A new cytotoxic guaianolide from Chrysanthemum boreale Ki Hun Park a , Min Suk Yang a , Moon Ki Park b , Sang Chan Kim c , Chae Ha Yang c , Sook Jahr Park c , Jong Rok Lee c, ⁎ a Division of Applied Life Science (BK21 program), EB-NCRC, Institute of Agriculture and Life Science, Gyeongsang National University, Jinju 660-701, Republic of Korea b Department of Herbalpharmaceutical Engineering, Daegu Haany University, Gyeongsan 712-715, Republic of Korea c College of Oriental Medicine (BK21 Program), Daegu Haany University, Daegu 706-060, Republic of Korea article info abstract Article history: Received 19 August 2008 Accepted in revised form 30 September 2008 Available online 14 October 2008 A new cytotoxic guaianolide was isolated from Chrysanthemum boreale Makino. The structure of guaianolide was elucidated as 8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (1). Compound 1 exhibited cytotoxic activity (IC 50 ≤ 4 μg/ml) against all five human cancer cell lines tested. © 2008 Elsevier B.V. All rights reserved. Keywords: Chrysanthemum boreale Makino Guaianolide 8-acetoxy-4,10-dihydroxy-2,11(13)- guaiadiene-12,6-olide Cytotoxic activity 1. Introduction Chrysanthemums are traditional oriental medicines com- monly used to clear heat and to improve eyesight in Asia [1]. They have been reported to exhibit anti-bacterial and anti-viral activities [2–5]. The dried flower and leaf of Chrysanthemum boreale Makino (C. boreale) have been used in the form of tea or wine to treat pyrexia, vertigo and red eyes in Korea. Chemical analysis with C. boreale has been rarely conducted compared to other chrysanthemum species including C. indicum. In our previous chemical investigations of C. boreale, cumanbrin A and handelin were the major chemicals. Additionally we reported several guaianolides with apoptosis inhibitory and cytotoxic activities [6–8]. In the course of our continuing search for new biological compounds from C. boreale, a new guaianolide deri- vative with cytotoxic activity was found from leaves and stems. Here, we report the isolation and identification of 8-acetoxy- 4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (1) and its cyto- toxic activities against human cancer cell lines. 2. Experimental 2.1. General Optical rotation values were recorded with a Perkin-Elmer polarimeter. IR spectra were recorded with a Bruker IFS66 infrared Fourier transform spectrophotometer (KBr). Low- resolution EIMS data were collected by a Jeol JMS-700 spectro- meter. Compound 1 was dissolved in CD 3 OD. 1 H and 13 C NMR and 2D NMR data were obtained with a Bruker AM 500 spectrometer. Elemental analysis was performed with LECO CHNS-932 elemental analyzer. 2.2. Plant C. boreale was collected in Hamyang (Korea), and a voucher specimen (Park, K.H. 108) of this raw material is deposited at Herbarium of Gyeongsang National University in Korea. 2.3. Extraction and isolation Dried leaves and stems (3 kg) of C. boreale were extracted with CHCl 3 (3 × 15 l) yielding a dark brown residue (87 g). The residue was subjected to a Si-gel CC (8 × 60 cm, 230–400 mesh, Fitoterapia 80 (2009) 54–56 ⁎ Corresponding author. College of Oriental Medicine, Daegu Haany University, 165 Sang-dong, Suseong-gu, Daegu 706-060, Republic of Korea. Tel.: +82 53 770 2297; fax: +82 53 768 6340. E-mail address: ssephia@hanmail.net (J.R. Lee). 0367-326X/$ – see front matter © 2008 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2008.09.013 Contents lists available at ScienceDirect Fitoterapia journal homepage: www.elsevier.com/locate/fitote