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DOI: 10.1055/s-2002-34404
© Georg Thieme Verlag Stuttgart · New York
New Cytotoxic Bis-labdanic Diterpenoids from Alpinia calcarata
Publication History
Received: November 30, 2001
Accepted: April 7, 2002
Publication Date:
30 September 2002 (online)
Abstract
Two novel bis-labdanic diterpenoids named calcaratarin D and calcaratarin E were isolated from the rhizomes of Alpinia calcarata. Their structures were elucidated as a pair of stereoisomers on the basis of the spectral evidence. 2D NMR techniques including 1H-1H COSY, HMQC, HMBC, NOESY spectra and HRFABMS were extensively applied to establish the structures. The two bis-labdanic diterpenoids showed cytotoxic activity against human KB cells in vitro.
Key words
Alpinia calcarata. - Zingiberaceae - bis-labdanic diterpenoids - calcaratarin D - calcaratarin E - cytotoxic activity
References
- 1 Jiangsu College of New Medicine, The Dictionary of the Traditional Chinese Medicine. Shanghai Press of Science & Technology Shanghai; 1977: 169-170
- 2 Nakatani N, Kikuzaki H, Yamaji H, Yoshio K, Kitora C, Okada K. et al . Labdane diterpenes from rhizomes of Hedychium coronarium . Phytochemistry. 1994; 37 1383-8
- 3 David J P, David J M, Yang S W, Cordell G A. A bis-labdenic diterpene from Moldenhawera nutans . Phytochemistry. 1999; 50 443-7
- 4 Kong L Y, Qin M J, Niwa M. Diterpenoids from the rhizomes of Alpinia calcarata . J Nat Prod. 2000; 63 939-42
- 5 Fatope M O, Zeng L, Ohayaga J E, Shi G, Mclaughlin J L. Selectively cytotoxic diterpenes from Euphorbia poisonii . J Med Chem. 1996; 39 1005-8
- 6 Alberto A, Umberta B, Gianluca N, Orso V P. Isolation and structure elucidation of tsugicolines A-D, novel protoilludane sesquiterpenes from Laurilia tsugicola . Tetrahedron. 1995; 51 13 357-64
- 7 Itokawa H, Yoshimoto S, Morita H. Diterpenes from the rhizomes of Alpinia formosana . Phytochemistry. 1988; 27 435-8
- 8 Kimbu S F, Nagadjui B, Sondengam L B, Njimi T K, Connolly J D, Fakunle C O. A new labdane diterpeniod from the seeds of Aframomum daniellii . J Nat Prod. 1987; 50 230-1
- 9 Singh S, Gray A I, Skelton B W, Waterman P G, White A H. (+)-14β-Hydroxylabda-8(17), 12-dieno-16,15-lactone [(+)-isocoronarin-D]: a new diterpene from Hedychium coronarium (Zingiberaceae). Austra J Chem. 1991; 44 1789-93
- 10 Sirat H M. Study on the terpenoids of Zingiber ottensii . Planta Med. 1994; 60 497
- 11 Sirat H M, Masri D, Rahman A A. The distribution of labdane diterpenes in the Zingiberaceae of Malaysia. Phytochemistry. 1994; 36 699-701
- 12 Sy L K, Brown G D. Labdane diterpenoids from Alpinia chinesis . J Nat Prod. 1997; 60 904-8
- 13 Zhao Q, Hao X J, Chen Y Z, Zou C. Diterpenoid constituents of Hedychium forrestii and their cytotoxic activity. Acta Pharmaceutica Sinica. 1995; 30 119-22
Prof. Dr. L.Y. Kong
Department of Natural Medicinal Chemistry
China Pharmaceutical University
Nanjing 210009
P. R. China
Email: lykong@jlonline.com
Fax: +86-25-5301528