Furaquinocin A
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| Category | Antibiotics |
| Catalog number | BBF-01460 |
| CAS | 125108-66-9 |
| Molecular Weight | 402.44 |
| Molecular Formula | C22H26O7 |
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Description
Furaquinocin A is originally isolated from Streptomyces sp. KO-3988. It can kill HeLa S3 and B16 melanoma cells, but has no antibacterial activity.
Specification
| Synonyms | (2R)-2α,3,8-Trimethyl-3α-[(1R,3Z)-1,5-dihydroxy-4-methyl-3-pentenyl]-4-hydroxy-7-methoxy-2,3,6,9-tetrahydronaphtho[1,2-b]furan-6,9-dione; 3-(1,5-Dihydroxy-4-methyl-3-pentenyl)-2,3-dihydro-4-hydroxy-7-methoxy-2,3,8-trimethylnaphtho(1,2-b)furan-6,9-dione |
| IUPAC Name | (2R,3S)-3-[(Z,1R)-1,5-dihydroxy-4-methylpent-3-enyl]-4-hydroxy-7-methoxy-2,3,8-trimethyl-2H-benzo[g][1]benzofuran-6,9-dione |
| Canonical SMILES | CC1C(C2=C(C=C3C(=C2O1)C(=O)C(=C(C3=O)OC)C)O)(C)C(CC=C(C)CO)O |
| InChI | InChI=1S/C22H26O7/c1-10(9-23)6-7-15(25)22(4)12(3)29-21-16-13(8-14(24)17(21)22)19(27)20(28-5)11(2)18(16)26/h6,8,12,15,23-25H,7,9H2,1-5H3/b10-6-/t12-,15-,22-/m1/s1 |
| InChI Key | FBOIBFWCHWNBOE-NKTCXQSFSA-N |
Properties
| Appearance | Yellow Acicular Crystalline |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 673.5°C at 760 mmHg |
| Melting Point | 182-183°C |
| Density | 1.34 g/cm3 |
Reference Reading
1. A gene cluster for prenylated naphthoquinone and prenylated phenazine biosynthesis in Streptomyces cinnamonensis DSM 1042
Yvonne Haagen, Kerstin Glück, Katja Fay, Bernd Kammerer, Bertolt Gust, Lutz Heide Chembiochem. 2006 Dec;7(12):2016-27. doi: 10.1002/cbic.200600338.
Streptomyces cinnamonensis DSM 1042 produces two classes of secondary metabolites of mixed isoprenoid/nonisoprenoid origin: the polyketide-isoprenoid compound furanonaphthoquinone I (FNQ I) and several prenylated phenazines, predominantly endophenazine A. We now report the cloning and sequence analysis of a 55 kb gene cluster required for the biosynthesis of these compounds. Several inactivation experiments confirmed the involvement of this gene cluster in the biosynthesis of FNQ I and endophenazine A. The six identified genes for endophenazine biosynthesis showed close similarity to phenazine biosynthetic genes from Pseudomonas. Of the 28 open reading frames identified in the adjacent FNQ I cluster, 13 showed close similarity to genes contained in the cluster for furaquinocin-a structurally similar metabolite from another Streptomyces strain. These genes included a type III polyketide synthase sequence, a momA-like monooxygenase gene, and two cloQ-like prenyltransferase genes designated fnq26 and fnq28. Inactivation experiments confirmed the involvement of fnq26 in FNQ I biosynthesis, whereas no change in secondary-metabolite formation was observed after fnq28 inactivation. The FNQ I cluster contains a contiguous group of five genes, which together encode all the enzymatic functions required for the recycling of S-adenosylhomocysteine (SAH) to S-adenosylmethionine (SAM). Two SAM-dependent methyltransferases are encoded within the cluster. Inactivation experiments showed that fnq9 is responsible for the 7-O-methylation and fnq27 for the 6-C-methylation reaction in FNQ I biosynthesis.
2. Biosynthesis of a natural polyketide-isoprenoid hybrid compound, furaquinocin A: identification and heterologous expression of the gene cluster
Takashi Kawasaki, Yutaka Hayashi, Tomohisa Kuzuyama, Kazuo Furihata, Nobuya Itoh, Haruo Seto, Tohru Dairi J Bacteriol. 2006 Feb;188(4):1236-44. doi: 10.1128/JB.188.4.1236-1244.2006.
Furaquinocin (FQ) A, produced by Streptomyces sp. strain KO-3988, is a natural polyketide-isoprenoid hybrid compound that exhibits a potent antitumor activity. As a first step toward understanding the biosynthetic machinery of this unique and pharmaceutically useful compound, we have cloned an FQ A biosynthetic gene cluster by taking advantage of the fact that an isoprenoid biosynthetic gene cluster generally exists in flanking regions of the mevalonate (MV) pathway gene cluster in actinomycetes. Interestingly, Streptomyces sp. strain KO-3988 was the first example of a microorganism equipped with two distinct mevalonate pathway gene clusters. We were able to localize a 25-kb DNA region that harbored FQ A biosynthetic genes (fur genes) in both the upstream and downstream regions of one of the MV pathway gene clusters (MV2) by using heterologous expression in Streptomyces lividans TK23. This was the first example of a gene cluster responsible for the biosynthesis of a polyketide-isoprenoid hybrid compound. We have also confirmed that four genes responsible for viguiepinol [3-hydroxypimara-9(11),15-diene] biosynthesis exist in the upstream region of the other MV pathway gene cluster (MV1), which had previously been cloned from strain KO-3988. This was the first example of prokaryotic enzymes with these biosynthetic functions. By phylogenetic analysis, these two MV pathway clusters were identified as probably being independently distributed in strain KO-3988 (orthologs), rather than one cluster being generated by the duplication of the other cluster (paralogs).
3. Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes
Tohru Dairi J Antibiot (Tokyo). 2005 Apr;58(4):227-43. doi: 10.1038/ja.2005.27.
Most Streptomyces strains are equipped with only the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for the formation of isopentenyl diphosphate, a common precursor of isoprenoids. In addition to this pathway, some Streptomyces strains possess the mevalonate (MV) pathway via which isoprenoid antibiotics are produced. We have recently cloned and analyzed the MV pathway gene clusters and their flanking regions from terpentecin, BE-40644, and furaquinocin A producers. All these clusters contained genes coding for mevalonate kinase, mevalonate diphosphate decarboxylase, phosphomevalonate kinase, type 2 IPP isomerase, HMG-CoA reductase, and HMG-CoA synthase. The order of each of the open reading frames (ORFs) is also the same, and the respective homologous ORFs show more than 70% amino acid identity with each other. In contrast to these conservative gene organizations, the biosynthetic genes of terpentecin, BE-40644, and furaquinocin A were located just upstream and/or downstream of the MV pathway gene cluster. These facts suggested that all the actinomycete strains possessing both the MV and MEP pathways produce isoprenoid compounds and the biosynthetic genes of one of these isoprenoids usually exist adjacent to the MV pathway gene cluster. Therefore, when the presence of the MV cluster is detected by molecular genetic techniques, isoprenoids may be produced by the cultivation of these actinomycete strains. During the course of these studies, we identified diterpene cyclases possessing unique primary structures that differ from those of eukaryotes and catalyze unique reactions.
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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 ╳
