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Glycosides and Xanthine Oxidase Inhibitors from Conyza Bonariensis

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Glycosides and Xanthine Oxidase Inhibitors from Conyza Bonariensis __________________________________________________________________________www.paper.edu.cn Phytochemistry 58 (2001) 645–651 www.elsevier.com/locate/phytochem Glycosides and xanthine oxidase inhibitors from Conyza bonariensis L.D. Konga, Z. Ablizb, C.X. Zhoua, L.J. Lib, C.H.K. Chengc, R.X. Tana,* aInstitute of Functional Biomolecule, State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing 210093, People’s Republic of China bDepartment of Instrumental Analysis for Determination of Chemical Structures, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People’s Republic of China cDepartment of Biochemistry, The Chinese University of Hong Kong, Shatin, N. T., Hong Kong Received in revised form 12 December 2000 Abstract Fractionation of the xanthine oxidase inhibitory methanol extract of Conyza bonariensis afforded three glycosides, in addition to nine known compounds including amyrin, b-sitostero1 daucosterol, syringic acid 3-hydroxy-5-methoxybenzoic acid, eugenol 4-O- glucopyranoside, and luteolin, apigenin and takakin 8-O-glucuronide. The structures of the glycosides were established by a com- bination of spectroscopic methods (IR, MS, 1Hand 13C NMR, DEPT, COSY, HMQC and HMBC) as 4-hydroxypyridin-3-car- boxylic acid 4-O-glucopyranoside, 8-hydroxy-6,7-dihydrolinalool 8-O-glucopyranoside and bonaroside [viz. 1,3,4,12-tetrahydroxy- 2-(9-hexadecenoylamino)octadecane 1-O-glucopyranoside]. The in vitro enzyme assay showed that syringic acid and takakin 8-O- glucuronide displayed weak inhibitory activity against xanthine oxidase with IC50 values of 500Æ41 mM and 170Æ12 mM, respec- tively. # 2001 Elsevier Science Ltd. All rights reserved. Keywords: Conyza bonariensis; Asteraceae; 4-Hydroxypyridin-3-carboxylic acid 4-O-glucopyranoside; 8-Hydroxy-6,7-dihydrolinalool 8-O-gluco- pyranoside; Bonaroside; Syringic acid; Takakin 8-O-glucuronide 1. Introduction three new glycosides (1–3), in addition to the known constituents amyrin, b-sitosterol, daucosterol, apigenin, Conyza bonariensis (L.) Crong (Asteraceae) has been luteolin, takakin 8-O-glucuronide, syringic acid and 3- phytochemically investigated (El-Karemy et al., 1986; hydroxy-5-methoxybenzoic acid. The in vitro evaluation Rizk et al., 1986; Ferraro et al., 1988; Sanz and Marco, of these isolates demonstrated that the enzyme inhibi- 1991). However, the species growing in China has not tors present in the title species were syringic acid and the been examined to date. In continuation of our investi- three flavonoids. gations of plant-derived xanthine oxidase inhibitors (Li The identification of amyrin, b-sitosterol and daucos- et al., 1999; Zhou et al., 1999), the methanol extract was terol was accomplished by direct comparisons (co-TLC, found to be active against the enzyme which is closely IR and EIMS) with authentic samples available in our related to the hyperuricemia and gout (Tsutomu et al., laboratory. The spectral data (IR, EIMS, 1Hand 13C 1991; Cos et al., 1998). We therefore analyzed the NMR) of the two acids revealed that they were syringic extract in detail in order to characterize the xanthine acid (Cuenca et al., 1992) and 3-hydroxy-5-methoxy- oxidase inhibitor(s). benzoic acid (Majumder et al., 1996), respectively. Syr- ingic acid was previously found to have antioxidant (Yoshiki et al., 1995), antibacterial (Fernandez et al., 2. Results and discussion 1996), antifungal (Lattanzio et al., 1994), properties, as well as being protective against cell damage induced by Repeated chromatography of the methanol extract of superoxide anion radicals in murine dermal fibroblasts C. bonariensis on silica gel and Sephadex LH-20 afforded (Masaki et al., 1995). The structures of apigenin and luteolin were ascertained by their IR, EIMS, 1Hand 13C * Corresponding author. Tel./fax: +86-25-359-3201. NMR spectra (Markham et al., 1978; Noro et al., 1983; E-mail address: [email protected] (R.X. Tan). Tosun and Akyuz, 1997). Both flavones were previously 0031-9422/01/$ - see front matter # 2001 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(01)00176-5 中国科技论文在线_________________________________________________________________________www.paper.edu.cn 646 L.D. Kong et al. / Phytochemistry 58 (2001) 645–651 investigated biologically and reported to be antioxidant the attachment of the glucopyranosyl group, the chemi- and anti-inflammatory (Maokn et al., 1996; Silvan et al., cal shift of the anomeric proton doublet (J=7.8 Hz) at 1996; Yokozawa et al., 1997). Furthermore, apigenin 4.91 supported the formulated glycosidation pattern if was found to inhibit tumor necrosis factor-induced compared with that of carboxylic ( 6.20) and phe- intercellular adhesion molecule-1 upregulation in vivo nolic (4.90) glucosides described previously (Jaku- (Panes et al., 1996), and to have anti-TPA-induced povic et al., 1991; Tan et al., 1993). Finally, the transformation, anti-protein kinase C activation and structure of glycoside 1 was reinforced by its FABMS anti-TPA-induced c-jun expression activities (Lee and spectrum which gave an intense protonated molecular Lin, 1997), whereas luteolin had cancer chemopreven- ion at m/z 302, accompanied by a strong fragment at tive and antiplatelet effects (Cai et al., 1997; Lin et al., m/z 140 produced through the elimination of the gluco- 1997). Furthermore, luteolin and apigenin have been syl moiety from the quasimolecular ion. reported to be xanthine oxidase inhibitors (Cos et al. The structure of glycoside 2 followed from its spectral 1998, Kasai et al., 1999). The flavone glycoside was data. The El mass spectrum of 2 was not informative. identified as takakin 8-O-glucuronide by the IR, EIMS, However, an intense quasimolecular ion was observed 1Hand 13C NMR spectral data (Chen et al., 1994). The at m/z 335 ([M+H]+) in its FABMS spectrum. Besides second glycoside was demonstrated to be eugenol 4-O- a set of proton resonances attributable to a glucopyr- glucopyranoside by its spectral data (FABMS, IR, 1H anosyl moiety, the 1HNMR spectrum of glycoside 2 and 13C NMR), characterized previously as the corre- exhibited a methyl singlet at 1.20, a three-proton sponding peracetate from Artemisia dracunculus (Jaku- doublet (J=6.7 Hz) at 0.91, a pair of double doublets povic et al., 1991). at 3.82 and 3.66 due to an oxygenated methylene In the 1HNMR spectrum of compound 1, a broa- group, and a set of signals at 5.88 (1 H, dd, J=17.4, dened singlet at 8.34 and a pair of mutually coupled 10.8 Hz), 5.15 (IH, dd, J=17.4, 1.5 Hz) and 4.98 (1H, doublets (J=5.6 Hz) at 8.15 and 6.61 indicated that it dd, J=10.8, 1.5 Hz) arising from a vinyl function. These was most likely a pyridine derivative carrying pre- 1HNMR spectroscopic data showed that compound 2 sumably 3-carbonyl and 4-hydroxyl (or amino) groups was most probably a 8-hydroxy-6,7-dihydrolinalool (Rasala, 1993). This hypothesis was subsequently con- glucoside (Tan et al., 1991; Schulz et al., 1997). This firmed by the 13C NMR spectrum of 1, which exhibited proposal was substantiated by its 13C NMR and DEPT a total of twelve carbon resonance lines consisting of one spectra. All carbon signals could be assigned by com- methylene, eight methine and three quaternary carbons. paring them with those of 6,7-dihydrolinalool analogs Subtracting a set of carbon signals due to a glucopyr- (Yu et al., 1989). The glucopyranosyloxy group was anosyl group, the rest was ascribable to the 4-hydroxy- shown to be at C-8 by the glycosidation induced down- pyridin-3-carboxylic acid nucleus (Yu et al., 1989). As to field shift ( 76.2) of the 8-oxygenated methylene carbon 中国科技论文在线_________________________________________________________________________www.paper.edu.cn L.D. Kong et al. / Phytochemistry 58 (2001) 645–651 647 signal. In conclusion, glycoside 2 was 8-hydroxy-6,7- 316. The 9,10-double bond was assigned to the hexa dihydrolinalool 8-O-glucopyranoside. decenoyl group on the basis of the typical fragment ion The molecular formula of compound 3 was found to be at m/z 500 which was formed by elimination of pentene 1 13 C40H77NO10 by its FABMS, Hand CNMR,andDEPT from that at m/z 570 through McLafferty rearrangement data and the HREIMS spectrum of the corresponding (Fig. 1). Obviously, the other aliphatic chain should peracetate (3a). The 1Hand 13C NMR spectra of 3 consist of eighteen carbons. Moreover, the presence of a indicated that it was also a glucopyranoside (Table 1). total of seven hydroxyl groups in the molecule was Furthermore, a carbonyl IR absorption at 1720 cmÀ1, deduced by comparison between the molecular ions and the six-proton triplet (J=7.0 Hz) at 0.86 and a pair appearing in the FABMS spectra of 3 and 3a. Accord- of olefinic proton signals at 5.34 and 5.42 in its 1HNMR ingly, after subtraction of the four hydroxyls involved in spectrum demonstrated that it possessed presumably two the glucopyranosyl group, the other three had to be 1 1 aliphatic chains, one of which carried a double bond. positioned in the C18 chain. The H– HCOSY spectrum Thus, the three unsaturations of the molecular formula of 3 showed that a pair of double doublets of an oxy- could be readily assigned to a double bond, a carbonyl genated methylene at 4.01 (dd, J=10.5, 6.2 Hz) and and a glucopyranosyl group. This hypothesis was sub- 3.76 (dd, J=10.5, 3.5 Hz) coupled to the oxygen-bearing sequently confirmed by the 13C NMR spectrum and methine signal at 4.24 (ddd, J=6.5, 6.2, 3.5 Hz). This FABMS of 3. In addition to the quasimolecular ion at resonance showed a correlation with the double doublet m/z 754 [M+Na]+, the FABMS spectrum of 3 exhib- (J=6.5, 6.0 Hz) at 3.56 which coupled further to the ited an intense fragment peak at m/z 570 which was signal at 3.48 (ddd, J=6.2, 6.5, 3.5 Hz).
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