Neoandrographolide
(Synonyms: 新穿心莲内酯; Neoandrographiside) 目录号 : GC36716
An anti-inflammatory diterpenoid
Cas No.:27215-14-1
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
Neoandrographolide is one of the principle diterpenoids isolated from A. paniculata, a well-recognized medicinal plant in Asia. Extracts from A. paniculata have been reported to exert a wide range of therapeutic actions, including immunosuppressant, antithrombotic, anti-inflammatory, antineoplastic, anti-viral, anti-bacterial, anti-diabetic, anti-oxidative stress, antipyretic, anti-edematogenic, and anti-nociceptive activities.1 Neoandrographolide has been shown to inhibit LPS-induced nitric oxide production in inflammatory macrophages after oral administration to mice (25 mg/kg) or by direct addition to cultured macrophages (IC50 = 35.5 ?M).2 At 25 ?M, it can reduce VEGF-induced proliferation of human umbilical vein endothelial cells.3 Neoandrographolide also inhibits the pro-protein convertase furin with an IC50 value of 53.5 ?M.4
1.Jarukamjorn, K., and Nemoto, N.Pharmacological aspects of Andrographis paniculata on health and its major diterpenoid constituent andrographolideJ. Health Sci.54(4)370-381(2008) 2.Batkhuu, J., Hattori, K., Takano, F., et al.Suppression of NO production in activated macrophages in vitro and ex vivo by neoandrographolide isolated from Andrographis paniculataBiol. Pharm. Bull.25(9)1169-1174(2002) 3.Gong, C., Xu, C., Ji, L., et al.A novel semi-synthetic andrographolide analogue A5 inhibits tumor angiogenesis via blocking the VEGFR2-p38/ERK1/2 signal pathwayBiosci. Trends7(5)230-236(2013) 4.Basak, A., Cooper, S., Roberge, A.G., et al.Inhibition of proprotein convertases-1, -7 and furin by diterpines of Andrographis paniculata and their succinoyl estersBiochem. J.338(Pt 1)107-113(1999)
| Cas No. | 27215-14-1 | SDF | |
| 别名 | 新穿心莲内酯; Neoandrographiside | ||
| Canonical SMILES | C[C@@]([C@@H]1CCC2=CCOC2=O)(CCC3)[C@@](CCC1=C)([H])[C@]3(C)CO[C@@H]([C@@H]([C@@H](O)[C@@H]4O)O)O[C@@H]4CO | ||
| 分子式 | C26H40O8 | 分子量 | 480.59 |
| 溶解度 | DMSO: ≥ 250 mg/mL (520.19 mM) | 储存条件 | 4°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 | 2.0808 mL | 10.4039 mL | 20.8078 mL |
| 5 mM | 0.4162 mL | 2.0808 mL | 4.1616 mL |
| 10 mM | 0.2081 mL | 1.0404 mL | 2.0808 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。
Dealkenylation of Neoandrographolide, a phytochemical from Andrographis paniculata stimulates FXR (Farnesoid X Receptor) and enhances gallstone dissolution
J Biomol Struct Dyn 2022 Mar 7;1-10.PMID:35253613DOI:10.1080/07391102.2022.2048078.
FXR (Farnesoid X Receptor) is one of the nuclear receptors expressed in the liver performing a significant role in the maintenance of bile acid concentration. An imbalance of cholesterol and bile acid ratio due to any undefined reason could cause gallstone formation. Hence, this paper aims to screen phytochemicals that could maintain a requisite balance of cholesterol and bile acid by targeting FXR and thereby contributing to the dissolution of gallstone. Nineteen phytochemicals were selected and queried for Pa and Pi in the way2drug online server for hepatoprotective property, cholesterol synthesis and absorption inhibition property, and β-glucuronidase inhibiting activity. Cianidanol, Neoandrographolide, cynarine, saponins, and tanins with satisfying stated properties were docked with the screened FXR (PDB ID- 1OSH) using HADDOCK server, followed by pharmacokinetics study utilizing SwissADME tool. Neoandrographolide fits best among the other selected literature-based phytochemicals with minor violation of 'Brenk's rule'. The violation was corrected with the removal of an alkene group in the provided ChemDraw space of SwissADME. This Dealkenylated compound was further docked with FXR. The promising response under the static condition of the Dealkenylated compound was analyzed for molecular dynamic simulation at physiological conditions for 100 ns. Dealkenylated Neoandrographolide (DN) exhibited hepatoprotective, cholesterol synthesis and absorption inhibition property, and β-glucuronidase inhibition activity with a superior binding score of -42.6+/-1.5 with FXR. The interaction of the FXR receptor and the DN showed exceptional stability at physiological conditions during MD simulation and fit for the ADME properties, therefore it could be a potent candidate to dissolve gallstones.Communicated by Ramaswamy H. Sarma.
Amelioratory effect of Neoandrographolide on myocardial ischemic-reperfusion injury by its anti-inflammatory and anti-apoptotic activities
Environ Toxicol 2021 Dec;36(12):2367-2379.PMID:34397165DOI:10.1002/tox.23350.
In the present study, we aimed to evaluate the cardioprotective effect of Neoandrographolide (Neo) on myocardial ischemia/reperfusion injury (I/R) models and explore its possible mechanism. We randomly and equally divided male mice into sham-operation, I/R, and I/R + Neo groups. H9C2 cell line and primary neonatal rat cardiomyocytes were induced into the simulated I/R's status and used to further validate the Neo's role in vitro. Heart systolic function, indexes of myocardial injury (IMI), infarct size, pathological change, cell apoptosis, inflammatory cytokines, and indexes related to apoptotic and NF-κB signaling pathways were analyzed in vivo or in vitro after the Neo treatment. Compared to the I/R group, Neo significantly suppressed IMI, infarct size, inflammatory cell infiltration, cell apoptosis, inflammatory cytokines, bax, cleaved caspase-3, P-IKBa, and P-NF-κB protein expressions, and the translocation of NF-kB subunit p65 from the cytoplasm to the nucleus in vivo or in vitro. Still, ejected fraction, fractional shortening, and the bcl-2 protein expression were notably increased after the Neo treatment. Neo could be developed into a new drug for treating myocardial I/R by inhibiting myocardial inflammation and apoptosis, which was closely related to suppressing the activation of bax/bcl-2 and NF-κB signaling pathways.
Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis
Org Lett 2018 Oct 5;20(19):5999-6002.PMID:30234309DOI:10.1021/acs.orglett.8b02146.
ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form Neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.
Neoandrographolide from Andrographis paniculata as a potential natural chemosensitizer
Planta Med 2010 Oct;76(15):1698-700.PMID:20446243DOI:10.1055/s-0030-1249876.
Extracts of the traditional medicinal herb Andrographis paniculata and its main constituents are described in the literature as showing anticancer activity. The aim of this study was to isolate the main constituents of a commercially available phytotherapeutic preparation of A. paniculata and to determine their chemosensitizing potential in a leukemia cell line. Chromatographic separation steps resulted in the isolation of the diterpenes andrographolide (1) and 14-deoxy-11,12-didehydroandrographolide (3) and the diterpene glucoside Neoandrographolide (2). The combination of these constituents with suboptimal concentrations of etoposide revealed compound 2 as chemosensitizer in S-Jurkat and X chromosome-linked inhibitor of apoptosis protein (XIAP)-overexpressing Jurkat cells, a model for chemoresistance.
Inhibitory effects of Neoandrographolide on nitric oxide and prostaglandin E2 production in LPS-stimulated murine macrophage
Mol Cell Biochem 2007 Apr;298(1-2):49-57.PMID:17109078DOI:10.1007/s11010-006-9349-6.
Activated macrophages express inducible isoforms of nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), produce excessive amounts of nitric oxide (NO) and prostaglandin E(2) (PGE(2)), which play key roles in the processes of inflammation. Andrographis paniculata Nees is a traditional Chinese herb commonly used for treatment of infection, inflammation, and diarrhea. However, the mechanism of its therapeutic function is not well known. In the present study, the effect of Neoandrographolide, one of bioactive components in A. paniculata, on iNOS-mediated NO production and COX-2-mediated PGE(2) in bacterial lipopolysaccharide (LPS) stimulated-murine macrophages was investigated. Neoandrographolide at concentrations (30-90 microM) significantly (p<0.05) inhibited the productions of NO and PGE(2) in LPS stimulated macrophages without inducing cytotoxicity. The effect of Neoandrographolide also has been investigated on iNOS and COX-2 expression in activated macrophage by using RT-PCR and immunoblotting. The inhibition of NO release by Neoandrographolide can be attributed to the block of iNOS mRNA transcription followed by inhibiting protein expression. However, Neoandrographolide inhibited COX-2 protein expression only but without inhibiting COX-2 mRNA expression, which was involved in the inhibitory activity against the PGE(2 )overproduction. This suggests that the effect of Neoandrographolide on iNOS expression may occur at the transcriptional level and the inhibition of COX-2 expression occurs at the translational level. Furthermore, we have found that the addition of Neoandrographolide inhibited the activation of p38 mitogen-activated protein kinase (MAPKs) instead of JNK, ERK1/2, or NF-kappaB. These results indicated that the anti-inflammatory properties of Neoandrographolide might result from the inhibition of iNOS and COX-2 expression through inhibiting p38 MAPKs activation. Therefore, Neoandrographolide isolated from A. paniculata could be offered as a leading compound for anti-inflammation.