Subscribe to RSS
DOI: 10.1055/s-0030-1250570
© Georg Thieme Verlag KG Stuttgart · New York
Labdane Diterpenoids and Shikimic Acid Derivatives from Araucaria cunninghamii
Publication History
received September 25, 2010
revised October 23, 2010
accepted October 27, 2010
Publication Date:
23 November 2010 (online)
Abstract
Four new (1–4) and two known compounds (5, 6) were isolated from the aerial parts of Araucaria cunninghamii. By analysis of UV, IR, MS, and NMR, the new compounds were identified as ent-19-(Z)-coumaroyloxylabda-8(17),13(16),14-triene (1), ent-19-(E)-coumaroyloxylabda-8(17),13(16),14-triene (2), shikimic acid n-butyl ester (3), and 5-(Z)-coumaroyloxyquinic acid n-butyl ester (4). Compounds 1 and 6 exhibited inhibitory activity against Escherichia coli, and compound 1 also exhibited moderate activity against human leukemia cells (HL-60) and human hepatoma cells (SMMC-7721) with IC50 values of 8.90 and 11.53 µM, respectively.
Key words
Araucaria cunninghamii - Araucariaceae - labdane derivatives - shikimic acid derivatives
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Caputo R, Dovinola V, Mangoni L. Diterpenoids of the Araucariaceae. II. New diterpenes from Araucaria cunninghami. Phytochemistry. 1974; 13 475-478
- 2 Rahman W, Bhatnagar S P. A new biflavonyl AC3 from Araucaria cunninghamii. Tetrahedron Lett. 1968; 6 675-678
- 3 Jung M, Ko I, Lee S, Choi S J, Youn B H, Kim S K. A concise synthesis and in vitro cytotoxicity of new labdane diterpenes. Bioorg Med Chem Lett. 1998; 8 3295-3298
- 4 Dimas K, Demetzos C, Marsellos M, Sotiriadou R, Malamas M, Kokkinopoulos D. Cytotoxic activity of labdane type diterpenes against human leukemic cell lines in vitro. Planta Med. 1998; 64 208-211
- 5 Tanaka R, Ohtsu H, Iwamoto M, Minami T, Tokuda H, Nishino H. Cancer chemopreventive agents, labdane diterpenoids from the stem bark of Thuja standishii (Gord.) Carr. Cancer Lett. 2000; 161 165-170
- 6 Liu C M, Wang H X, Wei S L, Gao K. Oleanane-type triterpenes from the flowers and roots of Saussurea muliensis. J Nat Prod. 2008; 71 789-792
- 7 Lin T C, Fang J M, Cheng Y S. Terpenes and lignans from leaves of Chamaecyparis formosensis. Phytochemistry. 1999; 51 793-801
- 8 Turner A, Chen S N, Nikolic D, Breemen R, Farnswort N R, Pauli G F. Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon). J Nat Prod. 2007; 70 253-258
- 9 David J P, David J M, Yang S W, Cordell G A. A bis-labdenic diterpene from Moldenhawera nutans. Phytochemistry. 1998; 50 443-447
- 10 Mambu L, Grellier P, Florent L, Joyeau R, Ramanitrahasimbola D, Rasoanaivo P, Frappier F. Clerodane and labdane diterpenoids from Nuxia sphaerocephala. Phytochemistry. 2006; 67 444-451
- 11 Perry N B, Weavers R T. Foliage diterpenes of Dacrydium intermedium: identification, variation and biosynthesis. Phytochemistry. 1985; 24 2899-2904
- 12 Fukuoka M. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor. Chem Pharm Bull. 1982; 30 3219-3224
- 13 Osawa K, Arakawa T, Shimura S, Takeya K. New quinic acid derivatives from the fruits of Chaenomeles sinensis (Chinese Quince). Nat Med. 2001; 55 255-257
- 14 Harada R, Kakisawa H, Kobayashi S, Musya M, Nakanishi K, Takahashi Y. Structure of pristimerin, a quinonoid triterpene. Tetrahedron Lett. 1962; 603-607
- 15 Mu L Y. Research methods of plant chemical protection. Beijing; Chinese Agricultural Press 1994: 72-82
- 16 Chen J J, Fei D Q, Chen S G, Gao K. Antimicrobial triterpenoids from Vladimiria muliensis. J Nat Prod. 2008; 71 547-550
- 17 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1990; 82 1107-1112
Prof. Kun Gao
Lanzhou University
College of Chemistry and Chemical Engineering
Tianshui South Road 222
Lanzhou 730000
China
Phone: +86 93 18 91 25 92
Fax: +86 93 18 91 25 82
Email: npchem@lzu.edu.cn
- www.thieme-connect.de/ejournals/toc/plantamedica