Ophiobolin C
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| Category | Antibiotics |
| Catalog number | BBF-02623 |
| CAS | 19022-51-6 |
| Molecular Weight | 386.57 |
| Molecular Formula | C25H38O3 |
| Purity | >98% by HPLC |
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Description
A member of the ophiobolin class of phytotoxic metabolites produced by many species of the genus bipolaris; inhibits human CCR5 binding to the envelope protein gp120 and CD4 that mediates HIV-1 entry into cells.
Specification
| Synonyms | Zizanin A |
| Storage | Store at -20°C |
| IUPAC Name | (1R,3S,4R,7S,8E,11S,12R)-4-hydroxy-1,4-dimethyl-12-[(2S)-6-methylhept-5-en-2-yl]-6-oxotricyclo[9.3.0.03,7]tetradec-8-ene-8-carbaldehyde |
| Canonical SMILES | CC(CCC=C(C)C)C1CCC2(C1CC=C(C3C(C2)C(CC3=O)(C)O)C=O)C |
| InChI | InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3/b18-9-/t17-,19+,20-,21-,23+,24+,25+/m0/s1 |
| InChI Key | PLWMYIADTRHIMY-BNFAVABNSA-N |
| Source | Bipolaris sp. |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi |
| Boiling Point | 512.4°C at 760 mmHg |
| Melting Point | 121°C |
| Flash Point | 277.8ºC |
| Density | 1.064 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining
Koji Narita, Katsuya Gomi, Ryota Chiba, Motoichiro Kodama, Hideaki Oikawa, Atsushi Minami, Isao Fujii Org Lett . 2016 May 6;18(9):1980-3. doi: 10.1021/acs.orglett.6b00552.
Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblBAc (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblBBm/oblBEv from the gene cluster of ophiobolin producers, with oblDBm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.
2. Isolation and structure of antagonists of chemokine receptor (CCR5)
Dennis W Stevenson, Lorraine Malkowitz, Hiranthi Jayasuriya, Suroojnauth Tiwari, Sal Siciliano, Manuel Sanchez, Anne W Dombrowski, Kithsiri B Herath, John G Ondeyka, Marty S Springer, Robert P Borris, Ziqiang Guan, Jon D Polishook, Gerald F Bills, Sheo B Singh J Nat Prod . 2004 Jun;67(6):1036-8. doi: 10.1021/np049974l.
Human CCR5 is a G-coupled receptor that binds to the envelope protein gp120 and CD4 and mediates the HIV-1 viral entry into the cells. The blockade of this binding by a small molecule receptor antagonist could lead to a new mode of action agent for HIV-1 and AIDS. Screening of natural product extracts led to the identification of anibamine (1), a novel pyridine quaternary alkaloid as a TFA salt, from Aniba sp.; ophiobolin C from fermentation extracts of fungi Mollisia sp.; and 19,20-epoxycytochalasin Q from Xylaria sp. Formation of the TFA salt of anibamine is plausibly an artifact of the isolation. The identity of the natural counterion is unknown. Anibamine.TFA competed for the binding of 125I-gp120 to human CCR5 with an IC50 of 1 microM. Ophiobolin C and 19,20-epoxycytochalasin Q exhibited binding IC50) values of 40 and 60 microM, respectively.
3. Ophiobolin O isolated from Aspergillus ustus induces G1 arrest of MCF-7 cells through interaction with AKT/GSK3β/cyclin D1 signaling
Cuiting Lv, Tonghan Zhu, Ruohua Chen, Caiguo Huang, Weiming Zhu, Wenxing Qin, Shanjian Wei, Kui Hong Mar Drugs . 2015 Jan 16;13(1):431-43. doi: 10.3390/md13010431.
Ophiobolin O is a member of ophiobolin family, which has been proved to be a potent anti-tumor drug candidate for human breast cancer. However, the anti-tumor effect and the mechanism of ophiobolin O remain unclear. In this study, we further verified ophiobolin O-induced G1 phase arrest in human breast cancer MCF-7 cells, and found that ophiobolin O reduced the phosphorylation level of AKT and GSK3β, and induced down-regulation of cyclin D1. The inverse docking (INVDOCK) analysis indicated that ophiobolin O could bind to GSK3β, and GSK3β knockdown abolished cyclin D1 degradation and G1 phase arrest. Pre-treatment with phosphatase inhibitor sodium or thovanadate halted dephosphorylation of AKT and GSK3β, and blocked ophiobolin O-induced G1 phase arrest. These data suggest that ophiobolin O may induce G1 arrest in MCF-7 cells through interaction with AKT/GSK3β/cyclin D1 signaling. In vivo, ophiobolin O suppressed tumor growth and showed little toxicity in mouse xenograft models. Overall, these findings provide theoretical basis for the therapeutic use of ophiobolin O.
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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 ╳
