Haliangicin B

Haliangicin B

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Category Antibiotics
Catalog number BBF-01305
CAS
Molecular Weight 376.49
Molecular Formula C22H32O5

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Description

It is produced by the strain of Haliangium luteum AJ-13395, H. ochraceum. It is similar to amphotericin B with anti-filamentous fungi activity (MIC 0.1-12.5 μg/mL), and it also has effect on oomycetes, but has no antibacterial activity. The antifungal activity of cis-trans isomer is similar, the activity of Haliangicin B and C is weaker than Haliangicin A, and the activity of Haliangicin D is weakest.

Specification

IUPAC Name methyl (2Z,4Z,6Z,8E,10R)-11-[(2S,3S)-3-ethenyl-2-methyloxiran-2-yl]-3,4-dimethoxy-6,9,10-trimethylundeca-2,4,6,8-tetraenoate
Canonical SMILES CC(CC1(C(O1)C=C)C)C(=CC=C(C)C=C(C(=CC(=O)OC)OC)OC)C
InChI InChI=1S/C22H32O5/c1-9-20-22(5,27-20)14-17(4)16(3)11-10-15(2)12-18(24-6)19(25-7)13-21(23)26-8/h9-13,17,20H,1,14H2,2-8H3/b15-10-,16-11+,18-12-,19-13-/t17-,20+,22+/m1/s1
InChI Key XIKGETOZQXNXHV-FBPBFTCHSA-N

Properties

Appearance Pale Yellow Oily Matter
Antibiotic Activity Spectrum Fungi
Solubility Soluble in Methanol

Reference Reading

1. Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 1. Fermentation and biological characteristics
R Fudou, T Iizuka, S Yamanaka J Antibiot (Tokyo). 2001 Feb;54(2):149-52. doi: 10.7164/antibiotics.54.149.
Haliangicin, a novel beta-methoxyacrylate antibiotic with a conjugated tetraene moiety, was isolated from the culture broth of a marine myxobacterium. A bacterium tentatively named as Haliangium luteum required 2-3% NaCl for the growth and production of haliangicin. Haliangicin inhibits the growth of a wide spectrum of fungi but was inactive against bacteria. In mitochondrial respiratory chains, haliangicin interfered the electron flow within the cytochrome b-c1 segment.
2. New haliangicin isomers, potent antifungal metabolites produced by a marine myxobacterium
Bangi A Kundim, Yu Itou, Youji Sakagami, Ryosuke Fudou, Takashi Iizuka, Shigeru Yamanaka, Makoto Ojika J Antibiot (Tokyo). 2003 Jul;56(7):630-8. doi: 10.7164/antibiotics.56.630.
Haliangicin is a beta-methoxyacrylate-type polyene antibiotic isolated from the unique marine myxobacterium Haliangium ochraceum. A further investigation of the extract of this microorganism has resulted in the isolation of haliangicin as well as its geometrical isomers. The configuration of the epoxide in haliangicin, which was unknown previously, was determined in this study. The planar structures with partial stereochemistry of these isomers were elucidated by spectroscopic analyses. The major isomer, cis-haliangicin, is a cis isomer of the epoxide portion of haliangicin. Haliangicins B approximately D are geometrical isomers of the polyene moiety, and present as an inseparable mixture of cis and trans epoxide isomers. Their antifungal activities were also evaluated in comparison with haliangicin.

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