FR 901235
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| Category | Antibiotics |
| Catalog number | BBF-03699 |
| CAS | 124190-19-8 |
| Molecular Weight | 344.31 |
| Molecular Formula | C18H16O7 |
| Purity | 95% |
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Description
This active molecular is an immunoactive substance produced by Paecilomyces carneus F-4882, an imperfect fungus. FR-901235 can lead the mitogen-induced lymphocyte proliferation to go back to a normal level after being suppressed by addition of immunosuppressive factor.
Specification
| Synonyms | FR-901235; (-)-2,4,9-Trihydroxy-6-methoxy-7-methyl-2-(2-oxopropyl)-1H-phenalene-1,3(2H)-dione |
| Shelf Life | 2 month in rt, long time |
| Storage | Store at -20°C |
| IUPAC Name | 2,4,9-trihydroxy-6-methoxy-7-methyl-2-(2-oxopropyl)phenalene-1,3-dione |
| Canonical SMILES | CC1=CC(=C2C3=C(C(=CC(=C13)OC)O)C(=O)C(C2=O)(CC(=O)C)O)O |
| InChI | InChI=1S/C18H16O7/c1-7-4-9(20)13-15-12(7)11(25-3)5-10(21)14(15)17(23)18(24,16(13)22)6-8(2)19/h4-5,20-21,24H,6H2,1-3H3 |
| InChI Key | LJOMNUOFKLTARM-UHFFFAOYSA-N |
Properties
| Appearance | Pale Yellow Flake Crystal |
| Boiling Point | 681.8°C at 760 mmHg |
| Melting Point | 168-170°C |
| Density | 1.501 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. A new immunomodulator, FR-901235
M Nishikawa, H Terano, S Takase, T Shibata, M Kohsaka, Y Tsurumi J Antibiot (Tokyo) . 1989 Sep;42(9):1356-61. doi: 10.7164/antibiotics.42.1356.
FR-901235 is a new type of immunoactive substance produced by an imperfect fungus, Paecilomyces carneus F-4882. The mitogen-induced lymphocyte proliferation which had been suppressed by addition of immunosuppressive factor, was restored to a normal level by the addition of FR-901235. Furthermore, the subsequent administration of FR-901235 partially restored the impaired delayed-type hypersensitivity to sheep red blood cells in tumor-bearing mice.
2. Polyketides from Penicillium sp. JP-1, an endophytic fungus associated with the mangrove plant Aegiceras corniculatum
Yuchun Fang, Zhenjian Lin, Tianjiao Zhu, Weiming Zhu, Qianqun Gu Phytochemistry . 2008 Mar;69(5):1273-8. doi: 10.1016/j.phytochem.2007.10.030.
Four polyketides, leptosphaerone C (1), penicillenone (2), arugosin I (3) and 9-demethyl FR-901235 (4), as well as five known compounds, bacillosporin A (5), bacillosporin C (6), sequoiamonascin D (7), sequoiatone A (8), and sequoiatone B (9) were isolated from the Penicillium sp. JP-1, an endophytic fungus isolated from Aegiceras corniculatum. Their structures were determined by spectroscopic methods, mainly by 2D NMR spectroscopic analyses. Compound 1 showed cytotoxicity against A-549 cells with an IC50 value of 1.45 microM, while compound 2 showed cytotoxicity against P388 cells with an IC50 value of 1.38 microM.
3. Total Syntheses of FR-901235, Auxarthrones A-D, and Lamellicolic Anhydride
Ayumi Imayoshi, Kazunori Tsubaki, Takuto Kayukawa, Kotaro Kiyotaki Org Lett . 2020 Dec 4;22(23):9220-9224. doi: 10.1021/acs.orglett.0c03401.
In our previous study, an unusual rearrangement reaction was discovered whereby dinaphthyl ketones with three hydroxy groups at restricted positions were transformed into a phenalenone ring and a benzene ring. Using the rearrangement as a key reaction, the first total syntheses of FR-901235 and auxarthrones A-D from an unstable triketone common intermediate are described. Furthermore, lamellicolic anhydride was synthesized from the triketone. This conversion is part of the putative biosynthetic pathway and was achieved experimentally for the first time.
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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 ╳
