Strobilurin G
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| Category | Antibiotics |
| Catalog number | BBF-03490 |
| CAS | 129145-64-8 |
| Molecular Weight | 442.54 |
| Molecular Formula | C26H34O6 |
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Description
Strobilurin G is an antibiotic produced by Bolina lutea Sacc. It has strong anti-fungal activity, and its in vitro anti-tumor proliferation IC50 is 0.01 µmol/L.
Specification
| Related CAS | 132056-04-3 |
| Synonyms | 6-(3,4-DIHYDRO-4,4-DIMETHYL-3-((3-METHYL-2-BUTENYL)OXY)-2H-1,5-BENZODIOXEPIN-7-YL)-2-(METHOXYMETHYLENE)-3-METHYL-, 3,5-HEXADIENOIC ACID METHYL ESTER; STROBILURIN G; 6-(3,4-dihydro-4,4-dimethyl-3-((3-methyl-2-butenyl)oxy)-2H-1,5-benzodioxepin-7-yl)-2-(metho |
| IUPAC Name | methyl (2E,3Z,5E)-6-[4,4-dimethyl-3-(3-methylbut-2-enoxy)-2,3-dihydro-1,5-benzodioxepin-7-yl]-2-(methoxymethylidene)-3-methylhexa-3,5-dienoate |
| Canonical SMILES | CC(=CCOC1COC2=C(C=C(C=C2)C=CC=C(C)C(=COC)C(=O)OC)OC1(C)C)C |
| InChI | InChI=1S/C26H34O6/c1-18(2)13-14-30-24-17-31-22-12-11-20(15-23(22)32-26(24,4)5)10-8-9-19(3)21(16-28-6)25(27)29-7/h8-13,15-16,24H,14,17H2,1-7H3/b10-8+,19-9-,21-16+ |
| InChI Key | CGBAOGDKJZIWTF-QILZHMQOSA-N |
Properties
| Appearance | Yellow Oil |
| Antibiotic Activity Spectrum | fungi; neoplastics (Tumor) |
| Boiling Point | 573.6°C at 760 mmHg |
| Density | 1.11 g/cm3 |
Reference Reading
1. Monochlorinated calocerins A-D and 9-oxostrobilurin derivatives from the basidiomycete Favolaschia calocera
Clara Chepkirui, Christian Richter, Josphat Clement Matasyoh, Marc Stadler Phytochemistry. 2016 Dec;132:95-101. doi: 10.1016/j.phytochem.2016.10.001. Epub 2016 Oct 13.
Eight previously undescribed compounds were isolated and characterised from the supernatant and mycelium of a culture of the basidiomycete Favolaschia calocera originating from Kakamega equatorial rainforest in Kenya. These were: 9- oxostrobilurins A, G, K and I and the four monochlorinated calocerins A, B, C and D. The calocerins extend our knowledge of halogenated compounds obtained from natural sources. Four further known compounds were also identified: strobilurin G, favolon, pterulinic acid and 2,3 -dihydro-1-benzoxepin derivative. The four oxostrobilurins exhibited prominent antifungal and cytotoxic activities while the four calocerins only showed 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. Biologically active metabolites from fungi 14 3-chloro-4-hydroxy-5-(3,7,11-trimethyldodeca-2,6,10-trienyl)-benzamide, a new antibacterial agent from a soil fungus
K Krohn, M John, H J Aust, S Draeger, B Schulz Nat Prod Lett. 2001;15(1):9-12. doi: 10.1080/10575630108041251.
The antibacterial 3-chloro-4-hydroxy-5-(3,7,11-trimethyldodeca-2,6,10-trienyl)-benzamide, and the antifungal strobilurins B and D were isolated from an unidentified South African soil fungus.
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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 ╳
