Strobilurin B
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| Category | Others |
| Catalog number | BBF-03079 |
| CAS | 65105-52-4 |
| Molecular Weight | 322.78 |
| Molecular Formula | C17H19ClO4 |
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Description
Strobilurin B is a compound produced by Strobilurus tenacellus No. 21602. It has the effect of anti-filamentous fungi and yeast, but not against bacteria. It can inhibit the synthesis of protein, RNA and DNA.
Specification
| IUPAC Name | methyl (2E,3Z,5E)-6-(4-chloro-3-methoxyphenyl)-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate |
| Canonical SMILES | CC(=CC=CC1=CC(=C(C=C1)Cl)OC)C(=COC)C(=O)OC |
| InChI | InChI=1S/C17H19ClO4/c1-12(14(11-20-2)17(19)22-4)6-5-7-13-8-9-15(18)16(10-13)21-3/h5-11H,1-4H3/b7-5+,12-6-,14-11+ |
| InChI Key | ZDIQYKMDNQULMX-PJUQCDRASA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | fungi; yeast |
| Boiling Point | 474.3°C at 760 mmHg |
| Melting Point | 95°C |
| Density | 1.158 g/cm3 |
Reference Reading
1. Bioactive metabolites from cultures of basidiomycete Favolaschia tonkinensis
Jittra Kornsakulkarn, Chawanee Thongpanchang, Rittikorn Chainoy, Wilunda Choowong, Sutichai Nithithanasilp, Tienthong Thongpanchang J Nat Prod. 2010 Apr 23;73(4):759-62. doi: 10.1021/np900777r.
Two strobilurins, 9-methoxystrobilurin B (1) and 9-methoxystrobilurin G (2), two monochlorinated 2,3-dihydro-1-benzoxepin derivatives, 3 and 4a, and butenolide 5, together with four known compounds, strobilurin B, 9-methoxystrobilurin A, and oudemansins A and B, were isolated from culture BCC 18689 of the fungus Favolaschia tonkinensis. 9-Methoxystrobilurins A, B (1), and G (2) and oudemansins A and B exhibited antimalarial, antifungal, and cytotoxic activities, while compounds 3, 4a, and 5 displayed only cytotoxic activity.
2. Investigations into the biosynthesis of the antifungal strobilurins
Zafar Iqbal, Li-Chen Han, Anna M Soares-Sello, Risa Nofiani, Gerald Thormann, Axel Zeeck, Russell J Cox, Christine L Willis, Thomas J Simpson Org Biomol Chem. 2018 Aug 1;16(30):5524-5532. doi: 10.1039/c8ob00608c.
The strobilurins are important antifungal metabolites isolated from a number of basidiomycetes and have been valuable leads for the development of commercially important fungicides. Isotopic labelling studies with early and advanced intermediates confirm for the first time that they are produced via a linear tetraketide, primed with the rare benzoate starter unit, itself derived from phenylalanine via cinnamate. Isolation of a novel biphenyl metabolite, pseudostrobilurin B, provides evidence for the involvement of an epoxide in the key rearrangement to form the β-methoxyacrylate moiety essential for biological activity. Formation of two bolineol related metabolites, strobilurins Y and Z, also probably involves epoxide intermediates. Time course studies indicate a likely biosynthetic pathway from strobilurin A, with the simplest non-subsubstituted benzoate ring, to strobilurin G with a complex dioxepin terpenoid-derived substituent. Precursor-directed biosynthetic studies allow production of a number of novel ring-halogenated analogues as well as a new pyridyl strobilurin. These studies also provide evidence for a non-linear biosynthetic relationship between strobilurin A and strobilurin B.
3. Hot off the Press
Robert A Hill, Andrew Sutherland Nat Prod Rep. 2018 Oct 17;35(10):1024-1028. doi: 10.1039/c8np90032a.
A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products such as huperphlegmine A from Huperzia phlegmaria.
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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 ╳
