Rumbrin
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| Category | Others |
| Catalog number | BBF-02216 |
| CAS | 148528-19-2 |
| Molecular Weight | 357.83 |
| Molecular Formula | C20H20ClNO3 |
| Purity | >98% |
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Description
Rumbrin is a cytoprotective substance produced by Auxarthron umbrinumn 13.
Specification
| Synonyms | 6-(8-(3-Chloro-1H-pyrrol-2-yl)-1-methyl-1,3,5,7-octatetraenyl)-4-methoxy-3-methyl-2H-pyran-2-one |
| IUPAC Name | 6-[(2Z,4E,6E,8E)-9-(3-chloro-1H-pyrrol-2-yl)nona-2,4,6,8-tetraen-2-yl]-4-methoxy-3-methylpyran-2-one |
| Canonical SMILES | CC1=C(C=C(OC1=O)C(=CC=CC=CC=CC2=C(C=CN2)Cl)C)OC |
| InChI | InChI=1S/C20H20ClNO3/c1-14(18-13-19(24-3)15(2)20(23)25-18)9-7-5-4-6-8-10-17-16(21)11-12-22-17/h4-13,22H,1-3H3/b6-4+,7-5+,10-8+,14-9- |
| InChI Key | TUFFAFAPFQNIRB-KDZWSXRISA-N |
Properties
| Appearance | Red Acicular Crystal |
| Boiling Point | 613.8±55.0°C at 760 mmHg |
| Melting Point | 170-171°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Production of anticancer polyenes through precursor-directed biosynthesis
Benjamin R Clark, Stephen O'Connor, Deirdre Fox, Jacques Leroy, Cormac D Murphy Org Biomol Chem. 2011 Sep 21;9(18):6306-11. doi: 10.1039/c1ob05667k. Epub 2011 Jul 26.
The biosynthesis of the pyrrolyl moiety of the fungal metabolite rumbrin originates from pyrrole-2-carboxylic acid. In an effort to produce novel derivatives with enhanced biological activity a series of substituted pyrrole-2-carboxylates were synthesised and incubated with the producing organism, Auxarthron umbrinum. Several 4-halo-pyrrole-2-carboxylic acids were incorporated into the metabolite yielding three new derivatives: 3-fluoro-, 3-chloro- and 3-bromo-isorumbrin, which were generated in milligram quantities enabling cytotoxicity assays to be conducted. The 3-chloro- and 3-bromo-isorumbrins had improved activity against HeLa cells compared with rumbrin; 3-bromoisorumbrin also showed dramatically improved activity towards a lung cancer cell line (A549).
2. Synthesis of polyenylpyrrole derivatives with selective growth inhibitory activity against T-cell acute lymphoblastic leukemia cells
Chihiro Yoshida, Tomoya Higashi, Yoshifumi Hachiro, Yuki Fujita, Takuya Yagi, Azusa Takechi, Chihiro Nakata, Kazuya Miyashita, Nobuo Kitada, Ryohei Saito, Rika Obata, Takashi Hirano, Takahiko Hara, Shojiro A Maki Bioorg Med Chem Lett. 2021 Apr 1;37:127837. doi: 10.1016/j.bmcl.2021.127837. Epub 2021 Feb 11.
T-cell acute lymphoblastic leukemia (T-ALL) is a hardly curable disease with a high relapse rate. 20 analogs were synthesized based on the structures of two kinds of fungi-derived polyenylpyrrole products (rumbrin (1) and auxarconjugatin-B (2)) to suppress the growth of T-ALL-derived cell line CCRF-CEM and tested for growth-inhibiting activity. The octatetraenylpyrrole analog gave an IC50 of 0.27 μM in CCRF-CEM cells, while it did not affect Burkitt lymphoma-derived cell line Raji and the cervical cancer cell line HeLa, or the oral cancer cell line HSC-3 (IC50 > 10 μM). This compound will be a promising compound for developing T-ALL-specific drugs.
3. Biosynthesis of rumbrins and inspiration for discovery of HIV inhibitors
Beifen Zhong, Jun Wan, Changhui Shang, Jiajia Wen, Yujia Wang, Jian Bai, Shan Cen, Youcai Hu Acta Pharm Sin B. 2022 Nov;12(11):4193-4203. doi: 10.1016/j.apsb.2022.02.005. Epub 2022 Feb 14.
Investigation on how nature produces natural compounds with chemical and biological diversity at the genetic level offers inspiration for the discovery of new natural products and even their biological targets. The polyketide rumbrin (1) is a lipid peroxide production and calcium accumulation inhibitor, which contains a chlorinated pyrrole moiety that is a rare chemical feature in fungal natural products. Here, we identify the biosynthetic gene cluster (BGC) rum of 1 and its isomer 12E-rumbrin (2) from Auxarthron umbrinum DSM3193, and elucidate their biosynthetic pathway based on heterologous expression, chemical complementation, and isotopic labeling. We show that rumbrins are assembled by a highly reducing polyketide synthase (HRPKS) that uniquely incorporates a proline-derived pyrrolyl-CoA starer unit, and followed by methylation and chlorination. Sequent precursor-directed biosynthesis was able to yield a group of rumbrin analogues. Remarkably, inspired by the presence of a human immunodeficiency virus (HIV)-Nef-associated gene in the rum cluster, we predicted and pharmacologically demonstrated rumbrins as potent inhibitors of HIV at the nanomolar level. This work enriches the recognition of unconventional starter units of fungal PKSs and provides a new strategy for genome mining-guided drug discovery.
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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 ╳
