Albaflavenone
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| Category | Antibiotics |
| Catalog number | BBF-00402 |
| CAS | |
| Molecular Weight | 218.33 |
| Molecular Formula | C15H22O |
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Description
It is produced by the strain of Streptomyces albido flavus. There was resistance to Bacillus thuringiensis with MIC 8-10 ㎍/mL.
Specification
| Synonyms | albaflavenone; (+)-epi-isozizaen-5-one; (3S,3aR,6S)-3,7,7,8-tetramethyl-2,3,4,5,6,7-hexahydro-1H-3a,6-methanoazulen-1-one; CHEBI:51460; LMPR0103700006; C17954; Q27122616 |
| IUPAC Name | (1R,2S,8S)-2,6,7,7-tetramethyltricyclo[6.2.1.01,5]undec-5-en-4-one |
| Canonical SMILES | CC1CC(=O)C2=C(C(C3CCC12C3)(C)C)C |
| InChI | InChI=1S/C15H22O/c1-9-7-12(16)13-10(2)14(3,4)11-5-6-15(9,13)8-11/h9,11H,5-8H2,1-4H3/t9-,11-,15+/m0/s1 |
| InChI Key | SHUZZAXJEJPUGA-CCUNJIBTSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Two new sesquiterpenoids from Dictyophora indusiata
Ying-Fang Zhang, Hang Xun, Quan Gao, Feng Tang, Fei-Fei Qi, Jia Sun J Asian Nat Prod Res. 2022 Aug 5;1-7. doi: 10.1080/10286020.2022.2106223. Online ahead of print.
Two new sesquiterpenoids, named 9,10-dihydroxy-albaflavenone (1) and 5-hydroxy-albaflavenone (2) were isolated from Dictyophora indusiata. Their structures and absolute configurations were determined by NMR, ECD and HRESIMS. Compounds 1 and 2 showed anti-inflammatory activity by inhibiting TNF-α and NO secretion to varying degrees.
2. Production of distinct labdane-type diterpenoids using a novel cryptic labdane-like cluster from Streptomyces thermocarboxydus K155
Silvia M Guzmán-Trampe, Haruo Ikeda, Pablo Vinuesa, Martha L Macías-Rubalcava, Baldomero Esquivel, Sara Centeno-Leija, Silvana M Tapia-Cabrera, Silvia I Mora-Herrera, Beatriz Ruiz-Villafán, Romina Rodríguez-Sanoja, Sergio Sanchez Appl Microbiol Biotechnol. 2020 Jan;104(2):741-750. doi: 10.1007/s00253-019-10240-3. Epub 2019 Dec 5.
Bioinformatic mining of the Streptomyces thermocarboxydus K155 genome predicted the presence of four synthases for the production of geosmin, hopene, albaflavenone, and a type B-type A diterpenoid system like that described for labdane-related diterpenoids (LRD). The lrd cluster was comprised by an operon of four genes (lrdABDC). This cluster seemed to be silent in the wild-type strain, as neither labdane nor terpene-like compounds were detected by UPLC-TOF-MS and GC-MS analyses in both culture supernatants and mycelial extracts. Heterologous expression of the lrdABDC cluster in a defective cyslabdan producer (Streptomyces cyslabdanicus K04-0144Δcld) generated 8,17-epoxy-7-hydroxy labda-12,14-diene and cyslabdan. The same cluster expressed in the strains Streptomyces coelicolor M1152, Streptomyces peucetius var. caesius, and Streptomyces avermitilis SUKA22 produced the general intermediary labda-8(17), 12(E),14-triene [(E)-biformene]. Besides (E)-biformene, S. coelicolor M1152 and S. avermitilis SUKA22 produced two and three different labdane-type diterpenoids, underlying the relevance of the genetic background of the Streptomyces host in product formation.
3. An Aromatic Cluster in the Active Site of epi-Isozizaene Synthase Is an Electrostatic Toggle for Divergent Terpene Cyclization Pathways
Trey A Ronnebaum, Sarah M Gardner, David W Christianson Biochemistry. 2020 Dec 22;59(50):4744-4754. doi: 10.1021/acs.biochem.0c00876. Epub 2020 Dec 3.
The sesquiterpene cyclase epi-isozizaene synthase (EIZS) catalyzes the cyclization of farnesyl diphosphate to form the tricyclic precursor of the antibiotic albaflavenone. The hydrophobic active site is largely defined by aromatic residues that direct a multistep reaction sequence through multiple carbocation intermediates. The previous substitution of polar residues for a key aromatic residue, F96, converts EIZS into a high-fidelity sesquisabinene synthase: the F96S, F96M, and F96Q variants generate 78%, 91%, and 97% sesquisabinene A, respectively. Here, we report high-resolution X-ray crystal structures of two of these reprogrammed cyclases. The structures of the F96M EIZS-Mg2+3-risedronate and F96M EIZS-Mg2+3-inorganic pyrophosphate-benzyltriethylammonium cation complexes reveal structural changes in the F96 aromatic cluster that redirect the cyclization pathway leading from the bisabolyl carbocation intermediate in catalysis. The structure of the F96S EIZS-Mg2+3-neridronate complex reveals a partially occupied inhibitor and an enzyme active site caught in transition between open and closed states. Finally, three structures of wild-type EIZS complexed with the bisphosphonate inhibitors neridronate, pamidronate, and risedronate provide a foundation for understanding binding differences between wild-type and variant enzymes. These structures provide new insight regarding active site flexibility, particularly with regard to the potential for subtle expansion and contraction to accommodate ligands of varying sizes as well as bound water molecules. Additionally, these structures highlight the importance of conformational changes in the F96 aromatic cluster that could influence cation-π interactions with carbocation intermediates in catalysis.
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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 ╳
