Deoxybrevianamide E
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| Category | Others |
| Catalog number | BBF-04600 |
| CAS | 34610-68-9 |
| Molecular Weight | 351.44 |
| Molecular Formula | C21H25N3O2 |
| Purity | >99% by HPLC |
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Description
An alkaloidal diketopiperazine derived from tryptophan and proline, isolated from aspergillus and penicillium species.
Specification
| Synonyms | L-Prolyl-2-(1,1-dimethylallyl)-L-tryptophan anhydride; (3S,8aS)-3-[[2-(1,1-Dimethyl-2-propen-1-yl)-1H-indol-3-yl]methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione; Prolyl-2-(1,1-dimethylallyl)tryptophyldiketopiperazine; (3S-trans)-3-[[2-(1,1-Dimethyl-2-propenyl)-1H-indol-3-yl]methyl]hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione; Desoxybrevianamide E; cyclo-2-(1,1-dimethylallyl)-L-tryptophyl-L-proline; cyclo-L-prolyl-2-(1,1-dimethylallyl)-L-tryptophan |
| Storage | Store at -20°C |
| IUPAC Name | (3S,8aS)-3-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione |
| Canonical SMILES | CC(C)(C=C)C1=C(C2=CC=CC=C2N1)CC3C(=O)N4CCCC4C(=O)N3 |
| InChI | InChI=1S/C21H25N3O2/c1-4-21(2,3)18-14(13-8-5-6-9-15(13)22-18)12-16-20(26)24-11-7-10-17(24)19(25)23-16/h4-6,8-9,16-17,22H,1,7,10-12H2,2-3H3,(H,23,25)/t16-,17-/m0/s1 |
| InChI Key | KUGNSEAHJVSMAJ-IRXDYDNUSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Off-white Solid |
| Boiling Point | 619.9±55.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E
Sachiko Tsukamoto, Takashi Nakahara, Hideharu Umaoka, Hikaru Kato, Robert M Williams, Yuichi Nakamura, Jennifer M Finefield Tetrahedron Lett . 2011 Dec 21;52(51):6923-6926. doi: 10.1016/j.tetlet.2011.10.065.
Two reverse-prenylated indole alkaloids, deoxybrevianamide E and 6-hydroxydeoxybrevianamide E, are proposed as biosynthetic precursors for advanced metabolites isolated from the marine-derived Aspergillus sp. In order to uncover the role of the alkaloids in the biosynthetic pathway, the feeding experiments of the [(13)C](2)-[(15)N]-labeled deoxybrevianamide E and 6-hydroxydeoxybrevianamide E were performed to afford the metabolites, which were produced by oxidation and successive pinacol-type rearrangement of the isoprenyl units.
2. The anti-TMV potency of the tobacco-derived fungus Aspergillus versicolor and its active alkaloids, as anti-TMV activity inhibitors
Jia-Meng Dai, Guang-Yu Yang, Du Gang, Zhen-Jie Li, Jian-Duo Zhang, Dong Miao, Xue-Mei Li, Hai-Ying Yang, Yin-Ke Li, Jin Wang, Qi-Li Mi, Qiu-Fen Hu Phytochemistry . 2023 Jan;205:113485. doi: 10.1016/j.phytochem.2022.113485.
Nicotiana tabacum (tobacco) has attracted interest as one of the most economically important industrial crops widely cultivated in China, whose dried leaves are popularly consumed medicinally and recreationally by human societies. In this study, five undescribed alkaloids derivatives, isoaspergillines A-E, together with eight known alkaloids, notoamide D, (1R,4S)-4-benzyl-1-isopropyl-2,4-dihydro-1H-pyrazino-[2,1-b]quinazoline-3,6-dione, protuboxepin K, notoamide C, notoamide M, deoxybrevianamide E, cyclo (D-Pro-L-Trp), and versicolamide B, were obtained from the culture of the Nicotiana tabacum-derived fungus Aspergillus versicolor. Their structures were mainly elucidated through comprehensive analyses of spectroscopic data. Bioactivity evaluation of all isolated compounds revealed that isoaspergilline A and notoamide M exhibited anti-TMV activities with IC50values of 20.0 and 22.8 μM, respectively. Molecular docking suggested that isoaspergilline A and notoamide M were well located into the active site of anti-TMV by interacting with SER138, SER143, and ASN73 residues. This study enlightens the therapeutic potential of the endophytic fungus A. versicolor and it is helpful to find undescribed anti-TMV activity inhibitors, as well as searching for new anti-TMV candidates from natural sources.
3. Biomimetic Diels-Alder cyclizations for the construction of the brevianamide, paraherquamide, sclerotamide, asperparaline and VM55599 ring systems
J F Sanz-Cervera, R M Williams, J A Marco, K M Halligan, F Sancenón Bioorg Med Chem . 1998 Aug;6(8):1233-41. doi: 10.1016/s0968-0896(98)00102-3.
A potentially bio-mimetic Diels-Alder cyclization to construct the bicyclo[2.2.2] ring system common to the paraherquamides, marcfortines, sclerotamides, brevianamides, VM55599, and asperparaline is reported. Epi-deoxybrevianamide E (22) is converted into the corresponding lactim ether (23) and then oxidized with DDQ to provide an azadiene (24) which is tautomerized in the presence of base to azadiene 25 which, spontaneously cyclizes to give a 2:1 mixture of cycloadducts 26 and 27. These cycloadducts are each in turn, converted into D,L-C-19-epi-brevianamide A (20) and D,L-brevianamide B (6). The stereochemical implications of the [4 + 2] cycloaddition is discussed in the context of a working hypothesis on the biosynthesis of this family, particularly VM55599.
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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 ╳
