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MedKoo Cat#: 414389 | Name: Nigranoic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nigranoic acid is a Triterpenoid from Schisandra sphaerandra that Inhibits HIV-1 Reverse Transcriptase

Chemical Structure

Nigranoic acid
CAS#39111-07-4

Theoretical Analysis

MedKoo Cat#: 414389

Name: Nigranoic acid

CAS#: 39111-07-4

Chemical Formula: C30H46O4

Exact Mass: 470.3396

Molecular Weight: 470.69

Elemental Analysis: C, 76.55; H, 9.85; O, 13.60

Price and Availability

Size Price Availability Quantity
1mg USD 230.00 2 Weeks
2mg USD 370.00 2 Weeks
5mg USD 600.00 2 Weeks
10mg USD 900.00 2 Weeks
25mg USD 1,450.00 2 Weeks
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Synonym
Nigranoic acid
IUPAC/Chemical Name
3,4-Secocycloarta-4(28),24-(Z)-diene-3,26-dioic acid
InChi Key
NJFOSFIPGRXARF-BRTULJEKSA-N
InChi Code
InChI=1S/C30H46O4/c1-19(2)22-10-11-24-28(6)14-12-23(20(3)8-7-9-21(4)26(33)34)27(28,5)16-17-30(24)18-29(22,30)15-13-25(31)32/h9,20,22-24H,1,7-8,10-18H2,2-6H3,(H,31,32)(H,33,34)/b21-9-/t20-,22+,23-,24+,27-,28+,29-,30+/m1/s1
SMILES Code
C=C([C@@H]1CC[C@@]2([H])[C@@]3(CC[C@@H]([C@]3(CC[C@@]24[C@@]1(C4)CCC(O)=O)C)[C@H](C)CC/C=C(C)\C(O)=O)C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nigranoic acid inhibits HIV-1 reverse transcriptase.
In vitro activity:
SBB1 induced Ca(2+) influx in a time- and concentration-dependent manner, which was significantly attenuated in Ca(2+) free media. SBB1 promoted the intracellular NO production which depended on increasing cytoplasmic Ca(2+) level. Moreover, SBB1 stimulated activation of ERK1/2 through Ca(2+)-CaMKII pathway. Reference: J Ethnopharmacol. 2014 May 14;153(3):725-31. https://pubmed.ncbi.nlm.nih.gov/24674947/
In vivo activity:
Rats in the nigranoic acid group were administered with 1 mg/kg intragastric nigranoic acid 6 and 2 h before brain ischemia, respectively. 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. Reference: Cell Biochem Biophys. 2015 Jan;71(1):345-51. https://pubmed.ncbi.nlm.nih.gov/25168103/

Preparing Stock Solutions

The following data is based on the product molecular weight 470.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yuan XX, Yang LP, Yang ZL, Xiao WL, Sun HD, Wu GS, Luo HR. Effect of nigranoic acid on Ca²⁺ influx and its downstream signal mechanism in NGF-differentiated PC12 cells. J Ethnopharmacol. 2014 May 14;153(3):725-31. doi: 10.1016/j.jep.2014.03.038. Epub 2014 Mar 24. PMID: 24674947. 2. Sun HD, Qiu SX, Lin LZ, Wang ZY, Lin ZW, Pengsuparp T, Pezzuto JM, Fong HH, Cordell GA, Farnsworth NR. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J Nat Prod. 1996 May;59(5):525-7. doi: 10.1021/np960149h. PMID: 8778243. 3. Feng T, Liu Y, Li C, Li Z. 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. doi: 10.1007/s12013-014-0204-1. PMID: 25168103.
In vitro protocol:
1. Yuan XX, Yang LP, Yang ZL, Xiao WL, Sun HD, Wu GS, Luo HR. Effect of nigranoic acid on Ca²⁺ influx and its downstream signal mechanism in NGF-differentiated PC12 cells. J Ethnopharmacol. 2014 May 14;153(3):725-31. doi: 10.1016/j.jep.2014.03.038. Epub 2014 Mar 24. PMID: 24674947. 2. Sun HD, Qiu SX, Lin LZ, Wang ZY, Lin ZW, Pengsuparp T, Pezzuto JM, Fong HH, Cordell GA, Farnsworth NR. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J Nat Prod. 1996 May;59(5):525-7. doi: 10.1021/np960149h. PMID: 8778243.
In vivo protocol:
1. Feng T, Liu Y, Li C, Li Z. 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. doi: 10.1007/s12013-014-0204-1. PMID: 25168103.
1: Feng T, Liu Y, Li C, Li Z. 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. doi: 10.1007/s12013-014-0204-1. PMID: 25168103. 2: Dong JY, Chen YG, Song HC, Zhu YH, Zhou YP, Li L, He YP, Cao J, Zhang KQ. Hydroxylation of the triterpenoid nigranoic acid by the fungus Gliocladium roseum YMF1.00133. Chem Biodivers. 2007 Feb;4(2):112-7. doi: 10.1002/cbdv.200790015. PMID: 17311223. 3: Han M, Qin D, Ye T, Yan X, Wang J, Duan X, Dong J. An endophytic fungus from Trichoderma harzianum SWUKD3.1610 that produces nigranoic acid and its analogues. Nat Prod Res. 2019 Jul;33(14):2079-2087. doi: 10.1080/14786419.2018.1486311. Epub 2018 Jun 13. PMID: 29897270. 4: Sun HD, Qiu SX, Lin LZ, Wang ZY, Lin ZW, Pengsuparp T, Pezzuto JM, Fong HH, Cordell GA, Farnsworth NR. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J Nat Prod. 1996 May;59(5):525-7. doi: 10.1021/np960149h. PMID: 8778243. 5: Huang G, Feng L, Liu B, He Y, Li Y, Chen Y. Synthesis and biological evaluation of nigranoic acid esters as novel human neutrophil elastase inhibitors. Nat Prod Res. 2015;29(17):1650-6. doi: 10.1080/14786419.2014.996149. Epub 2015 Jan 6. PMID: 25560928. 6: Wang L, Qin D, Zhang K, Huang Q, Liu S, Han MJ, Dong JY. 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. doi: 10.1080/14786419.2016.1255891. Epub 2016 Nov 10. PMID: 27830590. 7: Yuan XX, Yang LP, Yang ZL, Xiao WL, Sun HD, Wu GS, Luo HR. Effect of nigranoic acid on Ca²⁺ influx and its downstream signal mechanism in NGF- differentiated PC12 cells. J Ethnopharmacol. 2014 May 14;153(3):725-31. doi: 10.1016/j.jep.2014.03.038. Epub 2014 Mar 24. PMID: 24674947. 8: Qin D, Shen W, Wang J, Han M, Chai F, Duan X, Yan X, Guo J, Gao T, Zuo S, Dong J. Enhanced production of unusual triterpenoids from Kadsura angustifolia fermented by a symbiont endophytic fungus, Penicillium sp. SWUKD4.1850. Phytochemistry. 2019 Feb;158:56-66. doi: 10.1016/j.phytochem.2018.11.005. Epub 2018 Nov 23. PMID: 30476897. 9: Sun R, Song HC, Yang YH, Yang P, Yang DY, Shen KZ, Xu YB, Gao YX, Chen YG, Dong JY. Microbiological transformation of the triterpene nigranoic acid by the freshwater fungus Dictyosporium heptasporum. J Asian Nat Prod Res. 2013;15(5):433-40. doi: 10.1080/10286020.2013.778833. Epub 2013 Apr 22. PMID: 23600754. 10: Zhu L, Li B, Liu X, Meng X. Purification of two triterpenoids from Schisandra chinensis by macroporous resin combined with high-speed counter- current chromatography. J Chromatogr Sci. 2014 Oct;52(9):1082-8. doi: 10.1093/chromsci/bmt168. Epub 2013 Nov 12. PMID: 24220992.