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Planta Med 2007; 73(1): 84-90
DOI: 10.1055/s-2006-951773
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

Antibacterial Diterpenoids from Sagittaria pygmaea

Xue-Ting Liu1 , 2 , Yao Shi1 , Biao Yu2 , Ian D. Williams3 , Herman H.-Y. Sung3 , Qiong Zhang1 , Jing-Yu Liang1 , Nancy Y. Ip4 , Zhi-Da Min1
  • 1Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, P. R. China
  • 2State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China
  • 3Department of Chemistry, The Hong Kong University of Science and Technology, Hong Kong, P. R. China
  • 4Department of Biochemistry and Biotechnology Research Institute, The Hong Kong University of Science and Technology, Hong Kong, P. R. China
Further Information

Publication History

Received: August 29, 2006

Accepted: October 30, 2006

Publication Date:
18 December 2006 (online)

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Abstract

There were five new diterpenoids, 18-β-D-3′,4′-diacetoxyxylopyranosyl-ent-kaur-16-ene (1), 18-β-L-3′,5′-diacetoxyarabinofuranosyl-ent-kaur-16-ene (2), 18-β-D-3′,6′-diacetoxyglucopyranosyl-ent-kaur-16-ene (3), ent-isopimar-8(14),15-dien-19-oic acid (4), and 5α-hydroxy-ent-rosa-15-en-18-oic acid (5), isolated from the whole herb of Sagittaria pygmaea. Their structures and relative configurations were established based on spectroscopic studies, chemical methods, and X-ray crystallographic analysis. Compound 2 exhibited significant antibacterial activity against the oral pathogens, Streptococcus mutans ATCC 25 175 and Actinomyces viscosus ATCC 27 044, with MIC values against both pathogens of 15.6 μg/mL. Compound 3 was active against only A. viscosus ATCC 27 044 with an MIC value of 62.5 μg/mL. Compounds 4 and 5 were active against S. mutans ATCC 25 175 and A. viscosus ATCC 27 044, with MIC values against both pathogens of 125.0 μg/mL.

Key words

Sagittaria pygmaea - Alismaceae - ent-kaurane glycosides - ent-isopimarane - ent-rosane - antibacterial - oral pathogen

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Prof. Zhi-Da Min

Department of Natural Medicinal Chemistry

China Pharmaceutical University,

Nanjing 210009

People’s Republic of China

Phone: +86-25-8322-0992

Fax: +86-25-8327-1335

Email: zhdmin32@hotmail.com