Guanidylfungin A
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| Category | Antibiotics |
| Catalog number | BBF-01297 |
| CAS | 94116-22-0 |
| Molecular Weight | 1130.45 |
| Molecular Formula | C58H103N3O18 |
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Description
It is produced by the strain of Streptomyces hygroscopicus 662. It is a macrolide antibiotic. It has weak anti-gram-negative bacterial and fungal activity.
Specification
| IUPAC Name | 3-oxo-3-(((10Z,20E)-3,5,7,9,23,25,27,31,33,34,35-undecahydroxy-8,10,14,18,22,26,30-heptamethyl-15-((E)-4-methyl-10-(3-methylguanidino)dec-4-en-2-yl)-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,20-dien-19-yl)oxy)propanoic acid |
Properties
| Appearance | White Fine Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria; Fungi |
| Boiling Point | 1186.9 °C at 760 mmHg |
| Melting Point | >155 °C (dec.) |
| Density | 1.27 g/cm3 |
| Solubility | Insoluble in Water |
Reference Reading
1. Studies on new antifungal antibiotics, guanidylfungins A and B. II. Structure elucidation and biosynthesis
K Takesako, T Beppu J Antibiot (Tokyo). 1984 Oct;37(10):1170-86. doi: 10.7164/antibiotics.37.1170.
The structures of guanidylfungins A and B were elucidated from the physico-chemical properties of these compounds and the structures of the degradation products by ozonolysis and periodate oxidation. The guanidylfungins consist of a 36-membered polyhydroxyl lactone ring, a guanidine and a monoester of malonic acid. The labelling experiments with sodium [1-13C]acetate and sodium [1-13C]propionate revealed that twelve units of acetate and nine of propionate were incorporated into the molecule of guanidylfungin A.
2. Antifungal Substances from Streptomyces sp. A3265 Antagonistic to Plant Pathogenic Fungi
Nguyen Van Minh, E-Eum Woo, Ji-Yul Kim, Dae-Won Kim, Byung Soon Hwang, Yoon-Ju Lee, In-Kyoung Lee, Bong-Sik Yun Mycobiology. 2015 Sep;43(3):333-8. doi: 10.5941/MYCO.2015.43.3.333. Epub 2015 Sep 30.
In a previous study, we identified a Streptomyces sp., A3265, as exhibiting potent antifungal activity against various plant pathogenic fungi, including Botrytis cinerea, Colletotrichum gloeosporioides, and Rhizoctonia solani. This strain also exhibited a biocontrolling effect against ginseng root rot and damping-off disease, common diseases of ginseng and other crops. In this study, we isolated two antifungal substances responsible for this biocontrolling effect via Diaion HP-20 and Sephadex LH-20 column chromatography, medium pressure liquid chromatography, and high-performance liquid chromatography. These compounds were identified as guanidylfungin A and methyl guanidylfungin A by spectroscopic methods. These compounds exhibited potent antimicrobial activity against various plant pathogenic fungi as well as against bacteria.
3. Demalonyl derivatives of guanidylfungin A and copiamycin: their synthesis and antifungal activity
K Takesako, T Beppu, T Nakamura, A Obayashi J Antibiot (Tokyo). 1985 Oct;38(10):1363-70. doi: 10.7164/antibiotics.38.1363.
Guanidylfungin A was chemically modified by alkylation, reduction and/or demalonylation. Demalonylmethylguanidylfungin A became soluble in water and showed approximately eight-fold higher activity against fungi and Gram-positive bacteria than guanidylfungin A along with strongly fungicidal effect. Similarly, copiamycin was converted to demalonylmethylcopiamycin, which also showed higher antifungal activity than copiamycin itself.
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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 ╳
