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.
Key words
Blumea glomerata
- Compositae - diterpene - cytotoxicity - cell cycle - austroinulin - absolute configuration
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
