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DOI: 10.1055/s-2003-41123
© Georg Thieme Verlag Stuttgart · New York
Sesquiterpenes and Other Constituents from the Aerial Parts of Inula japonica
This work was supported by the National Natural Science Foundation of China NO. 29972017.Publication History
Received: November 27, 2002
Accepted: April 12, 2003
Publication Date:
04 August 2003 (online)
Abstract
Three new sesquiterpenes, 1β-hydroxy-8β-acetoxycostic acid methyl ester, 1β-hydroxy-8β-acetoxyisocostic acid methyl ester and 1β-hydroxy-4α,11α-eudesma-5-en-12,8β-olide, along with fourteen known compounds were isolated from the aerial parts of Inula japonica. The structures of these new compounds were elucidated by spectroscopic methods (IR, EIMS, HRMS, 1D and 2D NMR). 1,6α-dihydroxy-4αH-1,10-secoeudesma-5(10),11(13)-dien-12,8β-olide exhibited appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell) and HO-8910 (human ovarian carcinoma cell) with IC50 values of 52.22 and 21.32 μg/mL, while 5αH-eudesma-4(15),11(13)-dien-12,8β-olide showed remarkable cytotoxic activity against cultured SMMC-7721 and HO-8910 with IC50 values of 6.21 and 5.28 μg/mL, respectively.
Key words
Inula japonica - Compositae - sesquiterpene - eudesmane - cytotoxic activity
References
- 1 Jiangsu New Medical C ollege. A Dictionary of Traditional Chinese Drugs. Shanghai People's Press Shanghai; 1977: 324-6
- 2 Bohlmann F, Mahanta P K, Jakupovic J, Rastogi R C, Natu A. New sesquiterpene lactones from Inula species. Phytochemistry. 1978; 17 1165-72
- 3 Jeske F, Huneck S, Jakupovic J. Secoeudesmanolides from Inula japonica . Phytochemistry. 1993; 34 1647-9
- 4 Bohlmann F, Czerson H, Schöneweiβ S. New constituents of Inula viscose Ait. Chem Ber. 1977; 110 1330-4
- 5 Goyal R, Chhabra B R, Kalsi P S. Three oxygenated alantolides from Inula racemosa . Phytochemistry. 1990; 29 2341-3
- 6 Su B N, Takaishi Y, Yabuuchi T, Kusumi T. The structures and absolute configurations of macrophyllic acids A - E, five new rearranged eudesmane sesquiterpene acids from the bark of Inula macrophylla . Tetrahedron Letters. 2000; 41 2395-400
- 7 Shi Y P, Guo W, Yang C, Jia Z J. Two new aromatic monoterpene derivatives from Carpesium lipskyi . Planta Medica. 1998; 64 671-2
- 8 Yang C, Zhu Q X, Zhang Q, Wang Q, Jia Z J. Eudesmanolides, aromatic derivatives, and other constituents from Carpesium cernuum . Pharmazie. 2001; 56 825-7
- 9 Yang C, Shi Y P, Jia Z J. Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum . Planta Medica. 2002; 68 628-30
-
10 Chinese Academy of M edicine. Institute of Pharmacy. Traditional Chinese Medicine People's Health Press Beijing; 1984 3: 476-84
- 11 Herz W, Viswanathan N. Constituents of Iva species. II. The structures of asperilin and ivasperin, two new sesquiterpene lactones. J Org Chem. 1964; 29 1022-6
- 12 Herz W, Sumi Y, Sudarsanam V, Raulais D. Constituents of Iva species. X. Ivangulin, a novel secoeudesmanolide from Iva angustifolia Nutt. J Org Chem. 1967; 32 3658-62
- 13 Marcinek-Hüpen-Bestendonk C, Willuhn G, Steigel A. Germacranolides, guaianolides, and xanthanolides from the flowers of Arnica mollis and an X-ray structure analysis of baileyin acetate. Planta Medica. 1990; 56 104-10
- 14 Marshall J A, Cohen N. The structure of alantolactone. J Org Chem. 1964; 29 3727-9
- 15 Bohlmann F, Niedballa U, Schulz J. Über einige Thymolderivate aus Gaillardia- und Helenium-Arten. Chem Ber. 1969; 102 864-71
- 16 Greca M D, Monaco P, Previtera L. Stigmasterols from Typha latifolia . J Nat Prod. 1990; 53 1430-5
- 17 Li Y, Shi Y P, Hu Y. Chemical constituents of Artemisia roxburghiana Bess. Indian J Chem. 1994; 33B 302-4
- 18 Zdero C, Bohlmann F. Sesquiterpene lactones and other terpenes from Geigeria species. Phytochemistry. 1989; 28 3105-20
- 19 Öksüz S, Topcu G, Krawiec M, Watson W H. Eudesmanolides and other constituents of Inula thapsoides . Phytochemistry. 1997; 46 1131-4
- 20 Zdero C, Bohlmann F. Eremophilanolides, eudesmanolides, guaianolides and other constituents from Ondetia linearis . Phytochemistry. 1989; 28 1653-60
- 21 Dong Y F, Ding Y M. Sesquiterpene lactone from Carpesium abrotanoides . Acta Botanica Sinica. 1988; 30 71-5
- 22 Yang C, Yuan C S, Han Y F, Jia Z J. A new eudesmanoilde from Carpesium macrocephalum . Chin Chem Lett. 2001; 13 855-6
Prof. Zhong-Jian Jia
Department of Chemistry
Lanzhou University
Lanzhou
Gansu 730000
Peoples Republic of China
Fax: +86-0931-8912582
Email: Jiazj@lzu.edu.cn