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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O4
Molecular Weight 328.4029
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MACELIGNAN

SMILES

C[C@@]([H])(Cc1ccc(c(c1)OC)O)[C@]([H])(C)Cc2ccc3c(c2)OCO3

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

HIDE SMILES / InChI

Description
Curator's Comment:: 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.

Originator

Sources: Saengyak Hakhoechi (1986), 17, (3), 189-94. CODEN:SYHJAM ISSN:0253-3073.

Approval Year

PubMed

PubMed

TitleDatePubMed
Macelignan inhibits bee pathogenic fungi Ascophaera apis growth through HOG1 pathway.
2016 Jul 4
Patents

Patents

Sample Use Guides

Rats: 10 mg/kg/day
Route of Administration: Oral
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.
Name Type Language
MACELIGNAN
INCI  
INCI  
Official Name English
MACELIGNAN [INCI]
Common Name English
PHENOL, 4-((2S,3R)-4-(1,3-BENZODIOXOL-5-YL)-2,3-DIMETHYLBUTYL)-2-METHOXY-
Systematic Name English
(8R,8'S)-7-(3,4-METHYLENEDIOXYPHENYL)-7'-(4-HYDROXY-3-METHOXYPHENYL)-8,8'-DIMETHYLBUTANE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C52588
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
NCI_THESAURUS C28203
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
Code System Code Type Description
RXCUI
1872381
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
WIKIPEDIA
MACELIGNAN
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
NCI_THESAURUS
C92606
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
CAS
107534-93-0
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
MESH
C502026
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
DRUG BANK
DB14129
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
EPA CompTox
107534-93-0
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
FDA UNII
8PP3614Z43
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY
PUBCHEM
10404245
Created by admin on Sat Jun 26 05:10:54 UTC 2021 , Edited by admin on Sat Jun 26 05:10:54 UTC 2021
PRIMARY