Grifolin | CAS#6379-55-1 | antitumor

MedKoo Cat#: 584411 | Name: Grifolin

Description:

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

Grifolin is a secondary metabolite isolated from the fresh fruiting bodies of the mushroom Albatrellus confluens that has been shown to inhibit the growth of some cancer cell lines in vitro by induction of apoptosis via targeting DAPK1.

Chemical Structure

Grifolin

CAS#6379-55-1

Theoretical Analysis

MedKoo Cat#: 584411

Name: Grifolin

CAS#: 6379-55-1

Chemical Formula: C16H28O2

Exact Mass: 252.2089

Molecular Weight: 252.40

Elemental Analysis: C, 76.14; H, 11.18; O, 12.68

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

Grifolin; BRN 1782428

IUPAC/Chemical Name

5,7,11-Tridecatriene-3,4-diol, 3,8,12-trimethyl-

InChi Key

LYXITZQJPFABBF-ZZAMHKPASA-N

InChi Code

InChI=1S/C16H28O2/c1-6-16(5,18)15(17)12-8-11-14(4)10-7-9-13(2)3/h8-9,11-12,15,17-18H,6-7,10H2,1-5H3/b12-8+,14-11+

SMILES Code

CCC(O)(C)C(O)/C=C/C=C(C)/CC/C=C(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

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 252.40 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

1: Luo XJ, Li LL, Deng QP, Yu XF, Yang LF, Luo FJ, Xiao LB, Chen XY, Ye M, Liu JK, Cao Y. Grifolin, a potent antitumour natural product upregulates death-associated protein kinase 1 DAPK1 via p53 in nasopharyngeal carcinoma cells. Eur J Cancer. 2011 Jan;47(2):316-25. doi: 10.1016/j.ejca.2010.09.021. Epub 2010 Oct 11. PubMed PMID: 20943371. 2: Luo X, Yu X, Liu S, Deng Q, Liu X, Peng S, Li H, Liu J, Cao Y. The role of targeting kinase activity by natural products in cancer chemoprevention and chemotherapy (Review). Oncol Rep. 2015 Aug;34(2):547-54. doi: 10.3892/or.2015.4029. Epub 2015 Jun 4. Review. PubMed PMID: 26044950. 3: Liu LY, Li ZH, Ding ZH, Dong ZJ, Li GT, Li Y, Liu JK. Meroterpenoid pigments from the basidiomycete Albatrellus ovinus. J Nat Prod. 2013 Jan 25;76(1):79-84. doi: 10.1021/np300751m. Epub 2013 Jan 10. PubMed PMID: 23305465. 4: Luo XJ, Li W, Yang LF, Yu XF, Xiao LB, Tang M, Dong X, Deng QP, Bode AM, Liu JK, Cao Y. DAPK1 mediates the G1 phase arrest in human nasopharyngeal carcinoma cells induced by grifolin, a potential antitumor natural product. Eur J Pharmacol. 2011 Nov 30;670(2-3):427-34. doi: 10.1016/j.ejphar.2011.08.026. Epub 2011 Sep 6. PubMed PMID: 21914449. 5: Song J, Manir MM, Moon SS. Cytotoxic grifolin derivatives isolated from the wild mushroom Boletus pseudocalopus (Basidiomycetes). Chem Biodivers. 2009 Sep;6(9):1435-42. doi: 10.1002/cbdv.200800217. PubMed PMID: 19774605. 6: HIRATA Y, NAKANISHI K. Grifolin, an antibiotic from a basidiomycete. J Biol Chem. 1950 May;184(1):135-43. PubMed PMID: 15421982. 7: Liu LY, Li ZH, Wang GQ, Wei K, Dong ZJ, Feng T, Li GT, Li Y, Liu JK. Nine new farnesylphenols from the basidiomycete albatrellus caeruleoporus. Nat Prod Bioprospect. 2014 Apr;4(2):119-28. doi: 10.1007/s13659-014-0015-5. Epub 2014 Apr 23. PubMed PMID: 24858140; PubMed Central PMCID: PMC4004861. 8: Luo X, Yang L, Xiao L, Xia X, Dong X, Zhong J, Liu Y, Li N, Chen L, Li H, Li W, Liu W, Yu X, Chen H, Tang M, Weng X, Yi W, Bode A, Dong Z, Liu J, Cao Y. Grifolin directly targets ERK1/2 to epigenetically suppress cancer cell metastasis. Oncotarget. 2015 Dec 15;6(40):42704-16. doi: 10.18632/oncotarget.5678. PubMed PMID: 26516701; PubMed Central PMCID: PMC4767464. 9: Alves MJ, Ferreira IC, Dias J, Teixeira V, Martins A, Pintado M. A review on antifungal activity of mushroom (basidiomycetes) extracts and isolated compounds. Curr Top Med Chem. 2013;13(21):2648-59. Review. PubMed PMID: 24083794. 10: Quang DN, Hashimoto T, Arakawa Y, Kohchi C, Nishizawa T, Soma G, Asakawa Y. Grifolin derivatives from Albatrellus caeruleoporus, new inhibitors of nitric oxide production in RAW 264.7 cells. Bioorg Med Chem. 2006 Jan 1;14(1):164-8. Epub 2005 Sep 16. PubMed PMID: 16169234. 11: Ohta S, Nozaki A, Ohashi N, Matsukawa M, Okamoto M. A total synthesis of grifolin. Chem Pharm Bull (Tokyo). 1988 Jun;36(6):2239-43. PubMed PMID: 3240458. 12: Che X, Yan H, Sun H, Dongol S, Wang Y, Lv Q, Jiang J. Grifolin induces autophagic cell death by inhibiting the Akt/mTOR/S6K pathway in human ovarian cancer cells. Oncol Rep. 2016 Aug;36(2):1041-7. doi: 10.3892/or.2016.4840. Epub 2016 May 30. PubMed PMID: 27277722. 13: Hara T, Hirasawa A, Sun Q, Sadakane K, Itsubo C, Iga T, Adachi T, Koshimizu TA, Hashimoto T, Asakawa Y, Tsujimoto G. Novel selective ligands for free fatty acid receptors GPR120 and GPR40. Naunyn Schmiedebergs Arch Pharmacol. 2009 Sep;380(3):247-55. doi: 10.1007/s00210-009-0425-9. Epub 2009 May 27. PubMed PMID: 19471906. 14: Sugiyama K, Kawagishi H, Tanaka A, Saeki S, Yoshida S, Sakamoto H, Ishiguro Y. Isolation of plasma cholesterol-lowering components from ningyotake (Polyporus confluens) mushroom. J Nutr Sci Vitaminol (Tokyo). 1992 Aug;38(4):335-42. PubMed PMID: 1291638. 15: Nukata M, Hashimoto T, Yamamoto I, Iwasaki N, Tanaka M, Asakawa Y. Neogrifolin derivatives possessing anti-oxidative activity from the mushroom Albatrellus ovinus. Phytochemistry. 2002 Apr;59(7):731-7. PubMed PMID: 11909630. 16: Isobe M, Goto T. Synthesis of grifolin, an antibiotic from a Basidiomycete. Tetrahedron. 1968 Jan;24(2):945-8. PubMed PMID: 5637493. 17: Goto T, Kakisawa H, Hirata Y. The structure of grifolin, an antibiotic from a basidiomycete. Tetrahedron. 1963 Dec;19(12):2079-83. PubMed PMID: 5879215. 18: Liu XT, Winkler AL, Schwan WR, Volk TJ, Rott MA, Monte A. Antibacterial compounds from mushrooms I: a lanostane-type triterpene and prenylphenol derivatives from Jahnoporus hirtus and Albatrellus flettii and their activities against Bacillus cereus and Enterococcus faecalis. Planta Med. 2010 Feb;76(2):182-5. doi: 10.1055/s-0029-1186001. Epub 2009 Jul 30. PubMed PMID: 19644795. 19: Ohno N, Furukawa M, Miura NN, Adachi Y, Motoi M, Yadomae T. Antitumor beta glucan from the cultured fruit body of Agaricus blazei. Biol Pharm Bull. 2001 Jul;24(7):820-8. PubMed PMID: 11456124. 20: Ye M, Luo X, Li L, Shi Y, Tan M, Weng X, Li W, Liu J, Cao Y. Grifolin, a potential antitumor natural product from the mushroom Albatrellus confluens, induces cell-cycle arrest in G1 phase via the ERK1/2 pathway. Cancer Lett. 2007 Dec 18;258(2):199-207. PubMed PMID: 18029087.