Chemistry:Viriditoxin
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(-)-Viriditoxin
(M)-Viriditoxin | |
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3D model (JSmol)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Viriditoxin (VDT[1][2]) is a secondary metabolite produced by fungi.[3] Viriditoxin is a type of mycotoxin.[1] The biosynthesis of the compound has been investigated.[3]
Occurrence
It is produced by several Aspergillus species including A. aureoluteus,[4] A. brevipes,[5] and A. viridinutans in which it was first identified in 1971.[6] It has been isolated from Paecilomyces variotii, which was obtained from Nomura's jellyfish.[2] It is also produced by Cladosporium cladosporioides.[1]
Structure
Natural viriditoxin exists as a single atropisomer owing to restricted rotation about the C-C bond which joins the two naphthol rings. It has been confirmed by total synthesis to be twisted into the so-called M isomer.[6]
Biosynthesis
Viriditoxin is a secondary metabolite, a polyketide produced from multiple acetyl-CoA and malonyl-CoA units which are combined by a polyketide synthase (PKS) enzyme complex. A chain of eight acetate units are cyclised to give the three-ring system which forms half of the carbon framework of the final product. After selective methylation of one of the phenol groups and reduction of the pyrone ring, the resulting intermediate (semiviriditoxin) is dimerised by a laccase enzyme, generating specifically the minus M atropisomer.[7]
Uses
In nature, viriditoxin likely is used against microbial competition. On mangroves, P. variotii's production of viriditoxin was linked to antagonism against bacteria.[3]
A 2022 study found that it had potential as a leukemia treatment due to high cytotoxic potential and rapid kinetics of caspase activation when reacting to Jurkat leukemia and especially Ramos lymphoma cells; solid tumor cells were affected to a much lesser extent.Template:MEDCN[1] Tests of viriditoxin on pregnant mice found little effect on the survival of their pups and there was no increase of abnormalities.[better source needed][8]
References
- ↑ 1.0 1.1 1.2 1.3 [non-primary source needed] Stuhldreier, Fabian; Schmitt, Laura; Lenz, Thomas; Hinxlage, Ilka; Zimmermann, Marcel; Wollnitzke, Philipp; Schliehe-Diecks, Julian; Liu, Yang et al. (2022-11-08). "The mycotoxin viriditoxin induces leukemia- and lymphoma-specific apoptosis by targeting mitochondrial metabolism" (in en). Cell Death & Disease 13 (11): 938. doi:10.1038/s41419-022-05356-w. PMID 36347842.
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- ↑ 2.0 2.1 Kundu, Soma; Kim, Tae Hyung; Yoon, Jung Hyun; Shin, Han-Seung; Lee, Jaewon; Jung, Jee H.; Kim, Hyung Sik (2014-12-01). "Viriditoxin regulates apoptosis and autophagy via mitotic catastrophe and microtubule formation in human prostate cancer cells". International Journal of Oncology 45 (6): 2331–2340. doi:10.3892/ijo.2014.2659. PMID 25231051.
- ↑ 3.0 3.1 3.2 Urquhart, Andrew S.; Hu, Jinyu; Chooi, Yit-Heng; Idnurm, Alexander (2019). "The fungal gene cluster for biosynthesis of the antibacterial agent viriditoxin". Fungal Biology and Biotechnology 6: 2. doi:10.1186/s40694-019-0072-y. PMID 31304040. This article incorporates text from a free content work. Licensed under Creative Commons Attribution 4.0 To learn how to add open license text to HandWiki articles, please see this how-to page. For information on reusing text from HandWiki, please see the terms of use.
- ↑ Samson, R.A.; Hong, S.; Peterson, S.W.; Frisvad, J.C.; Varga, J. (2007). "Polyphasic taxonomy of Aspergillus section Fumigati and its teleomorph Neosartorya". Studies in Mycology 59: 147–203. doi:10.3114/sim.2007.59.14. PMID 18490953.
- ↑ Frederic, Lamoth; William J., Steinbach (2016). Advances in Aspergillus fumigatus pathobiology. Frontiers Media SA. ISBN 978-2-889-19789-7.
- ↑ 6.0 6.1 Smyth, Jamie E.; Butler, Nicholas M.; Keller, Paul A. (2015). "A twist of nature – the significance of atropisomers in biological systems". Natural Product Reports 32 (11): 1562–1583. doi:10.1039/c4np00121d. PMID 26282828. https://ro.uow.edu.au/cgi/viewcontent.cgi?article=4391&context=smhpapers. Retrieved June 12, 2023.
- ↑ Hüttel, Wolfgang; Müller, Michael (2021). "Regio- and stereoselective intermolecular phenol coupling enzymes in secondary metabolite biosynthesis". Natural Product Reports 38 (5): 1017–1020. doi:10.1039/d0np00010h. PMID 33196733.
- ↑ [non-primary source needed]Hood, R. D.; Hayes, A. W.; Scammell, J. G. (1976-01-01). "Effects of prenatal administration of citrinin and viriditoxin to mice" (in en). Food and Cosmetics Toxicology 14 (3): 175–178. doi:10.1016/S0015-6264(76)80419-1. PMID 950209. https://www.sciencedirect.com/science/article/pii/S0015626476804191.
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