Dendrobine (BioDeep_00000000268)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


7,5-(Epoxymethano)-1H-cyclopent[cd]indol-9-one,decahydro-1,7b-dimethyl-6-(1-methylethyl)-, (2aS,4aS,5R,6S,7R,7aS,7bR)-

化学式: C16H25NO2 (263.1885)
中文名称: 石斛碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 75%

分子结构信息

SMILES: CC(C)C1C2C3CCC4C3(C(C1OC2=O)N(C4)C)C
InChI: InChI=1S/C16H25NO2/c1-8(2)11-12-10-6-5-9-7-17(4)14(16(9,10)3)13(11)19-15(12)18/h8-14H,5-7H2,1-4H3/t9-,10+,11+,12-,13-,14-,16+/m1/s1

描述信息

Dendrobine is a member of indoles.
Dendroban-12-one is a natural product found in Dendrobium chrysanthum, Dendrobium linawianum, and Dendrobium nobile with data available.
Dendrobine is an alkaloid isolated from Dendrobium nobile. Dendrobine possesses antiviral activity against influenza A viruses, with IC50s of 3.39 μM, 2.16 μM and 5.32 μM for A/FM-1/1/47 (H1N1), A/Puerto Rico/8/34 H274Y (H1N1) and A/Aichi/2/68 (H3N2), respectively[1].
Dendrobine is an alkaloid isolated from Dendrobium nobile. Dendrobine possesses antiviral activity against influenza A viruses, with IC50s of 3.39 μM, 2.16 μM and 5.32 μM for A/FM-1/1/47 (H1N1), A/Puerto Rico/8/34 H274Y (H1N1) and A/Aichi/2/68 (H3N2), respectively[1].

同义名列表

7 个代谢物同义名

7,5-(Epoxymethano)-1H-cyclopent[cd]indol-9-one,decahydro-1,7b-dimethyl-6-(1-methylethyl)-, (2aS,4aS,5R,6S,7R,7aS,7bR)-; (1S,4S,7S,8R,11R,12R,13S)-2,12-Dimethyl-13-propan-2-yl-10-oxa-2-azatetracyclo[5.4.1.18,11.04,12]tridecan-9-one; dendrobine hydrochloride; Dendroban-12-one; A9N9FB9DPG; Dendrobine; Dendrobine



数据库引用编号

19 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 AIMP2, ANXA5, CASP3, CASP4, CAT, CDK5, CYP2C19, CYP3A4, FDPS, FOXP3, MVK
Peripheral membrane protein 4 ANXA5, CASP4, CPT2, CYP1B1
Endoplasmic reticulum membrane 4 CASP4, CYP1B1, CYP2C19, CYP3A4
Nucleus 7 AIMP2, CASP3, CDK5, FOXP3, GABPA, GPX4, PPARA
cytosol 11 ACOX1, AIMP2, ANXA5, CASP3, CASP4, CAT, CDK5, FDPS, FOXP3, GPX4, MVK
dendrite 1 CDK5
nucleoplasm 7 CASP3, CDK5, CPT2, FDPS, FOXP3, GABPA, PPARA
Cell membrane 1 CDK5
Cytoplasmic side 1 CASP4
lamellipodium 1 CDK5
Cell projection, growth cone 1 CDK5
Synapse 1 CDK5
cell junction 1 CDK5
glutamatergic synapse 1 CASP3
growth cone 1 CDK5
mitochondrial inner membrane 1 CPT2
neuromuscular junction 1 CDK5
neuronal cell body 2 CASP3, CDK5
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, CASP4
Presynapse 1 CDK5
plasma membrane 3 CASP4, CDK5, CYP2C19
Membrane 8 ACOX1, AIMP2, ANXA5, CAT, CDK5, CYP1B1, CYP3A4, FDPS
axon 2 CCK, CDK5
extracellular exosome 3 ANXA5, CAT, GPX4
endoplasmic reticulum 1 CASP4
extracellular space 2 CCK, IL6
mitochondrion 6 CASP4, CAT, CPT2, CYP1B1, GPX4, HMGCS2
protein-containing complex 4 CASP4, CAT, FOXP3, GPX4
intracellular membrane-bounded organelle 5 CAT, CYP1B1, CYP2C19, CYP3A4, MVK
Microsome membrane 2 CYP1B1, CYP3A4
filopodium 1 CDK5
postsynaptic density 2 CASP3, CDK5
protein kinase 5 complex 1 CDK5
Secreted 3 CASP4, CCK, IL6
extracellular region 5 ANXA5, CASP4, CAT, CCK, IL6
mitochondrial matrix 3 CAT, FDPS, HMGCS2
external side of plasma membrane 1 ANXA5
perikaryon 1 CDK5
nucleolus 1 CPT2
Cell projection, lamellipodium 1 CDK5
Mitochondrion inner membrane 1 CPT2
Matrix side 1 CPT2
focal adhesion 2 ANXA5, CAT
Peroxisome 4 ACOX1, CAT, FDPS, MVK
Peroxisome matrix 1 CAT
peroxisomal matrix 2 ACOX1, CAT
peroxisomal membrane 2 ACOX1, CAT
collagen-containing extracellular matrix 1 ANXA5
Inflammasome 1 CASP4
Zymogen granule membrane 1 ANXA5
neuron projection 1 CDK5
chromatin 3 FOXP3, GABPA, PPARA
nuclear envelope 1 GPX4
[Isoform 1]: Cytoplasm 1 CDK5
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 IL6
vesicle membrane 1 ANXA5
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
cyclin-dependent protein kinase holoenzyme complex 1 CDK5
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
endothelial microparticle 1 ANXA5
NLRP1 inflammasome complex 1 CASP4
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
non-canonical inflammasome complex 1 CASP4


文献列表

  • Yanzhe Xu, Miao Wang, Yi Luo, Hao Liu, Hua Ling, Yuqi He, Yanliu Lu. PPARα is one of the key targets for dendrobine to improve hepatic steatosis in NAFLD. Journal of ethnopharmacology. 2024 Apr; 323(?):117684. doi: 10.1016/j.jep.2023.117684. [PMID: 38171466]
  • Jia Xia, Jingyi Chen, Xinyue Xing, Jing Meng, Xiaoying Song, Danfei Lou. Dendrobine regulates STAT3 to attenuate mitochondrial dysfunction and senescence in vascular endothelial cells triggered by oxidized low-density lipoprotein. Drug development research. 2024 Feb; 85(1):e22152. doi: 10.1002/ddr.22152. [PMID: 38349255]
  • Meili Zhao, Yanchang Zhao, Zhenyu Yang, Feng Ming, Jian Li, Demin Kong, Yu Wang, Peng Chen, Meina Wang, Zhicai Wang. Metabolic Pathway Engineering Improves Dendrobine Production in Dendrobium catenatum. International journal of molecular sciences. 2023 Dec; 25(1):. doi: 10.3390/ijms25010397. [PMID: 38203567]
  • Yu-Sheng Shi, Ji-Cong Chen, Lin Lin, Ying-Zhe Cheng, Yang Zhao, Yan Zhang, Xiao-Dong Pan. Dendrobine rescues cognitive dysfunction in diabetic encephalopathy by inhibiting ferroptosis via activating Nrf2/GPX4 axis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Jul; 119(?):154993. doi: 10.1016/j.phymed.2023.154993. [PMID: 37567006]
  • Cheng-Chen Zhang, Yan-Li Kong, Mao-Sheng Zhang, Qin Wu, Jing-Shan Shi. Two new alkaloids from Dendrobium nobile Lindl. exhibited neuroprotective activity, and dendrobine alleviated Aβ1-42 -induced apoptosis by inhibiting CDK5 activation in PC12 cells. Drug development research. 2023 Jan; ?(?):. doi: 10.1002/ddr.22030. [PMID: 36658700]
  • Zhiheng Wang, Kuilong Zhou, Zhijie Liang, Huiting Zhang, Yangjie Song, Xiaomin Yang, Dongguo Xiang, Qingfan Xie. In Vitro Investigation on the Effect of Dendrobine on the Activity of Cytochrome P450 Enzymes. Planta medica. 2023 Jan; 89(1):72-78. doi: 10.1055/a-1806-2935. [PMID: 35523232]
  • Danfei Lou, Xinyue Xing, Yunyu Liang. Dendrobine modulates autophagy to alleviate ox-LDL-induced oxidative stress and senescence in HUVECs. Drug development research. 2022 08; 83(5):1125-1137. doi: 10.1002/ddr.21937. [PMID: 35417048]
  • Hong Pan, Fu-Guo Shi, Chao Fang, Jing-Shan Shi. Metabolic characterization of a potent natural neuroprotective agent dendrobine in vitro and in rats. Acta pharmacologica Sinica. 2022 Apr; 43(4):1059-1071. doi: 10.1038/s41401-021-00690-9. [PMID: 34183753]
  • Wende Deng, Zongbao Ding, Yiyuan Wang, Binhua Zou, Jiehuang Zheng, Yanhui Tan, Qin Yang, Minhong Ke, Yan Chen, Song Wang, Xiaojuan Li. Dendrobine attenuates osteoclast differentiation through modulating ROS/NFATc1/ MMP9 pathway and prevents inflammatory bone destruction. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Feb; 96(?):153838. doi: 10.1016/j.phymed.2021.153838. [PMID: 34801352]
  • Jing Meng, Xiaoying Song, Guoliang Yan, Haihui Wang, Haitao Li, Danfei Lou. Dendrobine suppresses endoplasmic reticulum stress-induced apoptosis through upregulating microRNA miR-381-3p to decrease caspase-4. Bioengineered. 2021 12; 12(1):4452-4463. doi: 10.1080/21655979.2021.1956672. [PMID: 34308746]
  • Dao-Yong Gong, Xing-Yue Chen, Shun-Xing Guo, Bo-Chu Wang, Biao Li. Recent advances and new insights in biosynthesis of dendrobine and sesquiterpenes. Applied microbiology and biotechnology. 2021 Sep; 105(18):6597-6606. doi: 10.1007/s00253-021-11534-1. [PMID: 34463801]
  • Xu Qian, Jieying Zhu, Qingjun Yuan, Qi Jia, Hui Jin, Jing Han, Surendra Sarsaiya, Leilei Jin, Jishuang Chen, Lanping Guo. Illumina Sequencing Reveals Conserved and Novel MicroRNAs of Dendrobium nobile Protocorm Involved in Synthesizing Dendrobine, a Potential Nanodrug. Journal of biomedical nanotechnology. 2021 Mar; 17(3):416-425. doi: 10.1166/jbn.2021.3036. [PMID: 33875076]
  • Jun-Qi Bai, Qian-Xiang Guo, Jing Zhang, Juan Huang, Wen Xu, Lu Gong, He Su, Yu-Bing Luo, Jian-Hua Li, Xiao-Hui Qiu, Zhi-Hai Huang. Metabolic Profile of Dendrobine in Rats Determined by Ultra-high-performance Liquid Chromatography/Quadrupole Time-of-flight Mass Spectrometry. Combinatorial chemistry & high throughput screening. 2021; 24(9):1364-1376. doi: 10.2174/1386207323666201023115744. [PMID: 33100199]
  • R Ci, K Zhang, A Zhu, W Zang. Dendrobine attenuates isoniazid- and rifampicin-induced liver injury by inhibiting miR-295-5p. Human & experimental toxicology. 2020 Dec; 39(12):1671-1680. doi: 10.1177/0960327120937047. [PMID: 32633153]
  • Dan Yang, Zhong-Quan Cheng, Bo Hou, Liu Yang, Cheng-Ting Zi, Fa-Wu Dong, Jiang-Miao Hu, Jun Zhou. Two unusual dendrobine-type alkaloids from Dendrobium findlayanum. Fitoterapia. 2020 Jul; 144(?):104607. doi: 10.1016/j.fitote.2020.104607. [PMID: 32387373]
  • Shigang Zheng, Yadong Hu, Ruoxi Zhao, Tingmei Zhao, Hongjie Li, Dan Rao, Ze Chun. Quantitative assessment of secondary metabolites and cancer cell inhibiting activity by high performance liquid chromatography fingerprinting in Dendrobium nobile. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Mar; 1140(?):122017. doi: 10.1016/j.jchromb.2020.122017. [PMID: 32050157]
  • Tian-He Song, Xiao-Xin Chen, Calvin Kai-Fai Lee, Stephen Cho-Wing Sze, Yi-Bin Feng, Zhi-Jun Yang, Hai-Yong Chen, Sheng-Tao Li, Li-Yan Zhang, Gang Wei, Jun Shi, Kai Xu, Tzi-Bun Ng, Ling-Ling Zhu, Kalin Yanbo Zhang. Dendrobine targeting JNK stress signaling to sensitize chemotoxicity of cisplatin against non-small cell lung cancer cells in vitro and in vivo. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 53(?):18-27. doi: 10.1016/j.phymed.2018.06.018. [PMID: 30668397]
  • Dan Yang, Zhong-Quan Cheng, Liu Yang, Bo Hou, Jing Yang, Xiao-Nian Li, Cheng-Ting Zi, Fa-Wu Dong, Zheng-Hua Liu, Jun Zhou, Zhong-Tao Ding, Jiang-Miao Hu. Seco-Dendrobine-Type Alkaloids and Bioactive Phenolics from Dendrobium findlayanum. Journal of natural products. 2018 02; 81(2):227-235. doi: 10.1021/acs.jnatprod.7b00150. [PMID: 29338260]
  • Chun-Wang Meng, Yu-Lin He, Cheng Peng, Xing-Jie Ding, Li Guo, Liang Xiong. Picrotoxane sesquiterpenoids from the stems of Dendrobium nobile and their absolute configurations and angiogenesis effect. Fitoterapia. 2017 Sep; 121(?):206-211. doi: 10.1016/j.fitote.2017.07.017. [PMID: 28778562]
  • Richan Li, Teng Liu, Miaomiao Liu, Feimin Chen, Shuwen Liu, Jie Yang. Anti-influenza A Virus Activity of Dendrobine and Its Mechanism of Action. Journal of agricultural and food chemistry. 2017 May; 65(18):3665-3674. doi: 10.1021/acs.jafc.7b00276. [PMID: 28417634]
  • Qing Li, Gang Ding, Biao Li, Shun-Xing Guo. Transcriptome Analysis of Genes Involved in Dendrobine Biosynthesis in Dendrobium nobile Lindl. Infected with Mycorrhizal Fungus MF23 (Mycena sp.). Scientific reports. 2017 03; 7(1):316. doi: 10.1038/s41598-017-00445-9. [PMID: 28331229]
  • Shuanghu Wang, Haiya Wu, Peiwu Geng, Yingying Lin, Zezheng Liu, Lijing Zhang, Jianshe Ma, Yunfang Zhou, Xianqin Wang, Congcong Wen. Pharmacokinetic study of dendrobine in rat plasma by ultra-performance liquid chromatography tandem mass spectrometry. Biomedical chromatography : BMC. 2016 Jul; 30(7):1145-1149. doi: 10.1002/bmc.3641. [PMID: 26525040]
  • X K Wang, T F Zhao. [Quantitative determination of spot size of dendrobine in thin-layer chromatography for Dendrobium nobile Lindl cultivated on trees]. Sichuan yi xue yuan xue bao = Acta Academiae Medicinae Sichuan. 1985 Sep; 16(3):249-53. doi: ". [PMID: 2874617]
  • X K Wang. [Gas chromatographic and mass spectrum analysis of the alkaloids of Dendrobium nobile cultivated on eleven trees]. Zhong yao tong bao (Beijing, China : 1981). 1985 Aug; 10(8):31-3, 35. doi: ". [PMID: 2869838]