spinasterol (BioDeep_00000637165)

Main id: BioDeep_00000000531

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3S,5S,9R,10S,13R,14R,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C29H48O (412.3705)
中文名称: α-Spinasterol
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@H](CC)C(C)C)CC[C@@]4([H])C3=CC[C@@]2([H])C[C@@H](O)C1
InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3/b9-8+/t20-,21+,22+,23+,25-,26+,27+,28+,29-/m1/s1

描述信息

α-Spinasterol, isolated from Melandrium firmum, has antibacterial activity[1]. α-Spinasterol is a transient receptor potential vanilloid 1 (TRPV1) antagonist, has anti-inflammatory, antidepressant, antioxidant and antinociceptive effects. α-Spinasterol inhibits COX-1 andCOX-2 activities with IC50 values of 16.17 μM and 7.76 μM, respectively[2].
α-Spinasterol, isolated from Melandrium firmum, has antibacterial activity[1]. α-Spinasterol is a transient receptor potential vanilloid 1 (TRPV1) antagonist, has anti-inflammatory, antidepressant, antioxidant and antinociceptive effects. α-Spinasterol inhibits COX-1 andCOX-2 activities with IC50 values of 16.17 μM and 7.76 μM, respectively[2].

同义名列表

20 个代谢物同义名

(3S,5S,9R,10S,13R,14R,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5S)-5-ethyl-6-methyl-hept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5S,9R,10S,13R,14R,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethylhex-2-enyl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; Stigmasta-7,22-dien-3-ol, (3-beta,5-alpha,22E)-; (3-beta,5-alpha,22E)-Stigmasta-7,22-dien-3-ol; 5-alpha-Stigmasta-7,22-dien-3-beta-ol, (E)-; Stigmasta-7,22E-dien-3beta-ol; alpha-Spinasterin; Alpha-Spinasterol; α-Spinasterol; Hitodesterol; LMST01040126; spinasterol; 481-18-5; C08840; 24S-ethyl-5alpha-cholesta-7,22E-dien-3beta-ol; Poriferasta-7,22E-dien-3beta-ol; ST 29:2;O; alpha-Spinasterol



数据库引用编号

15 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)

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PharmGKB(0)

220 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 9 AKT1, CAT, ESR1, IRS1, MAPK14, MSMP, PPARG, PTGS2, TP53
Peripheral membrane protein 2 ESR1, PTGS2
Endoplasmic reticulum membrane 4 ABCG1, HMGCR, HMOX1, PTGS2
Nucleus 8 AKT1, ESR1, HMOX1, IRS1, MAPK14, PDX1, PPARG, TP53
cytosol 11 ACOX1, AKT1, CAT, ESR1, HMOX1, IRS1, IRS2, MAPK14, PDX1, PPARG, TP53
centrosome 1 TP53
nucleoplasm 8 AKT1, ESR1, HMOX1, IRS1, MAPK14, PDX1, PPARG, TP53
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 5 ABCG1, AKT1, ESR1, TNF, TRPV1
Cytoplasmic side 2 ESR1, HMOX1
lamellipodium 1 AKT1
Multi-pass membrane protein 3 ABCG1, HMGCR, TRPV1
Golgi apparatus membrane 1 ABCG1
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 2 AKT1, MAPK14
Golgi apparatus 2 ABCG1, ESR1
Golgi membrane 2 ABCG1, INS
neuronal cell body 2 TNF, TRPV1
postsynapse 1 AKT1
Cytoplasm, cytosol 2 IRS2, PDX1
endosome 1 ABCG1
plasma membrane 7 ABCG1, AKT1, ESR1, IRS1, IRS2, TNF, TRPV1
Membrane 9 ABCG1, ACOX1, AKT1, CAT, ESR1, HMGCR, HMOX1, TP53, TRPV1
caveola 2 IRS1, PTGS2
extracellular exosome 1 CAT
endoplasmic reticulum 4 HMGCR, HMOX1, PTGS2, TP53
extracellular space 5 HMOX1, IL6, INS, MSMP, TNF
perinuclear region of cytoplasm 2 HMOX1, PPARG
mitochondrion 5 ABCG1, CAT, MAPK14, PDX1, TP53
protein-containing complex 5 AKT1, CAT, ESR1, PTGS2, TP53
intracellular membrane-bounded organelle 3 CAT, IRS1, PPARG
Microsome membrane 1 PTGS2
Secreted 3 IL6, INS, MSMP
extracellular region 6 CAT, DNAH9, IL6, INS, MAPK14, TNF
mitochondrial outer membrane 1 HMOX1
Mitochondrion matrix 1 TP53
mitochondrial matrix 3 CAT, PDX1, TP53
transcription regulator complex 2 ESR1, TP53
motile cilium 1 DNAH9
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
external side of plasma membrane 3 ABCG1, TNF, TRPV1
microtubule cytoskeleton 1 AKT1
nucleolus 1 TP53
cell-cell junction 1 AKT1
recycling endosome 2 ABCG1, TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
postsynaptic membrane 1 TRPV1
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 CAT
microtubule 1 DNAH9
spindle 1 AKT1
GABA-ergic synapse 1 TRPV1
Peroxisome 2 ACOX1, CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 2 ACOX1, CAT
peroxisomal membrane 3 ACOX1, CAT, HMGCR
Nucleus, PML body 1 TP53
PML body 1 TP53
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
axoneme 1 DNAH9
nuclear speck 2 MAPK14, PDX1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 TRPV1
receptor complex 1 PPARG
Cell projection, neuron projection 1 TRPV1
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 4 ESR1, PDX1, PPARG, TP53
phagocytic cup 1 TNF
spindle pole 1 MAPK14
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
site of double-strand break 1 TP53
endosome lumen 1 INS
euchromatin 1 ESR1
germ cell nucleus 1 TP53
replication fork 1 TP53
Peroxisome membrane 1 HMGCR
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
pyruvate dehydrogenase complex 1 PDX1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
Single-pass type IV membrane protein 1 HMOX1
[Isoform 1]: Nucleus 2 ESR1, TP53
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
insulin receptor complex 1 IRS1
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Farid Khallouki, Mohamed Ksila, Imen Ghzaiel, Soukaina Essadek, Mounia Tahri Joutey, Samah Maaloul, Wafa Zennouhi, Laila Benbacer, Mohamed Bourhia, Lhoussain Hajji, Amira Zarrouk, Leila Rezig, Sandrine Rup-Jacques, Raoudha Abdellaoui, Taoufik Ghrairi, Olfa Masmoudi-Kouki, Boubker Nasser, Pierre Andreoletti, Mustapha-Cherkaoui-Malki, Mohammad Samadi, Anne Vejux, Gérard Lizard. Chemical and Biochemical Features of Spinasterol and Schottenol. Advances in experimental medicine and biology. 2024; 1440(?):45-55. doi: 10.1007/978-3-031-43883-7_3. [PMID: 38036874]
  • Muhammed Majeed, Furkan Ahmad, Lakshmi Mundkur, Subramoniam Appian. Pharmacology of α-spinasterol, a phytosterol with nutraceutical values: A review. Phytotherapy research : PTR. 2022 Oct; 36(10):3681-3690. doi: 10.1002/ptr.7560. [PMID: 35802356]
  • Maqsood Ahmed, Allah Rakha Sajid, Ansar Javeed, Muhammad Aslam, Taswar Ahsan, Dilbar Hussain, Abdul Mateen, Xiuwei Li, Peiwen Qin, Mingshan Ji. Antioxidant, antifungal, and aphicidal activity of the triterpenoids spinasterol and 22,23-dihydrospinasterol from leaves of Citrullus colocynthis L. Scientific reports. 2022 03; 12(1):4910. doi: 10.1038/s41598-022-08999-z. [PMID: 35318417]
  • Maqsood Ahmed, Peiwen Qin, Mingshan Ji, Ran An, Hongxia Guo, Jamil Shafi. Spinasterol, 22,23-Dihydrospinasterol and Fernenol from Citrullus Colocynthis L. with Aphicidal Activity against Cabbage Aphid Brevicoryne Brassicae L. Molecules (Basel, Switzerland). 2020 May; 25(9):. doi: 10.3390/molecules25092184. [PMID: 32392823]
  • Olamide Elizabeth Adebiyi, James Olukayode Olopade, Funsho Olakitike Olayemi. Sodium metavanadate induced cognitive decline, behavioral impairments, oxidative stress and down regulation of myelin basic protein in mice hippocampus: Ameliorative roles of β-spinasterol, and stigmasterol. Brain and behavior. 2018 07; 8(7):e01014. doi: 10.1002/brb3.1014. [PMID: 29856129]
  • Indiara Brusco, Camila Camponogara, Fabiano Barbosa Carvalho, Maria Rosa Chitolina Schetinger, Mauro Schneider Oliveira, Gabriela Trevisan, Juliano Ferreira, Sara Marchesan Oliveira. α-Spinasterol: a COX inhibitor and a transient receptor potential vanilloid 1 antagonist presents an antinociceptive effect in clinically relevant models of pain in mice. British journal of pharmacology. 2017 Dec; 174(23):4247-4262. doi: 10.1111/bph.13992. [PMID: 28849589]
  • Ivan Haralampiev, Holger A Scheidt, Daniel Huster, Peter Müller. The Potential of α-Spinasterol to Mimic the Membrane Properties of Natural Cholesterol. Molecules (Basel, Switzerland). 2017 Aug; 22(8):. doi: 10.3390/molecules22081390. [PMID: 28829376]
  • Katarzyna Socała, Piotr Wlaź. Evaluation of the antidepressant- and anxiolytic-like activity of α-spinasterol, a plant derivative with TRPV1 antagonistic effects, in mice. Behavioural brain research. 2016 Apr; 303(?):19-25. doi: 10.1016/j.bbr.2016.01.048. [PMID: 26808607]
  • Alessio Cimmino, Véronique Mathieu, Marco Evidente, Marlène Ferderin, Laetitia Moreno Y Banuls, Marco Masi, Annelise De Carvalho, Robert Kiss, Antonio Evidente. Glanduliferins A and B, two new glucosylated steroids from Impatiens glandulifera, with in vitro growth inhibitory activity in human cancer cells. Fitoterapia. 2016 Mar; 109(?):138-45. doi: 10.1016/j.fitote.2015.12.016. [PMID: 26732071]
  • Katarzyna Socała, Dorota Nieoczym, Mateusz Pieróg, Piotr Wlaź. α-Spinasterol, a TRPV1 receptor antagonist, elevates the seizure threshold in three acute seizure tests in mice. Journal of neural transmission (Vienna, Austria : 1996). 2015 Sep; 122(9):1239-47. doi: 10.1007/s00702-015-1391-7. [PMID: 25764210]
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  • Mee-Young Lee, In-Sik Shin, Hwangbo Kyoung, Chang-Seob Seo, Jong-Keun Son, Hyeun-Kyoo Shin. α-Spinasterol from Melandrium firmum attenuates benign prostatic hyperplasia in a rat model. Molecular medicine reports. 2014 Jun; 9(6):2362-6. doi: 10.3892/mmr.2014.2081. [PMID: 24682042]
  • Youssef El Kharrassi, Mohammad Samadi, Tatiana Lopez, Thomas Nury, Riad El Kebbaj, Pierre Andreoletti, Hammam I El Hajj, Joseph Vamecq, Khadija Moustaid, Norbert Latruffe, M'Hammed Saïd El Kebbaj, David Masson, Gérard Lizard, Boubker Nasser, Mustapha Cherkaoui-Malki. Biological activities of Schottenol and Spinasterol, two natural phytosterols present in argan oil and in cactus pear seed oil, on murine miroglial BV2 cells. Biochemical and biophysical research communications. 2014 Apr; 446(3):798-804. doi: 10.1016/j.bbrc.2014.02.074. [PMID: 24582563]
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