Mesembrine (BioDeep_00000000643)

   

PANOMIX_OTCML-2023


代谢物信息卡片


(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one

化学式: C17H23NO3 (289.1678)
中文名称: 松叶菊碱, 蕃杏科生物碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 90.52%

分子结构信息

SMILES: CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
InChI: InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m0/s1

描述信息

Mesembrine is a member of pyrrolidines.
(-)-Mesembrine is a natural product found in Mesembryanthemum cordifolium, Oscularia deltoides, and other organisms with data available.

同义名列表

29 个代谢物同义名

(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one; 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aR,7aR)-rel-; 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, cis-(+/-)-; 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aS,7aS)-; 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3as-cis)-; (3aS*,7aS*)-3a-(3,4-dimethoxyphenyl) 1-methyloctahydro-6H-indol-6-one; (3aS*,7aS*)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-6H-indol-6-one; 6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, cis-; 4.alpha.,9.alpha.-Mesembrine; DAHIQPJTGIHDGO-IRXDYDNUSA-N; Mesembrine (+/-)-form [MI]; 4alpha,9alpha-Mesembrine; (+/-)-Mesembranone; Mesembrine, (+/-)-; Mesembrine, (-)-; (+/-)-Mesembrine; (-)-Mesembranone; Mesembrine [MI]; UNII-86E2ZU4ETY; (-)-Mesembrine; DL-Mesembrine; Mesembranone; NCI60_034735; 86E2ZU4ETY; Mesembrine; Mesembrin; AC1L97PM; AC1Q4FEO; Mesembrine



数据库引用编号

20 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 2 CNR2, GRIN2B
Peripheral membrane protein 1 ACHE
Endosome membrane 1 SLC6A4
Endoplasmic reticulum membrane 1 GRIN2B
Mitochondrion membrane 1 MAOA
Nucleus 1 ACHE
cytosol 1 MAOA
dendrite 3 ADORA2A, CNR2, SLC18A2
centrosome 1 SLC18A2
Cell membrane 6 ACHE, ADORA2A, FGFR3, GRID1, GRIN2B, SLC6A4
Cytoplasmic side 1 MAOA
Cell projection, axon 1 SLC18A2
Multi-pass membrane protein 5 ADORA2A, GRID1, GRIN2B, SLC18A2, SLC6A4
Synapse 2 ACHE, SLC6A4
cell surface 3 ACHE, FGFR3, GRIN2B
glutamatergic synapse 2 ADORA2A, GRID1
Golgi apparatus 2 ACHE, FGFR3
Golgi membrane 1 INS
neuromuscular junction 1 ACHE
neuronal cell body 1 ADORA2A
presynaptic membrane 2 ADORA2A, SLC6A4
synaptic vesicle 1 SLC18A2
Lysosome 1 GRIN2B
Presynapse 1 SLC6A4
plasma membrane 8 ACHE, ADORA2A, CNR2, FGFR3, GRID1, GRIN2B, SLC18A2, SLC6A4
presynaptic active zone 1 ADORA2A
synaptic vesicle membrane 1 SLC18A2
terminal bouton 1 SLC18A2
Membrane 7 ACHE, ADORA2A, FGFR3, GRIN2B, MAOA, SLC18A2, SLC6A4
axon 1 SLC18A2
extracellular exosome 1 GRID1
endoplasmic reticulum 2 CNR2, FGFR3
extracellular space 2 ACHE, INS
perinuclear region of cytoplasm 1 ACHE
mitochondrion 1 MAOA
intracellular membrane-bounded organelle 1 SLC18A2
postsynaptic density 1 GRIN2B
Single-pass type I membrane protein 1 FGFR3
Secreted 2 ACHE, INS
extracellular region 3 ACHE, FGFR3, INS
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 1 MAOA
Extracellular side 1 ACHE
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 SLC18A2
perikaryon 1 CNR2
postsynaptic membrane 5 ADORA2A, CNR2, GRID1, GRIN2B, SLC6A4
Membrane raft 1 SLC6A4
Cell junction, focal adhesion 1 SLC6A4
Cytoplasm, cytoskeleton 1 GRIN2B
focal adhesion 1 SLC6A4
axolemma 1 ADORA2A
GABA-ergic synapse 1 GRID1
basement membrane 1 ACHE
intermediate filament 1 ADORA2A
Postsynaptic cell membrane 2 GRID1, GRIN2B
Late endosome 1 GRIN2B
receptor complex 1 FGFR3
Cell projection, neuron projection 1 SLC6A4
neuron projection 2 GRIN2B, SLC6A4
cytoskeleton 1 GRIN2B
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 2]: Cell membrane 1 FGFR3
Endomembrane system 1 SLC6A4
endosome lumen 1 INS
Cell projection, dendrite 3 CNR2, GRIN2B, SLC18A2
side of membrane 1 ACHE
synaptic membrane 1 GRIN2B
secretory granule lumen 1 INS
secretory granule membrane 1 SLC18A2
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
transport vesicle 2 FGFR3, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 2 GRID1, GRIN2B
Single-pass type IV membrane protein 1 MAOA
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
synaptic cleft 1 ACHE
NMDA selective glutamate receptor complex 1 GRIN2B
dopaminergic synapse 1 SLC18A2
Cytoplasmic vesicle, secretory vesicle membrane 1 SLC18A2
asymmetric synapse 1 ADORA2A
[Isoform 4]: Cell membrane 1 FGFR3
clathrin-sculpted monoamine transport vesicle membrane 1 SLC18A2
[Isoform H]: Cell membrane 1 ACHE
serotonergic synapse 1 SLC6A4


文献列表

  • Borjana Sidjimova, Rumen Denev, Milena Nikolova, Jaume Bastida, Strahil Berkov. Dynamics of alkaloid accumulation in Narcissus cv. Hawera: a source of Sceletium-type alkaloids. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2024 Mar; 79(3-4):73-79. doi: 10.1515/znc-2023-0149. [PMID: 38516999]
  • Johané Gericke, Brian H Harvey, Lesha Pretorius, Tracey Ollewagen, Rohan M Benecke, Carine Smith. Sceletium tortuosum-derived mesembrine significantly contributes to the anxiolytic effect of Zembrin®, but its anti-depressant effect may require synergy of multiple plant constituents. Journal of ethnopharmacology. 2023 Sep; 319(Pt 1):117113. doi: 10.1016/j.jep.2023.117113. [PMID: 37660956]
  • Veronica B Maphanga, Krystyna Skalicka-Wozniak, Barbara Budzynska, Andriana Skiba, Weiyang Chen, Clement Agoni, Gill M Enslin, Alvaro M Viljoen. Mesembryanthemum tortuosum L. alkaloids modify anxiety-like behaviour in a zebrafish model. Journal of ethnopharmacology. 2022 May; 290(?):115068. doi: 10.1016/j.jep.2022.115068. [PMID: 35134486]
  • T L Olatunji, F Siebert, A E Adetunji, B H Harvey, J Gericke, J H Hamman, F Van der Kooy. Sceletium tortuosum: A review on its phytochemistry, pharmacokinetics, biological and clinical activities. Journal of ethnopharmacology. 2021 Nov; 280(?):114476. doi: 10.1016/j.jep.2021.114476. [PMID: 34333104]
  • A C Bennett, A Van Camp, V López, C Smith. Sceletium tortuosum may delay chronic disease progression via alkaloid-dependent antioxidant or anti-inflammatory action. Journal of physiology and biochemistry. 2018 Nov; 74(4):539-547. doi: 10.1007/s13105-018-0620-6. [PMID: 29520661]
  • Vamshi K Manda, Bharathi Avula, Mohammad K Ashfaq, Naohito Abe, Ikhlas A Khan, Shabana I Khan. Quantification of mesembrine and mesembrenone in mouse plasma using UHPLC-QToF-MS: Application to a pharmacokinetic study. Biomedical chromatography : BMC. 2017 Mar; 31(3):. doi: 10.1002/bmc.3815. [PMID: 27526669]
  • John L Krstenansky. Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacology. Journal of ethnopharmacology. 2017 Jan; 195(?):10-19. doi: 10.1016/j.jep.2016.12.004. [PMID: 27939420]
  • Marco Masi, Alet E van der Westhuyzen, Nurhayat Tabanca, Marco Evidente, Alessio Cimmino, Ivan R Green, Ulrich R Bernier, James J Becnel, Jeffrey R Bloomquist, Willem A L van Otterlo, Antonio Evidente. Sarniensine, a mesembrine-type alkaloid isolated from Nerine sarniensis, an indigenous South African Amaryllidaceae, with larvicidal and adulticidal activities against Aedes aegypti. Fitoterapia. 2017 Jan; 116(?):34-38. doi: 10.1016/j.fitote.2016.11.007. [PMID: 27864138]
  • A C Swart, C Smith. Modulation of glucocorticoid, mineralocorticoid and androgen production in H295 cells by Trimesemine™, a mesembrine-rich Sceletium extract. Journal of ethnopharmacology. 2016 Jan; 177(?):35-45. doi: 10.1016/j.jep.2015.11.033. [PMID: 26608706]
  • Dirk D Coetzee, Víctor López, Carine Smith. High-mesembrine Sceletium extract (Trimesemine™) is a monoamine releasing agent, rather than only a selective serotonin reuptake inhibitor. Journal of ethnopharmacology. 2016 Jan; 177(?):111-6. doi: 10.1016/j.jep.2015.11.034. [PMID: 26615766]
  • Golo M J Meyer, Carina S D Wink, Josef Zapp, Hans H Maurer. GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high "Kanna" isolated from Sceletium tortuosum. Analytical and bioanalytical chemistry. 2015 Jan; 407(3):761-78. doi: 10.1007/s00216-014-8109-9. [PMID: 25240931]
  • Melissa J Loria, Zulfiqar Ali, Naohito Abe, Kenneth J Sufka, Ikhlas A Khan. Effects of Sceletium tortuosum in rats. Journal of ethnopharmacology. 2014 Aug; 155(1):731-5. doi: 10.1016/j.jep.2014.06.007. [PMID: 24930358]
  • Jörg Roscher, Tjorben Nils Posch, Michael Pütz, Carolin Huhn. Forensic analysis of mesembrine alkaloids in Sceletium tortuosum by nonaqueous capillary electrophoresis mass spectrometry. Electrophoresis. 2012 Jun; 33(11):1567-70. doi: 10.1002/elps.201100683. [PMID: 22736358]
  • Emmanuel A Shikanga, Josias H Hamman, Weiyang Chen, Sandra Combrinck, Nigel Gericke, Alvaro M Viljoen. In vitro permeation of mesembrine alkaloids from Sceletium tortuosum across porcine buccal, sublingual, and intestinal mucosa. Planta medica. 2012 Feb; 78(3):260-8. doi: 10.1055/s-0031-1280367. [PMID: 22105579]
  • Alan L Harvey, Louise C Young, Alvaro M Viljoen, Nigel P Gericke. Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids. Journal of ethnopharmacology. 2011 Oct; 137(3):1124-9. doi: 10.1016/j.jep.2011.07.035. [PMID: 21798331]
  • Srinivas Patnala, Isadore Kanfer. HPLC analysis of mesembrine-type alkaloids in Sceletium plant material used as an African traditional medicine. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2010; 13(4):558-70. doi: 10.18433/j3dk5f. [PMID: 21486531]
  • Srinivas Patnala, Isadore Kanfer. Investigations of the phytochemical content of Sceletium tortuosum following the preparation of 'Kougoed' by fermentation of plant material. Journal of ethnopharmacology. 2009 Jan; 121(1):86-91. doi: 10.1016/j.jep.2008.10.008. [PMID: 18996176]
  • Srinivas Patnala, Isadore Kanfer. A capillary zone electrophoresis method for the assay and quality control of mesembrine in Sceletium tablets. Journal of pharmaceutical and biomedical analysis. 2008 Sep; 48(2):440-6. doi: 10.1016/j.jpba.2008.01.002. [PMID: 18280080]
  • J H Holmes, I Kanfer, H Zwarenstein. Effect of benzodiazepine derivatives on human blood cholinesterase in vitro. Research communications in chemical pathology and pharmacology. 1978 Aug; 21(2):367-70. doi: . [PMID: 29327]