Nigranoic acid
目录号 : GC61134
Nigranoicacid是五味子中分离得到的一种三萜类化合物。Nigranoicacid能抑制HIV-1逆转录酶。在脑缺血再灌注动物模型中，Nigranoicacid通过PARP/AIF信号通路保护大脑。
Cas No.:39111-07-4
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
Nigranoic acid is a triterpenoid separated from Schisandra chinensis. Nigranoic acid inhibits HIV-1 reverse transcriptase. Nigranoic acid exhibits protective effects on brain through PARP/AIF signaling pathway in cerebral ischemia-reperfusion animal model[1][2].
Nigranoic acid has a strong protective effect on rat cerebral ischemia-reperfusion injury, and acts by downregulating nerve cell apoptosis by preventing the overactivation of PARP and AIF nuclear translocation[2]. Nigranoic acid (1 mg/kg; i.g.; 6 hours and 2 hours before brain ischemia) significantly decreases apoptosis and the expression levels of AIF protein, PARP protein, and AIF mRNA at different time-points[2]. Animal Model: Sprague-Dawley rats (200-300 g), ischemia-reperfusion model[2]
[1]. Sun HD, et al. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J Nat Prod. 1996 May;59(5):525-7. [2]. Feng T, et al. Protective effects of nigranoic acid on cerebral ischemia-reperfusion injury and its mechanism involving apoptotic signaling pathway. Cell Biochem Biophys. 2015 Jan;71(1):345-51.
| Cas No. | 39111-07-4 | SDF | |
| Canonical SMILES | OC(CC[C@@]12[C@]3([C@](CC[C@H]2C(C)=C)([H])[C@]4([C@@](C)([C@]([C@H](C)CC/C=C(C)\C(O)=O)([H])CC4)CC3)C)C1)=O | ||
| 分子式 | C30H46O4 | 分子量 | 470.68 |
| 溶解度 | 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 | 2.1246 mL | 10.6229 mL | 21.2459 mL |
| 5 mM | 0.4249 mL | 2.1246 mL | 4.2492 mL |
| 10 mM | 0.2125 mL | 1.0623 mL | 2.1246 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。
Synthesis of Nigranoic acid and manwuweizic acid derivatives as HDAC inhibitors and anti-inflammatory agents
Bioorg Chem 2021 Apr;109:104728.PMID:33636436DOI:10.1016/j.bioorg.2021.104728.
As a successful anti-tumor drug target, the family of histone deacetylases (HDACs) is also a critical player in immune response, making the research of anti-inflammatory HDAC inhibitors an attractive new focus. In this report, triterpenoids Nigranoic acid (NA) and manwuweizic acid (MA) were identified as HDAC inhibitors through docking-based virtual screening and enzymatic activity assay. A series of derivatives of NA and MA were synthesized and assessed for their biological effects. As a result, hydroxamic acid derivatives of NA and MA showed moderately increased activity for HDAC1/2/4/6 inhibition (the lowest IC50 against HDAC1 is 1.14 μM), with no activity against HDAC8. In J774A.1 macrophage, compound 1-3, 13 and 17-19 demonstrated inhibitory activity against lactate dehydrogenase (LDH) and IL-1β production, without affecting cell viability. Compound 19 increased the histone acetylation level in J774A.1 cells, as well as inhibited IL-1β maturation and caspase-1 cleavage. These results indicated that compound 19 blocks the activation of NLRP3 inflammasome, probably related to HDAC inhibition. This work provided a natural scaffold for developing low-cytotoxic and anti-inflammatory HDAC inhibitors, as well as a class of tool molecules for studying the relationship between HDACs and NLRP3 activation.
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase
J Nat Prod 1996 May;59(5):525-7.PMID:8778243DOI:10.1021/np960149h.
An A ring-secocycloartene triterpenoid, Nigranoic acid (3,4-secocycloarta-4(28),24-(Z)-diene-3,-26-dioic acid, (1) was isolated from the stems of Schisandra sphaerandra, a Chinese traditional medicinal plant. Its structure elucidation and unambiguous NMR spectral assignment were achieved by the combination of 1D- and 2D-NMR techniques with the aid of computer modeling. Nigranoic acid showed activity in several anti-HIV reverse transcriptase and polymerase assays.
Protective effects of Nigranoic acid on cerebral ischemia-reperfusion injury and its mechanism involving apoptotic signaling pathway
Cell Biochem Biophys 2015 Jan;71(1):345-51.PMID:25168103DOI:10.1007/s12013-014-0204-1.
The goal of this study was to assess the expression of poly ADP-ribose polymerase (PARP) and apoptosis-inducing factor (AIF) in the hippocampal CA1 region, and to find out whether Nigranoic acid treatment exhibits protective effects on brain through PARP/AIF signaling pathway in cerebral ischemia-reperfusion animal model. Rats were randomly divided into three groups: Sham-surgery, ischemia-reperfusion, and nigranoic acid-treated. Rat models of middle cerebral artery occlusion were prepared using a way of thread occlusion. Rats in the Nigranoic acid group were administered with 1 mg/kg intragastric Nigranoic acid 6 and 2 h before brain ischemia, respectively. Following reperfusion, samples were collected at different time-points (6, 24, and 72 h) and each group was further divided into three subgroups. Apoptosis was measured using the terminal deoxynucleotidyl-transferase-mediated dUTP nick end labeling method. The protein expression levels of AIF and PARP were detected using Western blot and AIF mRNA quantity was evaluated using the reverse transcription-polymerase chain reaction. Apoptosis, levels of AIF and PARP protein expression, and levels of AIF mRNA expression were significantly increased in the ischemia-reperfusion group compared with the sham-surgery group. However, apoptosis and the expression levels of AIF protein, PARP protein, and AIF mRNA at different time-points were significantly decreased in the nigranoic acid-treated group compared with the model group. We can judge that Nigranoic acid has a strong protective effect on rat cerebral ischemia-reperfusion injury, and acts by downregulating nerve cell apoptosis by preventing the overactivation of PARP and AIF nuclear translocation.
Metabolites from the co-culture of Nigranoic acid and Umbelopsis dimorpha SWUKD3.1410, an endophytic fungus from Kadsura angustifolia
Nat Prod Res 2017 Jun;31(12):1414-1421.PMID:27830590DOI:10.1080/14786419.2016.1255891.
The ability of the endophytic fungus Umbelopsis dimorpha SWUKD3.1410 to transform the triterpene Nigranoic acid (3, 4-secocycloarta-4(28), 24-(Z)-diene-3, 26-dioic acid; 1) was investigated. Co-culture of Nigranoic acid with U. dimorpha SWUKD3.1410 yielded six major products, including a new triterpene (2) and 5 known compounds (3-7). Their structures were identified by the extensive 1D, 2D NMR and HR-ESI-MS Data analysis, and by comparison with those reported data. Among them, 2-4 were transformed from Nigranoic acid (1), while 5-7 were derived from the culture medium stimulated by the substrate. On the basis of the structures of 2-4, it was proposed that the transformative process probably involved isomerase and hydroxylase, in which the former was rare in fungi. Additionally, all the compounds (1-7) were evaluated for their cytotoxic activity. As a result, compounds 1, 3-5 exhibited weak cytotoxicity against the tested cell lines, while others showed no cytotoxicity.
Hydroxylation of the triterpenoid Nigranoic acid by the fungus Gliocladium roseum YMF1.00133
Chem Biodivers 2007 Feb;4(2):112-7.PMID:17311223DOI:10.1002/cbdv.200790015.
The ability of the fungus Gliocladium roseum YMF1.00133 to transform the bioactive Nigranoic acid (=(24Z)-9,19-cyclo-3,4-secolanosta-4(28),24-diene-3,26-dioic acid) was investigated. Three new products from the co-cultures of Nigranoic acid and G. roseum YMF1.00133 were obtained by employing a combination of Sephadex LH-20 and silica-gel column chromatography. The major metabolite was identified as 15beta-hydroxynigranoic acid, and the minor metabolites as 6alpha,15beta-dihydroxynigranoic acid and 7beta,15beta-dihydroxynigranoic acid by mass spectrometry and NMR spectroscopy. This is the first report of the biotransformation of the A-ring-secocycloartene triterpenoid, Nigranoic acid.