Germicidin B
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| Category | Bioactive by-products |
| Catalog number | BBF-01872 |
| CAS | 150973-78-7 |
| Molecular Weight | 182.22 |
| Molecular Formula | C10H14O3 |
| Purity | >95% by HPLC |
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Description
A pyranone isolated from streptomyces sp.; a potent autoregulator of the sporulation of the producing strain, and spores of closely related species.
Specification
| Synonyms | 2H-Pyran-2-one, 3-ethyl-4-hydroxy-6-(1-methylethyl)- |
| Storage | -20°C |
| IUPAC Name | 3-ethyl-4-hydroxy-6-propan-2-ylpyran-2-one |
| Canonical SMILES | CCC1=C(C=C(OC1=O)C(C)C)O |
| InChI | InChI=1S/C10H14O3/c1-4-7-8(11)5-9(6(2)3)13-10(7)12/h5-6,11H,4H2,1-3H3 |
| InChI Key | SZBDLUWYHDLLAG-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Tan Solid |
| Boiling Point | 326.1°C at 760 mmHg |
| Melting Point | 80°C |
| Density | 1.104 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Moderate water solubility. |
Reference Reading
1. α-Pyrone derivatives with cyto-protective activity from two Takla Makan desert soil derived actinomycete Nocardiopsis strains recovered in seawater based medium
Tingting Zhao, Tianjiao Zhu, Qianqun Gu, Qian Che, Jing Li, Yimin Chang, Dehai Li, Guojian Zhang Nat Prod Res . 2019 Sep;33(17):2498-2506. doi: 10.1080/14786419.2018.1455046.
In this paper, we described the discovery of twoNocardiopsisstrains HDN154-146 and HDN154-168 from Takla Makan desert soil samples using seawater based medium. Chemical investigation of these two strains led to the discovery of eight newα-pyrone derivatives named nocahypyrones A-H (1-8), together with one known analogue germicidin G (9). The structures of these compounds, including absolute configurations, were elucidated by extensive NMR, MS, and CD analyses. Compounds1-9were tested for their cyto-protective activities and for the first time we foundα-pyrones5and8exhibited capabilities to induce expression of phase II detoxifying enzymes.
2. Investigation on antimicrobial agents of the terrestrial Streptomyces sp. BCC71188
Pranee Rachtawee, Pattama Pittayakhajonwut, Paranee Sripreechasak, Khomsan Supong, Somboon Tanasupawat, Kannawat Danwisetkanjana Appl Microbiol Biotechnol . 2017 Jan;101(2):533-543. doi: 10.1007/s00253-016-7804-1.
The terrestrial actinomycete strain BCC71188 was identified as Streptomyces by its morphology (having spiral chain spore on the aerial mycelium), chemotaxonomy (containing LL-diaminopimelic acid in the cell wall), and 16S rRNA gene sequence analysis [showing high similarity values compared with Streptomyces samsunensis M1463T(99.85 %) and Streptomyces malaysiensis NBRC 16446T(99.40 %)]. The crude extract exhibited antimalarial against Plasmodium falciparum (IC500.19 μg/ml), anti-TB against Mycobacterial tuberculosis (MIC 6.25 μg/ml), and antibacterial against Bacillus cereus (MIC 1.56 μg/ml) activities. Therefore, chemical investigation was conducted by employing bioassay-guided method and led to the isolation of 19 compounds including two cyclic peptides (1-2), five macrolides (3-7), new naphthoquinone (8), nahuoic acid C (9), geldanamycin derivatives (10-13), cyclooctatin (14), germicidins A (15) and C (16), actinoramide A (17), abierixin, and 29-O-methylabierixin. These isolated compounds were evaluated for antimicrobial activity, such as antimalarial, anti-TB, and antibacterial activities, and for cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. Compounds 1-7, 10-14 exhibited antimalarial (IC500.22-7.14 μg/ml), and elaiophylin analogs (4-6) displayed anti-TB (MIC 0.78-12.00 μg/ml) and B. cereus (MIC 0.78-3.13 μg/ml) activities. Compounds 1, 2, 14, and abierixin displayed weak cytotoxicity, indicating a potential for antimicrobial agents.
3. Germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551
J W Metzger, H Zähner, F Petersen, R P Hummel, S Freund J Antibiot (Tokyo) . 1993 Jul;46(7):1126-38. doi: 10.7164/antibiotics.46.1126.
During germination spores of Streptomyces viridochromogenes NRRL B-1551 excrete a compound, germicidin, which has an inhibitory effect on the germination of its own arthrospores at a concentration as low as 200 pM (40 pg/ml). At higher concentrations germicidin inhibits porcine Na+/K(+)-activated ATPase and retards the germination of the cress Lepidium sativum. Germicidin is the first known autoregulative inhibitor of spore germination in the genus Streptomyces and was isolated from the supernatant of germinated spores, but also from the supernatant of the submerged culture. Spectroscopic analysis and derivatization reactions revealed germicidin to be 6-(2-butyl)-3-ethyl-4-hydroxy-2-pyrone (C11H16O3). Crude isolates of germicidin from the supernatant of submerged culture, but not from the spores, contained a second, structurally very similar compound (C10H14O3), in which in contrast to germicidin a 2-propyl instead of the 2-butyl chain was bound to C-6 and which did not show any activity in the germination and ATPase assay. The germination assay was evaluated as a new screening model for specifically active compounds.
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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 ╳
