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DOI: 10.1055/s-0030-1250683
© Georg Thieme Verlag KG Stuttgart · New York
Lignans and Other Constituents from the Roots of the Vietnamese Medicinal Plant Pseuderanthemum palatiferum
Publication History
received September 15, 2010
revised December 9, 2010
accepted December 11, 2010
Publication Date:
17 January 2011 (online)
Abstract
Two new lignans, palatiferin A (1) and palatiferin B (2), were isolated from the roots of Pseuderanthemum palatiferum, together with five known triterpenes, epifriedelanol (3), lupeol (4), lupenone (5), betulin (6), pomolic acid (7), and a dipeptide asperglaucide (8). Their structures were established from 2D NMR and mass spectroscopy. The absolute configuration of 1 and 2 was proposed based on the comparison of their optical rotation activities with those of compounds with similar structures such as wodeshiol and paulownin. The new lignans, palatiferin A (1) and palatiferin B (2) exhibited a moderate cytotoxicity against KB and HepG2 cell lines. However, betulin and lupeol, two abundant compounds from the roots of P. palatiferum, showed cytotoxic and antimicrobial activities.
Key words
Acanthaceae - Pseuderanthemum palatiferum - palatiferin - betulin - lupeol - cytotoxicity - antimicrobial
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References
- 1 Oanh L T L. Investigation of some biochemical characters of proteolytic activity of Pseuderanthemum palatiferum. J Mater Med (Vietnamese). 1999; 4 13-17
- 2 Huynh K D, Chau B L, Yamasaki S, Hirara H. The Effects of Pseuderanthemum palatiferum, a new medicinal plant, on growth performances and diarrhea of piglets. Jpn Agric Res Q. 2006; 40 85-90
- 3 Phan M G, Ha V B, Phan T S. Phytochemical investigation of Pseuderanthemum palatiferum (Nees) Radlk., (Acanthaceae). J Chem (Vietnamese). 2003; 2 115-118
- 4 Huynh K D. Phytochemical study of the leaves of Pseuderanthemum palatiferum. J Sci (Vietnamese). 2008; 9 232-240
- 5 Kundu J K, Rouf A S S, Nazmul-Hossain M D, Hasan C M, Rashid M A. Antitumor activity of epifriedelanol from Vitis trifolia. Fitoterapia. 2000; 71 577-579
- 6 Moriarity D M, Huang J, Yancey C A, Zhang P, Setzer W N, Lawton R O, Bates R B, Caldera S. Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. auerceti. Planta Med. 1998; 64 370-372
- 7 Siddiqui S, Hafeez F, Begum S, Siddiqui B S. Oleanderol, a new pentacyclic triterpene from the leaves of Nerium oleande. J Nat Prod. 1988; 51 229-233
- 8 Hisham A, Jaya-Kumar G, Fujimoto Y, Hara N. Salacianone and salacianol, two triterpenes from Salacia beddomei. Phytochemistry. 1995; 40 1227-1231
- 9 Numata A, Yang P, Takahashi C, Fujki R, Nabae M, Fujita E. Cytotoxic triterpenes from a Chinese medicine, Goreishi. Chem Pharm Bull. 1989; 37 648-651
- 10 Ishiguro K, Nagata S, Fukumoto H, Yamaki M, Takagi S, Isoi K. A dipeptide derivative from Hypericum japonicum. Phytochemistry. 1991; 30 3639-3641
- 11 Pelter A, Ward R S. General methods for the assignment of stereochemistry to 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans. Tetrahedron. 1976; 32 2783-2788
- 12 Kikuchi T, Matsuda S, Kadota S, Tai T. Studies on the constituents of medicinal and related plants in Sri Lanka. III. Novel sesquilignan from Hedyotis lawsoniae. Chem Pharm Bull. 1985; 33 1444-1451
- 13 HyperChem manual. Gainsville, FL; Hypercube, Inc. 2002
- 14 Anjaneyulu A S R, Rao K J, Rao V K, Row L R, Subrahmanyam C, Pelter A, Ward R S. The structures of lignans from Gmelina arborea Linn. Tetrahedron. 1975; 31 1277-1285
- 15 Okazaki M, Ishibashi F, Shuto Y, Taniguchi E. Total synthesis of (+)-paulownin. Biosci Biotechnol Biochem. 1997; 61 743-745
- 16 Anjaneyulu A S R, Ramaiah P A, Row L R, Pelter A, Ward R S. The structure of wodeshiol – the first of a new series of lignans. Tetrahedron Lett. 1975; 16 2961-2964
- 17 Han X, Corey E J. A catalytic enantioselective total synthesis of (−)-wodeshiol. Org Lett. 1999; 1 1871-1872
- 18 Yamashita K, Lu H, Lu J, Chen G, Yokoyama T, Sagara Y, Manabe M, Kodama H. Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta. 2002; 325 91-96
- 19 Sporn M B, Suh N. Chemoprevention of cancer. Carcinogenesis. 2000; 21 525-530
- 20 Saleem M, Maddodi N, Abu-Zaid M, Khan N, Hafeez B B, Asim M, Suh Y, Yun J M, Setaluri V, Mukhtar H. Lupeol inhibits growth of highly aggressive human metastatic melanoma cells in vitro and in vivo by inducing apoptosis. Clin Cancer Res. 2008; 14 2119-2127
- 21 Murtaza I, Saleem M, Adhami V M, Hafeez B B, Mukhtar H. Suppression of cFLIP by lupeol, a dietary triterpene, is sufficient to overcome resistance to TRAIL-mediated apoptosis in chemoresistant human pancreatic cancer cells. Cancer Res. 2009; 69 1156-1165
- 22 Mukherjee P K, Sahoo A K, Narayanan N, Kumar N S, Ponnusankar S. Lead finding from medicinal plants with hepatoprotective potentials. Expert Opin Drug Discov. 2009; 4 545-576
- 23 Yamashita K, Lu H, Lu J, Chen G, Yokoyama T, Sagara Y, Manabe M, Kodama H. Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta. 2002; 325 91-96
- 24 Saleem M, Murtaza I, Tarapore R S, Suh Y, Adhami V M, Johnson J J, Siddiqui I A, Khan N, Asim M, Hafeez B B, Shekhani M T, Li B, Mukhtar H. Lupeol inhibits proliferation of human prostate cancer cells by targeting β-catenin signaling. Carcinogenesis. 2009; 30 808-817
- 25 Zhang L, Zhang Y, Zhang L, Yang X, Lv Z. Lupeol, a dietary triterpene, inhibited growth, and induced apoptosis through downregulation of DR3 in SMMC7721 cells. Cancer Invest. 2009; 27 163-170
- 26 Alessia P, Gaetano P, Ugo T. Triterpenoids as new promising anticancer drugs. Anticancer Drugs. 2009; 20 880-892
- 27 Hadacek F, Greger H. Testing of antifungal natural products: methodologies, comparability of results and assay choice. Phytochem Anal. 2000; 11 137-147
- 28 Scudiero D A, Shoemaker R H, Kenneth D P, Monks A, Tierney S, Nofziger T H, Currens M J, Seniff D, Boyd M R. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 1988; 48 4827-4833
Dr. Huong Doan Thi Mai
Institute of Marine Biochemistry
Vietnam Academy of Science and Technology
18, Hoang Quoc Viet Road
Caugiay, Hanoi
Vietnam
Phone: +84 4 37 56 93 51
Fax: +84 4 38 36 12 83
Email: dtmhuong@ich.vast.ac.vn
Dr. Van Cuong Pham
Institute of Marine Biochemistry
Vietnam Academy of Science and Technology
18, Hoang Quoc Viet Road
Caugiay, Hanoi
Vietnam
Phone: +84 4 37 56 49 95
Fax: +84 4 38 36 12 83
Email: phamvc@ich.vast.ac.vn
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