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Arsenolipids, also known as arsenic containing lipids, are organoarsenic containing lipids, which are naturally produced in marine environments from inorganic arsenic such as arsenite and arsenate ions.
Structure and types
[edit]Over 50 structures of arsenolipid have been found, however, only some of them are found in the environment.[1] These arsenolipids can be subcategorised further based on their structure into groups such as arsenic-containing fatty acids (AsFAs), arsenic-containing hydrocarbons (AsHCs) and arsenic glycophospholipids (AsPLs).[2] These arsenolipids generally contain a two methyl groups bonded to the arsenic with a double bonded sulfur or oxygen.
| Name | Example diagram | Description |
|---|---|---|
| Arsenic-containing fatty acids (AsFA) |  |
Dimethyl arsenoyl or thioxo equivalent bonded to the end of a fatty acid. |
| Arsenic-containing hydrocarbons (AsHC) |  |
Dimethyl arsenoyl or thioxo equivalent bonded to a hydrocarbon. |
| Arsenic glycophospholipids (AsPL) |  |
Dimethyl arsenoyl or thioxo equivalent bonded to a glycophospholipid. |
Occurrence and synthesis
[edit]Arsenolipids are thought to be produced in marine environments by algae and cyanbacterium either due to the detoxification of arsenate ions,[3][4] or because of arsenics similarity to phosphorus, causing it to be mistakenly metabolised.[5][6] These arsenolipids can then be passed further up the food chain to larger animals.[6] Organophosphate containing arsenosugars can be converted into arsenosugar phospholipids by certain species of cyanobacterium such as members of the Synechocystis genus.[7][8]
Toxicity
[edit]Arsenolipids are proven to be toxic, with certain subclasses of them being shown to be possibly cytotoxic, predominately to bladder and intestinal cells, as well as being potentially neurotoxic.[1][9] Arsenolipids containing a double bonded sulfur are thought to be more toxic due to higher lipophilicity than the oxygen equivalent.[8]
References
[edit]- 1 2 Taylor, Vivien F.; Karagas, Margaret R. (June 1, 2022). "Exposure to arsenolipids and inorganic arsenic from marine-sourced dietary supplements". Chemosphere. 296 133930. Bibcode:2022Chmsp.29633930T. doi:10.1016/j.chemosphere.2022.133930. ISSN 0045-6535. PMC 9007862. PMID 35182530.
- ↑ Li, Caiyan; Chen, Jing; Wang, Zhuo; Song, Bingbing; Cheung, Kit-Leong; Chen, Jianping; Li, Rui; Liu, Xiaofei; Jia, Xuejing; Zhong, Sai-Yi (2024-02-01). "Speciation analysis and toxicity evaluation of arsenolipids—an overview focusing on sea food". Archives of Toxicology. 98 (2): 409–424. Bibcode:2024ArTox..98..409L. doi:10.1007/s00204-023-03639-5. ISSN 1432-0738. PMID 38099972.
- ↑ Dembitsky, Valery M.; Levitsky, Dmitrii O. (September 1, 2004). "Arsenolipids". Progress in Lipid Research. 43 (5): 403–448. Bibcode:2004PLipR..43..403D. doi:10.1016/j.plipres.2004.07.001. ISSN 0163-7827. PMID 15458814.
- ↑ Xue, Xi-Mei; Raber, Georg; Foster, Simon; Chen, Song-Can; Francesconi, Kevin A.; Zhu, Yong-Guan (2014-10-03). "Biosynthesis of arsenolipids by the cyanobacterium Synechocystis sp. PCC 6803". Environmental Chemistry. 11 (5): 506–513. Bibcode:2014EChem..11..506X. doi:10.1071/EN14069. ISSN 1448-2517.
- ↑ Heal, Katherine R.; Maloney, Ashley E.; Ingalls, Anitra E.; Bundy, Randelle M. (2022-02-16). "Diverse arsenic-containing lipids in the surface ocean". Limnology and Oceanography Letters. 7 (1): 43–51. Bibcode:2022LimOL...7...43H. doi:10.1002/lol2.10216. ISSN 2378-2242.
- 1 2 Sele, Veronika; Sloth, Jens J.; Lundebye, Anne-Katrine; Larsen, Erik H.; Berntssen, Marc H.G.; Amlund, Heidi (2012-08-01). "Arsenolipids in marine oils and fats: A review of occurrence, chemistry and future research needs". Food Chemistry. 133 (3): 618–630. Bibcode:2012FoodC.133..618S. doi:10.1016/j.foodchem.2012.02.004. ISSN 0308-8146.
- ↑ Xue, Xi-Mei; Ye, Jun; Raber, Georg; Rosen, Barry P.; Francesconi, Kevin; Xiong, Chan; Zhu, Zhe; Rensing, Christopher; Zhu, Yong-Guan (2019-01-15). "Identification of Steps in the Pathway of Arsenosugar Biosynthesis". Environmental Science & Technology. 53 (2): 634–641. Bibcode:2019EnST...53..634X. doi:10.1021/acs.est.8b04389. ISSN 0013-936X. PMC 6467767. PMID 30525501.
- 1 2 Christie, William (Bill) W. "Arsenolipids - hydrocarbons, fatty acids, phosphatidylarsenocholine, arseno-phosphoglycolipid - composition, biochemistry and toxicity". lipidmaps.org. Archived from the original on 2024-09-17. Retrieved 2026-05-15.
- ↑ Liu, Qingqing; Huang, Chengzhi; Li, Wenhui; Fang, Zhenzheng; Le, X. Chris (2021-03-16). "Discovery and Identification of Arsenolipids Using a Precursor-Finder Strategy and Data-Independent Mass Spectrometry". Environmental Science & Technology. 55 (6): 3836–3844. Bibcode:2021EnST...55.3836L. doi:10.1021/acs.est.0c07175. ISSN 0013-936X. PMC 8009509. PMID 33667084.