IL6
extracellular region 4 IL10, IL6, MAPK14, TNF
Single-pass membrane protein 1 RRBP1
mitochondrial matrix 1 GSR
transcription regulator complex 2 JUND, PARP1
centriolar satellite 1 PODXL
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
external side of plasma membrane 2 GSR, TNF
slit diaphragm 1 PODXL
nucleolus 2 PARP1, PODXL
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 PODXL
Cell projection, lamellipodium 1 PODXL
Mitochondrion inner membrane 2 CYP1A1, UCP1
Membrane raft 2 PODXL, TNF
Cytoplasm, cytoskeleton 1 DCTN4
focal adhesion 1 DCTN4
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, filopodium 1 PODXL
Cell projection, ruffle 1 PODXL
Cytoplasm, myofibril, sarcomere 1 DCTN4
ruffle 1 PODXL
sarcomere 1 DCTN4
neuron projection 1 PTGS2
ciliary basal body 1 PRKCA
chromatin 3 CDX1, JUND, PARP1
phagocytic cup 1 TNF
Chromosome 1 PARP1
brush border membrane 1 PRKCB
Nucleus, nucleolus 1 PARP1
spindle pole 2 DCTN4, MAPK14
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Cytoplasm, cell cortex 1 DCTN4
microvillus membrane 1 PODXL
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
microvillus 1 PODXL
phagophore assembly site 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
Cell projection, microvillus 1 PODXL
stress fiber 1 DCTN4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 2 IL6, PTGS2
transcription repressor complex 1 JUND
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
Single-pass type III membrane protein 1 RRBP1
cytoplasmic dynein complex 1 DCTN4
calyx of Held 1 PRKCB
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
spectrin 1 PRKCB
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
site of DNA damage 1 PARP1
presynaptic cytosol 1 PRKCB
ribosome 1 RRBP1
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
alphav-beta3 integrin-PKCalpha complex 1 PRKCA
interleukin-6 receptor complex 1 IL6
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
I-kappaB/NF-kappaB complex 1 NFKBIA
cytoplasmic side of mitochondrial outer membrane 1 BECN1
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Atsuyoshi Nishina, Motohiko Ukiya, Kazuki Motegi, Risa Kiryu, Daisuke Sato, Mitsuru Sada, Yuki Hori, Hideo Satsu, Kazuhiro Uemura, Mamoru Koketsu, Masayuki Ninomiya, Lwin Mon Mon Myint, Hirokazu Kimura. Promotion of ABCG2 gene expression by neolignans from Piper longum L. Bioscience, biotechnology, and biochemistry. 2023 Sep; ?(?):. doi: 10.1093/bbb/zbad132. [PMID: 37709570]
  • Jiaheng Xu, Xinlei Li, Zimin Yuan, Feng Li, Zhili Xu. Mitigative effects of dehydrodiisoeugenol on enteritis and co-occurring dysmotility in murine model. Pakistan journal of pharmaceutical sciences. 2022 Sep; 35(5):1347-1355. doi: . [PMID: 36451563]
  • Armelle T Mbaveng, Brice E N Wamba, Gabin T M Bitchagno, Simplice Beaudelaire Tankeo, İlhami Çelik, Brice C K Atontsa, Antoine H Nkuété Lonfouo, Victor Kuete, Thomas Efferth. Bioactivity of fractions and constituents of Piper capense fruits towards a broad panel of cancer cells. Journal of ethnopharmacology. 2021 May; 271(?):113884. doi: 10.1016/j.jep.2021.113884. [PMID: 33529639]
  • Cai-Wei Li, Yi-Cheng Chu, Chun-Yi Huang, Shu-Ling Fu, Jih-Jung Chen. Evaluation of Antioxidant and Anti-α-glucosidase Activities of Various Solvent Extracts and Major Bioactive Components from the Seeds of Myristica fragrans. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215198. [PMID: 33171671]
  • Dalila Junqueira Alvarenga, Laira Maria Faria Matias, Lucas Martins Oliveira, Luiz Paulo Melchior de Oliveira Leão, Jamie Anthony Hawkes, Breno Vilas Boas Raimundo, Lívia de Figueiredo Diniz Castro, Marli Matiko Anraku de Campos, Fallon Dos Santos Siqueira, Thiago Dos Santos, Diogo Teixeira Carvalho. Exploring how structural changes to new Licarin A derivatives effects their bioactive properties against rapid growing mycobacteria and biofilm formation. Microbial pathogenesis. 2020 Jul; 144(?):104203. doi: 10.1016/j.micpath.2020.104203. [PMID: 32304794]
  • Thiago R Morais, Geanne A Alves Conserva, Marina T Varela, Thais A Costa-Silva, Fernanda Thevenard, Vitor Ponci, Ana Fortuna, Amílcar C Falcão, Andre G Tempone, João Paulo S Fernandes, João Henrique G Lago. Improving the drug-likeness of inspiring natural products - evaluation of the antiparasitic activity against Trypanosoma cruzi through semi-synthetic and simplified analogues of licarin A. Scientific reports. 2020 03; 10(1):5467. doi: 10.1038/s41598-020-62352-w. [PMID: 32214193]
  • Uma Maheswari, Krishna Ghosh, Sudha Rani Sadras. Licarin A induces cell death by activation of autophagy and apoptosis in non-small cell lung cancer cells. Apoptosis : an international journal on programmed cell death. 2018 04; 23(3-4):210-225. doi: 10.1007/s10495-018-1449-8. [PMID: 29468481]
  • Dahyeon Yoon, Khan Mohammad Imran, Yong-Sik Kim. Distinctive effects of licarin A on lipolysis mediated by PKA and on formation of brown adipocytes from C3H10T1/2 mesenchymal stem cells. Toxicology and applied pharmacology. 2018 02; 340(?):9-20. doi: 10.1016/j.taap.2017.12.015. [PMID: 29288687]
  • Qian-Qian Lv, Xiao-Nan Yang, Dong-Mei Yan, Wei-Qing Liang, Hong-Ning Liu, Xiu-Wei Yang, Fei Li. Metabolic profiling of dehydrodiisoeugenol using xenobiotic metabolomics. Journal of pharmaceutical and biomedical analysis. 2017 Oct; 145(?):725-733. doi: 10.1016/j.jpba.2017.07.045. [PMID: 28806569]
  • Ji-Young Park, Su Hwan Lim, Bo Ram Kim, Hyung Jae Jeong, Hyung-Jun Kwon, Gyu-Yong Song, Young Bae Ryu, Woo Song Lee. Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of Myristica fragrans. Bioorganic & medicinal chemistry letters. 2017 07; 27(14):3060-3064. doi: 10.1016/j.bmcl.2017.05.055. [PMID: 28551100]
  • Jia-Rong Gao, Shuang-Zhi Xu, Yan-Quan Han, Liang-Bing Wei, Hui Jiang, Jun-Mei Song, Xue Xue. [Determination and pharmacokinetics of main components for Psoralea corylifolia-Myristica fragrants drug pair by using UPLC-MS/MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(9):1782-1786. doi: 10.19540/j.cnki.cjcmm.2017.0071. [PMID: 29082707]
  • Takuya Matsui, Chihiro Ito, Satoru Masubuchi, Masataka Itoigawa. Licarin A is a candidate compound for the treatment of immediate hypersensitivity via inhibition of rat mast cell line RBL-2H3 cells. The Journal of pharmacy and pharmacology. 2015 Dec; 67(12):1723-32. doi: 10.1111/jphp.12475. [PMID: 26376734]
  • Gui-Hua Tang, Zi-Wei Chen, Ting-Ting Lin, Min Tan, Xiao-Yun Gao, Jing-Mei Bao, Zhong-Bin Cheng, Zhang-Hua Sun, Gang Huang, Sheng Yin. Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells. Journal of natural products. 2015 Aug; 78(8):1894-903. doi: 10.1021/acs.jnatprod.5b00220. [PMID: 26226070]
  • Wei-Jern Tsai, Chien-Chang Shen, Tung-Hu Tsai, Lie-Chwen Lin. Lignans from the aerial parts of Saururus chinensis: isolation, structural characterization, and their effects on platelet aggregation. Journal of natural products. 2014 Jan; 77(1):125-31. doi: 10.1021/np400772h. [PMID: 24387347]
  • You-Bo Zhang, Li-Qiao Zhu, Xiu-Wei Yang. Cerebral nuclei distribution study of dehydrodiisoeugenol as an anxiogenic agent determined by RP-HPLC. Fitoterapia. 2013 Jan; 84(?):47-53. doi: 10.1016/j.fitote.2012.09.022. [PMID: 23059843]
  • Fei Li, Xiu-Wei Yang. Analysis of anti-inflammatory dehydrodiisoeugenol and metabolites excreted in rat feces and urine using HPLC-UV. Biomedical chromatography : BMC. 2012 Jun; 26(6):703-7. doi: 10.1002/bmc.1717. [PMID: 21932389]
  • Fei Li, Xiu-Wei Yang. Metabolism of the lignan dehydrodiisoeugenol in rats. Planta medica. 2011 Oct; 77(15):1712-7. doi: 10.1055/s-0030-1271063. [PMID: 21544774]
  • M M O Cabral, J M Barbosa-Filho, G L A Maia, M C O Chaves, M V Braga, W De Souza, R O A Soares. Neolignans from plants in northeastern Brazil (Lauraceae) with activity against Trypanosoma cruzi. Experimental parasitology. 2010 Mar; 124(3):319-24. doi: 10.1016/j.exppara.2009.11.007. [PMID: 19944690]
  • Letícia Ferrari L Barros, Andersson Barison, Marcos José Salvador, Renato de Mello-Silva, Elaine C Cabral, Marcos N Eberlin, Maria Elida A Stefanello. Constituents of the leaves of Magnolia ovata. Journal of natural products. 2009 Aug; 72(8):1529-32. doi: 10.1021/np900203y. [PMID: 19658431]
  • Shu Yang, Lai-Wei Li, Xiao-Dong Yang, Jing-Feng Zhao, LiIang Li. [Studies on the chemical constituents of Litsea lancifolia]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Jul; 31(7):985-7. doi: . [PMID: 18973009]
  • Fei Li, Xiu-Wei Yang. Simultaneous determination of diastereomers (+)-licarin A and isolicarin A from Myristica fragrans in rat plasma by HPLC and its application to their pharmacokinetics. Planta medica. 2008 Jun; 74(8):880-4. doi: 10.1055/s-2008-1074545. [PMID: 18523922]
  • E S Garcia, P Azambuja. Lignoids in insects: chemical probes for the study of ecdysis, excretion and Trypanosoma cruzi-triatomine interactions. Toxicon : official journal of the International Society on Toxinology. 2004 Sep; 44(4):431-40. doi: 10.1016/j.toxicon.2004.05.007. [PMID: 15302525]
  • P W Le Quesne, J E Larrahondo, R F Raffauf. Antitumor plants. X. Constituents of Nectandra rigida. Journal of natural products. 1980 May; 43(3):353-9. doi: 10.1021/np50009a006. [PMID: 7400821]