Rubiadin-1-methyl ether
(Synonyms: 甲基异茜草素-1-甲醚) 目录号 : GC60331
An anthraquinone with diverse biological activities
Cas No.:7460-43-7
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
Rubiadin-1 methyl ether is an anthraquinone that has been found in Heterophyllaea pustulata and has diverse biological activities.1,2,3,4 It generates superoxide radicals in isolated human neutrophils and monocytes when used at a concentration of 20 ?g/ml, an effect that can be enhanced by UV radiation.1 Rubiadin-1 methyl ether (0.1, 1, and 10 ?M) inhibits M-CSF- and RANKL-induced differentiation of osteoclasts.2 It inhibits C. tropicalis biofilm formation (MIC = 31.3 ?g/ml for a clinical isolate).3 Rubiadin-1 methyl ether (30 mg/kg) reduces LPS-induced increases in bronchoalveolar fluid (BALF) levels of TNF-α, IL-6, and IFN-γ in a mouse model of acute lung injury.4
1.Montoya, S.C.N., Comini, L.R., Sarmiento, M., et al.Natural anthraquinones probed as Type I and Type II photosensitizers: Singlet oxygen and superoxide anion productionJ. Photochem. Photobiol. B.78(1)77-83(2005) 2.He, Y.-Q., Zhang, Q., Shen, Y., et al.Rubiadin-1-methyl ether from Morinda officinalis How. Inhibits osteoclastogenesis through blocking RANKL-induced NF-κB pathwayBiochem. Biophys. Res. Commun.506(4)927-931(2018) 3.Marioni, J., da Silva, M.A., Cabrera, J.L., et al.The anthraquinones rubiadin and its 1-methyl ether isolated from Heterophyllaea pustulata reduces Candida tropicalis biofilms formationPhytomedicine23(12)1321-1328(2016) 4.Mohr, E.T.B., Nascimento, M.V.P.D.S., da Rosa, J.S., et al.Evidence that the anti-inflammatory effect of rubiadin-1-methyl ether has an immunomodulatory contextMediators Inflamm.6474168(2019)
| Cas No. | 7460-43-7 | SDF | |
| 别名 | 甲基异茜草素-1-甲醚 | ||
| Canonical SMILES | O=C1C2=C(C=CC=C2)C(C3=CC(O)=C(C)C(OC)=C13)=O | ||
| 分子式 | C16H12O4 | 分子量 | 268.26 |
| 溶解度 | DMSO : ≥ 125 mg/mL (465.97 mM) | 储存条件 | |
| 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 | 3.7277 mL | 18.6386 mL | 37.2773 mL |
| 5 mM | 0.7455 mL | 3.7277 mL | 7.4555 mL |
| 10 mM | 0.3728 mL | 1.8639 mL | 3.7277 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。
Evidence That the Anti-Inflammatory Effect of Rubiadin-1-methyl ether Has an Immunomodulatory Context
Mediators Inflamm 2019 Nov 3;2019:6474168.PMID:31780865DOI:10.1155/2019/6474168.
Background: In spite of the latest therapeutic developments, no effective treatments for handling critical conditions such as acute lung injuries have yet been found. Such conditions, which may result from lung infections, sepsis, multiple trauma, or shock, represent a significant challenge in intensive care medicine. Seeking ways to better deal with this challenge, the scientific community has recently devoted much attention to small molecules derived from natural products with anti-inflammatory and immunomodulatory effects. Aims: In this context, we investigated the anti-inflammatory effect of Rubiadin-1-methyl ether isolated from Pentas schimperi, using an in vitro model of RAW 264.7 macrophages induced by LPS and an in vivo model of acute lung injury (ALI) induced by LPS. Methods: The macrophages were pretreated with the compound and induced by LPS (1 μg/mL). After 24 h, using the supernatant, we evaluated the cytotoxicity, NOx, and IL-6, IL-1β, and TNF-α levels, as well as the effect of the compound on macrophage apoptosis. Next, the compound was administered in mice with acute lung injury (ALI) induced by LPS (5 mg/kg), and the pro- and anti-inflammatory parameters were analyzed after 12 h using the bronchoalveolar lavage fluid (BALF). Results: Rubiadin-1-methyl ether was able to inhibit the pro-inflammatory parameters studied in the in vitro assays (NOx, IL-6, and IL-1β) and, at the same time, increased the macrophage apoptosis rate. In the in vivo experiments, this compound was capable of decreasing leukocyte infiltration; fluid leakage; NOx; IL-6, IL-12p70, IFN-γ, TNF-α, and MCP-1 levels; and MPO activity. In addition, Rubiadin-1-methyl ether increased the IL-10 levels in the bronchoalveolar lavage fluid (BALF). Conclusions: These findings support the evidence that Rubiadin-1-methyl ether has important anti-inflammatory activity, with evidence of an immunomodulatory effect.
Rubiadin-1-methyl ether from Morinda officinalis How. Inhibits osteoclastogenesis through blocking RANKL-induced NF-κB pathway
Biochem Biophys Res Commun 2018 Dec 2;506(4):927-931.PMID:30392907DOI:10.1016/j.bbrc.2018.10.100.
Rubiadin-1-methyl ether (RBM) is a natural anthraquinone compound isolated from the root of Morinda officinalis How. In our previous study, RBM was found to have inhibitory effects on the TRAP activity of osteoclasts, which means that RBM may be a candidate for therapy of bone diseases characterized by enhanced bone resorption. However, the further effect of RBM on osteoclasts and the underlying mechanism remain unclear. In the present study, we investigated the effects of RBM isolated from Morinda officinalis How. on osteoclasts derived from bone marrow macrophages (BMMs) and the underlying mechanism in vitro. RBM at the dose that did not affect the viability of cells significantly inhibited RANKL-induced osteoclastogenesis and actin ring formation of osteoclast, while RBM performed a stronger effect at the early stage. In addition, RBM downregulated the expression of osteoclast-related proteins, including nuclear factor of activated T cells cytoplasmic 1 (NFATc1), cellular oncogene Fos (c-Fos), matrix metallopeptidase 9 (MMP-9) and cathepsin K (CtsK) as shown by Western blot. Furthermore, RBM inhibited the phosphorylation of NF-κB p65 and the degradation of IκBα as well as decreased the nuclear translocation of p65. Collectively, the results suggest that RBM inhibit osteoclastic bone resorption through blocking NF-κB pathway and may be a promising agent for the prevention and treatment of bone diseases characterized by excessive bone resorption.
Anthraquinones from the roots of Prismatomeris malayana
Nat Prod Res 2008;22(11):962-8.PMID:18629711DOI:10.1080/14786410701650261.
A novel anthraquinone, 1,3-dihydroxy-5,6-dimethoxy-2-methoxymethyl-9,10-anthraquinone (9) and a new natural product, 2-hydroxymethyl-1-methoxy-9,10-anthraquinone (8) were isolated from the roots of Prismatomeris malayana together with seven known anthraquinones, tectoquinone (1), 1-hydroxy-2-methyl-9,10-anthraquinone (2), rubiadin (3), Rubiadin-1-methyl ether (4), 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone (5), nordamnacanthal (6), and damnacanthal (7). Their structures were determined on the basis of spectroscopic data. Some of the anthraquinones were tested for anticancer, antifungal, and antimalarial activities.
Morindaquinone, a new bianthraquinone from Morinda coreia roots
Nat Prod Res 2021 Oct;35(20):3439-3445.PMID:31876434DOI:10.1080/14786419.2019.1705820.
Phytochemical investigation of the roots of Morinda coreia led to the isolation of one new bianthraquinone, morindaquinone (1), together with 12 known compounds, soranjidiol (2), Rubiadin-1-methyl ether (3), 2-methoxy-1,3,6-trihydroxyanthraquinone (4), 1-hydroxy-2-methylanthraquinone (5), tectoquinone (6), nordamnacanthal (7), damnacanthal (8), 2-formylanthraquinone (9), 3-hydroxy-2-hydroxymethylanthraquinone (10), lucidin-ω-methyl ether (11), scopoletin (12) and (+)-mellein (13). The structures of these compounds were determined on the basis of extensive spectroscopic analyses, as well as by comparison with literature reports. Compound 1 was the first example of bianthraquinone found in the genus Morinda, whereas compound 13 was firstly isolated from this genus. Among them, compounds 2, 7, 8 and 10 exhibited moderate to weak cytotoxicity against human cervical (HeLa), human colon (HT 29) and human breast (MCF-7) cell lines, while compounds 6 and 9 -11 showed weak anti-acetylcholinesterase activity.
Anthraquinones from Morinda officinalis roots enhance adipocyte differentiation in 3T3-L1 cells
Nat Prod Res 2012;26(18):1750-4.PMID:22008000DOI:10.1080/14786419.2011.608676.
To search for anti-diabetic and insulin-sensitising natural products, the effect on adipocyte differentiation was investigated by assessing fat accumulation in 3T3-L1 preadipocytes using Oil Red O staining. Fractionation and separation of n-hexane and CHCl₃ fractions of Morinda officinalis (Rubiaceae) using several chromatographic methods led to the isolation of three anthraquinones, 1,2-dimethoxyanthraquinone (1), alizarin-2-methyl ether (2) and Rubiadin-1-methyl ether (3). Among them, alizarin-2-methyl ether (2) showed the strongest enhancing activity, followed by Rubiadin-1-methyl ether (3) and 1,2-dimethoxyanthraquinone (1). At a concentration of 100 µM, alizarin-2-methyl ether (2) enhanced adipocyte differentiation by up to 131% (compared to insulin-treated cells). Thus, these compounds could be beneficial in the treatment of diabetes.