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Nigranoic acid
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Product Name Nigranoic acid
Price:
CAS No.: 39111-07-4
Catalog No.: CFN90253
Molecular Formula: C30H46O4
Molecular Weight: 470.69 g/mol
Purity: >=98%
Type of Compound: Triterpenoids
Physical Desc.: Powder
Source: The fruits of Schisandra chinensis
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
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Size /Price /Stock 10 mM * 1 mL in DMSO / Inquiry
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries
Biological Activity
Description: Nigranoic acid is able to promote NO production and stimulate phosphorylation of ERK1/2 through Ca(2+) influx, further impact expression of BDNF and c-fos, may be benefit to enhance mental and intellectual functions; it 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.Nigranoic acid exhibits significant inhibitory activity against HNE with the IC50 value of 3.77 μM, and six esters displayed considerable inhibitory effects on HNE with IC50 values in the range of 2.61-8.95 μM. Nigranoic acid shows activity in several anti-HIV reverse transcriptase and polymerase assays.
Targets: NO | ERK | BDNF | c-fos | PARP | HIV | AIF | Calcium Channel
In vitro:
J Nat Prod. 1996 May;59(5):525-7.
Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase.[Pubmed: 8778243]

METHODS AND RESULTS:
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.
CONCLUSIONS:
Nigranoic acid showed activity in several anti-HIV reverse transcriptase and polymerase assays.
Nigranoic acid Description
Source: The fruits of Schisandra chinensis
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
IF=22.415(2019)

PMID: 32004475

Mol Cell. 2017 Nov 16;68(4):673-685.e6.
doi: 10.1016/j.molcel.2017.10.022.
IF=14.548(2019)

PMID: 29149595

ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
IF=13.297(2019)

PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089
Calculate Dilution Ratios(Only for Reference)
1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1245 mL 10.6227 mL 21.2454 mL 42.4908 mL 53.1135 mL
5 mM 0.4249 mL 2.1245 mL 4.2491 mL 8.4982 mL 10.6227 mL
10 mM 0.2125 mL 1.0623 mL 2.1245 mL 4.2491 mL 5.3114 mL
50 mM 0.0425 mL 0.2125 mL 0.4249 mL 0.8498 mL 1.0623 mL
100 mM 0.0212 mL 0.1062 mL 0.2125 mL 0.4249 mL 0.5311 mL
* Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Kinase Assay:
Nat Prod Res. 2015 Jan 6:1-7.
Synthesis and biological evaluation of nigranoic acid esters as novel human neutrophil elastase inhibitors.[Pubmed: 25560928]
Human neutrophil elastase (HNE) has been implicated as a major contributor in the pathogenesis of diseases, such as lung disorders and other inflammatory diseases.
METHODS AND RESULTS:
A series of 12 new Nigranoic acid esters were regioselectively synthesised in good yields and evaluated for HNE inhibitory activity. Nigranoic acid exhibited significant inhibitory activity against HNE with the IC50 value of 3.77 μM, and six esters displayed considerable inhibitory effects on HNE with IC50 values in the range of 2.61-8.95 μM.
CONCLUSIONS:
The Nigranoic acid esters having phenyls substituted with bromine and trimethoxyls (3h and 3b) showed stronger inhibitory activity on HNE than Nigranoic acid.
Cell Research:
J Ethnopharmacol. 2014 May 14;153(3):725-31.
Effect of nigranoic acid on Ca²⁺ influx and its downstream signal mechanism in NGF-differentiated PC12 cells.[Pubmed: 24674947]
Schisandra chinensis has a long history of use as a famous traditional Chinese medicine. The plants of genus Schisandra, especially Schisandra neglecta, Schisandra rubriflora, and Schisandra sphaerandra are used in the same way as Schisandra chinensis in the folk medicine to treat insomnia, fatigue, increasing intelligence, and tranquilizing. Many studies showed that lignans were the major active components of Schisandra genus, whereas the bioactivity of abundant triterpenoids in Schisandra genus, such as Nigranoic acid (SBB1, 3,4-secocycloartene triterpenoid), has not been examined yet in neuropathology.
METHODS AND RESULTS:
After treating with Nigranoic acid, intracellular Ca(2+) concentration was analyzed by Ca(2+) fluorescent indicator (Fluo-4 AM) in NGF-differentiated PC12 cells. Intracellular nitric oxide (NO) level was analyzed using NO fluorescent indicator (DAF-FM). The expression of extracellular signal regulated kinase 1 and 2 (ERK1/2) was analyzed by western blotting, and the temporal mRNA for BDNF and c-fos was analyzed using reverse transcription quantitative PCR. We found that Nigranoic acid induced Ca(2+) influx in a time- and concentration-dependent manner, which was significantly attenuated in Ca(2+) free media. Nigranoic acid promoted the intracellular NO production which depended on increasing cytoplasmic Ca(2+) level. Moreover, Nigranoic acid stimulated activation of ERK1/2 through Ca(2+)-CaMKII pathway. In addition, we found that Nigranoic acid increased the expression of BDNF and c-fos mRNA.
CONCLUSIONS:
These results suggest that Nigranoic acid is able to promote NO production and stimulate phosphorylation of ERK1/2 through Ca(2+) influx, further impact expression of BDNF and c-fos, which provides evidence for the effects of Nigranoic acid that may be benefit to enhance mental and intellectual functions.
Animal Research:
Cell Biochem Biophys. 2015 Jan;71(1):345-51.
Protective effects of nigranoic acid on cerebral ischemia-reperfusion injury and its mechanism involving apoptotic signaling pathway.[Pubmed: 25168103]
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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.
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