Synthesis and studies of two marine indole alkaloids, barettin and caulersin

Phytochemistry Reviews

Volumn 12, Issue 3, 2013, Pages 487-494

  Bergman, J ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Algae; Anti fouling; Formylations; Reagents; Vilsmeier

Indexed keywords

BARETTIN; CAULERSIN; INDOLE ALKALOID; UNCLASSIFIED DRUG;

CHROMATOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; MARINE ENVIRONMENT; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REVIEW;

ALGAE;

EID: 84885298162     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-012-9238-4     Document Type: Review

References (47)

1. Aguilar-Santos G (1970) Caulerpin, a new red pigment from green algae of the genus Caulerpa. J Chem Soc C 1970:842-843
2. Alvarez M, Salas M, Joule JA (1991) Marine nitrogen-containing heterocyclic natural products. Structures and syntheses of compounds containing indole units. Heterocycles 32:1391-1429
3. Aygün A, Pindur U (2003) Chemistry and biology of new marine alkaloids from the indole and annelated indole series. Curr Med Chem 10:1113-1127
4. Bao B, Sun Q, Yao X, Hong J, Lee C-O, Sim CJ, Im KS, Jung JH (2005) Cytotoxic bisindole Alkaloids from a marine sponge Spongosorites sp. JNP 68:711-715
5. Barykina OV, Snider BB (2010) Synthesis of (±)-Eusynstyelamide A. Org Lett 12:2664-2667
6. Baran PS, Shenvi RA (2006) Total synthesis of (±)-Chartelline C. JACS 128:14028-14029
7. Bergander L, Wahlstrom N, Alsberg T, Bergman J, Rannug A, Rannug U (2003) Characterization of in vitro metabolites of the aryl hydrocarbon receptor ligand 6-formylindolo[3,2-b]carbazole by liquid chromatography-mass spectrometry and NMR. Drug Metab Dispos 31:230-241
8. Bergman J, Janosik T, Johnsson A-L (1999) Synthesis of hyrtiosin B, a bis-indole alkaloid from the Okinawan marine sponge Hyrtios erecta. Synthesis 1999:580-582
9. Bergman J, Janosik T, Wahlström N (2001) Indolocarbazoles. Adv Het Chem 80:1-71
10. Caballero E, Avendano C, Menendez JC (2003) Brief total synthesis of the cell cycle inhibitor tryprostatin B and related preparation of its alanine analogue. J Org Chem 68:6944-6951
11. Cui C-B, Kakeya H, Osada H (1996) Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketo-piperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures. J Antibiot 49:534-540
12. Endo T, Tsuda M, Fromont J, Kobayashi J (2007) Hyrtinadine A, a bis-indole alkaloid from a marine sponge. JNP 70:423-424
13. Fusetani N (2004) Bofouling and antifouling. NPR 21:94-104
14. Fusetani N (2011) Antifouling marine natural products. NPR 28:400-410
15. Garg NK, Caspi DD, Stoltz BM (2005) Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin F from a single enantiomer of quinic acid. JACS 127:5970-5978
16. Hedner E (2007) Bioactive compounds in the chemical defence of marine sponges; structure-activity relationships and pharmacological targets. Dissertation, University of Uppsala
17. Hedner E, Sjögren M, Frändberg P-A, Johansson T, Göransson U, Dahlström M, Jonsson P, Nyberg F, Bohlin L (2006) Brominated cyclodipeptides from the marine sponge Geodia barretti as selective 5-HT ligands. J Nat Prod 69:1421-1424
18. Hedner E, Sjögren M, Hodzic S, Andersson R, Göransson U, Jonsson PR, Bohlin L (2008) Antifouling activity of a dibrominated cyclopeptide from the marine sponge Geodia barretti. J Nat Prod 71:330-333
19. Johnson A-L, Janosik T, Bergman J, (2002) Synthesis of the diketopiperazine dipodazine. Arkivoc viii:57-61
20. Johnson A-L, Bergman J, Sjögren M, Bohlin L (2004) Synthesis of barettin. Tetrahedron 60:961-965
21. Kaur H, Heapy AM, Brimble M (2011) The synthesis of dehydrotryptophan and dehydrotryptophan-containing pepties. OBC 9:5897-5907
22. Kobayashi J, Murayama T, Ishibashi M, Kosuge S, Takamatsu M, Ohizumi Y, Kobayashi H, Ohta T, Nozoe S, Sasaki T (1990) Hyrtiosins A and B, new indole alkaloids from the Okinawan marine sponge Hyrtios erecta. Tetrahedron 46:7699-7702
23. Lidgren G, Bohlin L, Bergman J, 1986. Studies of Swedish marine organisms VII. A novel biologically active indole alkaloid from the sponge Geodia baretti. Tetrahedron Lett. 27:3283
24. Lieberknecht A, Griesser H (1987) What is the structure of barettin? Novel synthesis of unsaturated diketopiperazines. Tetrahedron Lett 28:4275-4281
25. Ma Q (2011) Influence of light on aryl hydrocarbon receptor signaling and consequences in drug metabolism, physiology and disease. Expert Opin Drug Metab Toxicol 7:1267-1293
26. Maiti BC, Thomson RH (1978) The structure of caulerpin, a pigment from Caulerpa algae. J Chem Res (M) 1978:1682-1693
27. Merkul E, Schaefer E, Mueller TJJ (2011) Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation-Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G. OBC 9:3139-3141
28. Moquin-Patte C, Guyot M (1989) Grossularine-1 and grossularine-2, cytotoxic a-carbolines from the tunicate: dendrodoa grossularia. Tetrahedron 45:3445-3450
29. Oikawa M, Ikoma M, Sasaki M (2011) Synthetic studies on dragmacidin D: synthesis and assembly of three fragments towards an advanced intermediate. Eur JOC 2011:4654-4666
30. Rafferty RJ, Williams RM (2012) Total synthesis of hapalindoles J and U. JOC 77:519-524
31. Rannug U, Rannug A, Sjöberg U, Li H, Westerholm R, Bergman J (1995) Structure elucidation of two tryptophan-derived, high affinity Ah receptor ligands. Chem Biol 2:841-845
32. Sammes PG, Weedon AC (1979) Pyrazine chemistry. Part 11. Chemical studies on cyclic tautomers of cyclo-l-propyl-l-tryptophyl and its derivatives. JCS Perkin TI 1979:3048-3052
33. Schwede JG, Cardellina JH II, Grode SH, James TR Jr, Blackman AJ (1987) Distribution of the pigment caulerpin in species of the green alga Caulerpa. Phytochemistry 26:155-158
34. Sjögren M, Göransson U, Johnson A-L, Dahlström M, Andersson R, Bergman J, Jonsson PR, Bohlin L (2004) Antifouling activity of brominated cyclopeptides from the marine sponge Geodia barretti. JNP 67:368-372
35. Sölter S, Dieckmann R, Blumenberg M, Francke W (2002) Barettin, revisited? Tetrahedron Lett 43:3385-3389
36. Somei M, Yamada F (2005) Simple indole alkaloids and those with a non-rearranged monoterpenoid unit. NPR 22:73-103
37. Su J-Y, Zhu Y, Zeng L-M, Xu X-H (1997) A new bisindole from alga Caulerpa serrulata. JNP 60:1043-1044
38. Sun C, Lin X, Weinreb SM (2006) Explorations on the total synthesis of the unusual marine alkaloid Chartelline A. JOC 71:3159-3166
39. Tadesse M, Tabudravu JN, Jaspars M, Strøm MB, Hansen E, Andersen JH, Kristiansen PE, Haug T (2011) The antibacterial ent-Eusynstyelamide B and Eusynstyelamides D, E, and F from the Arctic Bryozoan Tegella cf. spitzbergensis. JNP 74:837-841
40. Tapiolas DM, Bowden BF, Abou-Mansour E, Willis RH, Doyle JR, Muirhead AN, Liptrot C, Llewellyn LE, Wolff CWW, Wright AD, Motti CA (2009) Eusynstyelamides A, B, and C, nNOS inhibitors, from the ascidian Eusynstyela latericius. JNP 72:1115-1120
41. Tholander J, Bergman J (1998) Synthesis of 6-formylindolo[3,2-b] carbazole, an extremely potent ligand for the aryl hydrogen (Ah) receptor. Tetrahedron Lett 39:1619-1621
42. Tholander J, Bergman J (1999) Syntheses of 6-substituted indolo[3,2-b]carbazoles, including 6-formylindolo[3,2-b]carbazole, an extremely efficient ligand for the TCDD (Ah) receptor. Tetrahedron 55:6243-6260
43. Wahlström N, Romero I, Bergman J (2004a) Synthesis of metabolites of the Ah receptor ligand 6-formylindolo[3,2-b]carbazole. Eur J Org Chem 2004:2593-2602
44. Wahlström N, Stensland B, Bergman J (2004b) Synthesis of the marine alkaloid caulersin. Tetrahedron 60:2147-2153
45. Wei X, Henriksen NM, Skalicky JJ, Harper MK, Cheatham TE, Ireland CM, Van Wagoner RM (2011) Araiosamines A-D: trisbromo-indole cyclic guanidine alkaloids from the marine sponge Clathria (Thalysias) araiosa. JOC 76:5515-5523
46. Wincent E, Amini N, Luecke S, Glatt H, Bergman J, Crescenzi C, Rannug A, Rannug U (2009) The suggested physiologic aryl hydrocarbon receptor activator and cytochrome P4501 substrate 6-formyl-indolo[3,2-b]carbazole is present in humans. J Biol Chem 284:2690-2696
47. Yang C-G, Huang H, Jiang B (2004) Progress in studies of novel marine bis(indole) alkaloids. Curr Org Chem 8:1691-1720