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Barettin

From Wikipedia, the free encyclopedia
Barettin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C17H19BrN6O2/c18-10-3-4-11-9(8-22-13(11)7-10)6-14-16(26)23-12(15(25)24-14)2-1-5-21-17(19)20/h3-4,6-8,12,22H,1-2,5H2,(H,23,26)(H,24,25)(H4,19,20,21)/b14-6-/t12-/m0/s1
    Key: YYFNNPXWRXQUPR-JVXNRYDGSA-N
  • C1=CC2=C(C=C1Br)NC=C2C=C3C(=O)NC(C(=O)N3)CCCN=C(N)N
Properties
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).

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 and a cyclized tryptamine. The compound occurs naturally in certain sea sponges[3] and is known to interact with certain serotonin receptors.[4]

Natural occurrence

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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]

Pharmacology

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Geodia barretti (dried specimen).

Barettin shows affinity for the serotonin 5-HT2 receptors.[4] It has analgesic effects that are reversed by the serotonin 5-HT2A receptor antagonist ketanserin, suggesting that barettin's analgesic effects may be mediated by serotonin 5-HT2A receptor signaling.[4] Subsequently, barettin was found to act as an inverse agonist of the serotonin 5-HT2A receptor, with this action mediating its analgesic effects.[5] In accordance with its lack of activation of the serotonin 5-HT2A receptor, barettin failed to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[5]

Barettin seems to show antioxidant and anti-inflammatory properties which could be userful in treating diseases that affect the immune system and diseases that are caused by inflammation.[6] Atherosclerosis, a disease characterized by stiffening and a buildup of compounds in arteries,[7] may be prevented by barettin due to its anti-inflammatory properties.[6] 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).[8]

See also

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References

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  1. 1 2 3 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. 1 2 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.
  3. 1 2 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". Journal of Natural Products. 67 (3): 368–372. doi:10.1021/np0302403. ISSN 0163-3864. PMID 15043412.
  4. 1 2 3 Seekins, Caleb; Cárdenas, Paco; Streicher, John; Cartmell, Chris (2025). "Analgesic Properties of the Natural Product Barettin Are Mediated by the 5HT2A/C Receptors (Abstract ID: 165920)". The Journal of Pharmacology and Experimental Therapeutics. 392 (3) 101346. doi:10.1016/j.jpet.2024.101346. Retrieved 12 April 2025.
  5. 1 2 Seekins CA, Okine M, Forrest EG, Chavez T, Stump A, Kaleeswaran V, Carr JE, Hulme C, Cardenas P, Vanderah TW, Streicher JM, Cartmell C (March 2026). "Barettin, a Nonopioid, Nonhallucinogenic Marine Natural Product with Antihyperalgesic Properties Mediated by 5HT2A Inverse Agonism". J Nat Prod. doi:10.1021/acs.jnatprod.6c00169. PMID 41914263.
  6. 1 2 Lind, Karianne F.; Hansen, Espen; Østerud, Bjarne; Eilertsen, Karl-Erik; Bayer, Annette; Engqvist, Magnus; Leszczak, Kinga; Jørgensen, Trond Ø.; Andersen, Jeanette H. (2013-07-22). "Antioxidant and Anti-Inflammatory Activities of Barettin". Marine Drugs. 11 (7): 2655–2666. doi:10.3390/md11072655. ISSN 1660-3397. PMC 3736444. PMID 23880935.
  7. ↑ "Arteriosclerosis / atherosclerosis - Symptoms and causes". Mayo Clinic. Retrieved 2018-12-01.
  8. ↑ 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. S2CID 21255063.
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