Chapter 20
Three New Sesquiterpene Lactones from Inula britannica 1,2
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Naisheng Bai , Bing-Nan Zhou , Li Zhang , Shengmin Sang , Kan He , and Qun Yi Zheng
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Department of Food Science, Rutgers, The State University of New Jersey, 65 Dudley Road, New Brunswick, NJ 08901-8520 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Academia Sinica, Shanghai, People's Republic of China PureWorld Botanicals, Inc., 375 Huyler Street, South Hackensack, NJ 07606
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Three new sesquiterpene lactones were identified from the flowers of Inula britannica var. chinensis: britannilide, oxobritannilactone and eremobritanilin. Their structures were established by spectroscopic methods. Britannilide and eremobritanilin inhibited the growth of human P cell lines. 388
Inula, from Compositae, has more than 100 species in the world, mainly found in Europe, Africa and Asia. There are more than 20 species in China. Inula britannica is a wild plant found in Eastern Asia, including China, Korea, and Japan. In traditional Chinese medicine, Inula britannica and Inula japonica are called "Xuanfuhua" and the flowers have been used for the treatment of digestive disorders, bronchitis and inflammation. Its extracts are reported to have anti-inflammatory, anti-bacteria, anti-hepatitis and anti-tumorigenic activities U). In our previous studies on Chinese Inula species, we isolated sesquiterpene lactones from Inula britannica (2), /. salsoloides (3), I. hupehensis and /. © 2003 American Chemical Society In Oriental Foods and Herbs; Ho, C., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2003.
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helianthus-aquatica (4). Other compounds, such as kaurane glycosides, flavonoids and steroids have also been isolated from /. britannica (5). In these reports, the cytotoxic activities of nine sesquiterpene lactones were observed. In addition to our work, Park and Kim (6) reported four cytotoxic sesquiterpene lactones from /. britannica. The present paper describes the isolation and the structural determination of three new sesquiterpene lactones (1,2 and 3) named britannilide, oxobritannilactone and eremobritanilin, respectively. Their cytotoxicity is also discussed.
Experimental
General Instrumentation Mp: uncorr; [a] JASCO DIP-300 spectrophotometer; UV: Shimadzu UV300; IR: Perkin-Elmer 599 Β instrument; EIMS: MAT-711 and Finnigan MAT 4021 GC/MS; H NMR, COSY and NOE: Bruker AM-400; C NMR and DEPT: AC-100. D:
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Plant Material The flowers of Inula britannica var. chinensis were collected in July 1990 during the flowering stage, at the suburb of Yanan City, Shanxi Province, China. It was identified by Professor Tian-Lang Pan, Yanan Institute of Medicine Inspection, Shanxi Province, China. Voucher specimens are deposited in the Laboratory of Phytochemistry, Shanghai Institute of Materia Medica, Academia Sinica, Shanghai, China.
Extraction and Isolation of Compounds The flowers (60 Kg) of Inula britannica var. chinensis were extracted three times with 95% EtOH at room temperature. The CHCl -soluble part of the EtOH extract was chromatographed on a silica gel column and packed in CHC1 using an CHCl -Me CO gradient solvent system. The fractions from chloroformacetone (20; 1 to 10:1) were evaporated under vacuum and repeatedly chromatographed on silica gel column, to give 1 (15 mg), 2 (3 mg) and 3 (21 mg)3
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In Oriental Foods and Herbs; Ho, C., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2003.
273 Britannilide (1) Obtained as needles, C,5H 0 , mp 76-78° (CHC1 ), [
