Piloquinone
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| Category | Bioactive by-products |
| Catalog number | BBF-02418 |
| CAS | 25414-26-0 |
| Molecular Weight | 352.38 |
| Molecular Formula | C21H20O5 |
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Description
It is produced by the strain of Str. pilosus. It's a phenanthrene compound. It has inhibitory effect on mycobacterium and protozoa, but the effect is not strong.
Specification
| Synonyms | 9,10-Phenanthrenedione, 1,8-dihydroxy-2-methyl-3-(4-methyl-1-oxopentyl)-; 1,8-Dihydroxy-2-methyl-3-(4-methylpentanoyl)-9,10-phenanthrenedione |
| IUPAC Name | 1,8-dihydroxy-2-methyl-3-(4-methylpentanoyl)phenanthrene-9,10-dione |
| Canonical SMILES | CC1=C(C=C2C3=C(C(=CC=C3)O)C(=O)C(=O)C2=C1O)C(=O)CCC(C)C |
| InChI | InChI=1S/C21H20O5/c1-10(2)7-8-15(22)13-9-14-12-5-4-6-16(23)17(12)20(25)21(26)18(14)19(24)11(13)3/h4-6,9-10,23-24H,7-8H2,1-3H3 |
| InChI Key | UJTRABFYSZAGLW-UHFFFAOYSA-N |
Properties
| Appearance | Brown-red Acicular Crystal |
| Antibiotic Activity Spectrum | Mycoplasma; Parasites |
| Melting Point | 176-178°C |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Examination of Potential Exceptions to the F and S Biosynthetic Classification of Fused-Ring Aromatic Polyketides
Robert Thomas Chembiochem. 2016 Dec 2;17(23):2208-2215. doi: 10.1002/cbic.201600315. Epub 2016 Oct 18.
The reported acetate-derived labelling of the fungal naphthalene γ-pyrone fonsecin, two streptomycete dodecaketide αpyrones TW93f and TW93g, and the streptomycete phenanthraquinones piloquinone, murayaquinone and haloquinone appear to be exceptions to the generalisation that fungi and streptomycetes produce fused-ring aromatic polyketides by different modes of cyclisation. A review of their 1) originally assigned formulae, 2) [13 C2 ]acetate-derived labelling patterns, and 3) modes of cyclisation leads to the recognition of feasible alternative chemical structures or biosynthetic pathways, which are in accord with the originally proposed classification system.
2. Potent Inhibition of Monoamine Oxidase B by a Piloquinone from Marine-Derived Streptomyces sp. CNQ-027
Hyun Woo Lee, Hansol Choi, Sang-Jip Nam, William Fenical, Hoon Kim J Microbiol Biotechnol. 2017 Apr 28;27(4):785-790. doi: 10.4014/jmb.1612.12025.
Two piloquinone derivatives isolated from Streptomyces sp. CNQ-027 were tested for the inhibitory activities of two isoforms of monoamine oxidase (MAO), which catalyzes monoamine neurotransmitters. The piloquinone 4,7-dihydroxy-3-methyl-2-(4-methyl-1-oxopentyl)-6H-dibenzo[b,d]pyran-6-one (1) was found to be a highly potent inhibitor of human MAO-B, with an IC50 value of 1.21 µ; in addition, it was found to be highly effective against MAO-A, with an IC50 value of 6.47 µ. Compound 1 was selective, but not extremely so, for MAO-B compared with MAO-A, with a selectivity index value of 5.35. Compound 1,8-dihydroxy-2-methyl-3-(4-methyl-1-oxopentyl)-9,10-phenanthrenedione (2) was moderately effective for the inhibition of MAO-B (IC50 = 14.50 µ) but not for MAO-A (IC50 > 80 µ). There was no time-dependency in inhibition of MAO-A or -B by compound 1, and the MAO-A and -B activities were almost completely recovered in the dilution experiments with an excess amount of compound 1. Compound 1 showed competitive inhibition for MAO-A and -B, with Ki values of 0.573 and 0.248 µ, respectively. These results suggest that piloquinones from a microbial source could be potent reversible MAO inhibitors and may be useful lead compounds for developing MAO enzyme inhibitors to treat related disorders, such as depression, Parkinson's disease, and Alzheimer's disease.
3. A Versatile Transcription-Translation in One Approach for Activation of Cryptic Biosynthetic Gene Clusters
Qian Zhang, Jin-Wei Ren, Weishan Wang, Ji'an Zhai, Jing Yang, Ning Liu, Ying Huang, Yihua Chen, Guohui Pan, Keqiang Fan ACS Chem Biol. 2020 Sep 18;15(9):2551-2557. doi: 10.1021/acschembio.0c00581. Epub 2020 Aug 24.
The ever-growing drug resistance problem worldwide highlights the urgency to discover and develop new drugs. Microbial natural products are a prolific source of drugs. Genome sequencing has revealed a tremendous amount of uncharacterized natural product biosynthetic gene clusters (BGCs) encoded within microbial genomes, most of which are cryptic or express at very low levels under standard culture conditions. Therefore, developing effective strategies to awaken these cryptic BGCs is of great interest for natural product discovery. In this study, we designed and validated a Transcription-Translation in One (TTO) approach for activation of cryptic BGCs. This approach aims to alter the metabolite profiles of target strains by directly overexpressing exogenous rpsL (encoding ribosomal protein S12) and rpoB (encoding RNA polymerase β subunit) genes containing beneficial mutations for natural product production using a plug-and-play plasmid system. As a result, this approach bypasses the tedious screening work and overcomes the false positive problem in the traditional ribosome engineering approach. In this work, the TTO approach was successfully applied to activating cryptic BGCs in three Streptomyces strains, leading to the discovery of two aromatic polyketide antibiotics, piloquinone and homopiloquinone. We further identified a single BGC responsible for the biosynthesis of both piloquinone and homopiloquinone, which features an unusual starter unit incorporation step. This powerful strategy can be further exploited for BGC activation in strains even beyond streptomycetes, thus facilitating natural product discovery research in the future.
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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 ╳
