Barettin

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 [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.

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]

Geodia barretti (dried specimen)

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. ^ 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 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.
  5. ^ "Arteriosclerosis / atherosclerosis - Symptoms and causes". Mayo Clinic. Retrieved 2018-12-01.
  6. ^ 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.