Planta Med 2004; 70(12): 1170-1173
DOI: 10.1055/s-2004-835847
Original Paper
Biochemistry and Molecular Biology
© Georg Thieme Verlag KG Stuttgart · New York

Isolation of Austroinulin Possessing Cell Cycle Inhibition Activity from Blumea glomerata and Revision of Its Absolute Configuration

Takashi Ohtsuki1 , Takashi Koyano2 , Thaworn Kowithayakorn3 , Naoto Yamaguchi1 , Masami Ishibashi1
  • 1Graduate School of Pharmaceutical Sciences, Chiba University, Chiba, Japan
  • 2Temko Corporation, Nakano, Tokyo, Japan
  • 3Department of Horticulture, Faculty of Agriculture, Khon Kaen University, Khon Kaen, Thailand
Further Information

Publication History

Received: March 15, 2004

Accepted: June 13, 2004

Publication Date:
10 January 2005 (online)

Abstract

A labdane-diterpene, austroinulin (1), together with several known flavonoids and sesquiterpenes were isolated from leaves of Blumea glomerata (Compositae). Austroinulin (1) and most of the flavonoids showed cytotoxicity against HeLa cells, while austroinulin (1) exhibited a cell cycle inhibition effect at the G1 stage at the concentration of 15.2 μg/mL (47.2 μM). The absolute configuration of 1 was revised as 5S,6R,7S,8S,9R,10R on the basis of the modified Mosher’s method.

References

  • 1 Kawamoto S, Koyano T, Kowithayakorn T, Fujimoto H, Okuyama E. et al . Wrightiamines A and B, two new cytotoxic pregnane alkaloids from Wrightia javanica .  Chem Pharm Bull. 2003;  51 737-9
  • 2 Islam M T, Tahara S. Dihydroflavonols from Lannea coromandelica .  Phytochemistry. 2000;  54 901-7
  • 3 Ando M, Arai K, Kikuchi K, Isogai K. Synthetic studies of sesquiterpenes with cis-fused decalin system, 4. Synthesis of (+)-5βH-eudesma-3,11-diene, (-)-5βH-eudesmane-4β,11-diol, and (+)-5βH-eudesmane-4α,11-diol, and structure revision of a natural eudesmane-4,11-diol isolated from Pluchea arguta .  J Nat Prod. 1994;  57 1189-99
  • 4 Vasconcelos João M J, Silva Artur M S, Cavaleiro José A S. Chromones and flavanones from Artemisia campestris subsp. maritime .  Phytochemistry. 1998;  49 1421-4
  • 5 Ruangrungsi N, Tappayuthpijarn P, Tantivatana P. Traditional medicinal plants of Thailand. I. Isolation and structure elucidation of two new flavonoids, (2R,3R)-dihydroquercetin-4′-methyl ether and (2R,3R)-dihydroquercetin-4′,7′-dimethyl ether from Blumea balsamifera .  J Nat Prod. 1981;  44 541-5
  • 6 Iinuma M, Tanaka T, Matsuura S. Synthetic studies on the flavone derivatives 12. Synthesis of 2′,3′,5′- and 3′,4′,5′-trioxygenated flavones.  Chem Pharm Bull. 1984;  32 2296-300
  • 7 Kinoshita T, Firman K. Highly oxygenated flavonoids from Murraya paniculata .  Phytochemistry. 1996;  42 1207-10
  • 8 Le-van N, Cuong Phan T V. Two new flavones from Eupatorium coelestinum .  Phytochemistry. 1979;  18 1859-61
  • 9 Grande M, Piera F, Cuenca A, Torres P, Bellido I S. Flavonoids from Inula viscose .  Planta Medica. 1985;  51 414-9
  • 10 Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids.  J Am Chem Soc. 1991;  113 4092-6
  • 11 Larsson R, Kristensen J, Sandberg C, Nygren P. Laboratory detection of chemotherapeutic drug resistance in tumor cells from patients with leukemia, using a fluorometric microculture cytotoxicity assay (FMCA).  Int J Cancer. 1992;  50 177-85
  • 12 Yamaguchi N, Nakayama Y, Urakami T, Suzuki S, Nakamura T, Suda T. et al . Overexpression of the Csk homologous kinase (Chk tyrosine kinase) induces multinucleation: a possible role for chromosome-associated Chk in chromosome dynamics.  J Cell Sci. 2001;  114 1631-41
  • 13 Bohlmann F, Zdero C, Grenz M. Naturally occurring terpene derivatives, 81. Further constituents of representatives from the Eupatorium group.  Chem Ber. 1977;  110 1034-41
  • 14 Sholichin M, Yamasaki K, Miyama R, Yahara S, Tanaka O. Labdane-type diterpenes from Stevia rebaudiana .  Phytochemistry. 1980;  19 326-7
  • 15 Darise M, Kohda H, Mizutani K, Kasai R, Tanaka O. Chemical constituents of flowers of Stevia rebaudiana Bertoni.  Agric Biol Chem. 1983;  47 133-5
  • 16 Zdero C, Bohlmann F, Schmeda-Hirschmann G. Beyerene derivatives and other terpenoids from Stevia aristata .  Phytochemistry. 1987;  26 463-6

Prof. Masami Ishibashi

Graduate School of Pharmaceutical Sciences

Chiba University

1-33 Yayoi-cho

Inage-ku

Chiba 263-8522

Japan

Phone: +81-43-290-2913

Fax: +81-43-290-2913

Email: mish@p.chiba-u.ac.jp

    >