Aristolactams, 1-(2-C-Methyl-β-D-ribofuranosyl)-uracil and other bioactive constituents of Toussaintia orientalis

Natural Product Communications

Volumn 5, Issue 2, 2010, Pages 253-258

  Odalo, Josiah O ^a   Joseph, Cosam C ^a   Nkunya, Mayunga H H ^a   Sattler, Isabel ^b   Lange, Corinna ^b   Friedrich, Gollmick ^b   Dahse, Hans Martin ^b   Möllman, Ute ^b  

^a UNIVERSITY OF DAR ES SALAAM   (Tanzania)

^b HANS KNÖLL INSTITUTE   (Germany)

Author keywords

1 (2 C methyl D ribofuranosyl) uracil; Annonaceae; Antiinflammatory; Antimicrobials; Antiproliferative; Aristolactams; Cytotoxicity; Toussaintia orientalis

Indexed keywords

1 (2 C METHYL BETA DEXTRO RIBOFURANOSYL)URACIL; 3,4,5 TRIMETHOXYPHENYL BETA DEXTRO GLUCOPYRANOSIDE; AMPHOTERICIN; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ARISTOLACTAM AII; ARISTOLACTAM BII; ARISTOLACTAM FII; ARISTOLOLACTAM; CAMPTOTHECIN; CATECHINOID; CIPROFLOXACIN; COLCHICINE; EPICATECHIN 4BETA,8 EPICATECHIN; INDOMETACIN; NUCLEOSIDE DERIVATIVE; PACLITAXEL; PIPEROLACTAM C; TOUSSALACTAM; UNCLASSIFIED DRUG; 1 (2 C METHYL BETA D RIBOFURANOSYL) URACIL; 1-(2-C-METHYL-BETA-D-RIBOFURANOSYL)-URACIL; DRUG DERIVATIVE; INDOLE ALKALOID; LACTAM; URACIL;

AGAR DIFFUSION; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BARK; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; MEDICINAL PLANT; MOUSE; NONHUMAN; PLANT STEM; PROTON NUCLEAR MAGNETIC RESONANCE; TOUSSAINTIA ORIENTALIS; ANNONACEAE; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION;

ANNONACEAE;

ANNONACEAE; ANTI-BACTERIAL AGENTS; ANTI-INFLAMMATORY AGENTS; BACTERIA; INDOLE ALKALOIDS; LACTAMS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; URACIL;

EID: 77951889000     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1000500217     Document Type: Article

References (35)

1. Verdcourt B. (1971) Flora of Tropical East Africa - Annonaceae, Crown Agents, London, p. 1,9.
2. nd edition, Kenya Literature Bureau, Nairobi.
3. Verdcourt B. (1996) Sanrafaelia, a new genus of Annonaceae from Tanzania. Garcia de Orta, Series Botanica, 13, 43-44.
4. Couvreur TLP, Van Der Ham RWJM, Mbele YM, Mbago FM, Johnson DM. (2009) Molecular and morphological characterization of a new monotypic genus of Annonaceae, Mwasumbia, from Tanzania. Systematic Botany, 34, 266-276.
5. Deroin T, Luke Q. (2005) A new Toussaintia (Annonaceae) from Tanzania. Journal of East African Natural History, 94, 165-174.
6. Desai SJ, Prabhu BR, Mulchandani NB. (1988) Aristolactams and 4,5-dioxoaporphines from Piper longum. Phytochemistry, 27, 1511-1515.
7. Chia YC, Chang FR, Teng CM, Wu YC. (2000) Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii. Journal of Natural Products, 63, 1160-1163.
8. Sun NJ, Antoun M, Chang CJ, Cassady JM. (1987) New cytotoxic aristolactams from Pararistolochia flos-avis. Journal of Natural Products, 50, 843-846. (Pubitemid 17158670)
9. Beigelman LN, Ermolinsky BS, Gurskaya GV, Tsapkina EN, Karpeisky MY, Mikhailov SN. (1987) New synthesis of 2′-C-methylnucleosides starting from D-glucose and D-ribose. Carbohydrate Research, 166, 219-232.
10. Shimomura H, Sashida Y, Oohara M, Tenma H. (1988) Phenolic glucosides from Parabenzoin praecox. Phytochemistry, 27, 644-646.
11. Olsen CE, Tyagi OD, Boll PM, Hussaini FA, Parmar VS, Sharma NK, Teneja P, Jain SC, (1993) An aristolactam from Piper acutisleginum and revision of the structures of piperolactam B and D. Phytochemistry, 33, 518-520.
12. Chen YC, Chen JJ, Chang YL, Teng CM, Lin WY, Wu CC, Chen IS. (2004) A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense. Planta Medica, 70, 174-177.
13. Likhitwitayawuid K, Wiasathien L, Jongboonprasert V, Krungkrai J, Aimi N, Takayama H, Kitajima M. (1997) Antimalarial alkaloids from Goniothalamus tenuifolius. Pharmacology Letters, 7, 99-102.
14. Makriyannis A, Knittel JJ. (1979) The conformational analysis of aromatic methoxy groups from carbon-13 chemical shifts and spin-lattice relaxation times. Tetrahedron Letters, 20, 2753-2756.
15. Daneluttea AP, Costantina MB, Delgadob GE, Braz-Filho R, Kato MJ. (2005) Divergence of secondary metabolism in cell suspension cultures and differentiated plants of Piper cernuum and P. crassinervium. Journal of Brazilian Chemical Society, 16, 1425-1430.
16. Davies DB. (1978) Conformations of nucleosides and nucleotides. Progress of Nuclear Magnetic Resonance Spectroscopy, 12, 135-225.
17. Stevens JD, Fletcher HG. (1968) The proton magnetic resonance spectra of pentofuranose derivatives. Journal of Organic Chemistry, 33, 1799-1805.
18. Kam BL, Barascut JL, Imbach JL. (1979) A general method of synthesis and isolation, and an N.M.R.-spectroscopic study, of tetra-O-acetyl-D- aldopentofuranoses. Carbohydrates Research, 69, 135-142.
19. Jenkins SR, Arison B, Walton E. (1968) Branched-chain sugar nucleoside. IV. 2′-Methyladenosine. Journal of Organic Chemistry, 33, 2490-2494.
20. Guo FQ, Li Ai, Huang LF, Liang YZ, Chen BM. (2006) Identification and determination of nucleosides in Cordyceps sinesis and its substitutes by high performance liquid chromatography with mass spectrometric detection. Journal of Pharmacological and Biomedical Analysis, 40, 623-630.
21. Miles DW, Inskeep WH, Robins MJ, Winkley MW, Robins RK, Eyring H. (1970) Circular dichroism of nucleoside derivatives. IX. Vicinal effects on the circular dichroism of pyrimidine nucleosides. Journal of American Chemical Society, 92, 3872-3881.
22. Ingwall JS. (1972) Circular dichroism of nucleosides. I. Anomeric pairs of the D-pentofuranosides of adenine. Journal of American Chemical Society, 94, 5487-5495.
23. Searle PA, Molinski TF. (1995) Trachycladines A and B: 2′-C-methyl-5′-deoxyribofuranosyl nucleosides from the marine sponge Trachycladus laevispirulifer. Journal of Organic Chemistry, 60, 4296-4298.
24. Ichiba T, Nakao Y, Scheuer PJ, Sata NU, Kelly-Borges M. (1995) Kumusine, a chloroadenine riboside from a sponge, Theonella sp. Tetrahedron Letters, 36, 3977-3980.
25. De Clercq E. (2005) Antiviral drug discovery and development: Where chemistry meets with biomedicine. Antiviral Research, 67, 56-75.
26. De Clercq E. (2003) Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, andtenofovir intreatment of DNA virus and retrovirus infections. Clinical Microbiological Review, 16, 569-596.
27. Naesens L, De Clercq E. (2001) Recent developments in herpes virus therapy. Herpes, 8, 12-16.
28. Donia M, Hamann MT. (2003) Marine natural products and their potential applications as antiinfective agents. Lancet Infectious Diseases, 3, 338-348.
29. Suckling CJ. (1991) Chemical approaches to the discovery of new drugs. Science Progress, 75, 323-359.
30. Carroll SS, Tomassini JE, Bosserman M, Getty K, Stahlhut MW, Eldrup AB, Bhat B, Hall D, Simcoe AL, LaFemina R, Rutkowski CA, Wolanski B, Yang Z, Migliaccio G, De Francesco R, Kuo LC, MacCoss M, Olsen DB. (2003) Inhibition of hepatitis C virus RNA replication by 2′-modified nucleoside analogs. Journal of Biological Chemistry, 278, 11979-11984. (Pubitemid 36800172)
31. Stahl E. (1969) Thin-layer chromatography, a laboratory handbook. Springer-Verlag, New York, p. 857.
32. Meyer BN, Ferrigini RN, Jacobsen LB, Nicholas DE, McLaughlin JL. (1982) Brine shrimp: A convenient general bioassay for active plant constituents. Planta Medica, 45, 31-34.
33. Finney DJ. (1971) Probit analysis, 3rd ed., Cambridge University Press, Cambridge, 333 pp.
34. Penning TM. (1985) Inhibition of 5β-dihydrocotisone reduction in rat liver cytosol: A rapid spectrophotometric screen for nonsteroidal anti-inflammatory drug potency. Journal of Pharmacological Science, 74, 651-654.
35. Dahse HM, Schlegel B, Gräfe U. (2001) Differentiation between inducers of apoptosis and nonspecific cytotoxic drugs by means of cell analyzer and immunoassay using the cell lines K-562 (human chronic myeloid leukemia), and L-929 (mouse fibroblast) for antiproliferative effects and HeLa (human cervix carcinoma) for cytotoxic effects. Pharmazie, 56, 489-491.