Dehydrodiisoeugenol(DEH)是香豆蔻中具有代表性的主要苯并呋喃型新木质素,具有抗菌、抗炎、抗癌、抗氧化等特性。
Cas No.:2680-81-1
Sample solution is provided at 25 µL, 10mM.
Dehydrodiisoeugenol (DEH) is a representative and major benzofuran-type neolignan found in Myristica fragrans Houtt, possessing antibacterial, anti-inflammatory, anticancer, and antioxidant properties. Dehydrodiisoeugenol inhibits the proliferation of colorectal cancer cells and induces apoptosis, autophagy, endoplasmic reticulum stress and cell cycle arrest. Dehydrodiisoeugenol is commonly used in the research related to colorectal cancer, inflammatory diseases and ulcerative colitis[1][2][3].
In vitro, treatment with Dehydrodiisoeugenol (2.5, 5 and 10µM) for 24h inhibited the activation of the NF-κB and MAPK signaling pathways and dose-dependently suppressed the expression of inflammatory mediators, including NO, iNOS, COX-2, PGE₂, IL-1β, IL-6, and TNF-α in the LPS/IFNγ-induced RAW264.7 ulcerative colitis (UC) model[1]. Treatment with Dehydrodiisoeugenol (40, 80, and 100µM) for 24h significantly inhibited the viability of HCT116 and HT29 cells[1]. Treatment with Dehydrodiisoeugenol at 40µM for 24h induced apoptosis in HCT116 cells, suppressing Bcl-2 expression while upregulating Bax expression[1].
In vivo, oral administration of Dehydrodiisoeugenol at 40mg/kg for 20 days significantly inhibited tumor growth in BALB/c nude mice transplanted with HCT116 cells[1]. Oral gavage administration of Dehydrodiisoeugenol at 20mg/kg/d for 8 days significantly improved rectal bleeding in DSS-induced mice[1].
References:
[1] Yi F, Chen N, Zhao M, et al. Dehydrodiisoeugenol targets NOD2 exerting dual effects against colitis and colorectal cancer: a double-edged sword. Mol Med. 2025;31(1):221.
[2] Li C, Zhang K, Pan G, et al. Dehydrodiisoeugenol inhibits colorectal cancer growth by endoplasmic reticulum stress-induced autophagic pathways. J Exp Clin Cancer Res. 2021;40(1):125.
[3] Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I, Fujisawa S. Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Arch Biochem Biophys. 2005;434(2):326-332.
Dehydrodiisoeugenol(DEH)是香豆蔻中具有代表性的主要苯并呋喃型新木质素,具有抗菌、抗炎、抗癌、抗氧化等特性。Dehydrodiisoeugenol能抑制结直肠癌细胞增殖,诱导凋亡、自噬、内质网应激和细胞周期阻滞。Dehydrodiisoeugenol常用于结直肠癌、炎症性疾病和溃疡性结肠炎的相关研究[1][2][3]。
体内实验中,在LPS/IFN-γ诱导的RAW264.7溃疡性结肠炎(UC)模型中,用2.5、5和10µM Dehydrodiisoeugenol处理24小时,可抑制NF-κB和MAPK信号通路的激活,并以剂量依赖性方式抑制NO、iNOS、COX-2、PGE₂、IL-1β、IL-6和TNF-α等炎症因子的表达[1]。用Dehydrodiisoeugenol(40、80和100 µM)处理24小时可显著抑制HCT116和HT29细胞的活力[1]。以40µM的DEH处理HCT116细胞24小时可诱导细胞凋亡,抑制Bcl-2的表达,同时上调Bax的表达[1]。
体外实验中,以40mg/kg 剂量口服给予Dehydrodiisoeugenol20天,可显著抑制移植了HCT116细胞的BALB/c裸鼠中的肿瘤生长。以20mg/kg/d的Dehydrodiisoeugenol口服灌胃给药8天,可显著改善DSS诱导小鼠的直肠出血情况[1]。
| Cell experiment [1]: | |
Cell lines | RAW264.7 |
Preparation Method | RAW 264.7 cells were seeded overnight in a 96-well plate, and treated with the positive control drug (curcumin, 5µM) and Dehydrodiisoeugenol (2.5, 5, 10µM), following stimulated by LPS (0.5µg/ml) and recombinant IFNγ (10ng/ml) for 24h, determining the concentration of various inflammatory factors in cell culture supernatant. |
Reaction Conditions | 2.5, 5, 10µM; 24h |
Applications | Dehydrodiisoeugenol could inhibit the production of NO, iNOS, COX2, PGE2, IL-1β, IL-6, and TNFα in LPS/IFNγ-stimulated RAW264.7 cells in a dose-dependent manner. |
| Animal experiment [1]: | |
Animal models | BALB/c nude mice transplanted with HCT116 cells |
Preparation Method | BALB/c nude mice were subcutaneously injected with HCT116 cells into their bodies. About one week later, the successfully transplanted mice were randomly divided into the control group and the Dehydrodiisoeugenol (DEH) group. Then, the control group received intraperitoneal injection of 100µL PBS (containing 0.1% DMSO), while the mice in the DEH group were orally gavaged with DEH at 40mg/kg once daily for 20 consecutive days. Tumor sizes and body weights were measured and recorded every 5 days. The mice were euthanized, and tumors were excised, photographed, and weighed. |
Dosage form | 40mg/kg; 20d; p.o. |
Applications | There was no significant difference in average weight between the two groups of mice. However, tumor weight and volume were significantly smaller in the DEH (40mg/kg) treated group compared to the control group. |
References: | |
| 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 |
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0638 mL | 15.3191 mL | 30.6382 mL |
| 5 mM | 612.8 μL | 3.0638 mL | 6.1276 mL |
| 10 mM | 306.4 μL | 1.5319 mL | 3.0638 mL |
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