Glucopiericidin B
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| Category | Bioactive by-products |
| Catalog number | BBF-01264 |
| CAS | 108073-61-6 |
| Molecular Weight | 577.71 |
| Molecular Formula | C31H47NO6 |
| Purity | 95% |
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Description
It is produced by the strain of Streptomyces pactum S48727. Its antibacterial activity was stronger than Piericidin A1, and its inhibitory effect on antibody formation was also stronger than Piericidin A1.
Specification
| Synonyms | D-Glucopyranoside, 2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11,tridecatetraenyl)-5,6-dimethoxy-3-methyl-4-pyridinyl-, (R-(R*,R*(all E)))- |
| IUPAC Name | (2S,3R,4S,5S,6R)-2-((2-((2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl)-5,6-dimethoxy-3-methyl-1,4-dihydropyridin-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| Canonical SMILES | CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=C(C(=N1)OC)OC)OC2C(C(C(C(O2)CO)O)O)O)C)C)O |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 746.8 °C at 760 mmHg |
| Density | 1.187 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Ethyl Acetate |
Reference Reading
1. New piericidin glucosides, glucopiericidins A and B
M Matsumoto, K Mogi, K Nagaoka, S Ishizeki, R Kawahara, T Nakashima J Antibiot (Tokyo). 1987 Feb;40(2):149-56. doi: 10.7164/antibiotics.40.149.
The new piericidin group antibiotics, glucopiericidins A and B were isolated from the culture broth of Streptomyces pactum S48727 (FERM P-8117) as co-metabolite of piericidin A1. The structures of glucopiericidins A and B were determined as piericidin A1, 10-O-beta-D-glucoside and piericidin A1, 3'-O-D-glucoside on the basis of their spectral and chemical properties, respectively. Glucopiericidins were more potent in inhibiting antibody formation than piericidin A1 in vitro. In addition, these substances showed better antimicrobial activities than piericidin A1. Acute toxicities of these substances in mice were lower than that of piericidin A1. This indicates that D-glucose in glucopiericidin molecules is important in modulating their physiological activities.
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.
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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 ╳
