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Barettin

From Wikipedia, the free encyclopedia
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 mass419.283 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Barettin is abrominatedalkaloid made of adehydrogenatedbrominated derivative oftryptophan linked by twopeptide bonds to anarginineresidue, forming a2,5-diketopiperazinenucleus.[1][2] It is acyclicdipeptide and acyclized tryptamine. The compound occursnaturally in certainsea sponges[3] and is known to interact with certainserotonin receptors.[4]

Natural occurrence

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Barettin is the major compound in the deep-sea spongeGeodia 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 misspelledGeodia barretti with one 'r' in the original paper.[1]

Pharmacology

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Geodia barretti (dried specimen).

Barettin showsaffinity for theserotonin5-HT2 receptors.[4] It hasanalgesic effects that are reversed by the serotonin5-HT2A receptorketanserin, suggesting that barettin's analgesic effects may be mediated by serotonin 5-HT2A receptor activation.[4]

Barettin seems to showantioxidant andanti-inflammatory properties which could be userful in treating diseases that affect theimmune system and diseases that are caused byinflammation.[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 twoprotein kinases,receptor-interacting serine/threonine kinase 2 (RIPK2) andcalcium/calmodulin-dependent protein kinase 1α (CAMK1α).[7]

References

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  1. ^abcLidgren, 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. ^abSölter, 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. ^abSjögren, 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. ^abcSeekins, 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. Retrieved12 April 2025.
  5. ^abLind, 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. Retrieved2018-12-01.
  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.


5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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