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DOI: 10.1055/s-2007-981529
© Georg Thieme Verlag KG Stuttgart · New York
ent-Kaurane-Type Diterpenoids from a Cell Suspension Culture of the Liverwort Jungermannia subulata
Publication History
Received: October 22, 2006
Revised: April 15, 2007
Accepted: April 17, 2007
Publication Date:
01 June 2007 (online)
Abstract
A cell suspension culture of the liverwort Jungermannia subulata was established from callus tissue induced by culturing spores. From the suspension culture, three new ent-kaurane-type diterpenoids were isolated together with three previously reported ent-kaurane-type diterpenoids. Five ent-kaurane-type diterpenoids were isolated from the intact J. subulata, two of which were new compounds. Their structures were determined by spectroscopic methods, chemical reaction, and X-ray crystallographic analysis.
Key words
Jungermannia subulata - Jungermanniaceae - Hepaticae - liverwort - cell culture - kaurenes - diterpenes - isolation - X-ray
References
-
1 Asakawa Y. Chemical constitutes of Hepaticae. In: Herz W, Grisebach H, Kirby GW, editors
Progress in the chemistry of organic natural products, Vol. 42. New York; Springer 1982: 281-5. - 2 Matsuo A. Selected chemotaxonomic characteristics of liverwort sesquiterpenoids. J Hattori Bot Lab. 1982; 53 295-304.
-
3 Ohta Y, Kato K, Takeda R. Growth and secondary metabolites production in cultured cells of bryophytes. In: Chopra RN, Bhatla SC, editors
Bryophyte development: physiology and biochemistry. Boca Raton; CRC Press 1990: 209-23. - 4 Tazaki H, Adam K P, Becker H. Five lignan derivatives from in vitro cultures of the liverwort Janesoniella autumnalis . Phytochemistry. 1995; 40 1671-5.
- 5 Matsuo A, Ono K, Hamasaki K, Nozaki H. Phaeophytins from a cell suspension culture of the liverwort Plagiochila ovalifolia . Phytochemistry. 1996; 42 427-30.
- 6 Tazaki H, Iwasaki T, Nakasuga I, Kobayashi K, Koshino H, Tanaka M. et al . ent-Kaurane-type deterpenoids produced cell culture of the liverwort Jungermannia subulata . Phytochemistry. 1999; 52 1427-30.
- 7 Nagashima F, Toyota M, Asakawa Y. Terpenoids from some Japanese liverworts. Phytochemistry. 1990; 29 2169-74.
-
8 Matsuo A, Nakayama M, Hayashi S, Seki T, Amakawa T. A comparative study of the diterpenoids from several species of the genus Jungermannia
. In: Claude S, editor
Congress International de Bryologie, Bordeaux Nov. 21 - 23, Bryophytorum Bibliotheca, Vol. 13. Stuttgart; Schweizerbart Publishers 1977: 322-8. - 9 Asakawa Y. Chemosystematics of the Hepaticae. Phytochemistry. 2004; 65 623-69.
- 10 Nagashima F, Kondoh M, Kawase M, Simizu S, Osada H, Fujii M. et al . Apoptosis-inducing properties of ent-kaurene-type diterpenoids from the liverwort Jungermannia truncata . Planta Med. 2003; 69 377-9.
- 11 Suzuki I, Kondoh M, Harada M, Koizumi N, Fujii M, Nagashima F. et al . An ent-kaurene diterpene enhances apoptosis induced by tumor necrosis factor in human leukemia cells. Planta Med. 2004; 70 723-7.
- 12 Kondoh M, Nagashima F, Suzuki I, Harada M, Fujii M, Asakawa Y. et al . Induction of apoptosis by new ent-kaurene-type diterpenoids isolated from the New Zealand liverwort Jungermannia species. Planta Med. 2005; 71 1005-9.
- 13 Nagashima F, Kasai W, Kondoh M, Fujii M, Watanabe Y, Braggins J E. et al . New ent-kaurene-type diterpenoids possessing cytotoxicity from the New Zealand liverwort Jungermannia species. Chem Pharm Bull. 2003; 51 1189-92.
- 14 Yeh S H, Chang F R, Wu Y C, Yang Y L, Zhuo S K, Hwang T L. An anti-inflammatory ent-kaurane from the stems of Annona squamosa that inhibits various human neutrophil functions. Planta Med. 2005; 71 904-9.
- 15 Yang Y L, Chang F R, Wu C C, Wang W Y, Wu Y C. New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa . J Nat Prod. 2002; 65 1462-7.
- 16 Yang Y L, Chang F R, Hwang T L, Chang W T, Wu Y C. Inhibitory effects of ent-kauranes from the stems of Annona squamosa on superoxide anion generation by human neutrophils. Planta Med. 2004; 70 256-8.
- 17 Wu Y C, Hung Y C, Chang F R, Cosentino M, Wang H K, Lee K H. Identification of ent-16β, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa . J Nat Prod. 1996; 59 635-7.
- 18 Liu H J, Tseng S H, Wu J D, Wu C L. Kaurane-type diterpenoids from liverworts. J Chin Chem Soc (Taipei). 1997; 44 385-9.
- 19 Nagashima F, Suzuki M, Asakawa Y. Seco-cuparane-type sesquiterpenoid from the Japanese liverwort Jungermannia infusca . Phytochemistry. 2001; 56 807-10.
- 20 Murashige T, Skoog F. A revised media for rapid growth and bioassay with tobacco cultures. Physiol Plant. 1962; 15 473-97.
- 21 Fraga B M, Guillermo R, Hernandez M G. The microbiological transformation of two 15β-hydroxy-ent-kaurene diterpenes by Gibberella fujikuroi . J Nat Prod. 2004; 67 64-9.
- 22 Matsuo A, Kodama J, Nakayama M, Hayashi S. ent-Kaurene diterpenoids from the liverwort Jungermannia infusca . Phytochemistry. 1977; 16 489-90.
- 23 Buchana M S, Connolly J D, Kadir A A, Rycroft D S. Sesquiterpenoids and diterpenoids from the liverwort Jungermannia truncata . Phytochemistry. 1996; 42 1641-6.
- 24 Hayashi K, Kawaide H, Notomi M, Sakigi Y, Matsuo A, Nozaki H. Identification and functional analysis of bifunctional ent-kaurene synthase from the moss Physcomitrella patens . FEBS Lett.. 2006; 580 6175-81.
Prof. Dr. Hiroshi Nozaki
Department of Biochemistry
Okayama University of Science
1-1 Ridai-cho
Okayama City 700-0005
Japan
Phone: +81-86-256-9460
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Email: nozaki@dbc.ous.ac.jp