β-Aflatrem
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| Category | Mycotoxins |
| Catalog number | BBF-04461 |
| CAS | 144446-23-1 |
| Molecular Weight | 501.66 |
| Molecular Formula | C32H39NO4 |
| Purity | ≥98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04461 | 1 mg | $629 | In stock |
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Add to cartDescription
β-Aflatrem is a class of structurally-diverse secondary metabolites isolated from Aspergillus flavus. It is a mycotoxin that exhibits insecticidal activity.
Specification
| Synonyms | Aflatrem B; Beta-Aflatrem; 4H-3,15a-Epoxy-1-benzoxepino(6',7':6,7)indeno(1,2-b)indol-4-one, 10-(1,1-dimethyl-2-propenyl)-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-5b-hydroxy-2,2,13b,13c-tetramethyl-, (3alpha,5balpha,7abeta,13balpha,13cbeta,15aalpha)-(+)- |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-11-(2-methylbut-3-en-2-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8(13),9,11,20-pentaen-22-one |
| Canonical SMILES | CC1(C2C(=O)C=C3C4(CCC5CC6=C(C5(C4(CCC3(O2)O1)C)C)NC7=C6C=C(C=C7)C(C)(C)C=C)O)C |
| InChI | InChI=1S/C32H39NO4/c1-8-27(2,3)18-9-10-22-20(15-18)21-16-19-11-12-31(35)24-17-23(34)26-28(4,5)37-32(24,36-26)14-13-29(31,6)30(19,7)25(21)33-22/h8-10,15,17,19,26,33,35H,1,11-14,16H2,2-7H3/t19-,26-,29+,30+,31+,32-/m0/s1 |
| InChI Key | ONMXSHAELZXSPO-SDPXOEJRSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 663.6±55.0°C at 760 mmHg |
| Melting Point | 188-190°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei
Yi Wang, Peipei Liu, Kunlai Sun, Lei Guo, Weiming Zhu, Ye Li Mar Drugs . 2014 Jun 30;12(7):3970-81. doi: 10.3390/md12073970.
Two new indole-diterpenoids (1 and 2) and a new isocoumarin (3), along with the known β-aflatrem (4), paspalinine (5), leporin B (6), α-cyclopiazonic acid (7), iso-α-cyclopiazonic acid (8), ditryptophenaline (9), aflatoxin B1 (10), 7-O-acetylkojic acid (11) and kojic acid (12), were isolated from the fermentation broth of the marine-derived fungus, Aspergillus flavus OUCMDZ-2205. The structures of Compounds 1-12 were elucidated by spectroscopic analyses, quantum ECD calculations and the chemical method. New Compound 1 exhibited antibacterial activity against Staphylococcus aureus with a MIC value of 20.5 μM. Both new Compounds 1 and 2 could arrest the A549 cell cycle in the S phase at a concentration of 10 μM. Compound 1 showed PKC-beta inhibition with an IC50 value of 15.6 μM. In addition, the absolute configurations of the known compounds, 4-6 and leporin A (6a), were also determined for the first time.
2. Regiospecificities and prenylation mode specificities of the fungal indole diterpene prenyltransferases AtmD and PaxD
Tohru Dairi, Hideaki Oikawa, Hiroaki Toshima, Motoyoshi Noike, Chengwei Liu, Atsushi Minami Appl Environ Microbiol . 2013 Dec;79(23):7298-304. doi: 10.1128/AEM.02496-13.
We recently reported the function of paxD, which is involved in the paxilline (compound 1) biosynthetic gene cluster in Penicillium paxilli. Recombinant PaxD catalyzed a stepwise regular-type diprenylation at the 21 and 22 positions of compound 1 with dimethylallyl diphosphate (DMAPP) as the prenyl donor. In this study, atmD, which is located in the aflatrem (compound 2) biosynthetic gene cluster in Aspergillus flavus and encodes an enzyme with 32% amino acid identity to PaxD, was characterized using recombinant enzyme. When compound 1 and DMAPP were used as substrates, two major products and a trace of minor product were formed. The structures of the two major products were determined to be reversely monoprenylated compound 1 at either the 20 or 21 position. Because compound 2 and β-aflatrem (compound 3), both of which are compound 1-related compounds produced by A. flavus, have the same prenyl moiety at the 20 and 21 position, respectively, AtmD should catalyze the prenylation in compound 2 and 3 biosynthesis. More importantly and surprisingly, AtmD accepted paspaline (compound 4), which is an intermediate of compound 1 biosynthesis that has a structure similar to that of compound 1, and catalyzed a regular monoprenylation of compound 4 at either the 21 or 22 position, though the reverse prenylation was observed with compound 1. This suggests that fungal indole diterpene prenyltransferases have the potential to alter their position and regular/reverse specificities for prenylation and could be applicable for the synthesis of industrially useful 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 ╳
