SC-28762
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| Category | Antibiotics |
| Catalog number | BBF-03405 |
| CAS | 35483-50-2 |
| Molecular Weight | 662.6 |
| Molecular Formula | C34H30O14 |
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Description
SC-28762 is an antibiotic produced by Spicaria divaricata NRRL 5771. It has moderate activity against gram-positive, gram-negative bacteria and fungi.
Specification
| Synonyms | SC 28762; SC28762 |
| IUPAC Name | methyl 2-[8-[9,10-dihydroxy-7-methoxy-3-(2-methoxy-2-oxoethyl)-1-oxo-3,4-dihydrobenzo[g]isochromen-8-yl]-9,10-dihydroxy-7-methoxy-1-oxo-3,4-dihydrobenzo[g]isochromen-3-yl]acetate |
| Canonical SMILES | COC1=CC2=CC3=C(C(=C2C(=C1C4=C(C5=C(C6=C(CC(OC6=O)CC(=O)OC)C=C5C=C4OC)O)O)O)O)C(=O)OC(C3)CC(=O)OC |
| InChI | InChI=1S/C34H30O14/c1-43-19-9-15-5-13-7-17(11-21(35)45-3)47-33(41)25(13)29(37)23(15)31(39)27(19)28-20(44-2)10-16-6-14-8-18(12-22(36)46-4)48-34(42)26(14)30(38)24(16)32(28)40/h5-6,9-10,17-18,37-40H,7-8,11-12H2,1-4H3 |
| InChI Key | KPSSJZWNGXQOMD-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Melting Point | 263-267°C (dec.) |
Reference Reading
1. Lawsozaheer, a new chromone produced by an endophytic fungus Paecilomyces variotii isolated from Lawsonia Alba Lam. inhibits the growth of Staphylococcus aureus
Zaheer Abbas, Bina Shaheen Siddiqui, Saleem Shahzad, Samia Sattar, Sabira Begum, Anum Batool, Mohammad Iqbal Choudhary Nat Prod Res. 2021 Nov;35(22):4448-4453. doi: 10.1080/14786419.2020.1729148. Epub 2020 Feb 24.
One new chromone, lawsozaheer (1), and five known compounds 4-(2-hydroxyethyl) phenol (2), viriditoxin (3), stigmasta-4,6,8(14),22-tetraen-3-one (4), β-sitosterol (5) and stigmasterol (6) were isolated from the fungal broth of Paecilomyces variotii. Their structures were elucidated using spectroscopic data. The configuration of 1 was determined by Horeau's method. The broth extract and compound 1 showed highly selective activity against Staphylococcus aureus (NCTC 6571) bacterium with 83.19 and 84.26% inhibition respectively at 150 µg/mL, comparing well with that of standard drug ofloxacin (87.013% inhibition at 100 µg/mL). Broth extract also showed 75, and 40% inhibition of Candida albicans and Fusarium lini, respectively.
2. The mycotoxin viriditoxin induces leukemia- and lymphoma-specific apoptosis by targeting mitochondrial metabolism
Fabian Stuhldreier, Laura Schmitt, Thomas Lenz, Ilka Hinxlage, et al. Cell Death Dis. 2022 Nov 8;13(11):938. doi: 10.1038/s41419-022-05356-w.
Inhibition of the mitochondrial metabolism offers a promising therapeutic approach for the treatment of cancer. Here, we identify the mycotoxin viriditoxin (VDT), derived from the endophytic fungus Cladosporium cladosporioides, as an interesting candidate for leukemia and lymphoma treatment. VDT displayed a high cytotoxic potential and rapid kinetics of caspase activation in Jurkat leukemia and Ramos lymphoma cells in contrast to solid tumor cells that were affected to a much lesser extent. Most remarkably, human hematopoietic stem and progenitor cells and peripheral blood mononuclear cells derived from healthy donors were profoundly resilient to VDT-induced cytotoxicity. Likewise, the colony-forming capacity was affected only at very high concentrations, which provides a therapeutic window for cancer treatment. Intriguingly, VDT could directly activate the mitochondrial apoptosis pathway in leukemia cells in the presence of antiapoptotic Bcl-2 proteins. The mitochondrial toxicity of VDT was further confirmed by inhibition of mitochondrial respiration, breakdown of the mitochondrial membrane potential (ΔΨm), the release of mitochondrial cytochrome c, generation of reactive oxygen species (ROS), processing of the dynamin-like GTPase OPA1 and subsequent fission of mitochondria. Thus, VDT-mediated targeting of mitochondrial oxidative phosphorylation (OXPHOS) might represent a promising therapeutic approach for the treatment of leukemia and lymphoma without affecting hematopoietic stem and progenitor cells.
3. Viriditoxin Stabilizes Microtubule Polymers in SK-OV-3 Cells and Exhibits Antimitotic and Antimetastatic Potential
Mingzhi Su, Changhao Zhao, Dandan Li, Jiafu Cao, Zhiran Ju, Eun La Kim, Young-Suk Jung, Jee H Jung Mar Drugs. 2020 Aug 27;18(9):445. doi: 10.3390/md18090445.
Microtubules play a crucial role in mitosis and are attractive targets for cancer therapy. Recently, we isolated viriditoxin, a cytotoxic and antibacterial compound, from a marine fungus Paecilomyces variotii. Viriditoxin has been reported to inhibit the polymerization of bacterial FtsZ, a tubulin-like GTPase that plays an essential role in bacterial cell division. Given the close structural homology between FtsZ and tubulin, we investigated the potential antimitotic effects of viriditoxin on human cancer cells. Viriditoxin, like paclitaxel, enhanced tubulin polymerization and stabilized microtubule polymers, thereby perturbing mitosis in the SK-OV-3 cell line. However, the morphology of the stabilized microtubules was different from that induced by paclitaxel, indicating subtle differences in the mode of action of these compounds. Microtubule dynamics are also essential in cell movement, and viriditoxin repressed migration and colony formation ability of SK-OV-3 cells. Based on these results, we propose that viriditoxin interrupts microtubule dynamics, thus leading to antimitotic and antimetastatic activities.
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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 ╳
