Chemistry:Barettin
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| C17H19BrN6O2 | |
| Molar mass | 419.283 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Barettin is a brominated alkaloid made of a dehydrogenated brominated derivative of tryptophan linked by two peptide bonds to an arginine residue, forming a 2,5-diketopiperazine nucleus.[1][2] It is a cyclic dipeptide.
Barettin is the major compound in the deep-sea sponge Geodia barretti.[3] It was isolated for the first time in 1986 by Göran Lidgren, Lars Bohlin and Jan Bergman at Uppsala University, Sweden[1] but the correct chemical structure was determined later in 2002.[2] Barettin is written with one 'r' because the authors misspelled Geodia barretti with one 'r' in the original paper.[1]
Barettin seems to show antioxidant and anti-inflammatory properties which could be used in treating diseases that affect the immune system and diseases that are caused by inflammation.[4] Atherosclerosis, a disease characterized by stiffening and a buildup of compounds in arteries,[5] may be prevented by barettin due to its anti-inflammatory properties.[4] The effects barettin has on inflammation may be due to its inhibitory properties on two protein kinases, receptor-interacting serine/threonine kinase 2 (RIPK2) and calcium/calmodulin-dependent protein kinase 1α (CAMK1α).[6]
References
- ↑ 1.0 1.1 1.2 Lidgren, Göran; Bohlin, Lars; Bergman, Jan (January 1986). "Studies of swedish marine organisms VII. A novel biologically active indole alkaloid from the sponge Geodia baretti". Tetrahedron Letters 27 (28): 3283–3284. doi:10.1016/s0040-4039(00)84776-0. ISSN 0040-4039.
- ↑ 2.0 2.1 Sölter, Susanne; Dieckmann, Ralf; Blumenberg, Martin; Francke, Wittko (April 2002). "Barettin, revisited?". Tetrahedron Letters 43 (18): 3385–3386. doi:10.1016/s0040-4039(02)00470-7. ISSN 0040-4039.
- ↑ Sjögren, Martin; Göransson, Ulf; Johnson, Ann-Louise; Dahlström, Mia; Andersson, Rolf; Bergman, Jan; Jonsson, Per R.; Bohlin, Lars (March 2004). "Antifouling Activity of Brominated Cyclopeptides from the Marine SpongeGeodia barretti" (in en). Journal of Natural Products 67 (3): 368–372. doi:10.1021/np0302403. ISSN 0163-3864. PMID 15043412.
- ↑ 4.0 4.1 Lind, Karianne F.; Hansen, Espen; Østerud, Bjarne; Eilertsen, Karl-Erik; Bayer, Annette; Engqvist, Magnus; Leszczak, Kinga; Jørgensen, Trond Ø. et al. (2013-07-22). "Antioxidant and Anti-Inflammatory Activities of Barettin". Marine Drugs 11 (7): 2655–2666. doi:10.3390/md11072655. ISSN 1660-3397. PMID 23880935.
- ↑ "Arteriosclerosis / atherosclerosis - Symptoms and causes" (in en). Mayo Clinic. https://www.mayoclinic.org/diseases-conditions/arteriosclerosis-atherosclerosis/symptoms-causes/syc-20350569.
- ↑ Lind, Karianne Fredenfeldt; Østerud, Bjarne; Hansen, Espen; Jørgensen, Trond Ø; Andersen, Jeanette Hammer (2015). "The immunomodulatory effects of barettin and involvement of the kinases CAMK1α and RIPK2". Immunopharmacology and Immunotoxicology 37 (5): 458–464. doi:10.3109/08923973.2015.1082584. ISSN 1532-2513. PMID 26466644.
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