Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H24O4 |
Molecular Weight | 328.4022 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(C[C@H](C)[C@H](C)CC2=CC3=C(OCO3)C=C2)=CC=C1O
InChI
InChIKey=QDDILOVMGWUNGD-UONOGXRCSA-N
InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/23435944Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24927000 | https://www.ncbi.nlm.nih.gov/pubmed/18065517 | https://www.ncbi.nlm.nih.gov/pubmed/18940231
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23435944
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24927000 | https://www.ncbi.nlm.nih.gov/pubmed/18065517 | https://www.ncbi.nlm.nih.gov/pubmed/18940231
Macelignan is a neuroprotective lingan isolated from nutmeg (Myristica fragrans) that protects dopaminergic neurons from inflammatory degeneration. Macelignans have been shown to possess a broad range of pharmacological properties, including anti-bacterial, antiinflammatory, and anti-cancer activity. It has also been demonstrated that macelignans have anti-diabetes, hepatoprotective, and more importantly, neuroprotective properties. Apparently, the neuroprotective effect of macelignan is mediated by PPARγ activation and arginase-1 expression. Macelignan inhibits LPS induced production of NO as well and inflammatory cytokines including TNF and IL- 1β in primary cultures of microglia. Macelignan reduced serum glucose, insulin, triglycerides, free fatty acid levels, and triglycerides levels in the skeletal muscle and liver of db/db mice. Furthermore, macelignan significantly improved glucose and insulin tolerance in these mice, and without altering food intake, their body weights were slightly reduced while weights of troglitazone-treated mice increased. Macelignan increased adiponectin expression in adipose tissue and serum, whereas the expression and serum levels of tumor necrosis factor-alpha and interleukin-6 decreased. Macelignan downregulated inflammatory gene expression in the liver and increased AMP-activated protein kinase activation in the skeletal muscle of db/db mice. Strikingly, macelignan reduced endoplasmic reticulum (ER) stress and c-Jun NH2-terminal kinase activation in the liver and adipose tissue of db/db mice and subsequently increased insulin signaling.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18065517 |
4.221 µM [EC50] | ||
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18065517 |
5.405 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18940231
Rats: 10 mg/kg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24927000
Human dopaminergic neuroblastoma SH-SY5Y cells were used for activity evaluation. SH-SY5Y cells were maintained in DMEM culture medium (Solarbio, Beijing, China) with 10% calf serum (Sijiqing, Hangzhou, China), 100 U/mL penicillin, and 75 U/mL streptomycin in a 37 °C incubator (Heal Force HF-90, Hong Kong) in 5% CO2. Cells were trypsinized with 0.25% trypsin, counted, and seeded in 96-well culture plates (1 × 104 cells/well). After 24 h of incubation, the cells were pretreated with compound 8 (Macelignan) (0.08, 0.4, 2, and 10 μM) for 2 h before incubation in medium containing Aβ25−35 (1 μM). After 24 h of treatment, 15 μL of MTT (5 mg/mL) was added. For the MTT assays, the supernatant was discarded, and DMSO (100 μL/well) was added. The 96-well plate was vibrated on a microvibrator for 10 min, and the optical density at 570 nm was measured using a microplate reader.
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NCI_THESAURUS |
C52588
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NCI_THESAURUS |
C28203
Created by
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1872381
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8PP3614Z43
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MACELIGNAN
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C92606
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107534-93-0
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C502026
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DB14129
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DTXSID00148077
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8PP3614Z43
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10404245
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ACTIVE MOIETY