Caulerpin

• CAT Number: I024162
• CAS Number: 26612-48-6
• Molecular Formula: C24H18N2O4
• Molecular Weight: 398.42
• Purity: 98%
• Synonyms: Caulerpin
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Cycloocta(1,2-b:5,6-b')diindole-6,13-dicarboxylic acid, 5,12-dihydro-, dimethyl ester
• InChI: InChI=1S/C24H18N2O4/c1-29-23(27)17-11-15-13-7-3-6-10-20(13)26-22(15)18(24(28)30-2)12-16-14-8-4-5-9-19(14)25-21(16)17/h3-12,25-26H,1-2H3/b15-11-,16-12-,17-11+,18-12+,21-17-,22-18-
• InChIKey: PVWALMHWUOWPPA-HCOJNGAVSA-N
• SMILES: O=C(C1=C2NC3=C(C=CC=C3)C/2=C/C(C(OC)=O)=C4NC5=C(C=CC=C5)C/4=C/1)OC

Caulerpin is a biochemical from the pigment from green algae, Caulerpa lamourouxii.

Reference

1: Parvez M, Ara J, Sultana V, Qasim R, Ahmad VU. Caulerpin. Acta Crystallogr C. 2000 Mar 15;56(Pt 3):E96-7. doi: 10.1107/S0108270100001529. Epub 2000 Mar 15. PMID: 15263213.
2: Lunagariya J, Bhadja P, Zhong S, Vekariya R, Xu S. Marine Natural Product Bis-indole Alkaloid Caulerpin: Chemistry and Biology. Mini Rev Med Chem. 2019;19(9):751-761. doi: 10.2174/1389557517666170927154231. PMID: 28971770.
3: Yu H, Zhang H, Dong M, Wu Z, Shen Z, Xie Y, Kong Z, Dai X, Xu B. Metabolic reprogramming and AMPKα1 pathway activation by caulerpin in colorectal cancer cells. Int J Oncol. 2017 Jan;50(1):161-172. doi: 10.3892/ijo.2016.3794. Epub 2016 Dec 6. PMID: 27922662.
4: Lucena AMM, Souza CRM, Jales JT, Guedes PMM, de Miranda GEC, de Moura AMA, Araújo-Júnior JX, Nascimento GJ, Scortecci KC, Santos BVO, Souto JT. The Bisindole Alkaloid Caulerpin, from Seaweeds of the Genus Caulerpa, Attenuated Colon Damage in Murine Colitis Model. Mar Drugs. 2018 Sep 7;16(9):318. doi: 10.3390/md16090318. PMID: 30205459; PMCID: PMC6163434.
5: Magliozzi L, Maselli V, Almada F, Di Cosmo A, Mollo E, Polese G. Effect of the algal alkaloid caulerpin on neuropeptide Y (NPY) expression in the central nervous system (CNS) of Diplodus sargus. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2019 Apr;205(2):203-210. doi: 10.1007/s00359-019-01322-8. Epub 2019 Mar 9. PMID: 30852662.
6: Del Coco L, Felline S, Girelli CR, Angilè F, Magliozzi L, Almada F, D’Aniello B, Mollo E, Terlizzi A, Fanizzi FP. ¹H NMR Spectroscopy and MVA to Evaluate the Effects of Caulerpin-Based Diet on Diplodus sargus Lipid Profiles. Mar Drugs. 2018 Oct 18;16(10):390. doi: 10.3390/md16100390. PMID: 30340347; PMCID: PMC6213232.
7: de Souza ET, de Lira DP, de Queiroz AC, da Silva DJ, de Aquino AB, Mella EA, Lorenzo VP, de Miranda GE, de Araújo-Júnior JX, Chaves MC, Barbosa-Filho JM, de Athayde-Filho PF, Santos BV, Alexandre-Moreira MS. The antinociceptive and anti- inflammatory activities of caulerpin, a bisindole alkaloid isolated from seaweeds of the genus Caulerpa. Mar Drugs. 2009 Nov 26;7(4):689-704. doi: 10.3390/md7040689. PMID: 20098607; PMCID: PMC2810220.
8: Ahmed SA, Abdelrheem DA, El-Mageed HRA, Mohamed HS, Rahman AA, Elsayed KNM, Ahmed SA. Destabilizing the structural integrity of COVID-19 by caulerpin and its derivatives along with some antiviral drugs: An in silico approaches for a combination therapy. Struct Chem. 2020 Jul 23:1-22. doi: 10.1007/s11224-020-01586-w. Epub ahead of print. PMID: 32837118; PMCID: PMC7376526.
9: Liu Y, Morgan JB, Coothankandaswamy V, Liu R, Jekabsons MB, Mahdi F, Nagle DG, Zhou YD. The Caulerpa pigment caulerpin inhibits HIF-1 activation and mitochondrial respiration. J Nat Prod. 2009 Dec;72(12):2104-9. doi: 10.1021/np9005794. PMID: 19921787; PMCID: PMC2798910.
10: Canché Chay CI, Gómez Cansino R, Espitia Pinzón CI, Torres-Ochoa RO, Martínez R. Synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues. Mar Drugs. 2014 Mar 27;12(4):1757-72. doi: 10.3390/md12041757. PMID: 24681629; PMCID: PMC4012461.