Piericidin B
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Category | Antibiotics |
Catalog number | BBF-02416 |
CAS | 16891-54-6 |
Molecular Weight | 429.59 |
Molecular Formula | C26H39NO4 |
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Description
It is produced by the strain of Str. mobaraensis 16-24. It has anti-fungal, gram-positive bacteria and insect effects, but also has weak anti-gram-negative bacteria effect.
Specification
Synonyms | Piericidin B1; (-)-Piericidin B1; 4-Pyridinol, 2,3-dimethoxy-6-(10-methoxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5-methyl-, (S-(R*,R*-(all-E)))-; 4-Pyridinol, 2,3-dimethoxy-6-[(2E,5E,7E,9R,10R,11E)-10-methoxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5-methyl- |
IUPAC Name | 2,3-dimethoxy-6-[(2E,5E,7E,9R,10R,11E)-10-methoxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5-methyl-1H-pyridin-4-one |
Canonical SMILES | CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=O)C(=C(N1)OC)OC)C)C)OC |
InChI | InChI=1S/C26H39NO4/c1-10-19(4)24(29-7)20(5)16-18(3)13-11-12-17(2)14-15-22-21(6)23(28)25(30-8)26(27-22)31-9/h10-11,13-14,16,20,24H,12,15H2,1-9H3,(H,27,28)/b13-11+,17-14+,18-16+,19-10+/t20-,24+/m1/s1 |
InChI Key | PTKGTYKMTXCJOK-DDSKRPRESA-N |
Properties
Appearance | Yellow Viscous Oily Matter |
Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
Boiling Point | 586.2°C at 760 mmHg |
Density | 1.02 g/cm3 |
Solubility | Soluble in Methanol |
Reference Reading
1. New piericidin rhamnosides as potentiators of amphotericin B activity against Candida albicans produced by actinomycete strain TMPU-A0287
Akiho Yagi, Yuga Yamaguchi, Keiko Kawasaki, Eri Usui, Hiroyuki Yamazaki, Ryuji Uchida J Antibiot (Tokyo). 2023 Feb;76(2):65-74. doi: 10.1038/s41429-022-00581-z. Epub 2022 Dec 2.
Four new piericidin rhamnosides (2, 4-6) together with three known piericidins (1, 3, 7) were isolated from the culture broth of the unidentified actinomycete strain TMPU-A0287 as potentiators of antifungal amphotericin B (AmB) activity. The structures of piericidins were elucidated by spectroscopic analyses, including NMR and MS. Compounds 2 and 4-6 possessed a ketone at C-10 and one or two methoxy groups on the rhamnose in their structures. Compounds 1-7 did not exhibit antifungal activity against Candida albicans and all potentiated AmB activity. The MIC values of AmB against C. albicans combined with 1-7 (4.0 μg ml-1) decreased from 0.50 to 0.063 or 0.031 μg ml-1, yielding an 8- or 16-fold increase in AmB activity.
2. Cytotoxic Minor Piericidin Derivatives from the Actinomycete Strain Streptomyces psammoticus SCSIO NS126
Kunlong Li, Ziqi Su, Yongli Gao, Xiuping Lin, Xiaoyan Pang, Bin Yang, Huaming Tao, Xiaowei Luo, Yonghong Liu, Xuefeng Zhou Mar Drugs. 2021 Jul 28;19(8):428. doi: 10.3390/md19080428.
The mangrove-sediment-derived actinomycete strain Streptomyces psammoticus SCSIO NS126 was found to have productive piericidin metabolites featuring anti-renal cell carcinoma activities. In this study, in order to explore more diverse piericidin derivatives, and therefore to discover superior anti-tumor lead compounds, the NS126 strain was further fermented at a 300-L scale under optimized fermentation conditions. As a result, eight new minor piericidin derivatives (piericidins L-R (1-7) and 11-demethyl-glucopiericidin A (8)) were obtained, along with glucopiericidin B (9). The new structures including absolute configurations were determined by spectroscopic methods coupled with experimental and calculated electronic circular dichroism. We also proposed plausible biosynthetic pathways for these unusual post-modified piericidins. Compounds 1 and 6 showed selective cytotoxic activities against OS-RC-2 cells, and 2-5 exhibited potent cytotoxicity against HL-60 cells, with IC50 values lower than 0.1 μM. The new piericidin glycoside 8 was cytotoxic against ACHN, HL-60 and K562, with IC50 values of 2.3, 1.3 and 5.5 μM, respectively. The ability to arrest the cell cycle and cell apoptosis effects induced by 1 and 6 in OS-RC-2 cells, 2 in HL-60 cells, and 8 in ACHN cells were then further investigated. This study enriched the structural diversity of piericidin derivatives and confirmed that piericidins deserve further investigations as promising anti-tumor agents.
3. Effective Generation of Glucosylpiericidins with Selective Cytotoxicities and Insights into Their Biosynthesis
Zengzhi Liu, Fei Xiao, Siqi Cai, Chunni Liu, Huayue Li, Ting Wu, Yuechen Jiang, Xin Wang, Qian Che, Tianjiao Zhu, Dehai Li, Wenli Li Appl Environ Microbiol. 2021 Jun 11;87(13):e0029421. doi: 10.1128/AEM.00294-21. Epub 2021 Jun 11.
Exploring unknown glycosyltransferases (GTs) is important for compound structural glycodiversification during the search for drug candidates. Piericidin glycosides have been reported to have potent bioactivities; however, the GT responsible for piericidin glucosylation remains unknown. Herein, BmmGT1, a macrolide GT with broad substrate selectivity and isolated from Bacillus methylotrophicus B-9987, was found to be able to glucosylate piericidin A1 in vitro. Next, the codon-optimized GT gene sbmGT1, which was designed based on BmmGT1, was heterologously expressed in the piericidin producer Streptomyces youssoufiensis OUC6819. Piericidin glycosides thus significantly accumulated, leading to the identification of four new glucopiericidins (compounds 3, 4, 6, and 7). Furthermore, using BmmGT1 as the probe, GT1507 was identified in the genome of S. youssoufiensis OUC6819 and demonstrated to be associated with piericidin glucosylation; the overexpression of this gene led to the identification of another new piericidin glycoside, N-acetylglucosamine-piericidin (compound 8). Compounds 4, 7, and 8 displayed cytotoxic selectivity toward A549, A375, HCT-116, and HT-29 solid cancer cell lines compared to the THP-1 lymphoma cell line. Moreover, database mining of GT1507 homologs revealed their wide distribution in bacteria, mainly in those belonging to the high-GC Gram-positive and Firmicutes clades, thus representing the potential for identification of novel tool enzymes for compound glycodiversification. IMPORTANCE Numerous bioactive natural products are appended with sugar moieties and are often critical for their bioactivities. Glycosyltransferases (GTs) are powerful tools for the glycodiversification of natural products. Although piericidin glycosides display potent bioactivities, the GT involved in glucosylation is unclear. In this study, five new piericidin glycosides (compounds 3, 4, 6, 7, and 8) were generated following the overexpression of GT-coding genes in a piericidin producer. Three of them (compounds 4, 7, and 8) displayed cytotoxic selectivity. Notably, GT1507 was demonstrated to be related to piericidin glucosylation in vivo. Furthermore, mining of GT1507 homologs from the GenBank database revealed their wide distribution across numerous bacteria. Our findings would greatly facilitate the exploration of GTs to glycodiversify small molecules in the search for drug candidates.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳