YM-202204
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| Category | Antibiotics |
| Catalog number | BBF-01559 |
| CAS | |
| Molecular Weight | 646.8 |
| Molecular Formula | C37H58O9 |
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Description
YM-202204 is an antifungal antibiotic isolated from the culture broth of marine fungus Phoma sp. Q60596. It exhibited potent antifungal activities against Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus, and also inhibited glycosyl-phosphatidyl-inositol (GPI)-anchoring in yeast cells.
Specification
| Synonyms | 6'-(2,8-Dihydroxy-1,5,7,9,13,15,17-heptamethyl-nonadeca-3,5,11,13-tetraenyl)-3,4,4'-trihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-[2,3']bipyranyl-2'-one |
| IUPAC Name | 6-[(4E,6E,12E,14E)-3,9-dihydroxy-6,8,10,14,16,18-hexamethylicosa-4,6,12,14-tetraen-2-yl]-3-[3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxypyran-2-one |
| Canonical SMILES | CCC(C)CC(C)C=C(C)C=CCC(C)C(C(C)C=C(C)C=CC(C(C)C1=CC(=C(C(=O)O1)C2C(C(CC(O2)CO)O)O)O)O)O |
| InChI | InChI=1S/C37H58O9/c1-9-21(2)15-24(5)16-22(3)11-10-12-25(6)34(42)26(7)17-23(4)13-14-29(39)27(8)32-19-30(40)33(37(44)46-32)36-35(43)31(41)18-28(20-38)45-36/h10-11,13-14,16-17,19,21,24-29,31,34-36,38-43H,9,12,15,18,20H2,1-8H3/b11-10+,14-13+,22-16+,23-17+ |
| InChI Key | YGLKXOYPYOHGNS-YKCFUFIQSA-N |
Properties
| Appearance | Yellow Thick Liquid |
| Antibiotic Activity Spectrum | fungi; yeast |
Reference Reading
1. YM-202204, a new antifungal antibiotic produced by marine fungus Phoma sp
Koji Nagai, Kazuma Kamigiri, Hisao Matsumoto, Yasuhiro Kawano, Masakazu Yamaoka, Hitoshi Shimoi, Masato Watanabe, Kenichi Suzuki J Antibiot (Tokyo). 2002 Dec;55(12):1036-41. doi: 10.7164/antibiotics.55.1036.
A new antifungal antibiotic, YM-202204 (1), was found in the culture broth of marine fungus Phoma sp. Q60596. The structure of 1 was determined by several spectroscopic experiments as a new lactone compound. This antibiotic exhibited potent antifungal activities against Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus, and also inhibited glycosyl-phosphatidyl-inositol (GPI)-anchoring in yeast cells.
2. Bioprospecting Sponge-Associated Microbes for Antimicrobial Compounds
Anak Agung Gede Indraningrat, Hauke Smidt, Detmer Sipkema Mar Drugs. 2016 May 2;14(5):87. doi: 10.3390/md14050087.
Sponges are the most prolific marine organisms with respect to their arsenal of bioactive compounds including antimicrobials. However, the majority of these substances are probably not produced by the sponge itself, but rather by bacteria or fungi that are associated with their host. This review for the first time provides a comprehensive overview of antimicrobial compounds that are known to be produced by sponge-associated microbes. We discuss the current state-of-the-art by grouping the bioactive compounds produced by sponge-associated microorganisms in four categories: antiviral, antibacterial, antifungal and antiprotozoal compounds. Based on in vitro activity tests, identified targets of potent antimicrobial substances derived from sponge-associated microbes include: human immunodeficiency virus 1 (HIV-1) (2-undecyl-4-quinolone, sorbicillactone A and chartarutine B); influenza A (H1N1) virus (truncateol M); nosocomial Gram positive bacteria (thiopeptide YM-266183, YM-266184, mayamycin and kocurin); Escherichia coli (sydonic acid), Chlamydia trachomatis (naphthacene glycoside SF2446A2); Plasmodium spp. (manzamine A and quinolone 1); Leishmania donovani (manzamine A and valinomycin); Trypanosoma brucei (valinomycin and staurosporine); Candida albicans and dermatophytic fungi (saadamycin, 5,7-dimethoxy-4-p-methoxylphenylcoumarin and YM-202204). Thirty-five bacterial and 12 fungal genera associated with sponges that produce antimicrobials were identified, with Streptomyces, Pseudovibrio, Bacillus, Aspergillus and Penicillium as the prominent producers of antimicrobial compounds. Furthemore culture-independent approaches to more comprehensively exploit the genetic richness of antimicrobial compound-producing pathways from sponge-associated bacteria are addressed.
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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 ╳
