Lirioresinol-B dimethyl ether
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05591 |
| CAS | 80780-43-4 |
| Molecular Weight | 446.49 |
| Molecular Formula | C24H30O8 |
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Description
It is extracted from the seeds of Magnolia fargesii CHENG (Magnoliaceae). It inhibits NF-κB and COX-2 and activates IκBα expression in CCl4-induced hepatic fibrosis. It has anti-inflammatory and anti-cancer activities against HepG2 cells as well as in BALB/C male mice.
Specification
| Synonyms | NSC 83441; 1,4-bis(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan; Lirioresinol B, O,O-dimethyl-; (+)-O,O-Dimethyl lirioresinol-B; Syringaresinol dimethyl ether; Lirioresinol B dimethyl ether |
| IUPAC Name | 3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan |
| Canonical SMILES | COC1=CC(=CC(=C1OC)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC |
| InChI | InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3 |
| InChI Key | HRLFUIXSXUASEX-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 556.1°C at 760 mmHg |
| Density | 1.183 g/cm3 |
Reference Reading
1. Lirioresinol B dimethyl ether inhibits NF-κB and COX-2 and activates IκBα expression in CCl4-induced hepatic fibrosis
Adeeb Shehzad, Shagufta Rehmat, Salman Ul-Islam, Rizwan Ahmad, Meneerah Aljafary, Noor A Alrushaid, Ebtesam A Al-Suhaimi BMC Complement Med Ther. 2020 Feb 11;20(1):49. doi: 10.1186/s12906-020-2839-3.
Background: Inflammation is one of the key components in the initiation and progression of hepatic diseases. If not treated, inflammation may cause cell dysplasia, and ultimately cancer. In the current study, we investigated the anti-inflammatory and anti-cancer activities of plant isolated compound Lirioresinol B Dimethyl Ether (LBDE) extracted from the seeds of Magnolia fargesii CHENG (Magnoliaceae) against HepG2 cells as well as in BALB/C male mice. Methods: We assessed the antioxidant and anti-proliferative effects of plant compounds using DPPH assay and HepG2 cell lines. Carbon tetrachloride (CCl4) and Diethylnitrosamine (DEN) were used to induce liver cell dysplasia followed by hepatocellular carcinoma (HCC) in BALB/C male mice for 12 weeks. We investigated the underlying mechanism by using histopathology and immunoblot experiments. Results: Intraperitoneal injection of LBDE (50 mg/kg body weight/day) inhibited CCl4-induced HCC. Free radical scavenging assay shows the strong anti-oxidant activity of LBDE. Western blot results show that LBDE down-regulated nuclear factor kappa B (NFκB) and cyclooxygenase (COX-2) by preventing the phosphorylation of I kappa B alpha (IκBα) in CCl4 treated group. LBDE also improved liver function by decreasing Alkaline Phosphatase (ALP), aspartate aminotransferase (AST) and Alanine Aminotransferase (ALT) levels. Histopathology results revealed that LBDE decreased granulomas and express normal morphology of hepatocytes. Conclusions: These preliminary results show that LBDE has the potential to inhibit CCl4-induced liver cell dysplasia and prevents cancer development by regulating NFκB/COX-2 activation.
2. Molecular mechanism underlying anti-inflammatory activities of lirioresinol B dimethyl ether through suppression of NF-κB and MAPK signaling in in vitro and in vivo models
Yunshu Su, Sizheng Xiong, Hongwen Lan, Lijun Xu, Xiang Wei Int Immunopharmacol. 2019 Aug;73:321-332. doi: 10.1016/j.intimp.2019.05.020. Epub 2019 May 23.
The aim of the present study is to explore the anti-inflammatory mechanism of lirioresinol B dimethyl ether via inhibition of multiple signaling pathways in both in vitro and in vivo pharmacological models. To determine the anti-inflammatory activity of the lirioresinol B dimethyl ether, RAW 264.7 macrophages challenged with lipopolysaccharide (LPS) were treated with various concentrations of lirioresinol B dimethyl ether (5, 15, 25, and 50 μM). The results indicated that pretreatment with lirioresinol B dimethyl ether significantly suppressed nuclear factor kappa B (NF-κB) activation, nitric oxide (NO) production, the protein expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Lirioresinol B dimethyl ether inhibited LPS-induced activation of production of pro-inflammatory cytokines as well as prostaglandin E2 (PGE2) release. The results obtained by electrophoretic mobility shift assay (EMSA) demonstrated a concentration dependent reduction of the LPS-stimulated activation of NF-κB and activator protein-1 (AP-1) by lirioresinol B dimethyl ether in in vitro and in vivo models. Moreover, lirioresinol B dimethyl ether also reduced the expression of toll-like receptor (TLR)-4 protein and myeloid differentiation primary response gene 88 (MyD88) as well as promoted the degradation of IκBα. Lirioresinol B dimethyl ether also significantly down-regulated the phosphorylation of Jun N-terminal kinase (JNK), p-38 and extracellular signal-regulated kinase (ERK). Furthermore, the results of acute and chronic inflammation demonstrated that lirioresinol B dimethyl ether (10 and 50 mg per kg) reduced paw edema and mechanical hyperalgesia in carrageenan- and Complete Freund's Adjuvant (CFA)-induced in vivo mouse models, respectively. Hence, the current results indicate that lirioresinol B dimethyl ether either act by inhibiting pro-inflammatory mediators through down-regulation of mitogen activated protein kinases (MAPKs) signaling pathways and reduction of NF-κB activation.
3. Cytotoxic and Antimigration Activity of Etlingera alba (A.D.) Poulsen Rhizome
W Wahyuni, Ajeng Diantini, Mohammad Ghozali, Anas Subarnas, Euis Julaeha, Riezki Amalia, I Sahidin Adv Pharmacol Pharm Sci. 2021 Dec 28;2021:6597402. doi: 10.1155/2021/6597402. eCollection 2021.
Etlingera alba is one of the Etlingera plants that might have anticancer activity. This study aims to investigate the cytotoxic and antimetastatic activity of E. alba rhizome fractions and migration cell assay against MDA-MB-231 cell lines, which are used for triple-negative breast cancer (TNBC) treatment assay. The cytotoxic activity was assayed using CCK-8 assay, while the antimetastatic was assayed using migration cell assay for the fractions A-F. They were followed by LCMS/MS profiling to determine the chemical contents in the most active fraction. According to results obtained, fraction B was the most active fraction for cytotoxic activity with an IC50 value of 65.43 μg/mL, while fraction E was the most active fraction for antimetastasis activity against migration rate doses of 50, 100, and 200 ppm which were 6.80, 3.66, and 3.00%, respectively. Several compounds in fraction B, such as rengyolone, licochalcone A, sugiol, and spinasterol, might have been known to have activity against cancer cells, as well as aschantin and lirioresinol B dimethyl ether from fraction E. In conclusion, the chemical components from E. alba rhizome fractions provided potency for discovering new agents for cancer treatment, specifically for TNBC.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
