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Ophiobolin B (Synonyms: Cochliobolin B,Ophiobolsin A,Zizanin B)

Catalog No.GC15233

Helminthosporium oryzae의 sesterterpene 대사 산물인 Ophiobolin B는 옥수수 딱정벌레로부터 양성자 압출을 억제합니다.

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Ophiobolin B Chemical Structure

Cas No.: 5601-74-1

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1mg
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Sample solution is provided at 25 µL, 10mM.

Description of Ophiobolin B

Ophiobolins are a group of sesterterpene-type phytotoxins produced by fungi belonging to the genera Bipolaris, Drechslera, Cephalosporium and Aspergillus. Ophiobolins are secondary metabolites of fungi. To date, more than 25 ophiobolin analogues have been identified. Ophiobolins have been involved in various biological actions, such as phytotoxic, cytotoxic, nematocidal, antimicrobial and antiviral effects [1].

In vitro: In maize coleoptile tissues, Ophiobolin B inhibited proton extrusion. Ophiobolin B counteracted the biological activity of fusicoccin (FC). Ophiobolin B inhibited FC-promoted proton extrusion, potassium uptake and cell enlargement [2]. Calmodulin solutions preincubation with ophiobolin A caused an instantaneous quenching of the intrinsic tyrosine fluorescence in a time-dependent manner. The inhibitory effects of ophiobolin A could not be reversed by dialysis, dilution, nor denaturation by urea in the presence of methanol followed by renaturation. Ophiobolin A also inhibited spinach calmodulin [3]. In cultured CLL cells, treatment with increasing concentrations of Ophiobolin B for 24 h displayed bioactivity towards leukemia cells with induction of apoptosis at nanomolar concentrations [3]. Ophiobolins B exihibited antifungal effects on different zygomycetes with MIC value of 25-50 μg/ml [4].

References:
[1] Au T K, Chick W S H, Leung P C.  The biology of ophiobolins[J]. Life sciences, 2000, 67(7): 733-742.
[2] Gianani L, Cocucci S, Pardi D, et al.  Effects of ophiobolin B on cell enlargement and H+/K+ exchange in maize coleoptile tissues[J]. Planta, 1979, 146(3): 271-274.
[3] Bladt T T, Dürr C, Knudsen P B, et al.  Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells[J]. Molecules, 2013, 18(12): 14629-14650.
[4] Krizsán K, Bencsik O, Nyilasi I, et al.  Effect of the sesterterpene-type metabolites, ophiobolins A and B, on zygomycetes fungi[J]. FEMS microbiology letters, 2010, 313(2): 135-140.

Chemical Properties of Ophiobolin B

Cas No. 5601-74-1 SDF
Synonyms Cochliobolin B,Ophiobolsin A,Zizanin B
Chemical Name (1R,3aS,6aR,7S,9aR,10aS)-7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1,7-dihydroxy-1,9a-dimethyl-3-oxo-dicyclopenta[a,d]cyclooctene-4-carboxaldehyde
Canonical SMILES C[C@@]12C[C@@]([H])([C@]3(/C(C=O)=C\C[C@]1([C@](O)(CC2)[C@H](CC/C=C(C)\C)C)[H])[H])[C@](CC3=O)(C)O
Formula C25H38O4 M.Wt 402.6
Solubility DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Ophiobolin B

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1 mg 5 mg 10 mg
1 mM 2.4839 mL 12.4193 mL 24.8385 mL
5 mM 0.4968 mL 2.4839 mL 4.9677 mL
10 mM 0.2484 mL 1.2419 mL 2.4839 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 16 reference(s) in Google Scholar.)

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