From a methanol extract of the leaves of the Malian medicinal tree Terminalia macroptera, cis-polyisoprene (1), chebulic acid trimethyl ester (2), methyl gallate (3), shikimic acid (4), corilagin (5), rutin (6), narcissin (7), chebulagic acid (8) and chebulinic acid (9), were isolated. Cis-polyisoprene (1) was the major non-polar constituent. The novel compound 2 showed high radical scavenging activity (IC50 4.7 μg/mL), but was inactive as xanthine oxidase inhibitor. The major substituent of the crude extract, substance 5, showed a high radical scavenger effect (IC50 2.7 μg/mL) and weak xanthine oxidase inhibition (IC50 ca 105 μg/mL). The antioxidant and radical scavenging effects of some of the substances identified in this study may to some extent explain the medical use of this tree in West Africa.
SilvaO., GomesE.T., WolfenderJ.L., MarstonA., HostettmannK. (2000) Application of high performance liquid chromatography coupled with ultraviolet spectroscopy and electrospray mass spectrometry to the characterisation of ellagitannins from Terminalia macroptera roots. Pharmaceutical Research, 17, 1396–1401.
2.
SilvaO., FerreiraE., PatoM.V., CanicaM., GomesE.T. (2002) In vitro anti-Neisseria gonorrhoeae activity of Terminalia macroptera leaves. FEMS Microbiology Letters, 217, 271–274.
3.
MaydellH-J. (1990) Trees and shrubs of the Sahel: their characteristics and uses.Verlag Josef Margraf, Weikersheim.
4.
ArbonnierM. (2004) Trees, shrubs and lianas of West African dry zones.Margraf Publishers, Weikersheim, 276.
5.
NongoniermaR., ProliacA., RaynaudJ. (1990) O-Glycosyl flavonoids from the flowers of Terminalia-macroptera Guill. Et Perr. (Combretaceae). Pharmaceutica Acta Helvetiae, 65, 233–235.
6.
NongoniermaR., ProliacA., RaynaudJ. (1987) 2 Mono-C-glycosyl flavonoids from flowers of Terminalia macroptera Guill and Perr (Combretaceae). Pharmazie, 42, 871–872.
7.
ConradJ., VoglerB., KlaiberI., RoosG., WalterU., KrausW. (1998) Two triterpene esters from Terminalia macroptera bark. Phytochemistry, 48, 647–650.
8.
ConradJ., VoglerB., KlaiberI., ReebS., GuseJ.H., RoosG., KrausW. (2001) Vanillic acid 4-O-β-D-(6 ′-O-galloyl) glucopyranoside and other constituents from the bark of Terminalia macroptera Guill. et Perr. Natural Product Letters, 15, 35–42.
9.
ConradJ., VoglerB., ReebS., KlaiberI., PapajewskiS., RoosG., VasquezE., SetzerM.C., KrausW. (2001) Isoterchebulin and 4,6-O-isoterchebuloyl-D-glucose, novel hydrolyzable tannins from Terminalia macroptera. Journal of Natural Products, 64, 294–299.
10.
BatawilaK., KokouK., KoumagloK., GbéassorM., de FoucaultB., BouchetP., AkpaganaK. (2005) Antifungal activities of five Combretaceae used in Togolese traditional medicine. Fitoterapia, 76, 264–268.
ZhangY., DeWittD.L., MurugesanS., NairM.G. (2004) Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds. Chemistry and Biodiversity, 1, 426–441.
15.
ChungS.K., NamJ.A., JeonS.Y., KimS.I., LeeH.J., ChungT.H., SongK.S. (2003) A prolyl endopeptidase-inhibiting antioxidant from Phyllanthus ussurensis. Archives of Pharmacal Research, 26, 1024–1028.
16.
HanJ.T., BangM.H., ChunO.K., KimD.O., LeeC.Y., BaekN.I. (2004) Flavonol glycosides from the aerial parts of Aceriphyllum rossii and their antioxidant activities. Archives of Pharmacal Research, 27, 390–395.
17.
LeeE.H., KimH.J., SongY.S., JinC., LeeK-T, ChoJ., LeeY.S. (2003) Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Archives of Pharmacal Research, 26, 1018–1023.
18.
PfundsteinB., El DesoukyS.K., HullW.E., HaubnerR., ErbenG., OwenR.W. (2010) Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry, 71, 1132–1148.
19.
YangJ., SunF., LiZ., DuG., QinH. (2008) Chemical constituents from Terminalia chebula Retz. Tianran Chanwu Yanjiu Yu Kaifa, 20, 450–451.
20.
LeeH.S., JungS.H., YunB-S, LeeK-W. (2007) Isolation of chebulic acid from Terminalia chebula Retz. and its antioxidant effect in isolated rat hepatocytes. Archives of Toxicology, 81, 211–218.
21.
ChenL.G., HuangW.T., LeeL.T., WangC.C. (2009) Ellagitannins from Terminalia calamansanai induced apoptosis in HL-60 cells. Toxicology in Vitro, 23, 603–609.
AvulaB., WangY.H., SmillieT.J., KhanI.A. (2009) Determination of shikimic acid in fruits of Illicium species and various other plant samples by LC-UV and LC-ESI-MS. Chromatographia, 69, 307–314.
24.
OkudaT. (2005) Systematics and health effects of chemically distinct tannins in medicinal plants. Phytochemistry, 66, 2012–2031.
25.
ZhaoL., ZhangS-L, TaoJ-Y, PangR., JinF., GuoY-J, DongJ-H, YeP., ZhaoH-Y, ZhengG-H. (2008) Preliminary exploration on anti-inflammatory mechanism of corilagin (beta-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-D-glucose) in vitro. International Immunopharmacology, 8, 1059–1064.
26.
KinoshitaS., InoueY., NakamaS., IchibaT., AniyaY. (2007) Antioxidant and hepatoprotective actions of medicinal herb, Terminalia catappa L. from Okinawa island and its tannin corilagin. Phytomedicine, 14, 755–762.
27.
HuangR.L., HuangY.L., OuJ.C., ChenC.C., HsuF.L., ChangC. (2003) Screening of 25 compounds isolated from Phyllanthus species for anti-human Hepatitis B virus in vitro. Phytotherapy Research, 17, 449–453.
28.
ZhangY.J., NagaoT., TanakaT., YangC.R., OkabeH., KounoI. (2004) Antiproliferative activity of the main constituents from Phyllanthus emblica. Biological & Pharmaceutical Bulletin, 27, 251–255.
29.
FoglianiB., RaharivelomananaP., BianchiniJ.P., Bouraïma-MadjèbiS., HnawiaE. (2005) Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia. Phytochemistry, 66, 241–247.
30.
HatanoT., KusudaM., InadaK., OgawaT., ShiotaS., TsuchiyaT., YoshidaT. (2005) Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus. Phytochemistry, 66, 2047–2055.
31.
WangensteenH., SamuelsenA.B., MalterudK.E. (2004) Antioxidant activity in extracts from coriander. Food Chemistry, 88, 293–297.
