Fraxinellone
(Synonyms: 梣酮) 目录号 : GC38044
A liminoid degradant with diverse biological activities
Cas No.:28808-62-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Fraxinellone is a liminoid degradant that has been found in D. dasycarpus and has diverse biological activities.1,2,3 It has antifeedant activity against, and inhibits development of, armyworm (M. separata) larvae when applied to fresh wheat leaves at concentrations of 5, 10, or 20 mg/ml.1 Fraxinellone (6.25, 12.5, and 25 ?M) reduces LPS-induced nuclear translocation of the NF-κB subunit p65, as well as inhibits LPS-induced production of nitric oxide (NO) and prostaglandin E2 in RAW 264.7 cells.2 It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 30 or 100 mg/kg.3
1.Lü, M., Wu, W., and Liu, H.Insecticidal and feeding deterrent effects of fraxinellone from Dictamnus dasycarpus against four major pestsMolecules18(3)2754-2762(2013) 2.Kim, J.-H., Park, Y.-M., Shin, J.-S., et al.Fraxinellone inhibits lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by negatively regulating nuclear factor-kappa B in RAW 264.7 macrophages cellsBiol. Pharm. Bull.32(6)1062-1068(2009) 3.Xing, Y., Mi, C., Wang, Z., et al.Fraxinellone has anticancer activity in vivo by inhibiting programmed cell death-ligand 1 expression by reducing hypoxia-inducible factor-1α and STAT3Pharmacol. Res.135166-180(2018)
| Cas No. | 28808-62-0 | SDF | |
| 别名 | 梣酮 | ||
| Canonical SMILES | O=C1O[C@@H](C2=COC=C2)[C@]3(C)CCCC(C)=C31 | ||
| 分子式 | C14H16O3 | 分子量 | 232.28 |
| 溶解度 | DMSO: 100 mg/mL (430.51 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 | 4.3051 mL | 21.5257 mL | 43.0515 mL |
| 5 mM | 0.861 mL | 4.3051 mL | 8.6103 mL |
| 10 mM | 0.4305 mL | 2.1526 mL | 4.3051 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。
Fraxinellone: From pesticidal control to cancer treatment
Pestic Biochem Physiol 2020 Sep;168:104624.PMID:32711764DOI:10.1016/j.pestbp.2020.104624.
Fraxinellone (FRA) is a degraded limonoid isolated from the root bark of Dictamnus plants. The potent insecticidal activity of FRA has led to the synthesis of numerous derivatives (presented here with the structure-activity relationships) active against the oriental armyworm Mythimna separata Walker. In addition to its pesticidal activity, the natural product displays potent anti-inflammatory and immuno-modulatory effects at the origin of hepatoprotective and anticancer properties. This mini-review provides an update of the mechanism of action of FRA to highlight the recently discovered capacity of the compound to deactivate cancer-associated fibroblasts and thus to limit the immunosuppressive tumor microenvironment. The anticancer mode of action of FRA raises new ideas to better understand its primary insecticidal activity. The relationship between drug-induced cancer cell death and insect cell death is discussed. A drug interaction with the insect cytokine growth-blocking peptide (GBP), a member of the large EGF family, is proposed, supported by preliminary molecular modeling data. Altogether, the review shed light on the pharmacological properties of Fraxinellone as an antitumor agent and a natural insecticide.
Fraxinellone inhibits progression of glioblastoma via regulating the SIRT3 signaling pathway
Biomed Pharmacother 2022 Sep;153:113416.PMID:36076484DOI:10.1016/j.biopha.2022.113416.
Glioblastoma (GBM) is the most prevalent type of adult primary brain tumor and chemotherapy of GBM was limited by drug-resistance. Fraxinellone is a tetrahydro-benzofuranone derivative with various pharmacological activities. However, the pharmacological effects of Fraxinellone on GBM remains largely unknown. Here, we found that Fraxinellone inhibited the proliferation and growth of GBM cells in a dose-dependent manner in vitro. Subsequently, we found that Fraxinellone suppressed the migration and induced apoptosis of GBM cells in vitro. Using western blot and immunostaining, we further found that Fraxinellone downregulated the expressions of sirtuin 3 (SIRT3), and superoxide dismutase 2 (SOD2), a downstream of SIRT3 in GBM cells. Meanwhile, reactive oxygen species (ROS) were increased in these fraxinellone-treated GBM cells. Interestingly, overexpression of SIRT3 (SIRT3-OE) indeed partially restored the inhibition of both cell proliferation and migration of GBM cells induced by Fraxinellone. Finally, we found that Fraxinellone could inhibit the growth of GBM in xenograft model through the inactivation of SIRT3 signaling pathway. Taken together, these results suggest that Fraxinellone suppressed the growth and migration of GBM cells by downregulating SIRT3 signaling in vitro, and inhibited the tumorigenesis of GBMs in vivo.
Fraxinellone
Acta Crystallogr Sect E Struct Rep Online 2011 Jun 1;67(Pt 6):o1472.PMID:21754842DOI:10.1107/S1600536811018393.
In the title compound, C(14)H(16)O(3) [systematic name: (3R*,3aR*)-3-(3-furan-yl)-3a,7-dimethyl-3a,4,5,6-tetra-hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8 (2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, which generate [100] chains.
Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation
Toxicol Appl Pharmacol 2021 Jun 1;420:115530.PMID:33845055DOI:10.1016/j.taap.2021.115530.
Chronic Kidney Disease (CKD) is a serious threat to human health. In addition, kidney fibrosis is a key pathogenic intermediate for the progression of CDK. Moreover, excessive activation of fibroblasts is key to the development of kidney fibrosis and this process is difficult to control. Notably, Fraxinellone is a natural compound isolated from Dictamnus dasycarpus and has a variety of pharmacological activities, including hepatoprotective, anti-inflammatory and anti-cancer effects. However, the effect of Fraxinellone on kidney fibrosis is largely unknown. The present study showed that Fraxinellone could alleviate folic acid-induced kidney fibrosis in mice in a dose dependent manner. Additionally, the results revealed that Fraxinellone could effectively down-regulate the expression of CUGBP1, which was highly up-regulated in human and murine fibrotic renal tissues. Furthermore, expression of CUGBP1 was selectively induced by the Transforming Growth Factor-beta (TGF-β) through p38 and JNK signaling in kidney fibroblasts. On the other hand, downregulating the expression of CUGBP1 significantly inhibited the activation of kidney fibroblasts. In conclusion, these findings demonstrated that Fraxinellone might be a new drug candidate and CUGBP1 could be a promising target for the treatment of kidney fibrosis.
Fraxinellone Attenuates Rheumatoid Inflammation in Mice
Int J Mol Sci 2018 Mar 13;19(3):829.PMID:29533969DOI:10.3390/ijms19030829.
This study aimed to evaluate the therapeutic effect of Fraxinellone on inflammatory arthritis and identify the underlying mechanisms. Fraxinellone (7.5 mg/kg) or a vehicle control was injected into mice with collagen-induced arthritis (CIA). The severity of arthritis was evaluated clinically and histologically. The differentiation of CD4⁺ T cells and CD19⁺ B cells was investigated in the presence of Fraxinellone. Osteoclastogenesis after Fraxinellone treatment was evaluated by staining with tartrate-resistant acid phosphatase (TRAP) and by measuring the mRNA levels of osteoclastogenesis-related genes. Fraxinellone attenuated the clinical and histologic features of inflammatory arthritis in CIA mice. Fraxinellone suppressed the production of interleukin-17 and the expression of RAR-related orphan receptor γ t and phospho-signal transducer and activator of transcription 3 in CD4⁺ T cells. CD19⁺ B cells showed lower expression of activation-induced cytidine deaminase and B lymphocyte-induced maturation protein-1 after treatment with Fraxinellone. The formation of TRAP-positive cells and the expression of osteoclastogenesis-related markers were reduced in the presence of Fraxinellone. Inhibition of interleukin-17 and osteoclastogenesis was also observed in experiments using human peripheral mononuclear cells. Fraxinellone alleviated synovial inflammation and osteoclastogenesis in mice. The therapeutic effect of Fraxinellone was associated with the inhibition of cellular differentiation and activation. The data suggests that Fraxinellone could be a novel treatment for inflammatory arthritis, including rheumatoid arthritis.