FD-838
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-04405 |
| CAS | 110341-78-1 |
| Molecular Weight | 411.41 |
| Molecular Formula | C22H21NO7 |
| Purity | ≥98% |
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Description
FD-838 is produced from the mycelia of the basidiomycete Hericium erinaceum. FD-838 inhibits the growth of two plant fungal pathogens Botrytis cinerea and Glomerella cingulata. It has anti-tumor activity.
Specification
| Synonyms | Azaspirofuran A; Antibiotic FD-838; (5R,8S,9R)-2-(5-Ethyl-2-furyl)-3-methyl-8-benzoyl-8-methoxy-9-hydroxy-1-oxa-7-azaspiro[4.4]nona-2-ene-4,6-dione; 1-Oxa-7-azaspiro[4.4]non-2-ene-4,6-dione, 8-benzoyl-2-(5-ethyl-2-furanyl)-9-hydroxy-8-methoxy-3-methyl-, (5S,8S,9R)- |
| Storage | Store at -20°C |
| IUPAC Name | (5S,8S,9R)-8-benzoyl-2-(5-ethylfuran-2-yl)-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione |
| Canonical SMILES | CCC1=CC=C(O1)C2=C(C(=O)C3(O2)C(C(NC3=O)(C(=O)C4=CC=CC=C4)OC)O)C |
| InChI | InChI=1S/C22H21NO7/c1-4-14-10-11-15(29-14)16-12(2)17(24)21(30-16)19(26)22(28-3,23-20(21)27)18(25)13-8-6-5-7-9-13/h5-11,19,26H,4H2,1-3H3,(H,23,27)/t19-,21-,22-/m1/s1 |
| InChI Key | PXIIDWGMSCTXAQ-CEMLEFRQSA-N |
Properties
| Appearance | Pale Green Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 665.1±55.0°C at 760 mmHg |
| Melting Point | 98-99°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform, Benzene; Fairly soluble in Ether, Hexane |
Reference Reading
1. Total Synthesis of (-)-FD-838 and (-)-Cephalimysin A
Deokhee Jo, Sunkyu Han Org Lett. 2019 Aug 2;21(15):6045-6049. doi: 10.1021/acs.orglett.9b02203. Epub 2019 Jul 22.
We completed a nine-step total synthesis of (-)-FD-838 and (-)-cephalimysin A. Our synthesis features a biogenetically guided assembly of the highly oxidized spirocyclic core by Snider-type tandem epoxidations of the chiral substrate derived from an amino acid derivative. Our synthetic approach provides a general and versatile solution to access spirocyclic PKS-NRPS-based secondary fungal metabolites.
2. Cytotoxic compounds from the marine-derived fungus Aspergillus sp. recovered from the sediments of the Brazilian coast
Natália N Saraiva, Bárbara S F Rodrigues, Paula C Jimenez, Larissa A Guimarães, Maria C M Torres, Edson Rodrigues-Filho, Ludwig H Pfenning, Lucas M Abreu, Jair Mafezoli, Marcos C de Mattos, Letícia V Costa-Lotufo, Maria da Conceição F de Oliveira Nat Prod Res. 2015;29(16):1545-50. doi: 10.1080/14786419.2014.987772. Epub 2014 Dec 23.
A fungal strain of Aspergillus sp. (BRF 030) was isolated from the sediments collected in the northeast coast of Brazil, and the cytotoxic activity of its secondary metabolites was investigated against HCT-116 tumour cell line. The cytotoxicity-guided fractionation of the extracts from this fungus cultured in potato-dextrose-sea water for 14 days at room temperature yielded the hetero-spirocyclic γ-lactams pseurotin A (1), pseurotin D (2) and pseurotin FD-838 (7), the alkaloids fumitremorgin C (5), 12,13-dihydroxy fumitremorgin C (6), methylsulochrin (4) and bis(dethio)bis(methylthio)gliotoxin (3). Among them, fumitremorgin C (5) and 12,13-dihydroxy fumitremorgin C (6) were the most active. The cytotoxic activities of the extracts from Aspergillus sp. grown from 7 to 28 days were investigated, and they were associated with the kinetic production of the compounds. The most active extracts (14 and 21 days) were those with the highest relative concentrations of the compounds fumitremorgin C (5) and 12,13-dihydroxy fumitremorgin C (6).
3. Two New Spiro-Heterocyclic γ-Lactams from A Marine-Derived Aspergillus fumigatus Strain CUGBMF170049
Xiuli Xu, Jiahui Han, Yanan Wang, Rui Lin, Haijin Yang, Jiangpeng Li, Shangzhu Wei, Steven W Polyak, Fuhang Song Mar Drugs. 2019 May 14;17(5):289. doi: 10.3390/md17050289.
Two new spiro-heterocyclic γ-lactam derivatives, cephalimysins M (1) and N (2), were isolated from the fermentation cultures of the marine-derived fungus Aspergillus fumigatus CUGBMF17018. Two known analogues, pseurotin A (3) and FD-838 (4), as well as four previously reported helvolic acid derivatives, 16-O-propionyl-16-O-deacetylhelvolic acid (5), 6-O-propionyl-6-O-deacetylhelvolic acid (6), helvolic acid (7), and 1,2-dihydrohelvolic acid (8) were also identified. One-dimensional (1D), two-dimensional (2D) NMR, HRMS, and circular dichroism spectral analysis characterized the structures of the isolated 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 ╳
