Download PDF
Planta Med 2010; 76(15): 1710-1716
DOI: 10.1055/s-0030-1249957
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Highly Oxygenated Guaianolides from Artemisia dubia

Zheng-Sheng Huang1 , 3 , Yue-Hu Pei3 , Chu-Mei Liu1 , Sheng Lin1 , Jian Tang1 , Da-Sen Huang1 , 3 , Tai-Fa Song1 , Long-Hai Lu1 , Yan-Ping Gao1 , Wei-Dong Zhang1 , 2
  • 1Department of Phytochemistry, College of Pharmacy, Second Military Medical University, Shanghai, P. R. China
  • 2School of Pharmacy, Shanghai Jiao Tong University, Shanghai, P. R. China
  • 3School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, P. R. China
Further Information

Publication History

received October 12, 2009 revised April 8, 2010

accepted April 20, 2010

Publication Date:
19 May 2010 (online)

Also available at
    Permissions and Reprints

Abstract

Investigation of a Chinese folk medicine, Artemisia dubia (syn. Artemisia subdigitata), has resulted in the isolation of eight new guaianolides (artemdubolides A–H, 1–8), and nineteen known sesquiterpene lactones. Their structures were elucidated primarily on the basis of spectroscopic methods, including extensive 2D NMR experiments. The cytotoxic activities of compounds 1–8 were evaluated against A549 (human lung adenocarcinoma), Colo205 (human colon carcinoma), HepG2 (human hepatoma), and MDA‐MB‐435 (human melanoma) cell lines. Compounds 2 and 5 showed weak cell growth inhibition of Colo205 and MDA‐MB‐435 cells.

Key words

Artemisia dubia - Asteraceae - guaianolides - artemdubolides A–H - cytotoxic activities - sesquiterpene lactones

References

  • 1 Wang W C. Flora of China, Vol 76. Beijing; Science Press 1990: 1
    PubMedGoogle Scholar
  • 2 Wu Q X, Shi Y P, Jia Z J. Eudesmane sesquiterpenoids from the Asteraceae family.  Nat Prod Rep. 2006;  23 699-734
    CrossrefPubMedGoogle Scholar
  • 3 Macias F A, Varela R M, Torres A, Molinillo J G. Heliespirone. The first member of a novel family of bioactive sesquiterpenes.  Tetrahedron Lett. 1998;  39 427-430
    CrossrefPubMedGoogle Scholar
  • 4 Kim J H, Kim H K, Jeon S B, Son K H, Kim E H, Kang S K, Sung N D, Kwon B M. New sesquiterpene-monoterpene lactone, artemisolide, isolated from Artemisia argyi.  Tetrahedron Lett. 2002;  43 6205-6208
    CrossrefPubMedGoogle Scholar
  • 5 Irwin M A, Geissman T A. Novanin: a germacranolide from Artemisia nova.  Phytochemistry. 1973;  12 875-878
    CrossrefPubMedGoogle Scholar
  • 6 Marco J A, Sanz-Cervera J F, Morante M D, Garcia-Lliso V, Valles-Xirau J, Jakupovic J. Tricyclic sesquiterpenes from Artemisia chamaemlifolia.  Phytochemistry. 1996;  41 837-844
    CrossrefPubMedGoogle Scholar
  • 7 Marco J A, Sanz-Cervera J F, Manglano E, Sancenon F, Rustaiyan A, Kardar M. Sesquiterpene lactones from iranian Artemisia species.  Phytochemistry. 1993;  34 1561-1564
    CrossrefPubMedGoogle Scholar
  • 8 Bohlmann F, Zdero C, Jakupovic J, Greger H. Types of sesquiterpenes from Artemisia filifolia.  Phytochemistry. 1983;  22 503-507
    CrossrefPubMedGoogle Scholar
  • 9 Editorial Board of Zhong Hua Ben Cao of State Administration of Traditional Chinese Medicine .Zhong Hua Ben Cao. Shanghai; Shanghai Science and Technology Press 1999: 676
    PubMedGoogle Scholar
  • 10 Wu Z J, Xu X K, Shen Y H, Su J, Tian J M, Liang S, Li H L, Liu R H, Zhang W D. Ainsliadimer A, a new sesquiterpene lactone dimer with an unusual carbon skeleton from Ainsliaea macrocephala.  Org Lett. 2008;  10 2397-2400
    CrossrefPubMedGoogle Scholar
  • 11 Wang Y, Shen Y H, Jin H Z, Fu J J, Hu X J, Qin J J, Liu J H, Chen M, Yan S K, Zhang W D. Ainsliatrimers A and B, the first two guaianolide trimers from Ainsliaea fulvioides.  Org Lett. 2008;  10 5517-5520
    CrossrefPubMedGoogle Scholar
  • 12 Bohlmann F, Zdero C. Neue Furanoeremophilane und andere Sesquiterpene aus Vertretern der Gattung Euryops.  Phytochemistry. 1978;  17 1135-1153
    CrossrefPubMedGoogle Scholar
  • 13 Ober A G, Quuanno L, Urbatsch L E, Fischer N H. Guaianolides from Calea subcordata.  Phytochemistry. 1984;  23 1289-1292
    CrossrefPubMedGoogle Scholar
  • 14 Ober A G, Quuanno L, Urbatsch L E, Fischer N H. Guaianolides and chromenes from Calea species.  Phytochemistry. 1985;  24 795-799
    CrossrefPubMedGoogle Scholar
  • 15 Irwin M A, Geissman T A. Rupicolin-A and B, rupin-A and -B, and cumambrin-B oxide from Artemisia tripartite ssp. rupicola.  Phytochemistry. 1973;  12 863-869
    CrossrefPubMedGoogle Scholar
  • 16 Ito K, Sakakibara Y, Haruna M. Seven guaianolides from Eupatorium chinense.  Phytochemistry. 1982;  21 715-720
    CrossrefPubMedGoogle Scholar
  • 17 Fischer N H, Olivier E J, Fischer H D. Progress in the chemistry of organic natural products. Wien; Springer 1979
    PubMedGoogle Scholar
  • 18 Olivier E J, Perry D L, Fischer N H. Two new germacranolides from Melampodium leucanthum and their reductive and oxidative rearrangements.  J Org Chem. 1980;  45 4028-4034
    CrossrefPubMedGoogle Scholar
  • 19 Ohno N, Gershenzon Q, Roane C, Mabry T J. 11,13-Dehydrodesacetylmatricarin and other sesquiterpenes lactones from Artemisia ludoviciana var. ludoviciana and the identity of artecania and chyrsartemin B.  Phytochemistry. 1980;  19 103-106
    CrossrefPubMedGoogle Scholar
  • 20 Tan R X, Tang H Q, Hu J, Shuai B. Lignans and sesquiterpene lactones from Artemisia sieversiana and Inula racemosa.  Phytochemistry. 1998;  49 157-161
    CrossrefPubMedGoogle Scholar
  • 21 Singh P, Jakupovic J, Bohlmann F, King R M, Robinson H. Highly oxygenated guaianolides from Bishopanthus soliceps.  Phytochemistry. 1985;  24 2110-2112
    CrossrefPubMedGoogle Scholar
  • 22 Mata R, Delgado G, De Vivar A R. Sesquiterpene lactones of Artemisia klotzchiana.  Phytochemistry. 1985;  24 1515-1519
    CrossrefPubMedGoogle Scholar
  • 23 Bhadane N R, Shafizadeh F. Sesquiterpene lactones of sagebrush: the structure of artecanin.  Phytochemistry. 1975;  14 2651-2653
    CrossrefPubMedGoogle Scholar
  • 24 Zhang D Z. Studies on new sesquiterpenes in Artemisia sucrorum Lebed.  Guang Dong Wei Liang Yuan Su Ke Xue. 2006;  13 59-63
    PubMedGoogle Scholar
  • 25 Gonzalez A G, Bermejo J, Breton J L, Massanet G M, Triana J. Chlorohyssopifolin C, D, E and vahlenin, four new sesquiterpene lactones from Centaurea hyssopifolia.  Phytochemistry. 1974;  13 1193-1197
    CrossrefPubMedGoogle Scholar
  • 26 Osawa T, Suzuki A, Tamura S, Ohashi Y, Sasada Y. Structure of chlorochrymorin, a novel sesquiterpene lactone from chrysanthemum morifolium.  Tetrahedron Lett. 1973;  14 5135-5138
    CrossrefPubMedGoogle Scholar
  • 27 Gordon M M, Van Derveer D, Zalkow L H. New germacranolides from Artemisia herba alba. X-ray crystal structures of 3beta, 8alpha-dihydroxy-6beta H, 7alpha H, 11beta H-germacran-4(14), 9(10)-dien-6, 12-olide and the corresponding 3-oxo-olide.  J Nat Prod. 1981;  44 432-440
    CrossrefPubMedGoogle Scholar
  • 28 Yoshioka H, Renold W, Fischer N H, Higo A, Mabry T J. Sesquiterpene lactones from Ambrosia confertiflora (Compositae).  Phytochemistry. 1970;  9 823-832
    CrossrefPubMedGoogle Scholar
  • 29 White E H, Winter R E. Natural products from Achillea lanulosa.  Tetrahedron Lett. 1963;  4 137-140
    CrossrefPubMedGoogle Scholar
  • 30 White E H, Marx J N. The synthesis and stereochemistry of deacetoxymatricarin and achillin.  J Am Chem Soc. 1967;  89 5511-5513
    CrossrefPubMedGoogle Scholar
  • 31 Milosavljevic S, Macura S, Stefanovic M. Sesquiterpene lactones from Achillea crithmifolia.  J Nat Prod. 1994;  57 64-67
    CrossrefPubMedGoogle Scholar
  • 32 Jakupovic J, Tan R X, Bohlmann F, Boldt P E, Jia Z J. Sesquiterpene lactones from Artemisia ludooiciana.  Phytochemistry. 1991;  30 1573-1577
    CrossrefPubMedGoogle Scholar
  • 33 Todorova M N, Krasteva M L, Markova M M, Tsankova E T, Taskova R M, Peev D R. Terpenoids from Achillea clypeolata.  Phytochemistry. 1998;  49 2371-2374
    CrossrefPubMedGoogle Scholar
  • 34 Todorova M N, Krasteva M L. Sesquiterpene lactones from Artemisia lerchiana.  Phytochemistry. 1996;  42 1231-1233
    CrossrefPubMedGoogle Scholar
  • 35 Barrero A F, Oltra J E, Raslan D S, Saude D A. Microbial transformation of sesquiterpene lactones by the fungi Cunninghamella echinulata and Rhizopus oryzae.  J Nat Prod. 1999;  62 726-729
    CrossrefPubMedGoogle Scholar
  • 36 Hansen M B, Nielsen S E, Berg K. Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill.  J Immunol Methods. 1989;  119 203-210
    CrossrefPubMedGoogle Scholar

Prof. Wei-Dong Zhang

Department of Natural Product Chemistry
School of Pharmacy
Second Military Medical University

325 Guohe Road

Shanghai 200433

People's Republic of China

Phone: + 86 21 81 87 12 44

Fax: + 86 21 81 87 12 44

Email: wdzhangY@hotmail.com