Aflavazole
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| Category | Others |
| Catalog number | BBF-04465 |
| CAS | 2043963-70-6 |
| Molecular Weight | 417.58 |
| Molecular Formula | C28H35NO2 |
| Purity | 97.5% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04465 | 1 mg | $629 | In stock |
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Aflavazole is a metabolite of the sclerotia of Aspergillus flavus. It shows antifeedant activity against the fungivorous beetle Carpophilus hemipterus remarkably.
Specification
| Synonyms | (1R,4S,4aS,13dS,14R,16R,16aS)-1,2,3,4,5,6,9,13d,14,15,16,16a-Dodecahydro-1,7,14,16a-tetramethylphenanthro[2,1-c]carbazole-4,16-diol; (+)-Aflavazole; Benzo(4a,5)naphtho(2,1-c)carbazole-4,16-diol, 1,2,3,4,5,6,9,13d,14,15,16,16a-dodecahydro-1,7,14,16a-tetramethyl-, (1alpha,4alpha,4aS*,13dbeta,14alpha,16beta,16aalpha)-(+)-; Benzo(4a,5)naphtho(2,1-c)carbazole-4,16-diol,1,2,3,4,5,6,9,13d,14,15,16,16a-dodecahydro-1,7,16a-tetramethyl-, (1R,4S,4aS,13dS,14R,16R,16aS)-rel-(+)- |
| Storage | Store at -20°C |
| IUPAC Name | (2S,3R,5R,6S,7R,10S,11S)-3,6,7,15-tetramethyl-18-azahexacyclo[12.11.0.02,11.06,11.017,25.019,24]pentacosa-1(14),15,17(25),19,21,23-hexaene-5,10-diol |
| Canonical SMILES | CC1CCC(C23C1(C(CC(C2C4=C(CC3)C(=CC5=C4C6=CC=CC=C6N5)C)C)O)C)O |
| InChI | InChI=1S/C28H35NO2/c1-15-13-21-24(19-7-5-6-8-20(19)29-21)25-18(15)11-12-28-22(30)10-9-17(3)27(28,4)23(31)14-16(2)26(25)28/h5-8,13,16-17,22-23,26,29-31H,9-12,14H2,1-4H3/t16-,17-,22+,23-,26+,27-,28+/m1/s1 |
| InChI Key | CXQOHHTZVIKVEM-KOOUEZQKSA-N |
Properties
| Appearance | Light Yellow Crystal |
| Boiling Point | 630.6°C at 760 mmHg |
| Melting Point | 156-160°C |
| Density | 1.23 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Development of sexual structures influences metabolomic and transcriptomic profiles in Aspergillus flavus
Jane Marian Luis, Ignazio Carbone, Brian M Mack, Matthew D Lebar, Jeffrey W Cary, Matthew K Gilbert, Deepak Bhatnagar, Carol-Carter Wientjes, Gary A Payne, Geromy G Moore, Yaken Obaydeh Ameen, Peter S Ojiambo Fungal Biol. 2022 Mar;126(3):187-200. doi: 10.1016/j.funbio.2022.01.001. Epub 2022 Jan 31.
Sclerotium (female) fertility, the ability of a strain to produce ascocarps, influences internal morphological changes during sexual reproduction in Aspergillus flavus. Although sclerotial morphogenesis has been linked to secondary metabolite (SM) biosynthesis, metabolic and transcriptomic changes within A. flavus sclerotia during sexual development are not known. Successful mating between compatible strains may result in relatively high or low numbers of ascocarps being produced. Sclerotia from a high fertility cross (Hi-Fert-Mated), a low fertility cross (Lo-Fert-Mated), unmated strains (Hi-Fert-Unmated and Lo-Fert-Unmated) were harvested immediately after crosses were made and every two weeks until 8 weeks of incubation, then subjected to targeted metabolomics (n = 106) and transcriptomics analyses (n = 80). Aflatoxin B1 production varied between Hi-Fert-Mated and Hi-Fert-Unmated sclerotia, while it remained low or was undetected in Lo-Fert-Mated and Lo-Fert-Unmated sclerotia. Profiling of 14 SMs showed elevated production of an aflavazole analog, an aflavinine isomer, and hydroxyaflavinine in Hi-Fert-Mated sclerotia at 4 to 8 weeks. Similarly, genes ayg1, hxtA, MAT1, asd-3, preA and preB, and genes in uncharacterized SM gene clusters 30 and 44 showed increased expression in Hi-Fert-Mated sclerotia at these time points. These results broaden our knowledge of the biochemical and transcriptional processes during sexual development in A. flavus.
2. Total Syntheses of Aflavazole and 14-Hydroxyaflavinine
Hailong Li, Qifeng Chen, Zhaohong Lu, Ang Li J Am Chem Soc. 2016 Dec 7;138(48):15555-15558. doi: 10.1021/jacs.6b10880. Epub 2016 Nov 23.
The first total syntheses of aflavazole (6) and 14-hydroxyaflavinine (8), two sterically congested indole diterpenoids, were accomplished. AlI3-promoted alkyne Prins cyclization was exploited to construct their key structural motifs. An electrocyclization-aromatization sequence assembled the pentasubstituted arene of 6, and a Stille-Migita coupling furnished the tetrasubstituted olefin of 8. The benzylic and allylic C-O bonds were reductively cleaved at the late stage of the syntheses, respectively.
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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 ╳
