Planta Med 2002; 68(9): 813-817
DOI: 10.1055/s-2002-34404
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Cytotoxic Bis-labdanic Diterpenoids from Alpinia calcarata

Ling-Yi Kong1, 2 , Min-Jian Qin1 , Masatake Niwa2
  • 1Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, P.R. China
  • 2Faculty of Pharmacy, Meijo University, Nagoya, Japan
Further Information

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.

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