Linderalactone (BioDeep_00000000191)

 

Secondary id: BioDeep_00000269225

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00385309-01_C15H16O3_(1R)-3,8-Dimethyl-5,14-dioxatricyclo[10.2.1.0~2,6~]pentadeca-2(6),3,8,12(15)-tetraen-13-one

化学式: C15H16O3 (244.1099)
中文名称: 异乌药内酯, 乌药内酯, 钓樟内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 18.56%

分子结构信息

SMILES: C/C1=C\CCC2=C[C@@H](OC2=O)c2c(C)coc2C1
InChI: InChI=1S/C15H16O3/c1-9-4-3-5-11-7-13(18-15(11)16)14-10(2)8-17-12(14)6-9/h4,7-8,13H,3,5-6H2,1-2H3/t13-/m1/s1

描述信息

Isolinderalactone is a member of benzofurans. It has a role as a metabolite.
Isolinderalactone is a natural product found in Neolitsea villosa, Neolitsea hiiranensis, and other organisms with data available.
A natural product found in Neolitsea daibuensis.
Linderalactone is a natural product found in Neolitsea umbrosa, Neolitsea villosa, and other organisms with data available.
Isolinderalactone suppresses human glioblastoma growth and angiogenic activity through the inhibition of VEGFR2 activation in endothelial cells[1]. Isolinderalactone suppresses the expression of B-cell lymphoma 2 (Bcl-2), survi
Isolinderalactone suppresses human glioblastoma growth and angiogenic activity through the inhibition of VEGFR2 activation in endothelial cells[1]. Isolinderalactone suppresses the expression of B-cell lymphoma 2 (Bcl-2), survi
Linderalactone is an important sesquiterpene lactone isolated from Lindera aggregata. Linderalactone inhibits cancer growth by modulating the expression of apoptosis-related proteins and inhibition of JAK/STAT signalling pathway. Linderalactone also inhibits the proliferation of the lung cancer A-549 cells with an IC50 of 15 μM[1][2].
Linderalactone is an important sesquiterpene lactone isolated from Lindera aggregata. Linderalactone inhibits cancer growth by modulating the expression of apoptosis-related proteins and inhibition of JAK/STAT signalling pathway. Linderalactone also inhibits the proliferation of the lung cancer A-549 cells with an IC50 of 15 μM[1][2].

同义名列表

17 个代谢物同义名

(3aS,4R,8bR)-4,8-dimethyl-3-methylene-4-vinyl-3a,4,5,8b-tetrahydrobenzo[1,2-b:3,4-b]difuran-2(3H)-one; (3aS,4R,8bR)-4-ethenyl-4,8-dimethyl-3-methylidene-5,8b-dihydro-3aH-furo[2,3-e][1]benzofuran-2-one; isolinderalactone; Linderalactone; Germacra-1(10),4,7,11-tetraen-15-oic acid, 8,12-epoxy-6.alpha.-hydroxy-, .gamma.-lactone, (E)-(+)-; (R,7Z,10E)-3,11-dimethyl-4,8,9,12-tetrahydro-6H-4,7-(metheno)furo[3,2-c][1]oxacycloundecin-6-one; Germacra-1(10),4,7,11-tetraen-15-oic acid, 8,12-epoxy-6alpha-hydroxy-, gamma-lactone, (E)-(+)-; 6H-4,7-Methenofuro(3,2-c)oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, (4R,10E)-; (1R,8E)-3,8-dimethyl-5,14-dioxatricyclo[10.2.1.0?,?]pentadeca-2(6),3,8,12(15)-tetraen-13-one; 6H-4,7-Methenofuro(3,2-c)oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, (R-(E))-; 6H-4,7-Methenofuro[3,2-c]oxacycloundecin-6-one, 4,8,9,12-tetrahydro-3,11-dimethyl-, [R-(E)]-; (1R,8E)-3,8-dimethyl-5,14-dioxatricyclo[10.2.1.02,6]pentadeca-2(6),3,8,12(15)-tetraen-13-one; 3,11-Dimethyl-4,8,9,12-tetrahydro-6H-4,7-(metheno)furo[3,2-c]oxacycloundecin-6-one; LWCKQMHMTSRRAA-QGQQYVBWSA-N; NCGC00385309-01_C15H16O3_(1R)-3,8-Dimethyl-5,14-dioxatricyclo[10.2.1.0~2,6~]pentadeca-2(6),3,8,12(15)-tetraen-13-one; Linderalactone; Linderalactone



数据库引用编号

44 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)

54 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 13 AIMP2, ANG, BCL2, BIRC5, CASP3, CDC25C, KEAP1, MAPK8, PTPRF, SMAD3, STAT3, TGFB1, VEGFA
Peripheral membrane protein 1 GORASP1
Endoplasmic reticulum membrane 3 ATF6, BCL2, HMOX1
Nucleus 16 AIMP2, ANG, ATF6, BCL2, BIRC5, CASP3, CDC25C, GABPA, HMOX1, KEAP1, MAPK8, MPO, SMAD3, STAT3, TGFB1, VEGFA
cytosol 12 AIMP2, ANG, ATF6, BCL2, BIRC5, CASP3, CDC25C, HMOX1, KEAP1, MAPK8, SMAD3, STAT3
nucleoplasm 11 ATF6, BIRC5, CASP3, CDC25C, GABPA, HMOX1, KEAP1, MAPK8, MPO, SMAD3, STAT3
RNA polymerase II transcription regulator complex 2 ATF6, STAT3
Cell membrane 1 TNF
Cytoplasmic side 2 GORASP1, HMOX1
Golgi apparatus membrane 2 ATF6, GORASP1
Synapse 1 MAPK8
cell surface 3 TGFB1, TNF, VEGFA
glutamatergic synapse 1 CASP3
Golgi apparatus 3 ATF6, GORASP1, VEGFA
Golgi membrane 2 ATF6, GORASP1
growth cone 1 ANG
neuronal cell body 5 ANG, CASP3, PTPRF, TGFB1, TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 MPO
plasma membrane 5 PTPRF, SMAD3, STAT3, TGFB1, TNF
Membrane 6 AIMP2, ATF6, BCL2, HMOX1, PTPRF, VEGFA
axon 2 MAPK8, TGFB1
extracellular exosome 2 MPO, PTPRF
endoplasmic reticulum 5 ATF6, BCL2, HMOX1, KEAP1, VEGFA
extracellular space 6 ANG, HMOX1, MPO, TGFB1, TNF, VEGFA
perinuclear region of cytoplasm 2 CDC25C, HMOX1
adherens junction 1 VEGFA
mitochondrion 1 BCL2
protein-containing complex 2 BCL2, BIRC5
intracellular membrane-bounded organelle 1 MPO
postsynaptic density 1 CASP3
Secreted 3 ANG, TGFB1, VEGFA
extracellular region 5 ANG, MPO, TGFB1, TNF, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, PTPRF
mitochondrial outer membrane 2 BCL2, HMOX1
transcription regulator complex 2 SMAD3, STAT3
centriolar satellite 1 KEAP1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 2 TGFB1, VEGFA
actin cytoskeleton 1 ANG
microtubule cytoskeleton 1 BIRC5
nucleolus 1 ANG
midbody 2 BIRC5, KEAP1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 ATF6, TNF
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton, spindle 1 BIRC5
microtubule 1 BIRC5
spindle 1 BIRC5
cis-Golgi network 1 GORASP1
extracellular matrix 2 TGFB1, VEGFA
basement membrane 1 ANG
mitochondrial intermembrane space 1 CDC25C
collagen-containing extracellular matrix 1 TGFB1
secretory granule 3 MPO, TGFB1, VEGFA
interphase microtubule organizing center 1 BIRC5
nuclear inner membrane 1 SMAD3
receptor complex 1 SMAD3
neuron projection 1 PTPRF
chromatin 4 ATF6, GABPA, SMAD3, STAT3
phagocytic cup 1 TNF
Chromosome 2 ANG, BIRC5
centriole 1 BIRC5
Nucleus, nucleolus 1 ANG
nuclear chromosome 1 BIRC5
actin filament 1 KEAP1
blood microparticle 1 TGFB1
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 ATF6
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
myelin sheath 1 BCL2
azurophil granule 1 MPO
Golgi lumen 1 TGFB1
platelet alpha granule lumen 2 TGFB1, VEGFA
kinetochore 1 BIRC5
endocytic vesicle 1 ANG
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
chromosome, centromeric region 1 BIRC5
phagocytic vesicle lumen 1 MPO
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
heteromeric SMAD protein complex 1 SMAD3
SMAD protein complex 1 SMAD3
spindle microtubule 1 BIRC5
survivin complex 1 BIRC5
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Latency-associated peptide]: Secreted, extracellular space, extracellular matrix 1 TGFB1
[Transforming growth factor beta-1]: Secreted 1 TGFB1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
angiogenin-PRI complex 1 ANG
inclusion body 1 KEAP1
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[Processed cyclic AMP-dependent transcription factor ATF-6 alpha]: Nucleus 1 ATF6
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Xiaofei Shen, Hongqing Chen, Hai Zhang, Liuling Luo, Tian Wen, Lu Liu, Qiongying Hu, Lun Wang. A natural sesquiterpene lactone isolinderalactone attenuates lipopolysaccharide-induced inflammatory response and acute lung injury through inhibition of NF-κB pathway and activation Nrf2 pathway in macrophages. International immunopharmacology. 2023 Sep; 124(Pt B):110965. doi: 10.1016/j.intimp.2023.110965. [PMID: 37741124]
  • Ji Young Hwang, Jung Hwa Park, Min Jae Kim, Woo Jean Kim, Ki-Tae Ha, Byung Tae Choi, Seo-Yeon Lee, Hwa Kyoung Shin. Isolinderalactone regulates the BCL-2/caspase-3/PARP pathway and suppresses tumor growth in a human glioblastoma multiforme xenograft mouse model. Cancer letters. 2019 02; 443(?):25-33. doi: 10.1016/j.canlet.2018.11.027. [PMID: 30503550]
  • Meng-Chi Yen, Ying-Chu Shih, Ya-Ling Hsu, En-Shyh Lin, Yi-Shiuan Lin, Eing-Mei Tsai, Ya-Wen Ho, Ming-Feng Hou, Po-Lin Kuo. Isolinderalactone enhances the inhibition of SOCS3 on STAT3 activity by decreasing miR-30c in breast cancer. Oncology reports. 2016 Mar; 35(3):1356-64. doi: 10.3892/or.2015.4503. [PMID: 26707189]
  • Subhash C Joshi, Chandra S Mathela. Antioxidant and antibacterial activities of the leaf essential oil and its constituents furanodienone and curzerenone from Lindera pulcherrima (Nees.) Benth. ex hook. f. Pharmacognosy research. 2012 Apr; 4(2):80-4. doi: 10.4103/0974-8490.94721. [PMID: 22518079]
  • Su-Ling Wong, Hsun-Shuo Chang, Guei-Jane Wang, Michael Y Chiang, Hung-Yi Huang, Chu-Huang Chen, Shiow-Chwen Tsai, Chu-Hung Lin, Ih-Sheng Chen. Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity. Journal of natural products. 2011 Dec; 74(12):2489-96. doi: 10.1021/np100874f. [PMID: 22148193]
  • Li-She Gan, Yun-Liang Zheng, Jian-Xia Mo, Xin Liu, Xin-Hua Li, Chang-Xin Zhou. Sesquiterpene lactones from the root tubers of Lindera aggregata. Journal of natural products. 2009 Aug; 72(8):1497-501. doi: 10.1021/np900354q. [PMID: 19639966]
  • Xian-Long Cheng, Shuang-Cheng Ma, Feng Wei, Gang-Li Wang, Xin-Yue Xiao, Rui-Chao Lin. A new sesquiterpene isolated from Lindera aggregata (SIMS) KOSTERM. Chemical & pharmaceutical bulletin. 2007 Sep; 55(9):1390-2. doi: 10.1248/cpb.55.1390. [PMID: 17827769]
  • Yasuko Noda, Akitane Mori. Antioxidant activities of uyaku (lindera strychnifolia) leaf extract: a natural extract used in traditional medicine. Journal of clinical biochemistry and nutrition. 2007 Sep; 41(2):139-45. doi: 10.3164/jcbn2007019. [PMID: 18193108]
  • Chao-feng Zhang, Norio Nakamura, Supinya Tewtrakul, Masao Hattori, Qi-shi Sun, Zheng-tao Wang, Tamio Fujiwara. Sesquiterpenes and alkaloids from Lindera chunii and their inhibitory activities against HIV-1 integrase. Chemical & pharmaceutical bulletin. 2002 Sep; 50(9):1195-200. doi: 10.1248/cpb.50.1195. [PMID: 12237535]
  • Wataru Kobayashi, Toshio Miyase, Mitsuaki Sano, Kaoru Umehara, Tsutomu Warashina, Hiroshi Noguchi. Prolyl endopeptidase inhibitors from the roots of Lindera strychnifolia F. Vill. Biological & pharmaceutical bulletin. 2002 Aug; 25(8):1049-52. doi: 10.1248/bpb.25.1049. [PMID: 12186408]
  • C F Zhang, Q S Sun, Z T Wang, G X Chou. [Studies on constituents of the leaves of Lindera aggregata (Sims) Kosterm]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Nov; 26(11):765-7. doi: . [PMID: 12776349]
  • R Sekura, A Meister. Covalent interaction of L-2-amino-4-oxo-5-chloropentanoate at glutamate binding site of gamma-glutamylcysteine synthetase. The Journal of biological chemistry. 1977 Apr; 252(8):2606-10. doi: NULL. [PMID: 15993]
  • L K Hsu, A H Crisp, R S Kalucy, J Koval, C N Chen, M Carruthers, K J Zilkha. Early morning migraine. Nocturnal plasma levels of catecholamines, tryptophan, glucose, and free fatty acids and sleep encephalographs. Lancet (London, England). 1977 Feb; 1(8009):447-51. doi: 10.1016/s0140-6736(77)91942-0. [PMID: 65562]
  • E F Lavretskaia, Iu Sh Moshkovskii, I M Raĭkhman. [Effect of psychotropic and anticonvulsive preparations on transport ATPase in the renal tubules of the guinea pig]. Farmakologiia i toksikologiia. 1975 May; 38(3):272-5. doi: NULL. [PMID: 6303]