Reticulol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04595 |
| CAS | 26246-41-3 |
| Molecular Weight | 222.19 |
| Molecular Formula | C11H10O5 |
| Purity | >95% by HPLC |
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Description
An isocoumarin metabolite produced by selected species of streptomyces. It is a potent inhibitor of cyclic nucleotide phosphodiesterase. It also causes dose-dependent inhibition of lung metastasis in the B16F10 melanoma model.
Specification
| Synonyms | 6,8-Dihydroxy-7-methoxy-3-methylisocoumarin; 6,8-Dihydroxy-7-methoxy-3-methyl-1H-2-benzopyran-1-one; K 251-1; NSC 294978 |
| Storage | Store at -20°C |
| IUPAC Name | 6,8-dihydroxy-7-methoxy-3-methylisochromen-1-one |
| Canonical SMILES | CC1=CC2=CC(=C(C(=C2C(=O)O1)O)OC)O |
| InChI | InChI=1S/C11H10O5/c1-5-3-6-4-7(12)10(15-2)9(13)8(6)11(14)16-5/h3-4,12-13H,1-2H3 |
| InChI Key | LREZRXWUEZCZRU-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria |
| Boiling Point | 473.2±45.0°C (Predicted) |
| Melting Point | 193-193.5°C |
| Density | 1.424±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Polyketides from the Deep-Sea-Derived Fungus Graphostroma sp. MCCC 3A00421 Showed Potent Antifood Allergic Activities
Guangming Liu, Xian-Wen Yang, Chun-Lan Xie, Jin-Mei Xia, Zongze Shao, Zhu-Hua Luo, Qingmei Liu, Siwen Niu J Agric Food Chem . 2018 Feb 14;66(6):1369-1376. doi: 10.1021/acs.jafc.7b04383.
To discover antifood allergic components from deep-sea-derived microorganisms, we performed a systematic chemical investigation of the Atlantic hydrothermal fungus Graphostroma sp. MCCC 3A00421. Consequently, nine new (1-9) and 19 known (10-28) polyketides were isolated. The planar structures of the new compounds were elucidated mainly by detailed analysis of their nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data, while the absolute configurations were established using the modified Mosher's method in association with electronic circular dichroism spectra. Graphostrin A (1) is a novel chlorinated polyketide derivate bearing an oxazole moiety. All isolates were tested for antifood allergic bioactivities in immunoglobulin E-mediated rat basophilic leukemia-2H3 cells. Reticulol (10) significantly decreased the rates of degranulation and histamine release with IC50values of 13.5 and 13.7 μM, respectively, suggesting reticulol could be a potential antifood allergic medicine.
2. Antitumor efficacy of reticulol from Streptoverticillium against the lung metastasis model B16F10 melanoma. Lung metastasis inhibition by growth inhibition of melanoma
Si-Hwan Ko, Jeong-Hwan Kim, Yi-Sub Kwak, Won-Ho Yoon, Dae-Seog Lim, Chang-Han Kim Chemotherapy . 2003 Jun;49(3):146-53. doi: 10.1159/000070621.
Reticulol was isolated from the culture broth of the strain Streptoverticillium sp. NA-4803. Recticulol (M.W. 222.2) exhibited a potent in vitro cytotoxicity against A427, a human lung tumor cell line, and B16F10, a mouse melanoma cell line. In the trypan blue staining assay for B16F10 cells, the cell viability by reticulol treatment was significantly decreased in a dose-dependent manner. The in vivo assay for the lung metastasis-blocking effect showed that reticulol injected intravenously suppressed the increase in colonies on the lung in a dose-dependent manner. In addition, the survival rate of tumor-implanted mice treated with reticulol was closely associated with its antitumoral efficacy. Reticulol administered via the peritoneum of mice showed less metastasis inhibition than that injected intravenously. To demonstrate the mechanism for inhibition of metastasis, the inhibitory effect of reticulol for matrix metalloproteinase-2 or -9 involved in melanoma metastasis was investigated; however, they were not observed on zymogram gel. In addition, the antitumor efficacy of reticulol was not associated with cell cycle arrest or apoptosis. Therefore, it was inferred that reticulol known as a phosphodiesterase inhibitor directly inhibited the growth of B16F10 melanoma, showing necrotic response. These results suggest that reticulol protects its lung metastasis via the bloodstream by inhibiting the growth of B16F10 melanoma at the cellular level.
3. Bireticulol, a bioactive isocoumarin dimer from Streptomyces sp. BCC24731
Punsa Tobwor, Chanwit Suriyachadkun, Chollaratt Boonlarppradab, Sumalee Suphothina J Antibiot (Tokyo) . 2011 Mar;64(3):267-70. doi: 10.1038/ja.2010.171.
A new dimeric isocoumarin, bireticulol, was isolated from the terrestrial Streptomyces sp. and characterized as a 5-5' dimer of reticulol. In addition, reticulol and 8-hydroxy-6,7-dimethoxy-3-methyl isocoumarin, together with other known polyketides piericidin A, 2'-(2-hydroxyphenyl)-2,4'-bibenzoxazole-4-carboxylic acid methyl ester (UK-1) and 3-benzyl-4-hydroxy-5-methyldihydrofuran-2-one were also obtained. Bireticulol exhibited cytotoxic effects against KB (human epidermoid carcinoma, ATCC CCL-17) and NCI-H187 (human small cell lung cancer, ATCC CRL-5804) cell lines with IC(50) values of 24.4 and 8.31 μg ml(-1), respectively.
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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 ╳
