Download PDF
Planta Med 2010; 76(2): 189-194
DOI: 10.1055/s-0029-1186026
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Lupane-Type Triterpene Glycosides from the Leaves of Acanthopanax koreanum and Their In Vitro Cytotoxicity

Nguyen Xuan Nhiem1 , 2 , Phan Van Kiem2 , Chau Van Minh2 , Do Thi Ha1 , Buu Huu Tai1 , Pham Hai Yen2 , Nguyen Huu Tung1 , Jae-Hee Hyun3 , Hee-Kyoung Kang3 , Young Ho Kim3
  • 1College of Pharmacy, Chungnam National University, Daejeon, Korea
  • 2Institute of Natural Products Chemistry, VAST, Hanoi, Vietnam
  • 3School of Medicine, Institute of Medical Sciences, Cheju National University, Jeju, Korea
Further Information

Publication History

received May 4, 2009 revised July 8, 2009

accepted July 10, 2009

Publication Date:
10 August 2009 (online)

Also available at
    Permissions and Reprints

Abstract

Three new lupane triterpene glycosides, acankoreosides J–L (1–3), were isolated from the leaves of Acanthopanax koreanum. Based on the spectroscopic data, the chemical structures were determined as 3α-hydroxy-20-oxo-30-norlupane-23,28-dioic 28-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (1); 3α,20,29-trihydroxylupane-23,28-dioic 28-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (2); and (20S)-3α-hydroxy-29,29-dimethoxylupane-23,28-dioic 28-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (3). Compounds 1−3 were evaluated for their cytotoxicity and showed moderate activity against four cell lines, A549 (lung), HL-60 (leukemia), MCF-7 (breast), and U937 (leukemia), with IC50 values of 23.4, 36.5, 22.6, and 18.5 µM for 1; 6.8, 18.6, 23.1, and > 100 µM for 2; and 28.9, 21.8, 11.0, and 27.5 µM for 3, respectively.

Key words

Acanthopanax koreanum - Araliaceae - lupane glycoside - acankoreoside - in vitro cytotoxic activity

References

  • 1 Yook C S. Coloured medicinal plants of Korean. Seoul; Academy Publishing Co., Ltd 1993: 371-372
    Google Scholar
  • 2 Bae K. The medicinal plants of Korea. Seoul; Kyo-Hak Publishing 2000: 361
    Google Scholar
  • 3 Chang S Y, Yook C S, Nohara T. Two new lupane-triterpene glycosides from leaves of Acanthopanax koreanum.  Chem Pharm Bull. 1998;  46 163-165
    PubMedGoogle Scholar
  • 4 Chang S Y, Yook C S, Nohara T. Lupane-triterpene glycosides from leaves of Acanthopanax koreanum.  Phytochemistry. 1999;  50 1369-1374
    CrossrefPubMedGoogle Scholar
  • 5 Cai X F, Lee I S, Shen G, Dat N T, Lee J J, Kim Y H. Triterpenoids from Acanthopanax koreanum root and their inhibitory activities on NFAT transcription.  Arch Pharm Res. 2004;  27 825-828
    CrossrefPubMedGoogle Scholar
  • 6 Park S Y, Choi H S, Yook C S, Nohara T. A new lupane glycoside from the leaves of Acanthopanax koreanum.  Chem Pharm Bull. 2005;  53 97-99
    CrossrefPubMedGoogle Scholar
  • 7 Choi H S, Kim H J, Nam S G, Kim I S, Lee K T, Yook C S, Lee Y S. Lupane glycosides from the leaves of Acanthopanax koreanum.  Chem Pharm Bull. 2008;  56 1613-1616
    CrossrefPubMedGoogle Scholar
  • 8 Gauthier C, Legault J, Lebrun M, Dufour P, Pichette A. Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents.  Bioorg Med Chem. 2006;  14 6713-6725
    CrossrefPubMedGoogle Scholar
  • 9 Thibeault D, Gauthier C, Legault J, Bouchard J, Dufour P, Pichette A. Synthesis and structure-activity relationship study of cytotoxic germanicane – and lupane-type 3-beta-O-monodesmosidic saponins starting from betulin.  Bioorg Med Chem. 2007;  15 6144-6157
    CrossrefPubMedGoogle Scholar
  • 10 Sarek J, Klinot J, Dzubak P, Klinotova E, Noskova V, Krecek V, Korinkova G, Thomson J O, Janostakova A, Wang S, Parsons S, Fischer P M, Zhelev N Z, Hajduch M. New lupane derived compounds with pro-apoptotic activity in cancer cells: synthesis and structure-activity relationships.  J Med Chem. 2003;  46 5402-5415
    CrossrefPubMedGoogle Scholar
  • 11 Mutai C, Abatis D, Vagias C, Moreau D, Roussakis C, Roussis V. Cytotoxic lupane-type triterpenoids from Acacia mellifera.  Phytochemistry. 2004;  65 1159-1164
    CrossrefPubMedGoogle Scholar
  • 12 Hata K, Hor K, Ogasawara H, Takahashi S. Anti-leukemia activities of Lup-28-al-20(29), a lupane triperpene.  Toxicol Lett. 2003;  143 1-7
    CrossrefPubMedGoogle Scholar
  • 13 El-Gamal A A. Cytotoxic lupane-secolupane-, and oleanane-type triterpenes from Viburnum awabuki.  Nat Prod Res. 2008;  22 191-197
    CrossrefPubMedGoogle Scholar
  • 14 Fujioka T, Kashiwada Y, Kilkuskie R E, Cosentino L M, Ballas L M, Jiang J B, Janzen W P, Chen I S, Lee K H. Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids.  J Nat Prod. 1994;  57 243-247
    CrossrefPubMedGoogle Scholar
  • 15 Nusrat J, Wasim A, Abdul M. A lupane-type triterpene from Mimusops elengi. .  Phytochemistry. 1995;  39 255-257
    CrossrefPubMedGoogle Scholar
  • 16 Loc T V, Sung T V, Kamperdick C, Adam G. Synthesis of amino acid conjugates and further derivatives of 3α-hydroxylup-20(29)ene-23,28-dioic acid.  J Prakt Chem. 2000;  342 63-71
    PubMedGoogle Scholar
  • 17 Yoshikawa M, Zhang Y, Wang T, Nakamura S, Matsuda H. New triterpene constituents, foliasalacins A1–A4, B1–B3, and C, from the leaves of Salacia chinensis.  Chem Pharm Bull. 2008;  56 915-920
    CrossrefPubMedGoogle Scholar
  • 18 Corbett R E, Cong A N T, Wilkins A L, Thompson R A. Lichens and fungi. Part 17. The synthesis and absolute configuration at C-20 of the (R)- and (S)- epimers of some 29-substituted lupane derivatives and of some 30-norlupan-20-ol derivatives and the crystal structure of (20R)-3-acetoxylupan-29-ol.  J Chem Soc [Perkin I]. 1985;  10 2051-2056
    PubMedGoogle Scholar
  • 19 Ogura M, Cordell G A, Farnsworth R. Potential anticancer agents. IV. Constituents of Jacaranda caucana Pittier (Bignoniaceae).  Lloydia. 1977;  40 157-168
    PubMedGoogle Scholar
  • 20 Ryu S Y, Choi S U, Lee S H, Lee C O, No Z, Ahn J. Antitumor triterpenes from medicinal plants.  Arch Pharm Res. 1994;  17 375-377
    PubMedGoogle Scholar
  • 21 Hata K, Hori K, Ogasawara H, Takahashi S. Anti-leukemia activities of Lup-28-al-20(29)-en-3-one, a lupane triterpene.  Toxicol Lett. 2003;  143 1-7
    CrossrefPubMedGoogle Scholar
  • 22 Schmidt M L, Kuzmanoff K L, Ling-Indeck L, Pezzuto J M. Betulinic acid induces apoptosis in human neuroblastoma cell lines.  Eur J Cancer. 1997;  33 2007-2010
    CrossrefPubMedGoogle Scholar
  • 23 Sami A, Taru M, Salme K, Jari Y. Pharmacological properties of the ubiquitous natural product betulin.  Eur J Pharm Sci. 2006;  29 1-13
    CrossrefPubMedGoogle Scholar
  • 24 Carmichael J, DeGraff W G, Gazdar A F, Minna J D, Mitchell J B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of radiosensitivity.  Cancer Res. 1987;  47 943-946
    PubMedGoogle Scholar

Prof. Dr. Young Ho Kim

College of Pharmacy
Chungnam National University

305-764 Daejeon

Korea

Phone: + 82 4 28 21 59 33

Fax: + 82 4 28 23 65 66

Email: yhk@cnu.ac.kr