RSS-Feed abonnieren
DOI: 10.1055/s-0029-1240841
© Georg Thieme Verlag KG Stuttgart · New York
18,19-Secooleanane Type Triterpene Glycosyl Esters from the Bark of Terminalia arjuna
Publikationsverlauf
received August 26, 2009
revised Nov. 5, 2009
accepted January 4, 2010
Publikationsdatum:
28. Januar 2010 (online)
![](https://www.thieme-connect.de/media/plantamedica/201009/lookinside/thumbnails/10.1055-s-0029-1240841-1.jpg)
Abstract
Five novel 18,19-secooleanane-type triterpene glycosyl esters, namely arjunasides A–E, were isolated from the MeOH extract of the bark of Terminalia arjuna along with nine known oleanane triterpenoids. The structures of the new compounds were determined by spectroscopic analyses including 2D NMR, HRESIMS, and CD spectra.
Key words
Combretaceae - Terminalia arjuna - 18,19‐secooleanane triterpenoid‐triterpene glycosyl ester‐arjunasides A–E
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Dwivedi S. Terminalia arjuna Wright & Arn. – a useful drug for cardiovascular disorders. J Ethnopharmacol. 2007; 114 114-129
- 2 Bhattacharya S, Kamat J P, Bandyopadhyay S K, Chattopadhyay S. Comparative inhibitory properties of some Indian medicinal plant extracts against photosensitization-induced lipid damage. Food Chem. 2009; 113 975-979
- 3 Chen P S, Li J H, Liu T Y, Lin T C. Folk medicine Terminalia catappa and its major tannin component, punicalagin, are effective against bleomycin-induced genotoxicity in Chinese hamster ovary cells. Cancer Lett. 2000; 152 115-122
- 4 Pasquini R, Scassellati-Sforzolini G, Villarini M, Moretti M, Marcarelli M, Fatigoni C, Kaur S, Kumar S, Grover I S. In vitro protective effects of Terminalia arjuna bark extract against the 4-nitroquinoline-N-oxide genotoxicity. J Environ Pathol Toxicol Oncol. 2002; 21 33-44
- 5 Dwivedi S, Gupta D. Efficiency of Terminalia arjuna in chronic stable angina. Indian Heart J. 2002; 54 441
- 6 Bharani A, Ganguli A, Mathur L K, Jamra Y, Raman P G. Efficiency of Terminalia arjuna in chronic stable angina: a double-blind, placebo-controlled, cross over study comparing Terminalia arjuna with isosorbide mononitrate. Indian Heart J. 2002; 54 170-175
- 7 Dwivedi S, Jauhari R. Beneficial effects of Terminalia arjuna in coronary artery disease. Indian Heart J. 1997; 49 507-510
- 8 Lin T C, Ma Y T, Hsu F L. Tannins from the bark of Terminalia arjuna. Chin Pharm J (Taipei). 1996; 48 25-35
- 9 Sharma P N, Shoeb P N, Kapil R S, Popli S P. Arjunolone – a new flavone from stem bark of Terminalia arjuna. Indian J Chem. 1982; 21 B 263-264
- 10 Saxena M, Faridi U, Mishra R, Gupta M M, Darokar M P, Srivastava S K, Singh D, Luqman S, Khanuja S P S. Cytotoxic agents from Terminalia arjuna. Planta Med. 2007; 73 1486-1490
- 11 Prasad M V V, Anbalagan N, Patra A, Veluchamy G, Balakrishna K. Antiallergic and anti-asthmatic activities of the alcoholic extract of Terminalia arjuna and arjunolic acid. Nat Prod Sci. 2004; 10 240-243
- 12 Singh D V, Gupta M M, Tripathi A K, Prajapati V, Kumar S. Arjunetin from Terminalia arjuna as an insect feeding-deterrent and growth inhibitor. Phytother Res. 2004; 18 131-134
- 13 Ali A, Kaur G, Hamid H, Abdullah T, Ali M, Niwa M, Alam M S. Terminoside A, a new triterpene glycoside from the bark of Terminalia arjuna inhibits nitric oxide production in murine macrophages. J Asian Nat Prod Res. 2003; 5 137-142
- 14 Ali A, Abdullah S T, Hamid H, Ali M, Alam M S. Two new pentacyclic triterpenoid glycosides from the bark of Terminalia arjuna. Indian J Chem B. 2003; 42 B 2905-2908
- 15 Tripathi V K, Pandey V B, Udupa K N, Rücker G. Arjunolitin, a triterpene glycoside from Terminalia arjuna. Phytochemsitry. 1992; 31 349-351
- 16 Ahmad M U, Mullah K B, Nörin T, Ulla J K. Terminoic acid, a new trihydroxytriterpene carboxylic acid from bark of Terminalia arjuna. Indian J Chem B. 1983; 22 B 738-740
- 17 Upadhyay R K, Pandey M B, Jha R N, Singh V P, Pandey V B. Triterpene glycoside from Terminalia arjuna. J Asian Nat Prod Res. 2001; 3 207-212
- 18 Row L R, Murty P S, Rao G S R S, Sastry C S P, Rao K V J. Chemical examination of Terminalia species. XII. Isolation and structure determination of arjunic acid, a new trihydroxytriterpene carboxylic acid from Terminalia arjuna bark. Indian J Chem. 1970; 8 716-721
- 19 King F E, King T J, Ross J M. The chemistry of extractives from hardwoods. XVIII. The constitution of arjunolic acid, a triterpene from Terminalia arjuna. J Chem Soc. 1954; 3995-4003
- 20 Honda T, Murae T, Tsuyuki T, Takahashi T. The structure of arjungenin. A new sapogenin from Terminalia arjuna. Chem Pharm Bull. 1976; 24 178-180
- 21 Honda T, Murae T, Tsuyuki T, Takahashi T, Sawai M. Arjungenin, arjunglucoside I, arjunglucoside II. A new triterpene and new triterpene glucosides from Terminalia arjuna. Bull Chem Soc Jpn. 1976; 49 3213-3218
- 22 Tsuyuki T, Hamada Y, Honda T, Takahashi T, Matsushita K. A new triterpene glucoside from Terminalia arjuna. Arjunglucoside III. Bull Chem Soc Jpn. 1979; 52 3127-3128
- 23 Row L R, Murty P S, Rao G S R S, Sastry C S P, Rao K V J. Chemical examination of Terminalia species. XIII. Isolation and structure determination of arjunetin and Terminalia arjuna. Indian J Chem. 1970; 8 772-775
- 24 Bombardelli E, Bonati A, Gabetta B, Mustich G. Plants of Mozambique. VII. Triterpenoids of Terminalia sericea. Phytochemistry. 1974; 13 2559-2562
- 25 Jung S W, Shin M H, Jung J H, Kim N D, Im K S. A triterpene glucosyl ester from the roots of Rubus crataegifolius. Arch Pharm Res. 2001; 24 412-415
- 26 Wang W, Li X C, Ali Z, Khan I A. Two new C13 nor-isoprenoids from the leaves of Casearia sylvestris. Chem Pharm Bull. 2009; 57 636-638
- 27 Mustafa J, Khan S I, Ma G, Walker L A, Khan I A. Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin. Lipids. 2004; 39 167-172
- 28 Kakuno T, Yoshikawa K, Arihara S. Ilexosides A, B, C and D, antiallergic 18,19-seco-ursane glycosides from fruit of Ilex crenata. Tetrahedron Lett. 1991; 32 3535-3538
- 29 Li R T, Li J T, Wang J K, Han Q B, Zhu Z Y, Sun H D. Two new E-secoursane glycosides: bodiniosides A and B, isolated from Elsholtzia bodinieri. Helv Chim Acta. 2005; 88 252-257
Prof. Dr. Ikhlas A. Khan
National Center for Natural Products Research
School of Pharmacy
University of Mississippi
Oxford, MS 38677
USA
Telefon: + 1 66 29 15 78 21
Fax: + 1 66 29 15 79 89
eMail: ikhan@olemiss.edu
- www.thieme-connect.de/ejournals/toc/plantamedica