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MedKoo Cat#: 596339 | Name: Justicidin A

Description:

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

Justicidin A is a bioactive chemical isolaed from Justica procumbens.

Chemical Structure

Justicidin A
Justicidin A
CAS#25001-57-4

Theoretical Analysis

MedKoo Cat#: 596339

Name: Justicidin A

CAS#: 25001-57-4

Chemical Formula: C22H18O7

Exact Mass: 394.1053

Molecular Weight: 394.37

Elemental Analysis: C, 67.00; H, 4.60; O, 28.40

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Justicidin A; Justicidins; Justicidin;
IUPAC/Chemical Name
9-(benzo[d][1,3]dioxol-5-yl)-4,6,7-trimethoxynaphtho[2,3-c]furan-1(3H)-one
InChi Key
ANFSXHKDCKWWDB-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
SMILES Code
O=C1OCC2=C(OC)C3=CC(OC)=C(OC)C=C3C(C4=CC=C(OCO5)C5=C4)=C12
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 394.37 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
1: Youm J, Lee H, Choi Y, Yoon J. DW2008S and its major constituents from Justicia procumbens exert anti-asthmatic effect via multitargeting activity. J Cell Mol Med. 2018 May;22(5):2680-2691. doi: 10.1111/jcmm.13550. Epub 2018 Mar 7. PubMed PMID: 29512870; PubMed Central PMCID: PMC5908124. 2: Jiang J, Dong H, Wang T, Zhao R, Mu Y, Geng Y, Zheng Z, Wang X. A Strategy for Preparative Separation of 10 Lignans from Justicia procumbens L. by High-Speed Counter-Current Chromatography. Molecules. 2017 Nov 23;22(12). pii: E2024. doi: 10.3390/molecules22122024. PubMed PMID: 29168751. 3: Youm J, Lee H, Chang HB, Jeon J, Yoon MH, Woo JY, Choi MS, Hwang Y, Seong S, Na K, Yoon J. Justicia procumbens Extract (DW2008) Selectively Suppresses Th2 Cytokines in Splenocytes and Ameliorates Ovalbumin-Induced Airway Inflammation in a Mouse Model of Asthma. Biol Pharm Bull. 2017;40(9):1416-1422. doi: 10.1248/bpb.b17-00179. PubMed PMID: 28867724. 4: Chun YS, Kim J, Chung S, Khorombi E, Naidoo D, Nthambeleni R, Harding N, Maharaj V, Fouche G, Yang HO. Protective Roles of Monsonia angustifolia and Its Active Compounds in Experimental Models of Alzheimer's Disease. J Agric Food Chem. 2017 Apr 19;65(15):3133-3140. doi: 10.1021/acs.jafc.6b04451. Epub 2017 Apr 5. PubMed PMID: 28378593. 5: Snyder JC, Rochelle LK, Ray C, Pack TF, Bock CB, Lubkov V, Lyerly HK, Waggoner AS, Barak LS, Caron MG. Inhibiting clathrin-mediated endocytosis of the leucine-rich G protein-coupled receptor-5 diminishes cell fitness. J Biol Chem. 2017 Apr 28;292(17):7208-7222. doi: 10.1074/jbc.M116.756635. Epub 2017 Mar 8. PubMed PMID: 28275053; PubMed Central PMCID: PMC5409487. 6: Luo J, Hu Y, Qin J, Yang M. Ultra high performance liquid chromatography-electrospray ionization-tandem mass spectrometry and pharmacokinetic analysis of justicidin B and 6'-hydroxy justicidin C in rats. J Sep Sci. 2017 Feb;40(3):604-611. doi: 10.1002/jssc.201600961. Epub 2016 Dec 29. PubMed PMID: 27874243. 7: Hemmati S, Seradj H. Justicidin B: A Promising Bioactive Lignan. Molecules. 2016 Jun 23;21(7). pii: E820. doi: 10.3390/molecules21070820. Review. PubMed PMID: 27347906. 8: Gu MY, Kim J, Yang HO. The Neuroprotective Effects of Justicidin A on Amyloid Beta25-35-Induced Neuronal Cell Death Through Inhibition of Tau Hyperphosphorylation and Induction of Autophagy in SH-SY5Y Cells. Neurochem Res. 2016 Jun;41(6):1458-67. doi: 10.1007/s11064-016-1857-5. Epub 2016 Feb 18. PubMed PMID: 26887582. 9: Naresh G, Kant R, Narender T. Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products. Org Lett. 2015 Jul 17;17(14):3446-9. doi: 10.1021/acs.orglett.5b01477. Epub 2015 Jul 9. PubMed PMID: 26158760. 10: Kao TT, Lin CC, Shia KS. The Total Synthesis of Retrojusticidin B, Justicidin E, and Helioxanthin. J Org Chem. 2015 Jul 2;80(13):6708-14. doi: 10.1021/acs.joc.5b00866. Epub 2015 Jun 15. PubMed PMID: 26047161. 11: Zhou P, Luo Q, Ding L, Fang F, Yuan Y, Chen J, Zhang J, Jin H, He S. Preparative isolation and purification of lignans from Justicia procumbens using high-speed counter-current chromatography in stepwise elution mode. Molecules. 2015 Apr 20;20(4):7048-58. doi: 10.3390/molecules20047048. PubMed PMID: 25903362. 12: Wang YW, Chuang JJ, Chang TY, Won SJ, Tsai HW, Lee CT, Cheng HL, Tzai TS, Liu HS, Chow NH. Antiangiogenesis as the novel mechanism for justicidin A in the anticancer effect on human bladder cancer. Anticancer Drugs. 2015 Apr;26(4):428-36. doi: 10.1097/CAD.0000000000000203. PubMed PMID: 25569706. 13: Momekov G, Yossifov D, Guenova M, Michova A, Stoyanov N, Konstantinov S, Ionkov T, Sacheva P, Ionkova I. Apoptotic mechanisms of the biotechnologically produced arylnaphtalene lignan justicidin B in the acute myeloid leukemia-derived cell line HL-60. Pharmacol Rep. 2014 Dec;66(6):1073-6. doi: 10.1016/j.pharep.2014.07.005. Epub 2014 Aug 2. PubMed PMID: 25443737. 14: Won SJ, Yen CH, Liu HS, Wu SY, Lan SH, Jiang-Shieh YF, Lin CN, Su CL. Justicidin A-induced autophagy flux enhances apoptosis of human colorectal cancer cells via class III PI3K and Atg5 pathway. J Cell Physiol. 2015 Apr;230(4):930-46. doi: 10.1002/jcp.24825. PubMed PMID: 25216025. 15: Ilieva Y, Zhelezova I, Atanasova T, Zaharieva MM, Sasheva P, Ionkova I, Konstantinov S. Cytotoxic effect of the biotechnologically-derived justicidin B on human lymphoma cells. Biotechnol Lett. 2014 Nov;36(11):2177-83. doi: 10.1007/s10529-014-1612-4. Epub 2014 Jul 22. PubMed PMID: 25048236. 16: Luo J, Hu Y, Kong W, Yang M. Evaluation and structure-activity relationship analysis of a new series of arylnaphthalene lignans as potential anti-tumor agents. PLoS One. 2014 Mar 27;9(3):e93516. doi: 10.1371/journal.pone.0093516. eCollection 2014. PubMed PMID: 24675875; PubMed Central PMCID: PMC3968169. 17: Patel RM, Argade NP. Palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes: synthesis of justicidin B and retrojusticidin B. Org Lett. 2013 Jan 4;15(1):14-7. doi: 10.1021/ol3028658. Epub 2012 Dec 13. PubMed PMID: 23237050. 18: He XL, Zhang P, Dong XZ, Yang MH, Chen SL, Bi MG. JR6, a new compound isolated from Justicia procumbens, induces apoptosis in human bladder cancer EJ cells through caspase-dependent pathway. J Ethnopharmacol. 2012 Nov 21;144(2):284-92. doi: 10.1016/j.jep.2012.09.010. Epub 2012 Sep 15. PubMed PMID: 22985636. 19: Qiu F, Zhou S, Fu S, Kong W, Yang S, Yang M. LC-ESI-MS/MS analysis and pharmacokinetics of 6'-hydroxy justicidin A, a potential antitumor active component isolated from Justicia procumbens, in rats. J Pharm Biomed Anal. 2012 Nov;70:539-43. doi: 10.1016/j.jpba.2012.05.002. Epub 2012 May 15. PubMed PMID: 22651958. 20: Gudla V, Balamurugan R. Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation. J Org Chem. 2011 Dec 16;76(24):9919-33. doi: 10.1021/jo201918d. Epub 2011 Nov 14. PubMed PMID: 22029795.

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