Geodin
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| Category | Antibiotics |
| Catalog number | BBF-01870 |
| CAS | 427-63-4 |
| Molecular Weight | 399.18 |
| Molecular Formula | C17H12Cl2O7 |
| Purity | ≥95% |
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Description
An antibiotic produced by the strain of Aspergillus terreus, Geodin is resistant to gram-positive bacteria, negative bacteria (weak) and plant viruses.
Specification
| Synonyms | (+)-Estin; 5,7-dichloro-4-hydroxy-5'-methoxy-6-methyl-3,3'-dioxo-1'-spiro[benzofuran-2,6'-cyclohexa-1,4-diene]carboxylic acid methyl ester; (1'R)-5,7-dichloro-4-hydroxy-6'-methoxy-6-methyl-3,4'-dioxo-spiro[benzofuran-2(3H),1'-[2,5]cyclohexadiene]-2'-carboxylic acid, methyl ester |
| Storage | -20°C |
| IUPAC Name | methyl 5,7-dichloro-4-hydroxy-5'-methoxy-6-methyl-3,3'-dioxospiro[1-benzofuran-2,6'-cyclohexa-1,4-diene]-1'-carboxylate |
| Canonical SMILES | CC1=C(C(=C2C(=C1Cl)OC3(C2=O)C(=CC(=O)C=C3OC)C(=O)OC)O)Cl |
| InChI | InChI=1S/C17H12Cl2O7/c1-6-11(18)13(21)10-14(12(6)19)26-17(15(10)22)8(16(23)25-3)4-7(20)5-9(17)24-2/h4-5,21H,1-3H3 |
| InChI Key | LUBKKVGXMXTXOZ-UHFFFAOYSA-N |
Properties
| Appearance | Light Yellow Acicular Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; viruses |
| Boiling Point | 652.1°C at 760 mmHg |
| Melting Point | 228-231°C |
| Density | 1.61 g/cm3 |
Reference Reading
1. Improved lovastatin production by inhibiting (+)-geodin biosynthesis in Aspergillus terreus
Hanan Hasan, Muhamad Hafiz Abd Rahim, Leona Campbell, Dee Carter, Ali Abbas, Alejandro Montoya N Biotechnol. 2019 Sep 25;52:19-24. doi: 10.1016/j.nbt.2019.04.003. Epub 2019 Apr 14.
Lovastatin is widely prescribed to reduce elevated levels of cholesterol and prevent heart-related diseases. Cultivation of Aspergillus terreus (ATCC 20542) with carbohydrates or low-value feedstocks such as glycerol produces lovastatin as a secondary metabolite and (+)-geodin as a by-product. An A. terreus mutant strain was developed (gedCΔ) with a disrupted (+)-geodin biosynthesis pathway. The gedCΔ mutant was created by inserting the antibiotic marker hygromycin B (hyg) within the gedC gene that encodes emodin anthrone polyketide synthase (PKS), a primary gene responsible for initiating (+)-geodin biosynthesis. The effects of emodin anthrone PKS gene disruption on (+)-geodin and lovastatin biosynthesis and the production of the precursors acetyl-CoA and malonyl-CoA were investigated with cultures based on glycerol alone and in combination with lactose. The gedCΔ strain showed improved lovastatin production, particularly when cultivated on the glycerol-lactose mixture, increasing lovastatin production by 80% (113 mg/L) while simultaneously inhibiting (+)-geodin biosynthesis compared to the wild-type strain. This study thus shows that suppression of the (+)-geodin pathway increases lovastatin yield and demonstrates a practical approach of manipulating carbon flux by modulating enzyme activity.
2. Exploring the extremes: applying high concentration of yeast extract leads to drastic morphological changes and elimination of (+)-geodin and asterric acid production in Aspergillus terreus submerged cultures
Tomasz Boruta, Adrianna Górnicka, Iwona Grzybowska, Ida Stefaniak, Marcin Bizukojć Biotechnol Lett. 2021 Jan;43(1):61-71. doi: 10.1007/s10529-020-03018-5. Epub 2020 Oct 7.
Objective: Evaluation of morphology and secondary metabolites production in Aspergillus terreus ATCC 20542 cultures over a wide range of lactose and yeast extract concentrations from 0.2 up to an extremely high level of 200 g l-l. Results: The morphological differences of mycelial objects were quantified with the use of morphological parameters calculated by applying the tools of digital image analysis. At 200 g l-l of yeast extract clumps and loose hyphae were recorded instead of pellets commonly observed in submerged cultures of A. terreus. Under these conditions the biosynthesis of (+)-geodin and asterric acid was totally blocked, lovastatin formation was found to be at a relatively low level and biomass production turned out to be greater than in the remaining variants, where the pelleted growth was observed. At 200 g l-l of lactose the production of lovastatin, (+)-geodin and asterric acid was visibly stimulated compared to the media containing 0.2, 2 and 20 g l-l of the sugar substrate, but at the same time no traces of butyrolactone I could be detected in the broth. Lactose at the extremely high concentration of 200 g l-l did not induce the drastic morphological changes observed in the case of 200 g l-1 of yeast extract. It was proved that at the C/N values as low as 4 and as high as 374 A. terreus not only continued to display growth but also exhibited the production of secondary metabolites. The use of cultivation media representing the equivalent C/N ratios led to different metabolic and morphological outcomes depending on the concentration of lactose and yeast extract that contributed to the given C/N value. Conclusion: The extremely high concentration of yeast extract leads to marked morphological changes of A. terreus and the elimination of (+)-geodin and asterric production, while applying the excess of lactose is stimulatory in terms of lovastatin production.
3. Design, Semisynthesis, Insecticidal and Antibacterial Activities of a Series of Marine-Derived Geodin Derivatives and Their Preliminary Structure-Activity Relationships
Rong Chao, Gulab Said, Qun Zhang, Yue-Xuan Qi, Jie Hu, Cai-Juan Zheng, Ji-Yong Zheng, Chang-Lun Shao, Guang-Ying Chen, Mei-Yan Wei Mar Drugs. 2022 Jan 18;20(2):82. doi: 10.3390/md20020082.
To enhance the biological activity of the natural product geodin (1), isolated from the marine-derived fungus Aspergillus sp., a series of new ether derivatives (2-37) was designed and semisynthesized using a high-yielding one-step reaction. In addition, the insecticidal and antibacterial activities of all geodin congeners were evaluated systematically. Most of these derivatives showed better insecticidal activities against Helicoverpa armigera Hübner than 1. In particular, 15 showed potent insecticidal activity with an IC50 value of 89 μM, comparable to the positive control azadirachtin (IC50 = 70 μM). Additionally, 5, 12, 13, 16, 30 and 33 showed strong antibacterial activity against Staphylococcus aureus and Aeromonas salmonicida with MIC values in the range of 1.15-4.93 μM. The preliminary structure-activity relationships indicated that the introduction of halogenated benzyl especially fluorobenzyl, into 1 and substitution of 4-OH could be key factors in increasing the insecticidal and antibacterial activities of geodin.
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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 ╳
