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A new phenolic glycoside from the aerial parts of Solidago canadensis
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Phytochemical communication A new phenolic glycoside from the aerial parts of Solidago canadensis JinSong Zhang, XinQin Zhang, GuangQing Lei, Bo Li, JiaKuan Chen, TongShui Zhou ⁎ Research Center of Natural Medicines, School of Life Sciences, Fudan University, Shanghai 200433, PR China Received 15 August 2005; accepted 5 September 2005 Available online 23 September 2006 Abstract A new phenolic glycoside, 2′-hydroxy-4′,6′-di-O-β-D-glucopyranosyl-butyrrophenone (1), was isolated from the aerial parts of Solidago canadensis. The structure was elucidated on the basis of spectroscopic methods. © 2006 Elsevier B.V. All rights reserved. Keywords: Solidago canadensis;2′-Hydroxy-4′,6′-di-O-β-D-glucopyranosyl-butyrrophenone 1. Plant Solidago canadensis L. (Compositae), aerial parts were collected from Shanghai, PR China and identified by Prof. Bo Li (Fudan University, Shanghai). A voucher specimen was deposited in the Herbarium of Fudan University, PR China. 2. Uses in traditional medicine In European phytotherapy for the treatment of chronic nephritis, cystitis, urolithiasis, rhematism and as an antiphlogistic [1]. 3. Previously isolated constituents Flavonoids [2], sesquiterpenes [3], diterpenes [4], triterpenes [5] and saponins [6]. Fitoterapia 78 (2007) 69 – 71 www.elsevier.com/locate/fitote ⁎ Corresponding author. Tel./fax: +86 21 65642206. E-mail address: [email protected] (T. Zhou). 0367-326X/$ - see front matter © 2006 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2005.09.001
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Transcript of A new phenolic glycoside from the aerial parts of Solidago canadensis
Fitoterapia 78 (2007) 69–71www.elsevier.com/locate/fitote
Phytochemical communication
A new phenolic glycoside from the aerial partsof Solidago canadensis
JinSong Zhang, XinQin Zhang, GuangQing Lei, Bo Li,JiaKuan Chen, TongShui Zhou ⁎
Research Center of Natural Medicines, School of Life Sciences, Fudan University, Shanghai 200433, PR China
Received 15 August 2005; accepted 5 September 2005Available online 23 September 2006
Abstract
A new phenolic glycoside, 2′-hydroxy-4′,6′-di-O-β-D-glucopyranosyl-butyrrophenone (1), was isolated from the aerial parts ofSolidago canadensis. The structure was elucidated on the basis of spectroscopic methods.© 2006 Elsevier B.V. All rights reserved.
Keywords: Solidago canadensis; 2′-Hydroxy-4′,6′-di-O-β-D-glucopyranosyl-butyrrophenone
1. Plant
Solidago canadensis L. (Compositae), aerial parts were collected from Shanghai, PR China and identified by Prof.Bo Li (Fudan University, Shanghai). A voucher specimen was deposited in the Herbarium of Fudan University, PRChina.
2. Uses in traditional medicine
In European phytotherapy for the treatment of chronic nephritis, cystitis, urolithiasis, rhematism and as anantiphlogistic [1].
3. Previously isolated constituents
Flavonoids [2], sesquiterpenes [3], diterpenes [4], triterpenes [5] and saponins [6].
⁎ Corresponding author. Tel./fax: +86 21 65642206.E-mail address: [email protected] (T. Zhou).
0367-326X/$ - see front matter © 2006 Elsevier B.V. All rights reserved.doi:10.1016/j.fitote.2005.09.001
Fig. 1. Compound 1.
70 J. Zhang et al. / Fitoterapia 78 (2007) 69–71
4. New isolated constituents
2′-Hydroxy-4′,6′-di-O-β-D-glucopyranosyl-butyrrophenone (1) (20 mg from 20 kg of fresh material) (Fig. 1):colourless amorphous solid; UVmax (MeOH): 285 nm; HRESI-MSm/z: 543.4701 [M+Na]+ (calcd. for C22H32O14+Na,543.4709); 1H NMR (DMSO-d6, 500 MHz), 13C NMR (DMSO-d6, 125 MHz) and 2D NMR see Table 1.
Table 11H and 13C NMR data of compound 1 (J in Hz)
C δC δH COSY HMBC
1 206.52 46.1 3.02 (2H, t, J 7.35) 1.60 206.5, 17.93 17.9 1.60 (2H, m) 3.02, 0.91 46.1, 14.14 14.1 0.91 (3H, t, J 7.35) 1.60 17.91′ 107.72′ 163.0 13.09 (1H, s, OH)3′ 94.7 6.15 (1H, d, J 2.0) 6.33 163.0, 164.34′ 164.35′ 98.0 6.33 (1H, d, J 2.0) 6.15 164.3, 160.26′ 160.21″ 99.8 4.95 (1H, d, J 7.2) 3.33 164.32″ 73.5 3.33 (1H, m) 4.95, 3.22, 5.32
5.32 (1H, d, J 5.0, OH) 3.333″ 77.9 3.22 (1H, m) 3.33, 5.09
5.09 (1H, d, J 5.0, OH) 3.224″ 70.3 3.33 (1H, m) 3.12, 3.22, 5.17
5.17 (1H, d, J 5.0, OH) 3.335″ 77.0 3.12 (1H, m) 3.33, 3.45, 3.746″ 61.3 3.74 (1H, m, H-6″a) 3.45, 3.12, 4.72
3.45 (1H, m, H-6″b) 3.73, 3.12, 4.724.72 (1H, t, J 5.0, OH) 3.45, 3.74
1″′ 100.8 4.99 (1H, d, J 7.3) 3.33 160.22″′ 73.7 3.33(1H, m) 4.99, 3.22, 5.35
5.35 (1H, d, 5.0, OH) 3.333″′ 77.5 3.22 (1H, m) 3.33, 3.12, 5.06
5.06 (1H, d, J 5.0, OH) 3.224″′ 70.3 3.33 (1H, m) 3.22, 3.12, 5.12
5.12 (1H, d, J 5.0, OH) 3.335″′ 77.3 3.12 (1H, m) 3.33, 3.45, 3.74,6″′ 61.3 3.74 (1H, m, H-6″′a) 3.12, 3.45, 4.67
3.45 (1H, m, H-6″′b) 3.12, 3.74, 4.674.67 (1H, t, J 5.0, OH) 3.45, 3.74
All the signals were assigned by 1D and 2D NMR.
71J. Zhang et al. / Fitoterapia 78 (2007) 69–71
Acknowledgement
This research was supported by the Shanghai Commission of Science and Technology (Grant no. 014319316).
References
[1] Apáti P, Szentmihályi K, Kristó ST, Papp I, Vinkler P, Szoke E, et al. J Pharm Biomed Anal 2003;32:1045.[2] Batyuk VS, Kovaleva SN. Khim Prir Soed 1985;566.[3] Kasali AA, Ekundayo O, Paul C, Konig WA. Phytochemistry 2002;59:805.[4] Lu T, Menelaou MA, Vargas D, Fronczed FR, Fischer NH. Phytochemistry 1993;32:1483.[5] Chaturvedula VSP, Zhou BN, Gao ZJ, Thomas SJ, Hecht SM, Kingston DGI. Bioorg Med Chem 2004;12:6271.[6] Reznicek G, Jurenitsch J, Plasun M, Korhammer S, Kaslinger E, Hiller K, et al. Phytochemistry 1991;30:1629.
