Feigrisolide C
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-00907 |
| CAS | 313949-18-7 |
| Molecular Weight | 400.50 |
| Molecular Formula | C21H36O7 |
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Description
Feigrisolide C is a lactone produced by Streptomyces griseus.
Specification
| IUPAC Name | (1S,2S,5S,8R,9R,12S,14R)-8-hydroxy-5-[(2R)-2-hydroxybutyl]-2,9,12-trimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione |
| Canonical SMILES | CCC(CC1CCC(C(C(=O)OC(CC2CCC(O2)C(C(=O)O1)C)C)C)O)O |
| InChI | InChI=1S/C21H36O7/c1-5-15(22)11-17-6-8-18(23)13(3)20(24)26-12(2)10-16-7-9-19(27-16)14(4)21(25)28-17/h12-19,22-23H,5-11H2,1-4H3/t12-,13+,14-,15+,16+,17-,18+,19-/m0/s1 |
| InChI Key | HQBGZNNKSCTNKH-JWFKEXIPSA-N |
Properties
| Appearance | Powder |
Reference Reading
1. Bonactin and Feigrisolide C Inhibit Magnaporthe oryzae Triticum Fungus and Control Wheat Blast Disease
S M Fajle Rabby, Moutoshi Chakraborty, Dipali Rani Gupta, Mahfuzur Rahman, Sanjoy Kumar Paul, Nur Uddin Mahmud, Abdullah Al Mahbub Rahat, Ljupcho Jankuloski, Tofazzal Islam Plants (Basel). 2022 Aug 12;11(16):2108. doi: 10.3390/plants11162108.
Wheat blast caused by the Magnaporthe oryzaeTriticum (MoT) pathotype is one of the most damaging fungal diseases of wheat. During the screening of novel bioactive secondary metabolites, we observed two marine secondary metabolites, bonactin and feigrisolide C, extracted from the marine bacteria Streptomyces spp. (Act 8970 and ACT 7619), remarkably inhibited the hyphal growth of an MoT isolate BTJP 4 (5) in vitro. In a further study, we found that bonactin and feigrisolide C reduced the mycelial growth of this highly pathogenic isolate in a dose-dependent manner. Bonactin inhibited the mycelial development of BTJP 4 (5) more effectively than feigrisolide C, with minimal concentrations for inhibition being 0.005 and 0.025 µg/disk, respectively. In a potato dextrose agar (PDA) medium, these marine natural products greatly reduced conidia production in the mycelia. Further bioassays demonstrated that these secondary metabolites could inhibit the MoT conidia germination, triggered lysis, or conidia germinated with abnormally long branched germ tubes that formed atypical appressoria (low melanization) of BTJP 4 (5). Application of these natural products in a field experiment significantly protected wheat from blast disease and increased grain yield compared to the untreated control. As far as we are aware, this is the first report of bonactin and feigrisolide C that inhibited mycelial development, conidia production, conidial germination, and morphological modifications in the germinated conidia of an MoT isolate and suppressed wheat blast disease in vivo. To recommend these compounds as lead compounds or biopesticides for managing wheat blast, more research is needed with additional MoT isolates to identify their exact mode of action and efficacy of disease control in diverse field conditions.
2. Dinactin from a new producer, Streptomyces badius gz-8, and its antifungal activity against the rubber anthracnose fungus Colletotrichum gloeosporioides
Kai Zhang, Liushuang Gu, Yuefeng Zhang, Zhiqiang Liu, Xiaoyu Li Microbiol Res. 2020 Nov;240:126548. doi: 10.1016/j.micres.2020.126548. Epub 2020 Jul 6.
Colletotrichum gloeosporioides is a main cause of rubber anthracnose, which results in very large losses for the natural rubber industry. In this study, an actinomycete strain gz-8 was isolated and had strong antagonistic activity against C. gloeosporioides, with an inhibition rate of 72.5 %. Strain gz-8 was identified as Streptomyces badius. Three active compounds were separated from S. badius gz-8 and identified as feigrisolide B, feigrisolide C and dinactin according to the mass spectrometry and NMR-spectra results. In the three compounds, dinactin exhibited the best antifungal activity against C. gloeosporioides, with an EC50 value of 2.55 μg/mL, and its minimum inhibitory concentration was 44 μg/mL. Dinactin had broad inhibitory activities against nine other pathogenic fungi, and it also had an obvious control effect on rubber anthracnose comparable to that of chlorothalonil. Dinactin could inhibit the conidiogenesis and spore germination of C. gloeosporioides. This report will contribute to understanding the antifungal activity of dinactin against C. gloeosporioides.
3. Inhibitory Effects of Macrotetrolides from Streptomyces spp. On Zoosporogenesis and Motility of Peronosporomycete Zoospores Are Likely Linked with Enhanced ATPase Activity in Mitochondria
Md Tofazzal Islam, Hartmut Laatsch, Andreas von Tiedemann Front Microbiol. 2016 Nov 18;7:1824. doi: 10.3389/fmicb.2016.01824. eCollection 2016.
The release of zoospores from sporangia and motility of the released zoospores are critical in the disease cycle of the Peronosporomycetes that cause devastating diseases in plants, fishes, animals and humans. Disruption of any of these asexual life stages eliminates the possibility of pathogenesis. In the course of screening novel bioactive secondary metabolites, we found that extracts of some strains of marine Streptomyces spp. rapidly impaired motility and caused subsequent lysis of zoospores of the grapevine downy mildew pathogen Plasmopara viticola at 10 μg/ml. We tested a number of secondary metabolites previously isolated from these strains and found that macrotetrolide antibiotics such as nonactin, monactin, dinactin and trinactin, and nactic acids such as (+)-nonactic acid, (+)-homonactic acid, nonactic acid methyl ester, homonactic acid methyl ester, bonactin and feigrisolide C impaired motility and caused subsequent lysis of P. viticola zoospores in a dose- and time-dependent manners with dinactin being the most active compound (MIC 0.3 μg/ml). A cation channel-forming compound, gramicidin, and a carrier of monovalent cations, nigericin also showed similar biological activities. Among all 12 compounds tested, gramicidin most potently arrested the motility of zoospores at concentrations starting from 0.1 μg/ml. All macrotetrolide antibiotics also displayed similar motility impairing activities against P. viticola, Phytophthora capsici, and Aphanomyces cochlioides zoospores indicating non-specific biological effects of these compounds toward peronosporomyctes. Furthermore, macrotetrolide antibiotics and gramicidin also markedly suppressed the release of zoospores from sporangia of P. viticola in a dose-dependent manner. As macrotetrolide antibiotics and gramicidin are known as enhancers of mitochondrial ATPase activity, inhibition of zoosporogenesis and motility of zoospores by these compounds are likely linked with hydrolysis of ATP through enhanced ATPase activity in mitochondria. This is the first report on motility inhibitory and lytic activities of macrotetrolide antibiotics and nactic acids against the zoospores of peronosporomycete phytopathogens.
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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 ╳
