(−)-Viriditoxin

(−)-Viriditoxin

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(−)-Viriditoxin
Category Mycotoxins
Catalog number BBF-03765
CAS 1381782-08-6
Molecular Weight 662.59
Molecular Formula C34H30O14
Purity ≥98%

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Description

(−)-Viriditoxin is a mycotoxin originally isolated from A. viridinutans. Exhibits broad activity against Gram-positive bacteria. Bacterial cell division protein FtsZ inhibitor (IC50=8.2µg/ml). Inhibits the GTPase activity of FtsZ in vitro (IC50 = 7.0 µg/ml). Induces apoptosis and autophagy and inhibits cell growth at G2/M in human prostate cancer cells. Activates ATP hydrolysis and induces calcium sensitized swelling of rat liver mitochondria.

Specification

Related CAS 35483-50-2 36619-29-1
Synonyms UNII-6TAK972FMC; 6TAK972FMC
Storage Store at 2-8°C
IUPAC Name methyl 2-[(3S)-6-[(3S)-9,10-dihydroxy-7-methoxy-3-(2-methoxy-2-oxoethyl)-1-oxo-3,4-dihydrobenzo[g]isochromen-6-yl]-9,10-dihydroxy-7-methoxy-1-oxo-3,4-dihydrobenzo[g]isochromen-3-yl]acetate
Canonical SMILES COC1=C(C2=C(C(=C1)O)C(=C3C(=C2)CC(OC3=O)CC(=O)OC)O)C4=C(C=C(C5=C4C=C6CC(OC(=O)C6=C5O)CC(=O)OC)O)OC
InChI InChI=1S/C34H30O14/c1-43-21-11-19(35)27-17(7-13-5-15(9-23(37)45-3)47-33(41)25(13)31(27)39)29(21)30-18-8-14-6-16(10-24(38)46-4)48-34(42)26(14)32(40)28(18)20(36)12-22(30)44-2/h7-8,11-12,15-16,35-36,39-40H,5-6,9-10H2,1-4H3/t15-,16-/m0/s1
InChI Key GMCZVCXZGZGZPX-HOTGVXAUSA-N

Properties

Appearance Solid Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 904.6±65.0°C(Predicted)
Density 1.477±0.06 g/cm3(Predicted)
Solubility Soluble in DMSO, Ethanol

Reference Reading

1. 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.
2. Fungal Dirigent Protein Controls the Stereoselectivity of Multicopper Oxidase-Catalyzed Phenol Coupling in Viriditoxin Biosynthesis
Jinyu Hu, Hang Li, Yit-Heng Chooi J Am Chem Soc. 2019 May 22;141(20):8068-8072. doi: 10.1021/jacs.9b03354. Epub 2019 May 8.
Paecilomyces variotii produces the antibacterial and cytotoxic ( M)-viriditoxin (1) together with a trace amount of its atropisomer ( P)-viriditoxin 1'. Elucidation of the biosynthesis by heterologous pathway reconstruction in Aspergillus nidulans identified the multicopper oxidase (MCO) VdtB responsible for the regioselective 6,6'-coupling of semiviriditoxin (10), which yielded 1 and 1' at a ratio of 1:2. We further uncovered that VdtD, an α/β hydrolase-like protein lacking the catalytic serine, directs the axial chirality of the products. Using recombinant VdtB and VdtD as cell-free extracts from A. nidulans, we demonstrated that VdtD acts like a dirigent protein to control the stereoselectivity of the coupling catalyzed by VdtB to yield 1 and 1' at a ratio of 20:1. Furthermore, we uncovered a unique Baeyer-Villiger monooxygenase (BVMO) VdtE that could transform the alkyl methylketone side chain to methyl ester against the migratory aptitude.
3. 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.

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