Planta Med 2010; 76(4): 345-349
DOI: 10.1055/s-0029-1186143
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Naphthoquinones, Anthraquinones and Naphthalene Derivatives from the Bulbs of Eleutherine americana

Wilawan Mahabusarakam1 , 3 , Chulida Hemtasin1 , Suda Chakthong1 , Supayang Piyawan Voravuthikunchai2 , 3 , Ifesan Beatrice Olawumi2
  • 1Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand
  • 2Department of Microbiology, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand
  • 3Natural Product Research Center, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla, Thailand
Further Information

Publication History

received April 11, 2009 revised August 10, 2009

accepted August 18, 2009

Publication Date:
23 September 2009 (online)

Abstract

A new naphthoquinone, named eleuthinone A (8), two new anthraquinones, named eleuthraquinone A and B (12, 13), a naphthalene derivative, named eleucanarol (14) were isolated from the bulbs of Eleutherine americana, together with two new natural products previously synthesized, and nine known compounds. Their structures were established based on spectroscopic evidence. Their antibacterial activities against Staphylococcus aureus ATCC25923 and ATCC27664, an enterotoxin producing strain were investigated.

References

  • 1 Komura H, Mizukawa K, Minakata H, Huan H, Qin G, Xu R. New anthraquinones from Eleutherine americana.  Chem Pharm Bull. 1983;  31 4206-4208
  • 2 Chen Z, Huang H, Wang C, Li Y, Ding J, Ushio S, Hiroshi N, Yoichi I. Hongconin, a new naphthalene derivative from Hong-Cong the rhizome of Eleutherine americana Merr and Heyne (Iridaceae).  Chem Pharm Bull. 1986;  34 2743-2746
  • 3 Hara H, Maruyama N, Yamashita S, Hayashi Y, Lee K H, Bastow F K, Chirul, Marumoto N, Imakura Y. Elecanacin, a novel new naphthoquinone from the bulb of Eleutherine americana.  Chem Pharm Bull. 1997;  45 1714-1716
  • 4 Jinzhong X, Feng Q, Gexia Q, Naili W, Xinsheng Y. Studies on antifungal constituents isolated from Eleutherine americana.  Zhongguo Yaowu Huaxue Zazhi. 2005;  15 157-161
  • 5 Limsuwan S, Voravuthikunchai S P. Boesenbergia pandurata (Roxb.) Schltr., Eleutherine americana Merr and Rhodomyrtus tomentosa (Aiton) Hassk as antibiofilm producing and antiquorum sensing in Streptococcus pyogenes.  Immunol Med Microbiol. 2008;  53 429-436
  • 6 Ifesan B O, Hamtasin C, Mahabusarakam W, Voravuthikunchai S P. Assessment of antistaphylococcal activity of partially-purified fractions and pure compounds from Eleutherine americana.  J Food Protect. 2009;  72 354-359
  • 7 Ifesan B O, Hamtasin C, Mahabusarakam W, Voravuthikunchai S P. Inhibitory effect of Eleutherine americana Merr extract on Staphylococcus aureus isolated from food.  J Food Sci. 2009;  74 M31-M36
  • 8 Jinzhong X, Feng Q, Wenjuan D, Gexia Q, Naili W, Xinsheng Y. New bioactive constituents from Eleutherine americana.  Front Chem China. 2006;  3 320-323
  • 9 Christopher D D, Melvyn G, Leonie M T. Synthesis of pyran and pyranone natural products.  Molecules. 2004;  9 498-512
  • 10 Alves T M A, Helmut K. Eleutherinone, a novel fungitoxic naphthoquinone from Eleutherine bulbosa (Iridaceae).  Mem Inst Oswaldo Cruz. 2003;  98 709-712
  • 11 Han A R, Min H Y, Nam J W, Lee N Y, Wiryawan A, Suprapto W, Lee S K, Lee K R, Seo E K. Identification of a new naphthalene and its derivatives from the bulb of Eleutherine americana with inhibitory activity on lipopolysaccharide-induced nitric oxide production.  Chem Pharm Bull. 2008;  56 1314-1316
  • 12 Tieteze L F, Gericke K M, Guentenes C. First total synthesis of the bioactive anthraquinones kwanzoquinone C and related natural products by a Diels-Alder approach.  Eur J Org Chem. 2006;  21 4910-4915

Assoc. Prof. Dr. Wilawan Mahabusarakam

Department of Chemistry
Faculty of Science
Prince of Songkla University

Hat Yai

Songkhla 90112

Thailand

Phone: + 66 74 28 84 32

Fax: + 66 74 21 29 18

Email: wilawan.m@psu.ac.th

    >