Dihydroxyaflavinine
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| Category | Mycotoxins |
| Catalog number | BBF-04468 |
| CAS | 76410-56-5 |
| Molecular Weight | 437.61 |
| Molecular Formula | C28H39NO3 |
| Purity | 98.0% |
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Description
Dihydroxyaflavinine is a metabolite of Aspergillus flavus and is a fungal toxin. It inhibits non-competitively GABAA receptor channel expressed in Xenopus oocytes. It displays oral toxicity to the corn earworm (Heliothis zea) and fall armyworm (Spodoptera frugiperda).
Specification
| Synonyms | 20,25-Dihydroxyaflavinine; 1H-Benzo[d]naphthalene-1,5-diol, 2,3,4,4a,5,6,7,7a,10,11-decahydro-9-[(1R)-2-hydroxy-1-methylethyl]-8-(1H-indol-3-yl)-4,4a,7-trimethyl-, (1R,4S,4aR,5S,7S,7aR,11aR)-rel-; 1H-Benzo(d)naphthalene-1,5-diol, 2,3,4,4a,5,6,7,7a,10,11-decahydro-9-(2-hydroxy-1-methylethyl)-8-(1H-indol-3-yl)-4,4a,7-trimethyl-, (1alpha,4alpha,4aalpha,5beta,7alpha,7abeta,9(R*),11aR*)- |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4R,4aS,5R,7R,7aS)-9-[(2S)-1-hydroxypropan-2-yl]-8-(1H-indol-3-yl)-4,4a,7-trimethyl-1,2,3,4,5,6,7,7a,10,11-decahydrobenzo[d]naphthalene-1,5-diol |
| Canonical SMILES | CC1CCC(C23C1(C(CC(C2C(=C(CC3)C(C)CO)C4=CNC5=CC=CC=C54)C)O)C)O |
| InChI | InChI=1S/C28H39NO3/c1-16-13-24(32)27(4)18(3)9-10-23(31)28(27)12-11-19(17(2)15-30)25(26(16)28)21-14-29-22-8-6-5-7-20(21)22/h5-8,14,16-18,23-24,26,29-32H,9-13,15H2,1-4H3/t16-,17-,18-,23+,24-,26+,27-,28?/m1/s1 |
| InChI Key | ZMEZVDUXYBOYTB-KNFQJDNVSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 634.9±55.0°C (Predicted) |
| Melting Point | 254-256°C |
| Density | 1.20±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. [Fungal toxin dihydroxyaflavinine inhibits non-competitively GABAA receptor channel expressed in Xenopus oocytes]
Y Yao, Y Li Sheng Li Xue Bao. 1991 Jun;43(3):227-35.
Dihydroxyaflavinine is an indole-derived metabolite of Aspergillus flavus. Its action on GABA-induced response was quantitatively studied on the GABAA receptor expressed in Xenopus oocytes after injection of chick brain mRNA under voltage-clamp conditions. Dihydroxyaflavinine inhibits GABA-induced current non-competitively with KI = 12 mumol/L. This blockage is rapidly reversible. In comparison, the inhibitory effect of penicillin on GABAA receptor is enhanced by increasing GABA concentration. Ro 15-1788 (a benzodiazepine ligand with KD = 0.6--2 nmol/L) of concentration as high as 1 mumol/L, does not mask the action of 10 mumol/L dihydroxyaflavinine, indicating that dihydroxyaflavinine acts on a site different from benzodiazepines. Dihydroxyaflavinine appears to expedite desensitization of the receptor, which is similar to the action of picrotoxin and in contrast with that of penicillin and bicuculline.
2. Chromolaena laevigata (Asteraceae) as a source of endophytic non-aflatoxigenic Aspergillus flavus: chemical profile in different culture conditions and biological applications
Rodolfo B Balbinot, Josiane A M de Oliveira, et al. Braz J Microbiol. 2021 Sep;52(3):1201-1214. doi: 10.1007/s42770-021-00502-6. Epub 2021 Apr 30.
Endophytes are microorganisms that form symbiotic relationships with their host. These microorganisms can produce a variety of secondary metabolites, some of which have inhibitory effects on pests and pathogens or even act to promote plant growth. Due to these characteristics, these microorganisms are used as sources of biologically active substances for a wide range of biotechnological applications. Based on that, the aim of this study was to evaluate the production of metabolites of the endophytic Aspergillus flavus CL7 isolated from Chromolaena laevigata, in four different cultivation conditions, and to determine the antimicrobial, cytotoxic, antiviral, and antioxidant potential of these extracts. The multiphasic approach used to identify this strain was based on morphology and ITS gene sequence analysis. The chemical investigation of A. flavus using potato dextrose and minimal medium, using both stationary and agitated methods, resulted in the isolation of kojic acid, α-cyclopiazonic acid, and 20,25-dihydroxyaflavinine. Another 18 compounds in these extracts were identified by UHPLC-HRMS/MS, of which dideacetyl parasiticolide A has been described for the first time from A. flavus. Aflatoxins, important chemomarkers of A. flavus, were not detected in any of the extracts, thus indicating that the CL7 strain is non-aflatoxigenic. The biological potential of all extracts was evaluated, and the best results were observed for the extract obtained using minimal medium against Trichophyton rubrum and Mycobacterium tuberculosis.
3. Aspergillus flavus aswA, a gene homolog of Aspergillus nidulans oefC, regulates sclerotial development and biosynthesis of sclerotium-associated secondary metabolites
Perng-Kuang Chang, Leslie L Scharfenstein, Robert W Li, Natalia Arroyo-Manzanares, Sarah De Saeger, José Diana Di Mavungu Fungal Genet Biol. 2017 Jul;104:29-37. doi: 10.1016/j.fgb.2017.04.006. Epub 2017 Apr 22.
Aspergillus flavus aswA (AFLA_085170) is a gene encoding a Zn(II)2Cys6 DNA-binding domain and a transcriptional activation domain, DUF3468. Disruption of aswA yielded strains that made a truncated gene transcript and generated a fungus that produced a greatly increased number of sclerotia. These sclerotia were odd-shaped and non-pigmented (white) and different from oval and pigmented (dark brown to black) mature sclerotia. Transcriptomic analysis of the ΔaswA strain grown on potato dextrose agar plates and Wickerham agar plates showed that expression of clustering genes involved in the biosynthesis of three sclerotium-associated secondary metabolites was down-regulated. These included gene clusters of asparasone, aflatrem, and aflavarin. In contrast, those of aflatoxin, cyclopiazonic acid and kojic acid were not affected. Metabolite analyses confirmed that the non-pigmented sclerotia contained aflatoxin and cyclopiazonic acid but not other aforementioned metabolites, three asparasone analogs and dihydroxyaflavinine commonly present in mature sclerotia. Impairment in aswA gene function stalls normal sclerotial development, which in turn prevents biosynthesis and accumulation of sclerotium-specific metabolites.
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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 ╳
