The new aristolactam alkaloid toussalactam {2-hydroxy-1,6-dimethoxy-5H-dibenzo[cdf]indol-4-one} and the known ones, namely aristolactam AII, aristolactam BII, piperolactam C and aristolactam FII; 1-(2-C-methyl-β-D-ribofuranosyl)-uracil, 3,4,5-trimethoxyphenyl-β-D-glucopyranoside, and three catechinoids were isolated from the cytotoxic Toussaintia orientalis Verdc stem and root bark extracts, and their structures established based on analysis of spectroscopic data. The aristolactams exhibited antimicrobial and antiinflammatory activity, aristolactam FII showing almost the same level of activity as the standard anti-inflammatory agent Indomethacin. The compounds also exhibited either mild or no antiproliferative and cytotoxic activities, except aristolactam FII that showed the same level of cytotoxicity as the standard drug Camptothecin. 1-(2-C-Methyl-β-D-ribofuranosyl)-uracil, which is being reported for the first time as a natural product, was inactive in the antibacterial, antifungal, antiinflammatory, antiproliferative and cytotoxicity assays.
VerdcourtB. (1971) Flora of Tropical East Africa - Annonaceae, Crown Agents, London, p. 1,9.
2.
KokwaroJO. (1993) Medicinal Plants of East Africa, 2nd edition, Kenya Literature Bureau, Nairobi.
3.
VerdcourtB. (1996) Sanrafaelia, a new genus of Annonaceae from Tanzania. Garcia de Orta, Series Botanica, 13, 43–44.
4.
CouvreurTLP, Van Der HamRWJM, MbeleYM, MbagoFM, JohnsonDM. (2009) Molecular and morphological characterization of a new monotypic genus of Annonaceae, Mwasumbia, from Tanzania. Systematic Botany, 34, 266–276.
5.
DeroinT, LukeQ. (2005) A new Toussaintia (Annonaceae) from Tanzania. Journal of East African Natural History, 94, 165–174.
6.
DesaiSJ, PrabhuBR, MulchandaniNB. (1988) Aristolactams and 4,5-dioxoaporphines from Piper longum. Phytochemistry, 27, 1511–1515.
7.
ChiaYC, ChangFR, TengCM, WuYC. (2000) Aristolactams and dioxoaporphines from Fissistigma balansae and Fissistigma oldhamii. Journal of Natural Products, 63, 1160–1163.
8.
SunNJ, AntounM, ChangCJ, CassadyJM. (1987) New cytotoxic aristolactams from Pararistolochia flos-avis. Journal of Natural Products, 50, 843–846.
9.
BeigelmanLN, ErmolinskyBS, GurskayaGV, TsapkinaEN, KarpeiskyMY, MikhailovSN. (1987) New synthesis of 2′-C-methylnucleosides starting from D-glucose and D-ribose. Carbohydrate Research, 166, 219–232.
OlsenCE, TyagiOD, BollPM, HussainiFA, ParmarVS, SharmaNK, TenejaP, JainSC, (1993) An aristolactam from Piper acutisleginum and revision of the structures of piperolactam B and D. Phytochemistry, 33, 518–520.
12.
ChenYC, ChenJJ, ChangYL, TengCM, LinWY, WuCC, ChenIS. (2004) A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense. Planta Medica, 70, 174–177.
MakriyannisA, KnittelJJ. (1979) The conformational analysis of aromatic methoxy groups from carbon-13 chemical shifts and spin-lattice relaxation times. Tetrahedron Letters, 20, 2753–2756.
15.
DanelutteaAP, CostantinaMB, DelgadobGE, Braz-FilhoR, KatoMJ. (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.
DaviesDB. (1978) Conformations of nucleosides and nucleotides. Progress of Nuclear Magnetic Resonance Spectroscopy, 12, 135–225.
17.
StevensJD, FletcherHG. (1968) The proton magnetic resonance spectra of pentofuranose derivatives. Journal of Organic Chemistry, 33, 1799–1805.
18.
KamBL, BarascutJL, ImbachJL. (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.
JenkinsSR, ArisonB, WaltonE. (1968) Branched-chain sugar nucleoside. IV. 2′-Methyladenosine. Journal of Organic Chemistry, 33, 2490–2494.
20.
GuoFQ, LiAi, HuangLF, LiangYZ, ChenBM. (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.
MilesDW, InskeepWH, RobinsMJ, WinkleyMW, RobinsRK, EyringH. (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.
IngwallJS. (1972) Circular dichroism of nucleosides. I. Anomeric pairs of the D-pentofuranosides of adenine. Journal of American Chemical Society, 94, 5487–5495.
23.
SearlePA, MolinskiTF. (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.
IchibaT, NakaoY, ScheuerPJ, SataNU, Kelly-BorgesM. (1995) Kumusine, a chloroadenine riboside from a sponge, Theonella sp. Tetrahedron Letters, 36, 3977–3980.
25.
De ClercqE. (2005) Antiviral drug discovery and development: Where chemistry meets with biomedicine. Antiviral Research, 67, 56–75.
26.
De ClercqE. (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.
NaesensL, De ClercqE. (2001) Recent developments in herpes virus therapy. Herpes, 8, 12–16.
28.
DoniaM, HamannMT. (2003) Marine natural products and their potential applications as antiinfective agents. Lancet Infectious Diseases, 3, 338–348.
29.
SucklingCJ. (1991) Chemical approaches to the discovery of new drugs. Science Progress, 75, 323–359.
30.
CarrollSS, TomassiniJE, BossermanM, GettyK, StahlhutMW, EldrupAB, BhatB, HallD, SimcoeAL, LaFeminaR, RutkowskiCA, WolanskiB, YangZ, MigliaccioG, De FrancescoR, KuoLC, MacCossM, OlsenDB. (2003) Inhibition of hepatitis C virus RNA replication by 2′-modified nucleoside analogs. Journal of Biological Chemistry, 278, 11979–11984.
31.
StahlE. (1969) Thin-layer chromatography, a laboratory handbook. Springer-Verlag, New York, p. 857.
32.
MeyerBN, FerriginiRN, JacobsenLB, NicholasDE, McLaughlinJL. (1982) Brine shrimp: A convenient general bioassay for active plant constituents. Planta Medica, 45, 31–34.
33.
FinneyDJ. (1971) Probit analysis, 3rd ed., Cambridge University Press, Cambridge, 333 pp.
34.
PenningTM. (1985) Inhibition of 5ß-dihydrocotisone reduction in rat liver cytosol: A rapid spectrophotometric screen for nonsteroidal anti-inflammatory drug potency. Journal of Pharmacological Science, 74, 651–654.
35.
DahseHM, SchlegelB, GräfeU. (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.
