Haliangicin D
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| Category | Antibiotics |
| Catalog number | BBF-01307 |
| 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 (2E,4E,6E,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-YBIVBRJXSA-N |
Properties
| Appearance | Pale Yellow Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Solubility | Soluble in Methanol |
Reference Reading
1. Heterologous Production of the Marine Myxobacterial Antibiotic Haliangicin and Its Unnatural Analogues Generated by Engineering of the Biochemical Pathway
Yuwei Sun, Zhiyang Feng, Tomohiko Tomura, Akira Suzuki, Seishi Miyano, Takashi Tsuge, Hitoshi Mori, Joo-Won Suh, Takashi Iizuka, Ryosuke Fudou, Makoto Ojika Sci Rep. 2016 Feb 26;6:22091. doi: 10.1038/srep22091.
Despite their fastidious nature, marine myxobacteria have considerable genetic potential to produce novel secondary metabolites. The marine myxobacterium Haliangium ochraceum SMP-2 produces the antifungal polyketide haliangicin (1), but its productivity is unsatisfactory. The biosynthetic gene cluster hli (47.8 kbp) associated with 1 was identified and heterologously expressed in Myxococcus xanthus to permit the production of 1 with high efficiency (tenfold greater amount and threefold faster in growth speed compared with the original producer), as well as the generation of bioactive unnatural analogues of 1 through gene manipulation. A unique acyl-CoA dehydrogenase was found to catalyse an unusual γ,δ-dehydrogenation of the diketide starter unit, leading to the formation of the terminal alkene moiety of 1. Biological evaluation of the analogues obtained through this study revealed that their bioactivities (anti-oomycete and cytotoxic activities) can be modified by manipulating the vinyl epoxide at the terminus opposite the β-methoxyacrylate pharmacophore.
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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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 ╳
