Dactylfungin B

Dactylfungin B

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Dactylfungin B
Category Antibiotics
Catalog number BBF-00779
CAS 146935-36-6
Molecular Weight 700.94
Molecular Formula C41H64O9

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Description

Dactylfungin is an antifungal antibiotic produced by Dactylaria parvispora D500, and two components A and B are separated. A and B have no antibacterial activity. B is resistant to individual Candida and Saccharomyces fungi (MIC 3.1-6.2 μg/mL), and has a weak effect on important pathogenic fungi such as Candida albicans (MIC >100μg/mL).

Specification

Synonyms 4H-Pyran-4-one, 3-(4-deoxy-beta-xylo-hexopyranosyl)-2-hydroxy-6-(2-hydroxy-7-(hydroxymethyl)-1,1,5,9,11,13,17,19-octamethyl-3,5,13,15,17-heneicosapentaenyl)-
Storage Store at -20°C
IUPAC Name 3-((2S,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2-hydroxy-6-((4E,6E,14E,16E,18E)-3-hydroxy-8-(hydroxymethyl)-2,6,10,12,14,18,20-heptamethyldocosa-4,6,14,16,18-pentaen-2-yl)-4H-pyran-4-one
Canonical SMILES CCC(C)\C=C(/C)\C=C\C=C(/C)\CC(C)CC(C)CC(CO)\C=C(/C)\C=C\C(O)C(C)(C)C1=CC(=O)C(=C(O)O1)[C@@H]2O[C@H](CO)C[C@H](O)[C@H]2O
InChI InChI=1S/C41H64O9/c1-10-25(2)16-26(3)12-11-13-27(4)17-29(6)18-30(7)20-31(23-42)19-28(5)14-15-35(46)41(8,9)36-22-33(44)37(40(48)50-36)39-38(47)34(45)21-32(24-43)49-39/h11-16,19,22,25,29-32,34-35,38-39,42-43,45-48H,10,17-18,20-21,23-24H2,1-9H3/b12-11+,15-14+,26-16+,27-13+,28-19+/t25?,29?,30?,31?,32-,34-,35?,38+,39-/m0/s1
InChI Key XBOURDXDRVZWJC-CKGFFVAASA-N

Properties

Antibiotic Activity Spectrum fungi
Melting Point 173-174°C(dec.)
Solubility Soluble in Methanol, Chloroform, DMSO

Reference Reading

1. Dactylfungins, novel antifungal antibiotics produced by Dactylaria parvispora
J Xaio, S Kumazawa, N Yoshikawa, T Mikawa, Y Sato J Antibiot (Tokyo). 1993 Jan;46(1):48-55. doi: 10.7164/antibiotics.46.48.
Novel antifungal antibiotics, designated as dactylfungins A (1) and B (3), were isolated from the culture broth of Dactylaria parvispora D500. Dactylfungins A and B were found to be new substances containing an alpha-pyrone and a gamma-pyrone ring, respectively, which conjoined with a polyalcohol moiety and a long side chain, based on NMR spectral analyses. The antibiotics were active against Candida pseudotropicalis and other fungi, with an MIC value at less than 10 micrograms/ml.

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