ES-242-4

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Category Antibiotics
Catalog number BBF-02821
CAS
Molecular Weight 578.61
Molecular Formula C32H34O10

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Description

ES 242-4 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 25μmol/L.

Specification

Synonyms (aS)-3,3'-Dimethyl-7,7',9,9'-tetramethoxy-3,3',4,4'-tetrahydro-5,5'-bi[1H-naphtho[2,3-c]pyran]-4,4',10,10'-tetraol
IUPAC Name 5-(4,10-dihydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl)-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-4,10-diol
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)O)O
InChI InChI=1S/C32H34O10/c1-13-29(33)27-19(11-41-13)31(35)23-17(7-15(37-3)9-21(23)39-5)25(27)26-18-8-16(38-4)10-22(40-6)24(18)32(36)20-12-42-14(2)30(34)28(20)26/h7-10,13-14,29-30,33-36H,11-12H2,1-6H3
InChI Key AVAQRWVGWWNBIN-UHFFFAOYSA-N

Properties

Appearance Colorless Acicular Crystal
Melting Point 184-185°C

Reference Reading

1. 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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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