Synthesis and biological activities of marine terpene-adenine hybrids and synthetic analogs

Phytochemistry Reviews

Volumn 12, Issue 3, 2013, Pages 467-486

  Gundersen, Lise Lotte ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

Agelasimine; Agelasine; Antimicrobial agents; Antineoplastic agents; Asmarine

Indexed keywords

2 OXOAGELASINE B; 2 OXOAGELASINE D; ADENINE DERIVATIVE; AGELASIMINE A; AGELASIMINE B; AGELASIN B; AGELASINE A; AGELASINE C; AGELASINE D; AGELASINE E; AGELASINE F; AGELASINE G; AGELASINE H; AGELASINE I; AGELASINE J; AGELASINE K; AGELASINE L; AGELASINE M; AGELOXIME D; ASMARINE A; ASMARINE B; ASMARINE C; ASMARINE D; ASMARINE E; ASMARINE F; GELASINE A; GELASINE B; METHYL KOLAVENATE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ASPERGILLUS NIGER; BACILLUS SUBTILIS; BACTEROIDES FRAGILIS; BACTEROIDES THETAIOTAOMICRON; BIOFILM; CANDIDA ALBICANS; CANDIDA KRUSEI; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ENTEROCOCCUS FAECIUM; ESCHERICHIA COLI; HUMAN; IC 50; LEISHMANIA INFANTUM; LEUKEMIA CELL; LEUKEMIA P 388; LYMPHOMA CELL; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; MYELOMA CELL; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; REVIEW; SACCHAROMYCES CEREVISIAE; SMOOTH MUSCLE CONTRACTION; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI;

AGELAS; RASPAILIA;

EID: 84885320337     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-012-9236-6     Document Type: Review

References (64)

1. Appenzeller J, Mihci G, Martin MT et al (2008) Agelasines J, K, and L from the Solomon Islands marine sponge Agelas cf. mauritiana. J Nat Prod 71:1451-1454
2. Asao K, Iio H, Tokoroyama T (1989a) Stereoselective cyclization of (E)- and (Z)-5,6-dimethyl-8-trimethylsilyl-6-octenals. Tetrahedron Lett 30:6397-6400
3. Asao K, Iio H, Tokoroyama T (1989b) Total synthesis of (±)-ageline A, a physiologically active constituent of Agelas sponges. Tetrahedron Lett 30:6401-6404
4. Bakkestuen AK, Gundersen L-L (2003) Synthesis of (+)-trixagol, the enantiomer of the (-)-agelasine E terpenoid side chain. Tetrahedron 59:115-121
5. Bakkestuen AK, Gundersen L-L, Petersen D et al (2005) Synthesis and antimycobacterial activity of agelasine E and analogs. Org Biol Chem 3:1025-1033
6. Blunt JW, Copp BR, Hu WP et al (2009) Marine natural products. Nat Prod Reports 26:170-244
7. Butler MS (2004) The role of natural product chemistry in drug discovery. J Nat Prod 67:2141-2153
8. Calcul L, Tenney K, Ratnam J et al (2010) Structural variations to the 9-N-methyladeninium deterpenoid hybrid commonly isolated from Agelas sponges. Aust J Chem 63:915-921
9. Capon RJ, Faulkner DJ (1984) Antimicrobial metabolites from a Pacific sponge, Agelas sp. J Am Chem Soc 106:1819-1822
10. Constantino V, Fattorusso E, Menna M et al (2004) Chemical diversity of bioactive marine natural products: an illustrative case study. Curr Med Chem 11:1671-1692
11. Cullen E, Devlin JP (1975) Agelasine: a novel quaternary 9-methyladenine from the sponge Agelas dispar. Can J Chem 53:1690-1691
12. Demain AL, Vaishnav P (2011) Natural products for cancer chemotherapy. Microb Biotech 4:687-699
13. Elkin GJ, Rojas JJ, Martinez A (2011) Pharmacological developments obtained from marine natural products and current pipeline perspective. Nat Prod Commun 6:287-300
14. Fathi-Afshar R, Allen TM (1988) Biologically active metabolites from Agelas mauritania. Can J Chem 66:45-50
15. Fathi-Afshar R, Allen TM, Krueger DA et al (1989) Some pharmalogical activities of novel adenine-related compounds isolated from a marine sponge Agelas mauritania. Can J Physiol Pharmacol 67:276-281
16. Fehr C, Galindo J (1995) Syntheses of the enantiomers of γ-cyclogeranic acid, γ-cyclocitral, and γ-damascone: enantioselective protonation of enolates. Helv Chim Acta 78:539-552
17. Fu X, Schmitz FJ, Tanner RS et al (1998) Agelasine H and I, 9-methyladenine-containing diterpenoids from an Agelas sponge. J Nat Prod 61:548-550
18. Fujii T, Itaya T, Wu CC et al (1971) Purines-III. Rearrangement of 1-alkoxy-9-alkyladenines to 6-alkoxyamino-9-alkylpurines through isolable N′-alkoxy-1-alkyl-5-formamidoimidazole-4-carboxamidines. Tetrahedron 27:2415-2423
19. Garcia A, Bocanegra-Garcia V, Palma-Nicolas JP et al (2012) Recent advances in antitubercular natural products. Eur J Med Chem 49:1-23
20. Griengl H, Hayden W, Plessing A (1984) C(6)-N(7)-Cyclized purines. J Heterocycl Chem 21:333-336
21. Hattori T, Adachi K, Shizuri YJ (1997) New agelasine compound from the marine sponge Agelas mauretania as an antifouling substance against macroalgae. J Nat Prod 60:411-413
22. Hertiani T, Edraaada-Ebel R, Ortlepp S et al (2010) From anti-fouling to biofilm inhibition: new cytotoxic secondary metabolites from two Indonesian Agelas sponges. Bioorg Med Chem 18:1297-1311
23. Iio H, Asao K, Tokoroyama T (1985) Syntheses of agelasine B and its analogues. J Chem Soc Chem Commun 774-775
24. Iio H, Monden M, Okada K et al (1987) Asymmetric synthesis of clerodane diterpenoids: total synthesis of (-)-methyl kolavenate. J Chem Soc Chem Commun 358-359
25. Ishida K, Ishibashi M, Shigemori H et al (1992) Agelasine G, a new antileukemic alkaloid from the Okinawan marine sponge Agelas sp. J Chem Pharm Bull 40:766-767
26. Iwagawa T, Kaneko M, Okamura H et al (1998) New alkaloids from the Papua New Guinean sponge Agelas nakamurai. J Nat Prod 61:1310-1312
27. Jähne G, Kroha H, Müller A et al (1994) Regioselective synthesis and antiviral activity of purine nucleoside analogs acyclically substituted at N7. Angew Chem Int Ed Engl 33:562-563
28. +-ATPase by agelasidines and agelasines from a sea sponge. Arch Biochem Biophys 259:179-184
29. Lindel T, Hoffmann H, Hochgürtel M et al (2000) Structure-activity relationship of inhibition of fish feeding by sponge-derived and synthetic pyrrole-imidazole alkaloids. J Chem Ecol 26:1477-1496
30. Manglindan GC, Talaue MT, Cruz LJ et al (2000) Agelasine F from a Philippine Agelas sp. sponge exhibits in vitro antituberculosis activity. Planta Med 66:364-365
31. Marcos IS, Garcia N, Sexmero MJ (2005) Synthesis of (+)-agelasine C. A structural revision. Tetrahedron 61:11672-11678
32. Nakamura H, Wu H, Ohizumi Y et al (1984) Agelasine-A, -B, -C and -D, novel bicyclic diterpenoids with a 9-methyladeninium unit possessing inhibitory effects on Na,K-ATPase from the Okinawan sea sponge Agelas sp. Tetrahedron Lett 25:2989-2992
33. Ohba M, Tashiro T (2002) Preparatory study for the synthesis of the marine sponge alkaloids asmarines A-F: synthesis of their heterocyclic portion. Heterocycles 57:1235-1238
34. Ohba M, Kawase N, Fujii T et al (1995) Racemic syntheses of agelasimine-A and agelasimine-B, bicyclic diterpenoids from the marine sponge Agelas mauritania. Tetrahedron Lett 36:6101-6104
35. Ohba M, Kawase N, Fujii T (1996) Total syntheses of (±)- agelasimine-A, (±)-agelasimine-B, and (±)-purino-diterpene and the structure of diacetylagelasimine-A. J Am Chem Soc 118:8250-8257
36. Ohba M, Iizuka K, Ishibashi H et al (1997) Syntheses and absolute configuration of the marine sponge purines (+)-agelasimine-A and (+)-agelasimine-B. Tetrahedron 53:16977-16986
37. Pappo D, Kashman Y (2003) Synthesis of 9-substituted tetrahydrodiazepinopurines - asmarine A analogues. Tetrahedron 59:6493-6501
38. Pappo D, Rudi A, Kashman Y (2001) A synthetic approach towards the synthesis of asmarine analogues. Tetrahedron Lett 42:5941-5943
39. Pappo D, Shimony S, Kashman Y (2005) Synthesis of 9-substituted tetrahydrodiazepinopurines: studies toward the total synthesis of asmarines. J Org Chem 70:199-206
40. 3Sn function as a readily removable "anchoring" group in the synthesis of enantiomerically pure bicyclic alchohols and ketones. Tetrahedron Lett 32:5219-5222
41. Piers E, Roberge JY (1992) Total syntheses of the diterpenoids (-)-kolavenol and (-)-agelasine B. Tetrahedron Lett 33:6923-6926
42. Piers E, Breau ML, Han X et al (1995) Total synthesis of diterpenoids: (-)-agelasine A and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide. J Chem Soc Perkin Trans 1:963-966
43. 2+ concentration and induces apoptosis in human breast cancer cells (MCF-7). Cancer Chemother Pharmacol 69:71-83
44. Proksch P, Edrada-Ebel R, Ebel R (2003) Drugs from the sea - opportunities and obstacles. Mar Drugs 1:5-17
45. Proszenyak A, Charnock C, Hedner E et al (2007) Synthesis and antimicrobial and antineoplastic activities of agelasine and agelasimine analogs with a β-cyclocitral derived substituent. Arch Pharm Chem Life Sci 340:625-634
46. Proszenyak A, Brændvang M, Charnock C et al (2009) The first synthesis of ent-Agelasine F. Tetrahedron 65:194-199
47. Rodgen SA, Schaus SE (2006) Efficient construction of the clerodane decalin core by an asymmetric Morita-Baylis-Hillman reaction/Lews acid promoted strategy. Angew Chem Int Ed Engl 45:4929-4932
48. Roggen H, Charnock C, Burman R et al (2011) Antimicrobial and antineoplastic activities of agelasine analogs modified in the purine 2-position. Arch Pharm Chem Life Sci 344:50-55
49. Rudi A, Shalom H, Schleyer M et al (2004a) Asmarines G and H and barekol, three new compounds from the marine sponge Raspailia sp. J Nat Prod 67:106-109
50. Rudi A, Aknin M, Gaydou E et al (2004b) Asmarines I, J, and K and Nosyberkol: Four new compounds from the marine sponge Raspailia sp. J Nat Prod 67:1932-1935
51. Schumacher M, Kelkel M, Dicato M et al (2011) A survey of marine natural compounds and their derivatives with anti-cancer activity reported in 2010. Molecules 16:5629-5646
52. Sjögren M, Dahlström M, Hedner E et al (2008) Antifouling activity of the sponge metabolite agelasine D and synthesized analogs on Balanus improvisus. Biofouling 24:251-258
53. Soladie G, Hutt J (1987) Total synthesis of dihydrovitamin DHV3 and dihydrotachysterol DHT3. Application of the low-valent titanium induced reductive elimination. J Org Chem 52:3560-3566
54. Steiner U, Willhalm B (1952) Synthesis of ethyl 2,2-dimethyl-6- oxocyclohexanecarboxylate. Helv Chim Acta 35:1752-1756
55. Tempone AG, Martins de Oliveira C, Berlinck RGS (2011) Current approaches to discover marine antileishmanial natural products. Planta Med 77:572-585
56. Utenova BT, Gundersen L-L (2004) Synthesis of (+)-agelasine D from (+)-manool. Tetrahedron Lett 45:4233-4235
57. Vik A, Gundersen L-L (2007) Synthetic studies directed towards asmarines; construction of the tetrahydrodiazepinopurine moiety by ring closing metathesis. Tetrahedron Lett 48:1931-1934
58. Vik A, Hedner E, Charnock C et al (2006) (+)-Agelasine D: improved synthesis and evaluation of antibacterial and cytotoxic activities. J Nat Prod 69:381-386
59. Vik A, Hedner E, Charnock C et al (2007) Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs. Bioorg Med Chem 15:4016-4037
60. Vik A, Proszenyak A, Vermeersch M et al (2009) Screening of agelsine D and analogs for inhibitory activity against pathogenic protozoa; identification of hits for treatment of visceral leishmaniasis and Chagas disease. Molecules 14:279-288
61. Wu H, Nakamura H, Kobayashi J et al (1984) Agelasine-E and -F, novel monocyclic diterpenoids with a 9-methyladeninium unit possessing inhibitory effects on Na,K-ATPase from the Okinawan sea sponge Agelas nakamurai Hoshino. Tetrahedron Lett 25:3719-3722
62. Wu H, Nakamura H, Kobayashi J et al (1986) Structures of agelasines, diterpenes having a 9-methyladeninium chromophore isolated from the Okinawan sea sponge Agelas nakamurai Hoshino. Bull Chem Soc Jpn 59:2495-2504
63. Yosief T, Rudi A, Stein Z et al (1998) Asmarines A-C; Three novel cytotoxic metabolites from the marine sponge Raspailia sp. Tetrahedron Lett 39:3323-3326
64. Yosief T, Rudi A, Kashman Y (2000) Asmarines A-F; Novel cytotoxic compounds from the marine sponge Raspailia species. J Nat Prod 63:299-304