Grifolin
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| Category | Antibiotics |
| Catalog number | BBF-01804 |
| CAS | 6903-07-7 |
| Molecular Weight | 328.50 |
| Molecular Formula | C22H32O2 |
| Purity | 98.0% |
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Description
It is produced by the strain of Grifolin confluens. It is mainly anti-gram-positive bacteria and mycobacterium activity (weak).
Specification
| Synonyms | 2-Farnesyl-5-methylresorcinol; 1,3-Benzenediol, 5-methyl-2-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-, (E,E)-; E,E,5-Methyl-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol |
| IUPAC Name | 5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,3-diol |
| Canonical SMILES | CC1=CC(=C(C(=C1)O)CC=C(C)CCC=C(C)CCC=C(C)C)O |
| InChI | InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+ |
| InChI Key | PZHNKNRPGLTZPO-VZRGJMDUSA-N |
Properties
| Appearance | Colorless Fine Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Melting Point | 43 °C |
| Solubility | Soluble in organic solvents; Insoluble in Water |
Reference Reading
1. Pharmacological Effects of Grifolin: Focusing on Anticancer Mechanisms
Abdelhakim Bouyahya, Aicha El Allam, Ikrame Zeouk, Douae Taha, Gokhan Zengin, Bey Hing Goh, Michelina Catauro, Domenico Montesano, Nasreddine El Omari Molecules. 2022 Jan 3;27(1):284. doi: 10.3390/molecules27010284.
Grifolin is a volatile compound contained in essential oils of several medicinal plants. Several studies show that this substance has been the subject of numerous pharmacological investigations, which have yielded interesting results. Grifolin demonstrated beneficial effects for health via its multiple pharmacological activities. It has anti-microbial properties against bacteria, fungi, and parasites. In addition, grifolin exhibited remarkable anti-cancer effects on different human cancer cells. The anticancer action of this molecule is related to its ability to act at cellular and molecular levels on different checkpoints controlling the signaling pathways of human cancer cell lines. Grifolin can induce apoptosis, cell cycle arrest, autophagy, and senescence in these cells. Despite its major pharmacological properties, grifolin has only been investigated in vitro and in vivo. Therefore, further investigations concerning pharmacodynamic and pharmacokinetic tests are required for any possible pharmaceutical application of this substance. Moreover, toxicological tests and other investigations involving humans as a study model are required to validate the safety and clinical applications of grifolin.
2. Efficient Synthesis of Cannabigerol, Grifolin, and Piperogalin via Alumina-Promoted Allylation
Nicholas G Jentsch, Xiong Zhang, Jakob Magolan J Nat Prod. 2020 Sep 25;83(9):2587-2591. doi: 10.1021/acs.jnatprod.0c00131. Epub 2020 Sep 10.
The synthesis of three phenolic natural products has been accomplished with unprecedented efficiency using a new alumina-promoted regioselective aromatic allylation reaction. Cannabigerol and grifolin were prepared in one step from the inexpensive 5-alkyl-resorcinols olivetol and orcinol. Piperogalin was synthesized, for the first time, via two sequential allylations of orcinol with geraniol and prenol.
3. Design and synthesis of water-soluble grifolin prodrugs for DNA methyltransferase 1 (DNMT1) down-regulation
Liguo Wang, Yue Wu, Zhenzhen Li, Tianlong Lan, Xu Zhao, Wenxing Lv, Feng Shi, Xiangjian Luo, Yu Rao, Ya Cao RSC Adv. 2021 Dec 3;11(61):38907-38914. doi: 10.1039/d1ra06648j. eCollection 2021 Nov 29.
DNA methylation and gene silencing play indispensable roles in the epigenetic landscape and gene expression. DNA methyltransferase 1 (DNMT1), a member of the DNMT family, which catalyzes the addition of methyl groups on DNA has been identified to have a close relationship with tumorigenesis. But DNMT1 inhibitors are rare except for the highly toxic nucleoside derivates. Grifolin is a unique natural product which down-regulates DNMT1 and has low toxicity. However, the poor solubility and stability of grifolin limit its application. Herein, we synthesized PEG5-Grifolin as a water-miscible prodrug of grifolin. The half-life of PEG5-Grifolin at 25 °C was considerably extended, revealing excellent stability. Meanwhile, PEG5-Grifolin suppressed tumor growth of by downregulating DNMT1 and reactivating the expression of several tumor suppressor genes in vivo. PEG5-Grifolin might be a promising demethylation agent for DNMT1 associated diseases and benefit much against various types of DNMT1 associated cancer.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
