Barettin

In today's article we will talk about Barettin, a topic that has become increasingly relevant in recent years. Barettin has become a point of interest for many people, whether due to its impact on society, its historical relevance or its influence on popular culture. Throughout this article we will explore different aspects related to Barettin, from its origin and evolution, to its current and future projection. We will discover its importance in people's lives and how it has been setting standards in various areas. Without a doubt, Barettin is a topic that generates great interest and from which we can learn a lot.

Barettin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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 , 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

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

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 ketanserin, suggesting that barettin's analgesic effects may be mediated by serotonin 5-HT2A receptor activation.[4]

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.[5] Atherosclerosis, a disease characterized by stiffening and a buildup of compounds in arteries,[6] may be prevented by barettin due to its anti-inflammatory properties.[5] 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).[7]

References

  1. ^ a b c 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. ^ a b 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. ^ a b 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. ^ a b c 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. ^ a b 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.
  6. ^ "Arteriosclerosis / atherosclerosis - Symptoms and causes". Mayo Clinic. Retrieved 2018-12-01.
  7. ^ 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.