Dehydrodiisoeugenol
(Synonyms: 脱氢二异丁香酚) 目录号 : GC38184
Dehydrodiisoeugenol, a naturally occurring lignan from Aristolochia taliscana (Aristolochiaceae), acts as a potent anti-inflammatory agent and shows various pharmacological activities, including anti-lipid peroxidation, anti-bacteial function, and hepatic drug metabolism enzyme inhibition.
Cas No.:2680-81-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dehydrodiisoeugenol, a naturally occurring lignan from Aristolochia taliscana (Aristolochiaceae), acts as a potent anti-inflammatory agent and shows various pharmacological activities, including anti-lipid peroxidation, anti-bacteial function, and hepatic drug metabolism enzyme inhibition.
| Cas No. | 2680-81-1 | SDF | |
| 别名 | 脱氢二异丁香酚 | ||
| Canonical SMILES | OC1=CC=C(C2OC3=C(OC)C=C(/C=C/C)C=C3C2C)C=C1OC | ||
| 分子式 | C20H22O4 | 分子量 | 326.39 |
| 溶解度 | DMSO: ≥ 250 mg/mL (765.95 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0638 mL | 15.3191 mL | 30.6382 mL |
| 5 mM | 0.6128 mL | 3.0638 mL | 6.1276 mL |
| 10 mM | 0.3064 mL | 1.5319 mL | 3.0638 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Dehydrodiisoeugenol inhibits colorectal cancer growth by endoplasmic reticulum stress-induced autophagic pathways
J Exp Clin Cancer Res 2021 Apr 10;40(1):125.PMID:33838688DOI:10.1186/s13046-021-01915-9.
Background: Dehydrodiisoeugenol (DEH), a novel lignan component extracted from nutmeg, which is the seed of Myristica fragrans Houtt, displays noticeable anti-inflammatory and anti-allergic effects in digestive system diseases. However, the mechanism of its anticancer activity in gastrointestinal cancer remains to be investigated. Methods: In this study, the anticancer effect of DEH on human colorectal cancer and its underlying mechanism were evaluated. Assays including MTT, EdU, Plate clone formation, Soft agar, Flow cytometry, Electron microscopy, Immunofluorescence and Western blotting were used in vitro. The CDX and PDX tumor xenograft models were used in vivo. Results: Our findings indicated that treatment with DEH arrested the cell cycle of colorectal cancer cells at the G1/S phase, leading to significant inhibition in cell growth. Moreover, DEH induced strong cellular autophagy, which could be inhibited through autophagic inhibitors, with a rction in the DEH-induced inhibition of cell growth in colorectal cancer cells. Further analysis indicated that DEH also induced endoplasmic reticulum (ER) stress and subsequently stimulated autophagy through the activation of PERK/eIF2α and IRE1α/XBP-1 s/CHOP pathways. Knockdown of PERK or IRE1α significantly decreased DEH-induced autophagy and retrieved cell viability in cells treated with DEH. Furthermore, DEH also exhibited significant anticancer activities in the CDX- and PDX-models. Conclusions: Collectively, our studies strongly suggest that DEH might be a potential anticancer agent against colorectal cancer by activating ER stress-induced inhibition of autophagy.
Synthesis and Biological Activities of Dehydrodiisoeugenol: A Review
Pharmaceuticals (Basel) 2022 Oct 31;15(11):1351.PMID:36355523DOI:10.3390/ph15111351.
Dehydrodiisoeugenol (DHIE) is a neolignan found in more than 17 plant species, including herbs, fruit, and root. DHIE was, for the first time, isolated from Myristica fragrans bark in 1973. Since then, many methodologies have been used for the obtention of DHIE, including classical chemistry synthesis using metal catalysts and biocatalytic synthesis; employing horseradish peroxidase; peroxidase from Cocos nucifera; laccase; culture cells of plants; and microorganisms. Increasing evidence has indicated that DHIE has a wide range of biological activities: anti-inflammatory, anti-oxidant, anti-cancerogenic, and anti-microbial properties. However, evidence in vivo and in human beings is still lacking to support the usefulness potential of DHIE as a therapeutic agent. This study's review was created by searching for relevant DHIE material on websites such as Google Scholar, PubMed, SciFinder, Scholar, Science Direct, and others. This reviews the current state of knowledge regarding the different synthetical routes and biological applications of DHIE.
Metabolic profiling of Dehydrodiisoeugenol using xenobiotic metabolomics
J Pharm Biomed Anal 2017 Oct 25;145:725-733.PMID:28806569DOI:10.1016/j.jpba.2017.07.045.
Dehydrodiisoeugenol (DDIE), a representative and major benzofuran-type neolignan in Myristica fragrans Houtt., shows anti-inflammatory and anti-bacterial actions. In order to better understand its pharmacological properties, xenobiotic metabolomics was used to determine the metabolic map of DDIE and its influence on endogenous metabolites. Total thirteen metabolites of DDIE were identified through in vivo and in vitro metabolism, and seven of them were reported for the first time in the present study. The identity of DDIE metabolites was achieved by comparison of the MS/MS fragmentation pattern with DDIE using ultra-performance chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (UPLC-ESI- QTOFMS). Demethylation and ring-opening reaction were the major metabolic pathways for in vivo metabolism of DDIE. Recombinant cytochrome P450s (CYPs) screening revealed that CYP1A1 is a primary enzyme contributing to the formation of metabolites D1-D4. More importantly, the levels of two endogenous metabolites 2,8-dihydroxyquinoline and its glucuronide were significantly elevated in mouse urine after DDIE exposure, which explains in part its modulatory effects on gut microbiota. Taken together, these data contribute to the understanding of the disposition and pharmacological activities of DDIE in vivo.
Mitigative effects of Dehydrodiisoeugenol on enteritis and co-occurring dysmotility in murine model
Pak J Pharm Sci 2022 Sep;35(5):1347-1355.PMID:36451563doi
The actions and mechanisms of Dehydrodiisoeugenol (DEH) on releasing clinical symptoms such as diarrhea caused by inflammatory bowel diseases or colorectal cancer is still unclear. The main purpose is to reveal the mechanism and describe the impacts of DEH on enteritis and accompanying intestinal dysmotility in murine model. The animal model of diarrhea was established through being given acetic acid by intracolonic instillation and restraint stress and the weight of the diarrhea mouse, diarrhea index (the product of stool rate and stool grade) evaluation and then, myeloperoxidase (MPO) activity were determined after administrated with DEH. Meanwhile, the expression of myosin light chain kinase (MLCK) was research by WB method. Moreover, the isolated jejunal segment (IJS) of rats was separated from the intact jejunum and the contractility was measured through BL-420F physiological recording system. DEH could significantly inhibit the intestinal transit in normal mice or diarrhea-predominated mice and reduce the diarrhea index and the level of MPO in mice. DEH concentration-dependently inhibited motility of IJS in different states. DEH significantly markedly ameliorated the histopathology condition and reduce the MLCK expression in acetic acid induced diarrhea mice. DEH simultaneously improved enteritis and co-occurring dysmotility in diarrhea mice characterized by reducing the contractility and MLCK contents in acetic acid induced diarrhea mice.
Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages
Arch Biochem Biophys 2005 Feb 15;434(2):326-32.PMID:15639233DOI:10.1016/j.abb.2004.11.013.
o-Methoxyphenols such as eugenol and isoeugenol exhibit anti-oxidant and anti-inflammatory activities, but at higher concentrations act as oxidants and potent allergens. We recently demonstrated the eugenol dimer bis-eugenol to be an efficient inhibitor of lipopolysaccharide (LPS)-induced inflammatory cytokine expression in macrophages without cytotoxicity. This result suggested that dimer compound of o-methoxyphenols may possess anti-inflammatory activity. Thus, we further synthesized Dehydrodiisoeugenol and alpha-diisoeugenol from isoeugenols, and investigated whether these dimers could inhibit LPS-stimulated nuclear factor kappa B (NF-kappaB) activation and cyclooxygenase (COX)-2 gene expression, both of which are closely involved in inflammation and mutagenesis. The expression of the COX-2 gene was strongly inhibited by Dehydrodiisoeugenol in RAW264.7 murine macrophages stimulated with LPS. In contrast, isoeugenol and alpha-diisoeugenol did not inhibit it. Dehydrodiisoeugenol also significantly inhibited LPS-stimulated phosphorylation-dependent proteolysis of inhibitor kappaB-alpha and transcriptional activity of NF-kappaB in the cells. These findings suggest that Dehydrodiisoeugenol acts as a potent anti-inflammatory agent.