Deflectin

A deflectin is one of a family of antibiotic chemicals produced by Aspergillus deflectus which contain a 6H-furo[2,3-h]-2-benzopyran-6,8(6aH)-dione core.

Deflectin
Identifiers
3D model (JSmol)
ChEMBL
  • 1a: InChI=1S/C21H24O5/c1-4-5-6-7-8-9-16(22)18-19-15-12-25-13(2)10-14(15)11-17(23)21(19,3)26-20(18)24/h10-12H,4-9H2,1-3H3/t21-/m0/s1
    Key: YNVKQPJBOAUYIJ-NRFANRHFSA-N
  • 1b: InChI=1S/C24H30O5/c1-4-5-6-7-8-9-10-11-12-19(25)21-22-18-15-28-16(2)13-17(18)14-20(26)24(22,3)29-23(21)27/h13-15H,4-12H2,1-3H3/t24-/m0/s1
    Key: FKBCHWDBWGUJBS-DEOSSOPVSA-N
  • 2b: InChI=1S/C26H34O5/c1-5-6-7-8-9-10-11-12-13-17(2)24(28)22-23-20-16-30-18(3)14-19(20)15-21(27)26(23,4)31-25(22)29/h14-17H,5-13H2,1-4H3/t17-,26-/m0/s1
    Key: VWGYSDWIZCHBOH-QLXKLKPCSA-N
  • 1a: CCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)[C@@]2(OC1=O)C)C
  • 1b: CCCCCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)[C@@]2(OC1=O)C)C
  • 2b: CCCCCCCCCC[C@H](C)C(=O)C1=C2C3=COC(=CC3=CC(=O)[C@@]2(OC1=O)C)C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Deflectins are yellow coloured crystalline substances when pure. They react with ammonia, by replacing an oxygen atom in the six-membered ring with an NH group. They are weak acids. On adding a strong base to an alcoholic solution of deflectin, it show a red colour for a short time.[1] Deflectin 1a contains a 1-oxooctyl side chain. It has a melting point of 161 °C. Deflectin 1b contains a ten carbon side chain and melts at 152 °C. Deflectin 1c has a 12-atom side chain and melts at 141 °C.[1]

Deflectin 2a melts at 122 °C. It has a 10 carbon atom side chain with a 2-methyl branch. Deflectin 2b is similar but the side chain is 2 atoms longer. It melts at 111 °C.[2]

Chemical structures
Deflectin 1a Deflectin 1b Deflectin 1c Deflectin 2a Deflectin 2b

References
  1. Anke, H.; Kremmer, T.; Ho..fle, G. (August 1981). "Deflectins, New Antimicrobial Azaphilones From Aspergillus deflectus". The Journal of Antibiotics. 34 (8): 923–928. doi:10.7164/antibiotics.34.923. PMID 7319924.
  2. Bycroft, Barrie W. (1987). Dictionary of Antibiotics & Related Substances. CRC Press. p. 258. ISBN 9780412254505.
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