Verrucarin J

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

MedKoo CAT#: 558675

CAS#: 4643-58-7

Description: Verrucarin J is a natural inhibitor of cancer stem cell (CSC) self-renewal signalling pathways, which induces cell apoptosis with concomitant down regulation of key CSC specific genes- ALDH1, LGR5, OCT4 and CD133 in a dose-dependent manner.


Price and Availability

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Verrucarin J is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 558675
Name: Verrucarin J
CAS#: 4643-58-7
Chemical Formula: C27H32O8
Exact Mass: 484.2097
Molecular Weight: 484.55
Elemental Analysis: C, 66.93; H, 6.66; O, 26.41


Synonym: Verrucarin J

IUPAC/Chemical Name: (4'E,10'E,12'Z)-5',16a',21'-trimethyl-6',7',16',16a',19a',22'-hexahydro-1'H,3'H,18'H,23'H-spiro[oxirane-2,17'-[16,18]methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene]-3',9',14'-trione

InChi Key: GXCGYHWSYNQVHU-LWYZCPILSA-N

InChi Code: InChI=1S/C27H32O8/c1-17-8-10-26-15-32-24(30)13-18(2)9-11-31-22(28)6-4-5-7-23(29)35-19-14-21(34-20(26)12-17)27(16-33-27)25(19,26)3/h4-7,12-13,19-21H,8-11,14-16H2,1-3H3/b6-4+,7-5-,18-13+

SMILES Code: CC1=CC2C3(COC(/C=C(C)/CCOC(/C=C/C=C\C(OC4C3(C)C5(C(O2)C4)CO5)=O)=O)=O)CC1


Technical Data

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:
>3 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).

Harmonized System Code:
2934.99.90.01


References

1: Udoh K, Parte S, Carter K, Mack A, Kakar SS. Targeting of Lung Cancer Stem Cell Self-Renewal Pathway by a Small Molecule Verrucarin J. Stem Cell Rev. 2019 Aug;15(4):601-611. doi: 10.1007/s12015-019-09874-7. PubMed PMID: 30835047; PubMed Central PMCID: PMC6626573.

2: Pal D, Tyagi A, Chandrasekaran B, Alattasi H, Ankem MK, Sharma AK, Damodaran C. Suppression of Notch1 and AKT mediated epithelial to mesenchymal transition by Verrucarin J in metastatic colon cancer. Cell Death Dis. 2018 Jul 23;9(8):798. doi: 10.1038/s41419-018-0810-8. PubMed PMID: 30038258; PubMed Central PMCID: PMC6056562.

3: Liu Y, Zhou X, Naman CB, Lu Y, Ding L, He S. Preparative Separation and Purification of Trichothecene Mycotoxins from the Marine Fungus Fusarium sp. LS68 by High-Speed Countercurrent Chromatography in Stepwise Elution Mode. Mar Drugs. 2018 Feb 24;16(2). pii: E73. doi: 10.3390/md16020073. PubMed PMID: 29495262; PubMed Central PMCID: PMC5852501.

4: Chandrasekaran B, Tyagi A, Sharma AK, Cai L, Ankem M, Damodaran C. Molecular insights: Suppression of EGFR and AKT activation by a small molecule in non-small cell lung cancer. Genes Cancer. 2017 Sep;8(9-10):713-724. doi: 10.18632/genesandcancer.154. PubMed PMID: 29234489; PubMed Central PMCID: PMC5724805.

5: Carter K, Rameshwar P, Ratajczak MZ, Kakar SS. Verrucarin J inhibits ovarian cancer and targets cancer stem cells. Oncotarget. 2017 Oct 6;8(54):92743-92756. doi: 10.18632/oncotarget.21574. eCollection 2017 Nov 3. PubMed PMID: 29190952; PubMed Central PMCID: PMC5696218.

6: Aleksic B, Draghi M, Ritoux S, Bailly S, Lacroix M, Oswald IP, Bailly JD, Robine E. Aerosolization of Mycotoxins after Growth of Toxinogenic Fungi on Wallpaper. Appl Environ Microbiol. 2017 Aug 1;83(16). pii: e01001-17. doi: 10.1128/AEM.01001-17. Print 2017 Aug 15. PubMed PMID: 28646113; PubMed Central PMCID: PMC5541226.

7: Mondol MA, Surovy MZ, Islam MT, Schüffler A, Laatsch H. Macrocyclic Trichothecenes from Myrothecium roridum Strain M10 with Motility Inhibitory and Zoosporicidal Activities against Phytophthora nicotianae. J Agric Food Chem. 2015 Oct 14;63(40):8777-86. doi: 10.1021/acs.jafc.5b02366. Epub 2015 Sep 29. PubMed PMID: 26320597.

8: Zhang SY, Li ZL, Guan LP, Wu X, Pan HQ, Bai J, Hua HM. Structure determination of two new trichothecenes from a halotolerant fungus Myrothecium sp. GS-17 by NMR spectroscopy. Magn Reson Chem. 2012 Sep;50(9):632-6. doi: 10.1002/mrc.3845. Epub 2012 Jul 16. PubMed PMID: 22806769.

9: Zhao L, Liu L, Wang N, Wang SJ, Hu JC, Gao JM. Potent toxic macrocyclic trichothecenes from the marine-derived fungus Myrothecium verrucaria Hmp-F73. Nat Prod Commun. 2011 Dec;6(12):1915-6. PubMed PMID: 22312738.

10: García CC, Rosso ML, Bertoni MD, Maier MS, Damonte EB. Evaluation of the antiviral activity against Junin virus of macrocyclic trichothecenes produced by the hypocrealean epibiont of Baccharis coridifolia. Planta Med. 2002 Mar;68(3):209-12. PubMed PMID: 11914955.

11: Rubezhniak IG. [Changes in the composition of dendrochines in the cultivation dynamics of Dendrodochium toxicum 100115]. Mikrobiol Z. 2001 Jul-Aug;63(4):37-44. Russian. PubMed PMID: 11692676.

12: Abbas HK, Tak H, Boyette CD, Shier WT, Jarvis BB. Macrocyclic trichothecenes are undetectable in kudzu (Pueraria montana) plants treated with a high-producing isolate of Myrothecium verrucaria. Phytochemistry. 2001 Sep;58(2):269-76. PubMed PMID: 11551550.

13: Namikoshi M, Akano K, Meguro S, Kasuga I, Mine Y, Takahashi T, Kobayashi H. A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau. J Nat Prod. 2001 Mar;64(3):396-8. PubMed PMID: 11277768.

14: el-Maghraby OM, Bean GA, Jarvis BB, Aboul-Nasr MB. Macrocyclic trichothecenes produced by Stachybotrys isolated from Egypt and eastern Europe. Mycopathologia. 1991 Feb;113(2):109-15. PubMed PMID: 2034259.

15: Hughes BJ, Hsieh GC, Jarvis BB, Sharma RP. Effects of macrocyclic trichothecene mycotoxins on the murine immune system. Arch Environ Contam Toxicol. 1989 May-Jun;18(3):388-95. PubMed PMID: 2786385.

16: Harrach B, Bata A, Sándor G, Ványi A. Isolation of macrocyclic and non-macrocyclic trichothecenes (stachybotrys and fusarium toxins) from the Environment of 200 III Sport Horses. Mycotoxin Res. 1987 Sep;3(2):65-8. doi: 10.1007/BF03191991. PubMed PMID: 23604940.

17: Jarvis BB, Lee YW, Cömezoglu SN, Yatawara CS. Trichothecenes produced by Stachybotrys atra from Eastern Europe. Appl Environ Microbiol. 1986 May;51(5):915-8. PubMed PMID: 3729393; PubMed Central PMCID: PMC238987.

18: Bata A, Harrach B, Ujszászi K, Kis-Tamás A, Lásztity R. Macrocyclic trichothecene toxins produced by Stachybotrys atra strains isolated in Middle Europe. Appl Environ Microbiol. 1985 Mar;49(3):678-81. PubMed PMID: 4039551; PubMed Central PMCID: PMC373570.

19: McDougal PG, Schmuff NR. Chemical synthesis of the trichothecenes. Fortschr Chem Org Naturst. 1985;47:153-219. Review. PubMed PMID: 3896992.

20: Smitka TA, Bunge RH, Bloem RJ, French JC. Two new trichothecenes, PD 113,325 and PD 113,326. J Antibiot (Tokyo). 1984 Aug;37(8):823-8. PubMed PMID: 6548218.