Ramentaceone | CAS#14787-38-3 | antineoplastic

MedKoo Cat#: 596316 | Name: Ramentaceone

Description:

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

Ramentaceone is a naphthoquinone compound primarily found in Drosera (sundew) species. Here’s a summary of its known bioactivities: 1. Antimicrobial Activity Exhibits antibacterial properties, particularly against Gram-positive bacteria like Staphylococcus aureus. Shows antifungal activity against Candida species and dermatophytes. 2. Anticancer Activity Demonstrates cytotoxic effects on various cancer cell lines, including melanoma and lung carcinoma. Mechanism likely involves oxidative stress induction and interference with cellular redox balance. 3. Anti-inflammatory and Antioxidant Effects Modulates inflammatory pathways by inhibiting pro-inflammatory cytokines. Acts as a reactive oxygen species (ROS) scavenger, reducing oxidative damage. 4. Enzyme Inhibition Reported to inhibit topoisomerase and other enzymes linked to DNA replication and repair, contributing to its anticancer potential. 5. Potential for Drug Development Due to its cytotoxic and antimicrobial properties, ramentaceone is being studied as a lead compound for anticancer and antibacterial agents.

Chemical Structure

Ramentaceone

CAS#14787-38-3

Theoretical Analysis

MedKoo Cat#: 596316

Name: Ramentaceone

CAS#: 14787-38-3

Chemical Formula: C11H8O3

Exact Mass: 188.0473

Molecular Weight: 188.18

Elemental Analysis: C, 70.21; H, 4.29; O, 25.51

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ramentaceone; NSC 208733; NSC-208733; NSC208733; NSC 624625; NSC-624625; NSC624625; 7-Methyljuglon;

IUPAC/Chemical Name

5-hydroxy-7-methylnaphthalene-1,4-dione

InChi Key

OZUSCVSONBBWOR-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H8O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h2-5,14H,1H3

SMILES Code

O=C1C=CC(C2=C1C=C(C)C=C2O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 188.18 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.

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

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Free Radic Biol Med. 2017 Jul;108:433-444. doi: 10.1016/j.freeradbiomed.2017.04.010. Epub 2017 Apr 14. PubMed PMID: 28414098. 5: Rauf A, Uysal S, Hadda TB, Uddin G, Nawaz MA, Khan H, Siddiqui BS, Raza M, Bawazeer S, Zengin G. In vivo and in silico sedative-hypnotic like activity of 7-methyljuglone isolated from Diospyros lotus L. Biomed Pharmacother. 2017 Mar;87:678-682. doi: 10.1016/j.biopha.2017.01.021. Epub 2017 Jan 12. PubMed PMID: 28088734. 6: Uddin Z, Song YH, Curtis-Long MJ, Kim JY, Yuk HJ, Park KH. Potent bacterial neuraminidase inhibitors, anthraquinone glucosides from Polygonum cuspidatum and their inhibitory mechanism. J Ethnopharmacol. 2016 Dec 4;193:283-292. doi: 10.1016/j.jep.2016.08.026. Epub 2016 Aug 21. PubMed PMID: 27553976. 7: Kawiak A, Lojkowska E. Ramentaceone, a Naphthoquinone Derived from Drosera sp., Induces Apoptosis by Suppressing PI3K/Akt Signaling in Breast Cancer Cells. PLoS One. 2016 Feb 3;11(2):e0147718. doi: 10.1371/journal.pone.0147718. eCollection 2016. PubMed PMID: 26840401; PubMed Central PMCID: PMC4739616. 8: Sun W, Bao J, Lin W, Gao H, Zhao W, Zhang Q, Leung CH, Ma DL, Lu J, Chen X. 2-Methoxy-6-acetyl-7-methyljuglone (MAM), a natural naphthoquinone, induces NO-dependent apoptosis and necroptosis by H2O2-dependent JNK activation in cancer cells. Free Radic Biol Med. 2016 Mar;92:61-77. doi: 10.1016/j.freeradbiomed.2016.01.014. Epub 2016 Jan 21. PubMed PMID: 26802903. 9: Rauf A, Uddin G, Khan H, Arfan M, Siddiqui BS. Bioassay-guided isolation of antibacterial constituents from Diospyros lotus roots. Nat Prod Res. 2016;30(4):426-8. doi: 10.1080/14786419.2015.1013957. Epub 2015 Feb 23. PubMed PMID: 25702900. 10: Rauf A, Uddin G, Khan H, Siddiqui BS, Arfan M. Anti-hyperalgesic activity of crude extract and 7-methyljuglone of Diospyros lotus roots. Nat Prod Res. 2015;29(23):2226-9. doi: 10.1080/14786419.2014.1003297. Epub 2015 Jan 21. PubMed PMID: 25604725. 11: Kishore N, Binneman B, Mahapatra A, van de Venter M, du Plessis-Stoman D, Boukes G, Houghton P, Marion Meyer JJ, Lall N. Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines. Bioorg Med Chem. 2014 Sep 1;22(17):5013-9. doi: 10.1016/j.bmc.2014.06.013. Epub 2014 Jul 4. PubMed PMID: 25059501. 12: Uddin G, Rauf A, Siddiqui BS, Muhammad N, Khan A, Shah SU. Anti-nociceptive, anti-inflammatory and sedative activities of the extracts and chemical constituents of Diospyros lotus L. Phytomedicine. 2014 Jun 15;21(7):954-9. doi: 10.1016/j.phymed.2014.03.001. Epub 2014 Apr 3. PubMed PMID: 24703326. 13: Mbaveng AT, Kuete V. Review of the chemistry and pharmacology of 7-Methyljugulone. Afr Health Sci. 2014 Mar;14(1):201-5. doi: 10.4314/ahs.v14i1.31. Review. PubMed PMID: 26060480; PubMed Central PMCID: PMC4449069. 14: Karkare S, Chung TT, Collin F, Mitchenall LA, McKay AR, Greive SJ, Meyer JJ, Lall N, Maxwell A. The naphthoquinone diospyrin is an inhibitor of DNA gyrase with a novel mechanism of action. J Biol Chem. 2013 Feb 15;288(7):5149-56. doi: 10.1074/jbc.M112.419069. Epub 2012 Dec 28. PubMed PMID: 23275348; PubMed Central PMCID: PMC3576119. 15: Egan PA, van der Kooy F. Coproduction and ecological significance of naphthoquinones in carnivorous sundews (Drosera). Chem Biodivers. 2012 Jun;9(6):1033-44. doi: 10.1002/cbdv.201100274. PubMed PMID: 22700223. 16: Kawiak A, Zawacka-Pankau J, Wasilewska A, Stasilojc G, Bigda J, Lojkowska E. Induction of apoptosis in HL-60 cells through the ROS-mediated mitochondrial pathway by ramentaceone from Drosera aliciae. J Nat Prod. 2012 Jan 27;75(1):9-14. doi: 10.1021/np200247g. Epub 2012 Jan 17. PubMed PMID: 22250825. 17: Landa P, Kutil Z, Temml V, Vuorinen A, Malik J, Dvorakova M, Marsik P, Kokoska L, Pribylova M, Schuster D, Vanek T. Redox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinones. 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