Antimicrobial Pentacyclic Triterpenoids from Terminalia superba

Abstract

Antibacterial bioassay-guided fractionation of the methanol extract of the stem bark of Terminalia superba led to the isolation of four new triterpene glucosides (1–4) which were characterized as 2α,3β-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (1), 2α,3β, 21β-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (2), 2α,3β, 29-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (3) and 2α,3β,23,27-tetrahydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside (4) together with the known triterpene 2α,3β,23-trihydroxyolean-12-en-28-oic acid (5). Structures were established by spectroscopic methods including one- and two-dimensional NMR, EI‐MS and HR‐EI‐MS. The antibacterial activity of 1–5 was also investigated against two gram-positive (Bacillus subtilis, Staphylococcus aureus), and four gram-negative (Escherichia coli, Shigella flexenari, Pseudomonas aeruginosa, Salmonella typhi) bacterial strains.

Key words

Terminalia superba - Combretaceae - triterpenoids - antibacterial activity

References

• 1 Cao S, Brodie P J, Miller J S, Randrianaivo R, Ratovoson F, Birkinshaw C, Andriantsiferana R, Rasamison V E, Kingston D G. Antiproliferative xanthones of Terminalia calcicola from the Madagascar rain forest.  J Nat Prod. 2007;  70 679-681
• 2 Han Q, Song J, Qiao C, Wong L, Xu H. Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography.  J Sep Sci. 2006;  29 1653-1657
• 3 Wansi J D, Lallemand M C, Chiozem D D, Toze F AA, Mbaze L M, Khan S N, Choudhary M I, Tillequin F, Wandji J, Fomum Z T. α-Glucosidase inhibitory constituents from stem bark of Terminalia superba (Combretaceae).  Phytochemistry. 2007;  68 2096-3000
• 4 Katerere D R, Gray A I, Nash R J, Waigh R D. Antimicrobial activity of pentacyclic triterpenes isolated from African Combretaceae.  Phytochemistry. 2003;  63 81-88
• 5 Pawar R S, Bhutani K K. Effect of oleanane triterpenoids from Terminalia arjuna – a cardioprotective drug on the process of respiratory oxyburst.  Phytomedicine. 2005;  12 391-393
• 6 Kloucek P, Polesny Z, Svobodova B, Vlkova E, Kokoska L. Antibacterial screening of some Peruvian medicinal plants used in Calleria District.  J Ethnopharmacol. 2005;  99 309-312
• 7 Tshikalange T E, Meyer J J, Hussein A A. Antimicrobial activity, toxicity and the isolation of a bioactive compound from plants used to treat sexually transmitted diseases.  J Ethnopharmacol. 2005;  96 515-519
• 8 Rani P, Khullar N. Antimicrobial evaluation of some medicinal plants for their anti-enteric potential against multi-drug resistant Salmonella typhi.  Phytother Res. 2004;  18 670-673
• 9 Adjanohoun J E, Aboubakar N, Dramane K, Ebot M E, Ekpere J A, Enow-Orock E G, Focho D, Gbile Z O, Kamanyi A, Kamsu K J, Keita A, Mbenkum T, Mbi C N, Mbiele A L, Mbome I L, Mubiru N K, Nancy W L, Nkongmeneck B, Satabie B, Sofowora A, Tamze V, Wirmum C K. Traditional medicine and pharmacopoeia, contribution to ethnobotanical and floristic studies in Cameroon. Porto-Novo, Benin; CNPMS 1996: 85
• 10 Tabopda T K, Ngoupayo J, Liu J, Ali M S, Khan S N, Ngadjui B T, Luu B. α-Glucosidase inhibitors ellagic acid derivatives with immunoinhibitory properties from Terminalia superba.  Chem Pharm Bull. 2008;  56 847-850
• 11 Carron R, Moran A, Montero J M, Fernandez-Lago L, Dominguez A. Propriétés antimicrobiennes des différents extraits obtenus de quelques plantes méditerranéennes d'intérêt médicinal.  Plantes Médicinales et Phytothérapie. 1987;  XXI 195-202
• 12 Zhang Y, DeWitt D L, Murugesan S, Nair M G. Cyclooxygenase-2 enzyme inhibitory triterpenoids from Picrorhiza kurroa seeds.  Life Sci. 2005;  77 3222-3230
• 13 Mitaine-Offer A C, Marouf A, Hanquet B, Birlirakis N, Lacaille-Dubois M A. Two triterpene saponins from Achyranthes bidentata.  Chem Pharm Bull. 2001;  49 1492-1494
• 14 Karliner J, Djerassi C. Terpenoids. LVII. Mass spectal and nuclear magnetic resonance studies of pentacyclic triterpene hydrocarbons.  J Org Chem. 1966;  31 1945-1955
• 15 Weis R, Seebacher W. Complete assignment of ¹H and ¹³C NMR spectra of new pentacyclic triterpene acid benzyl esters.  Magn Reson Chem. 2002;  40 455-457
• 16 Majumdar K, Biswas M, Som U K, Das S. Chemical constituents of the bark of Terminalia myriocarpa.  J Indian Chem Soc. 2005;  82 673-674
• 17 Garcez F R, Garcez W S, Mighel D LS, Serea A AT, Prado F C. Chemical constituents from Terminalia glabrescens.  J Braz Chem Soc. 2003;  14 461-465
• 18 Chauhan S MS, Parkah S, Kaushik R. Isolation of 3β-hydroxyolean-12-ene and related triterpenoids from the leaves of Terminalia arjuna.  Indian J Chem B. 1997;  36 B 297-298
• 19 Tewari N C, Ayengar K NN, Rangaswami S. Structure of sapogenins of Caccinia glauca. Caccigenin, caccigenin lactone, and 23-deoxycaccigenin.  Indian J Chem. 1970;  8 593-597
• 20 Yang J H, Wang Y-S, Huang R, Luo S-D, Zhang H-B, Li L. New polyoxygenated triterpenoids from Stachyurus himalaicus var. himalaicus.  Helv Chim Acta. 2006;  89 2830-2835