ES-242-2
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| Category | Antibiotics |
| Catalog number | BBF-02819 |
| CAS | |
| Molecular Weight | 662.68 |
| Molecular Formula | C36H38O12 |
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Description
ES 242-2 is produced by the strain of Verticillium sp. SPC-15898. It inhibited the [3H] thienyl cyclohexypiperidine ([3H] TCP) binding membrane of rat cell process by IC50 of 2.9 μmol/L.
Specification
| Synonyms | (aR)-4,4'-Diacetoxy-3,3'-dimethyl-7,7',9,9'-tetramethoxy-3,3',4,4'-tetrahydro-5,5'-bi[1H-naphtho[2,3-c]pyran]-10,10'-diol |
| IUPAC Name | [5-(4-acetyloxy-10-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl)-10-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-4-yl] acetate |
| Canonical SMILES | CC1C(C2=C(C3=C(C(=CC(=C3)OC)OC)C(=C2CO1)O)C4=C5C(C(OCC5=C(C6=C4C=C(C=C6OC)OC)O)C)OC(=O)C)OC(=O)C |
| InChI | InChI=1S/C36H38O12/c1-15-35(47-17(3)37)31-23(13-45-15)33(39)27-21(9-19(41-5)11-25(27)43-7)29(31)30-22-10-20(42-6)12-26(44-8)28(22)34(40)24-14-46-16(2)36(32(24)30)48-18(4)38/h9-12,15-16,35-36,39-40H,13-14H2,1-8H3 |
| InChI Key | PEDZYCDSAWVMRN-UHFFFAOYSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Melting Point | 161-162°C |
Reference Reading
1. ES-242-2, -3, -4, -5, -6, -7, and -8, novel bioxanthracenes produced by Verticillium sp., which act on the N-methyl-D-aspartate receptor
S Toki, K Ando, I Kawamoto, H Sano, M Yoshida, Y Matsuda J Antibiot (Tokyo). 1992 Jul;45(7):1047-54. doi: 10.7164/antibiotics.45.1047.
Verticillium sp. SPC-15898 was found to produce novel metabolites, designated ES-242-2-(-)8, which were structurally related to ES-242-1. These compounds were isolated from the culture broth and the physico-chemical and biochemical properties were examined. ES-242-2-(-)8 inhibited [3H]thienyl cyclohexypiperidine ([3H]TCP) binding to rat crude synaptic membranes (CSM) with IC50 values of 0.116, 2.9, ca. 2.9, 25.3, 1.0, 59, 24, and 13 microM, respectively. None of these compounds showed inhibitory effects against the binding of [3H]kainate to its receptor, which is another subtype of the excitatory amino acid receptor.
2. ES-242 derivatives and cycloheptapeptides from Cordyceps sp. strains BCC 16173 and BCC 16176
Masahiko Isaka, Urarat Srisanoh, Nattapat Lartpornmatulee, Tanapong Boonruangprapa J Nat Prod. 2007 Oct;70(10):1601-4. doi: 10.1021/np070357h. Epub 2007 Sep 22.
Five new ES-242 analogues ( 1- 5) were isolated together with nine known compounds ( 6- 14) from the insect pathogenic fungus Cordyceps sp. BCC 16173. A closely related strain, BCC 16176, provided cordyheptapeptide A ( 15) and small amount of its new analogue, cordyheptapeptide B ( 16), along with known ES-242s. Structures of the new bioxanthracenes, 1- 5, were determined to be 6'- O-desmethyl analogues of 6 (ES-242-4), 8, 9 (ES-242-2), 12, and 13, respectively, primarily by spectroscopic analyses. Cordyheptapeptide B ( 16) has an N-methyl- l-phenylalanine residue instead of the N-methyl- l-tyrosine in 15.
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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 ╳
