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A New Furobenzopyranone and Other Constituents from Anaphalis Lactea

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A New Furobenzopyranone and Other Constituents from Anaphalis Lactea ORIGINAL ARTICLES National Laboratory of Applied Organic Chemistry1, College of Chemistry and Chemical Engineering, College of Biological Science2, Lanzhou University, Lanzhou, P.R. China A new furobenzopyranone and other constituents from Anaphalis lactea Ai-Xia Wang1, Qi Zhang2, Zhong-Jian Jia1 Received September 9, 2003, accepted November 1, 2003 Prof. Zhong-Jian Jia, Department of Chemistry, Lanzhou University, Lanzhou Gansu 730000, People’s Republic of China [email protected] Pharmazie 59: 807–811 (2004) Together with twenty-one known compounds, a new furobenzopyranone was isolated from the whole plant of Anaphalis lactea. Their structures were elucidated by spectroscopic methods MS, IR, UV, NMR, including 2D-NMR techniques. The anti-bacterial activity of compounds 1, 4–6, 14, 15 and the anti-tumor activity of compounds 4–6 were tested. 1. Introduction 6-(40-hydroxystyryl)-4-methoxy-2-pyrone (14) (Talapatra et al. 1976), 6-(40-O-b-d-glucopyranose-styryl)-4-meth- There are about 80 species of Anaphalis (Compositae) all oxy-2-pyrone (15) (Romo et al. 1972), (E)-3-(3,4-dihy- over the world and more than 50 species distributed in droxyphenyl)-propenoic acid (16) (Asahi Research Cen- China (Editorial Committee of Zhongguozhiwuzhi, Chi- ter 1986), (E)-3-(3,4-dihydroxy phenyl)-propenoic acid nese Academy of Sciences 1979). But only a few have methyl ester (17), methyl 3,4-dihydroxy benzoate (18) been studied chemically. The whole plant of Anaphalis (Luo et al. 2001), 4-hydroxy benzoic acid (19) (Asahi Re- lactea Maxim. has long been used as a Tibetan medicine search Center 1985), inositol (20), 1-methyl- inositol (21) for invigorating the circulation of blood, relieving phlegm and stearic acid (22). The structure of the new compound and hemostasia (Jiangsu College of New Medicine 1977), 1 was identified by EI-MS, FAB-MS, IR, UV, 1H NMR, however, its chemical constituents have not been pre- 13C NMR, HMBC spectroscopic methods and comparing viously investigated. In this paper, we report the isolation with the spectral data of similar compounds. The struc- and structural elucidation of a new furobenzopyranone (1) tures of the known compounds 2–10 and 13–19 were and twenty-one known compounds (2–22). Compound 9 elucidated by comparison with their spectral data (EI-MS, was a new one which was isolated and identified from FAB-MS, IR, 1H NMR and 13C NMR) with those pub- Ligularia dolichobotrys by our research group (Li et al. in lished in the literature. In addition, compounds 11, 12 and press). Almost the the same time, we obtained it from 20-22 were determined on the basis of their physical prop- A. lactea. In addition, six of the compounds isolated (1, erties by comparison with those of authentic samples, re- 4–6, 14, 15) were assayed against Bacillus subtilis, Sta- spectively. phylococcus aureus and Escherichia coli, three kaempferol Compound 1 was obtained as colorless gum, its FAB-MS flavonoids (4–6) were screened against human hepatoma gave quasi-molecular ion peaks at m/z 239.2 [M þ Li]þ (Bel-7402) and human ovaria carcinoma (HO-8910) cell and m/z 255.1 [M þ Na]þ, combined with the peak of EI- lines. MS ([M]þ at m/z 232), the molecular formula of 1 was deduced to be C13H12O4, which was supported by 1 13 2. Investigations, results and discussion H NMR, C NMR and DEPT data (Table 1). The IR spectrum (KBr) showed the presence of hydroxyl From the acetone extract of the whole plant of A. lactea, a (3528 cmÀ1), a,b-unsaturated g-lactone (1723 cmÀ1), ben- new furobenzopyranone anaphalisol (1) was isolated and zene ring (1635, 1600, 1464 cmÀ1) and C––O––C bond elucidated, together with twenty-one known compounds: (1335, 1152, 1046 cmÀ1). Its 1H NMR spectrum gave the clovane-2b,9a-diol (2) (Heymann et al. 1994), flavone (3) typical signals of 2,2-dimethyl-chromene derivative at d (Iinuma et al. 1980), kaempferol-3-O-b-d-glucopyranoside 6.15 (1 H, d, 9.9 Hz), 5.63 (1 H, d, 9.9 Hz), 1.46 (6 H, s), (4) (Markham et al. 1978), kaempferol-3-O-[600-O-(trans- two independent signals at d 6.35 (1 H, s), 5.25 (2 H, s) p-coumaroyl)]-b-d-glucopyranoside (5) (Zhang et al. 1997; and an aromatic hydroxyl signal at d 7.65 (1 H, brs) 00 13 Zhou et al. 2001), kaempferol-3-O-[6 -O-(trans-p-co- which disappeared on addition of D2O. C NMR and 00 umaroyl)-4 -O-acetyl]-b-d-glucopyranoside (6) (Romussi DEPT spectra revealed 13 carbons (2 Â CH3,1Â CH2, et al. 1988), 1-hydroxyl-2,3,4,5-tetramethoxyxanthone (7) 3 Â CH, 7 Â C) (Table 1). The signals at d 161.1 (C), (Ghosal et al. 1975; Li et al. 1998), 3b-oleanolic acid (8) 157.6 (C), 143.0 (C), 108.6 (C), 104.0 (C) and 103.9 (CH) (Liu et al. 1999), 3b,7a,22-trihydroxy-5-en-stigmast (9) (benzene ring), at d 129.8, 116.6 (2 Â CH, the sp2 double (Li et al. in press), 3b,7a-dihydroxy-5-en-stigmast (10) bond), 78.1 (C) and 28.5 (2 Â CH3), further confirmed the (Greca et al. 1990), b-sitosterol (11), daucosterol (12), skeleton of 2,2-dimenthyl-chromene. Apart from the car- 3a-spinasterol (13) (Itoh et al. 1981; Xu et al. 1998), bon signals corresponding to the above mentioned groups, Pharmazie 59 (2004) 10 807 ORIGINAL ARTICLES 14 13 5 6 14 H 6 HO 12 O 4 15 7 4 7 3 5 1 10 12 15 O 13 8 2 8 11 9 3 HO 1 11 9 OH O 10 2 1 2 O HO O OH O OH OH O OH O HO OH 3 4 2' 3' 2''' 3''' 8 1 1' 4' 7''' 1''' 4''' HO 9 O 2 OH OOH 7 6' 5' 6'' 9''' 8''' 6''' 5''' 6 3 O 5 10 4 OO1'' 5'' 4'' OR OH O HO 2'' OH 3'' 5R=H 6R=Ac OOH 8 1 7 8a 9a 2 OMe 9 COOH 6 3 10a O 4a 4 OMe 5 10 OMe OMe HO 7 8 29 R 28 21 22 23 26 19 24 25 12 20 11 18 13 17 27 1 16 2 9 10 814 15 HO3 4 5 6 7 OH RO 9R=OH 11 R=H 10 R=H 12 R=GLC the 13C NMR and DEPT spectra also displayed a carbonyl Table 1: 1HNMR, 13C NMR, DEPT data and HMBC correla- carbon at d 172.5 and a oxygen-bearing carbon methylene tions of 1 (d, ppm, TMS, CDCl3) at d 69.4, which could be due to a g-lactone moiety, as 1 13 followed by the molecular formula and the IR spectrum. No. H NMR C NMR (DEPT) HMBC Moreover, the significant absorption band at 245 nm in 1 5.25 (s) 69.4 (CH2) C-3, 10, 11, 12, 13 the UV spectrum also supported a g-lactone benzofurane 3 – 172.5 (C) – ring. Considered a single signal of aromatic proton in 4 – 157.6 (C) – 1H NMR spectrum and a signal of hydroxy in 1H NMR 5 6.35 (s) 103.9 (CH) C-4, 10, 12, 13 and IR spectra, the benzene ring had five substitutions 7 – 78.1 (C) – including a hydroxy. From the above data, the structure of 8 5.63 (d, J ¼ 9.9 Hz) 129.8 (CH) C-7, 9, 13, 14, 15 compound 1 was deduced as furobenzopyranone. In addi- 9 6.15 (d, J ¼ 9.9 Hz) 116.6 (CH) C-7, 8, 11, 12, 13 tion, its HMBC spectrum gave the long-range correlations 10 – 104.0 (C) – between d 6.35 (H-5) with d 161.1 (C-12), 157.6 (C-4), 11 – 143.0 (C) – 108.6 (C-13), 104.0 (C-10); d 6.15 (H-9) with d 161.1 12 – 161.1 (C) – 13 – 108.6 (C) – (C-12), 143.0 (C-11), 108.6 (C-13); d 5.25 (H-1) with d 14 1.46 (s) 28.5 (CH ) C-7, 8, 15 172.5 (C-3), 143.0 (C-11), 108.6 (C-13), 104.0 (C-10) 3 15 1.46 (s) 28.5 (CH3) C-7, 8, 14 (Table 1). Therefore, compound 1 was established and OH 7.65 (brs) – – named anaphalisol. Moreover, compared the 1H NMR 808 Pharmazie 59 (2004) 10 ORIGINAL ARTICLES OMe 22 5 23 3' 2' 6 4 4' 1' 7 3 RO 8 O 2 1 8 5' 6' O 7 HO 3 14 R=H 13 15 R=GLC O 2' 3 3' HO 1 OR HO COOMe 1' 2 4' HO 6' HO 5' 16 R=H 18 17 R=Me OH OH HO HO COOH OR HO OH 20 R=H 19 21 R=OMe CH3(CH2)14COOH 22 spectrum of compound 1 with that of the known com- by comparision with the standard vincristin sulphate. But pound phthalidochromene (Jakupovic et al. 1987), the they showed no effect on the growth of the cell lines at a only difference between them was that phthalidochromene concentration of 50 ug/ml, so they exhibited little anti-tu- had a signal at d 3.93 (OMe), but compound 1 had a mor activities against the cell lines. signal at d 7.65 (Ar––OH). So their structure’s difference was the group at C-4, the phthalidochromene was OMe (d 3.93), however, anaphalisol was OH (d 7.65).
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