A new ursane triterpene, torment (2α,3β,19α-trihydroxyurs-12-en) (1), was isolated from the fruits of Terminalia arjuna along with four known ursane and oleane triterpenes. The structures were established on the basis of extensive NMR (1D & 2D) and MS (EI & ESI) studies. Tormentic acid (2), 19α-hydroxy asiatic acid (3) and olean-12-en-2α,3β-diol (4) were isolated for the first time from this species. Compounds 1 and 2 lacked significant enzyme inhibition, cytotoxicity, immunomodulatory and antiglycation activities.
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2.
(a) OberoiL., AkiyamaT., LeeK.L., LiuS.J. (2011) The aqueous extract, not organic extracts, of Terminalia arjuna bark exerts cardiotonic effect on adult ventricular myocytes. Phytomedicine, 18, 259–265; (b) Shaila HP, Udupa SL, Udupa AL. (1998) Hypolipidemic activity of three indigenous drugs in experimentally induced atherosclerosis, International Journal of Cardiology, 67, 119–124; (c) Ram A, Lauria P, Gupta R, Kumar P, Sharma VN. (1997) Hypocholesterolaemic effects of Terminalia arjuna tree bark. Journal of Ethnopharmacology, 55, 165–169.
3.
DeviR.S., NarayanS., VaniG., SrinivasanP., MohanK.V., SabithaK.E., DeviC.S.S. (2007) Ulcer protective effect of Terminalia arjuna on gastric mucosal defensive mechanism in experimental rats. Phytotherapy Research, 21, 762–767.
4.
(a) SivalokanathanS., IlayarajaM., BalasubramanianM.P. (2006) Antioxidant activity of Terminalia arjuna bark extract on N-nitrosodiethylamine induced hepatocellular carcinoma in rats. Molecular and Cellular Biochemistry, 281, 87–93; (b) Pettit GR, Hoard MS, Doubek DL, Schmidt JM, Pettit RK, Tackett LP, Chapuis J-C. (1996) Antineoplastic agents 338. The cancer cell growth inhibitory. Constituents of Terminalia arjuna (Combretaceae). Journal of Ethnopharmacology, 53, 57–63; (c) Sivalokanathan S, Vijayababu MR, Balasubramanian MP. (2006) Effects of Terminalia arjuna bark extract on apoptosis of human hepatoma cell line HepG2. World Journal of Gastroenterology, 12, 1018–1024; (d) Kuo PL, Hsu YL, Lin TC, Lin LT, Chang JK, Lin CC. (2005) Casuarinin from the bark of Terminalia arjuna induces apoptosis and cell cycle arrest in human breast adenocarcinoma MCF-7 cells. Planta Medica, 71, 237–243; (e) Kuo PL, Hsu YL, Lin TC, Chang JK, Lin CC. (2005) Induction of cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells by casuarinin from the bark of Terminalia arjuna Linn. Anticancer Drugs, 16, 409–415.
5.
(a) TripathiV.K., SinghB. (1996) Terminalia arjuna- its present status (a review). Oriental Journal of Chemistry, 12, 1–16; (b) Saxena M, Yadav S, Bawankule DU, Srivastava SK, Pal A, Mishra R, Gupta MM, Darokar MP, Priyanka, Khanuja SPS. (2008) An immunomodulator from Terminalia arjuna and biological evaluation of its derivatives. Natural Product Communications, 3, 891–894.
6.
JainS., YadavP.P., GillV., VasudevaN., SinglaN. (2009) Terminalia arjuna a sacred medicinal plant: phytochemical and pharmacological profile. Phytochemistry Reviews, 8, 491–502.
7.
(a) YangM.-H, BlundenG., O'NeillM.J., LewisJ.A. (1992) Tormentic acid and 2α-hydroxyursolic acid from Arnebia euchroma. Planta Medica, 58, 227; (b) Braca A, Sortino C, Mendez J, Morelli I. (2001) Triterpenes from Licania licaniaeflora. Fitoterapia, 72, 585–587; (c) Honda T, Murae T, Tsuyuki T, Takahashi T, Sawai M. (1976) Arjungenin, arjunglucoside I, and arjunglucoside II. A new triterpene and new triterpene glucosides from Terminalia arjuna. Bulletin of the Chemical Society of Japan, 49, 3213–3218; (d) Nandy AK, Podder G, Sahu, NP, Mahato SB. (1989) Triterpenoids and their glucosides from Terminalia bellerica. Phytochemistry, 28, 2769–2772.
8.
BisoliE., GarcezS.G., HamerskiL., TieppoC., GarcezF.R. (2008) Bioactive pentacyclic triterpenes from the stems of Combretum laxum. Molecules, 13, 2717–2728.
9.
(a) Atta-ur-Rahman, ZareenS., ChoudharyM.I., AkhtarM.N., ShujaatS., NgounouF.N. (2005) Some chemical constituents of Terminalia glaucescens and their enzyme inhibition activity. Zeitschrift für Naturforschung, 60B, 347–350; (b) Ngounou FN, Atta-ur-Rahman, Choudhary MI, Malik S, Zareen S, Ali R, Lontsi D, SondengamBL. (1999) Two saponins from Pteleopsis hylodendron, Phytochemistry, 52, 917–921.
