Roburic acid
(Synonyms: 栎樱酸) 目录号 : GC38151
Roburic acid 是秦艽中的四环三萜类化合物，作为一种 COX 的抑制剂，对 COX-1 和 COX-2 的 IC50 值分别为 5 和 9 μM。
Cas No.:6812-81-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Roburic acid, a tetracyclic triterpenoid found in Gentiana macrophylla, acts as an inhibitor of COX, with IC50s of 5 and 9 μM for COX-1 and COX-2, respectively[1].
[1]. Cao H, et al. Discovery of cyclooxygenase inhibitors from medicinal plants used to treat inflammation. Pharmacol Res. 2010 Jun;61(6):519-24.
| Cas No. | 6812-81-3 | SDF | |
| 别名 | 栎樱酸 | ||
| Canonical SMILES | C[C@](C1=CC2)(CC[C@]3(C)[C@@]1([H])[C@@H](C)[C@H](C)CC3)[C@@](CC[C@H]4C(C)=C)(C)[C@@]2([H])[C@@]4(C)CCC(O)=O | ||
| 分子式 | C30H48O2 | 分子量 | 440.7 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C,protect from light |
| 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 | 2.2691 mL | 11.3456 mL | 22.6912 mL |
| 5 mM | 0.4538 mL | 2.2691 mL | 4.5382 mL |
| 10 mM | 0.2269 mL | 1.1346 mL | 2.2691 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。
Roburic acid Targets TNF to Inhibit the NF-κB Signaling Pathway and Suppress Human Colorectal Cancer Cell Growth
Front Immunol 2022 Feb 9;13:853165.PMID:35222445DOI:10.3389/fimmu.2022.853165.
Tumor necrosis factor (TNF)-stimulated nuclear factor-kappa B (NF-κB) signaling plays very crucial roles in cancer development and progression, and represents a potential target for drug discovery. Roburic acid is a newly discovered tetracyclic triterpene acid isolated from oak galls and exhibits anti-inflammatory activity. However, whether Roburic acid exerts antitumor effects through inhibition of TNF-induced NF-κB signaling remains unknown. Here, we demonstrated that Roburic acid bound directly to TNF with high affinity (KD = 7.066 μM), blocked the interaction between TNF and its receptor (TNF-R1), and significantly inhibited TNF-induced NF-κB activation. Roburic acid exhibited antitumor activity in numerous cancer cells and could effectively induce G0/G1 cell cycle arrest and apoptosis in colorectal cancer cells. Importantly, Roburic acid inhibited the TNF-induced phosphorylation of IKKα/β, IκBα, and p65, degradation of IκBα, nuclear translocation of p65, and NF-κB-target gene expression, including that of XIAP, Mcl-1, and Survivin, in colorectal cancer cells. Moreover, Roburic acid suppressed tumor growth by blocking NF-κB signaling in a xenograft nude mouse model of colorectal cancer. Taken together, our findings showed that Roburic acid directly binds to TNF with high affinity, thereby disrupting its interaction with TNF-R1 and leading to the inhibition of the NF-κB signaling pathway, both in vitro and in vivo. The results indicated that Roburic acid is a novel TNF-targeting therapeutics agent in colorectal cancer as well as other cancer types.
Roburic acid attenuates osteoclastogenesis and bone resorption by targeting RANKL-induced intracellular signaling pathways
J Cell Physiol 2022 Mar;237(3):1790-1803.PMID:34796915DOI:10.1002/jcp.30642.
Excessive activity of osteoclasts contributes to skeletal diseases such as osteoporosis and osteolysis. However, current drugs targeting osteoclast have various deficiencies, placing natural compounds as substitutions of great potential. Roburic acid (RA) is a triterpenoid exacted from Radix Gentianae Macrophyllae, which exhibits inhibitory effects on inflammation and oxidation. By employing an in vitro osteoclastogenesis model, this study investigates the effects and mechanisms of RA on intracellular signaling induced by receptor activator of nuclear factor-κB ligand (RANKL). As expected, RA at a concentration scope from 1 to 10 μM dampened the osteoclast differentiation of bone marrow macrophages (BMMs) but without cell toxicity. Interestingly, RA showed no effect on osteoblastogenesis in vitro. Furthermore, RA mitigated F-actin ring formation, hydroxyapatite resorption, and gene expression in osteoclasts. Mechanistically, RA suppressed TNF receptor-associated factor 6 (TRAF6), the crucial adaptor protein following RANKL-RANK binding. On the one hand, RA downregulated the nuclear factor-κB (NF-κB) activity, extracellular regulated protein kinases (ERK) phosphorylation, and calcium oscillations. On the other hand, RA upregulated the antioxidative response element (ARE) response and the protein expression of heme oxygenase (HO)-1. These upstream alterations eventually led to the suppression of the nuclear factor of activated T cells 1 (NFATc1) activity and the expression of proteins involved in osteoclastogenesis and bone resorption. Furthermore, by using an ovariectomized (OVX) mice model, RA was found to have therapeutic effects against bone loss. On account of these findings, RA could be used to restrain osteoclasts for treating osteoporosis and other osteolytic diseases.
Roburic acid Suppresses NO and IL-6 Production via Targeting NF-κB and MAPK Pathway in RAW264.7 Cells
Inflammation 2017 Dec;40(6):1959-1966.PMID:28761990DOI:10.1007/s10753-017-0636-z.
In the present study, we investigated the anti-inflammatory effect of Roburic acid on production of nitric oxide (NO) and interlukin-6 (IL-6) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. We found that Roburic acid reduced production of NO and IL-6, and the expression of inducible nitric oxide synthases (iNOS). Meanwhile, phosphorylation of inhibitor of κBα (IκBα) and IκB kinase α/β (IKKα/β), as well as translocation of nuclear factor-κB (NF-κB) to the nucleus, was suppressed by Roburic acid treatment. In addition, phosphorylation of mitogen-activated protein kinase (MAPKs) including p38 and c-Jun-NH2-terminal kinase (JNK) was inhibited. Roburic acid exhibited inhibitory activities on production of NO and IL-6 via blocking IKK/IκB/NF-κB and MAPKs pathway, suggesting the potential application as a drug candidate for therapy of inflammatory diseases.
Inhibitory effect of Roburic acid in combination with docetaxel on human prostate cancer cells
J Enzyme Inhib Med Chem 2022 Dec;37(1):542-553.PMID:34986722DOI:10.1080/14756366.2021.2018684.
Roburic acid (ROB) is a naturally occurred tetracyclic triterpenoid, and the anticancer activity of this compound has not been reported. Docetaxel (DOC) is the first-line chemotherapeutic agent for advanced stage prostate cancer but toxic side effects and drug resistance limit its clinical success. In this study, the potential synergistic anticancer effect and the underlying mechanisms of ROB in combination with DOC on prostate cancer were investigated. The results showed that ROB and DOC in combination synergistically inhibited the growth of prostate cancer cells. The combination also strongly induced apoptosis, and suppressed cell migration, invasion and sphere formation. Mechanistic study showed that the combined effects of ROB and DOC on prostate cancer cells were associated with inhibition of NF-κB activation, down regulation of Bcl-2 and up regulation of Bax. Knockdown of NF-κB by small interfering RNA (siRNA) significantly decreased the combined effect of ROB and DOC. Moreover, we found that esomeprazole (ESOM), a proton pump inhibitor (PPI), strongly enhanced the effectiveness of ROB and DOC on prostate cancer cells in acidic culture medium. Since acidic micro environment is known to impair the efficacy of current anticancer therapies, ESOM combined with ROB and DOC may be an effective approach for improving the treatment of prostate cancer patients.
Seven new chemical constituents from the roots of Gentiana macrophylla pall
Fitoterapia 2020 Mar;141:104476.PMID:31927012DOI:10.1016/j.fitote.2020.104476.
Gentimilegenins A, B (1, 2), (6R, 8R)-6-hydroxy swerimuslactone A (3), (6R, 8S)-6-hydroxy swerimuslactone A (4), 4-hydroxy Roburic acid methyl ester (5), (±) 3'-hydroxy gentioxepine (6), N-heptacosanoyl anthranilic acid (7a), N-nonacosanoyl anthranilic acid (7b), together with 40 known compounds were isolated from the roots of Gentiana macrophylla Pall. Their structures were elucidated on the basis of comprehensive analysis of HRESIMS, IR, 1D-, 2D-NMR and X-ray diffraction. The anti-inflammatory effects of selected compounds were also evaluated through the detection of their inhibitory effects on NO production in LPS-induced RAW264.7 macrophage cells.