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A new phenolic glycoside from the roots of Lygodium japonicum
Fitoterapia 78 (2007) 600 – 601 www.elsevier.com/locate/fitote
Phytochemical communication
A new phenolic glycoside from the roots of Lygodium japonicum Wencai Ye a,b,⁎, Chunlin Fan a , Leihong Zhang a , Zhiqi Yin a , Shouxun Zhao a b
a Department of Phytochemistry, China Pharmaceutical University, Nanjing, 210009, PR China Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, PR China
Received 25 June 2005; accepted 4 April 2007 Available online 10 May 2007
Abstract A new phenolic glycoside, 3,4-dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside (1), was isolated from the roots of Lygodium japonicum. The structure was elucidated on the basis of spectroscopic methods. © 2007 Elsevier B.V. All rights reserved. Keywords: Lygodium japonicum; 3,4-Dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside; Spectroscopic methods
1. Plant Lygodium japonicum (Thunb.) Sw. (Lygodiaceae), roots collected in Wuhu City, Anhui province of China, in November 2003 were identified by Prof. M. J. Qin (China Pharmaceutical University). A voucher specimen (no. 20031112) was deposited in the Herbarium of China Pharmaceutical University, Nanjing, PR China. 2. Uses in traditional medicine The roots of L. japonicum (Chinese name ‘Hai-Jin-Sha’) are used in traditional Chinese medicine for the treatment of pneumonia, acute gastroenteritis, dysentery, and urinary tract infection [1]. 3. Previously isolated constituents Some plant growth regulators such as gibberellin A9 methyl ester, gibberellin A73 methyl ester, and phenolic acids were isolated from the spores of L. japonicum [2–7]. 4. New-isolated constituents 3,4-Dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside (1, Fig. 1) (120 mg from 5.8 kg of plant material), white needles (MeOH), mp 205–207 °C; [α]27D − 87.2° (c 0.065, MeOH); UV max (MeOH): 213 nm; IR ⁎ Corresponding author. Department of Phytochemistry, China Pharmaceutical University, Nanjing, 210009, PR China. Tel.: +86 20 85228369; fax: +86 20 85221559. E-mail address: [email protected] (W. Ye). 0367-326X/$ - see front matter © 2007 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2007.04.003
W. Ye et al. / Fitoterapia 78 (2007) 600–601
601
Fig. 1. Compound 1.
(KBr): 3291, 1705, 1601, 1455, 1303, 1240, 1105, 986, 765 cm−1; ESI-MS m/z: 331 [M + 1]+; HR-ESI-MS: m/z 331.1021. Calculated for C14H18O9 + H+: 331.1023; 1H NMR (500 MHz, CD3OD), 13C NMR (125 MHz, CD3OD) and 2D NMR (Table 1). Acknowledgments The authors thank Prof. Minjian Qin for identification of plant material. We are also grateful to Prof. Wenbin Shen for providing NMR date (Analytical Center, China Pharmaceutical University). References [1] New Medical College of Jiangsu. Dictionary of Chinese Materia Medica, vol. 2. Shanghai: Shanghai Science and Technology press; 1977. p. 1949. [2] Yamane N, Takahashi N, Takeno K, Furuya M. Planta Med 1979;147:251. [3] Yamane N, Satoh Y, Nohara K, Nakayama M, Murofushi N, Takahashi N, et al. Tetrahedron Lett 1988;29:3959. [4] Armin R, Gemmrich K. Phytochemistry 1977;16:1044. [5] Matsuda H, Yamazaki M, Naruo S, Asanuma Y, Kubo M. Biol Pharm Bull 2002;25:622. [6] Yamane H, Sato Y, Takahashi N, Takeno K, Furuya M. Agric Biol Chem 1980;44:1697. [7] Bernard V. Bull Soc Bot Fr 1976;123:219.
Table 1 H and 13C NMR data for 1 (500 and 125 MHz, CD3OD, J in Hz) a
1
δH 1 2 3 4 5 6 7 1′ 2′ 3′ 4′ 5′ 6′
7.51 (d, 2.0)
7.19 (d, 8.3) 7.49 (dd, 2.0, 8.3)
OMe a
4.88 (d, 7.6) 3.53 (dd, 7.6, 9.4) 3.60 (dd, 8.8, 9.4) 3.22 (dd, 8.8, 9.7) 3.45 (ddd, 2.1, 4.7, 9.7) 3.72 (dd, 4.7, 12.1) 3.86 (dd, 2.1, 12.1) 3.58 (s)
δC 126.8 123.3 147.9 150.6 117.3 118.4 169.6 103.1 74.9 77.4 80.6 77.5 62.1
All the signals were established by interpretation of 1D and 2D.
60.9
HMBC
NOESY
C-1, C-3, C-7
C-4, C-6 C-1, C-5, C-7
H-1′, H-5′, H-6 H-5
C-4, C-5′ C-1′, C-3′ C-2′, C-4′ C-5′, C-6′, OMe C-4′, C-6′, C-1′ C-4′, C-5′
H-3′, H-5′, H-5 H-4′ H-1′, OMe H-6′, OMe H-1′, H-6′, OMe H-4′, H-5′
C-4′
H-3′, H-4′, H-5′
Phytochemical communication
A new phenolic glycoside from the roots of Lygodium japonicum Wencai Ye a,b,⁎, Chunlin Fan a , Leihong Zhang a , Zhiqi Yin a , Shouxun Zhao a b
a Department of Phytochemistry, China Pharmaceutical University, Nanjing, 210009, PR China Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, PR China
Received 25 June 2005; accepted 4 April 2007 Available online 10 May 2007
Abstract A new phenolic glycoside, 3,4-dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside (1), was isolated from the roots of Lygodium japonicum. The structure was elucidated on the basis of spectroscopic methods. © 2007 Elsevier B.V. All rights reserved. Keywords: Lygodium japonicum; 3,4-Dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside; Spectroscopic methods
1. Plant Lygodium japonicum (Thunb.) Sw. (Lygodiaceae), roots collected in Wuhu City, Anhui province of China, in November 2003 were identified by Prof. M. J. Qin (China Pharmaceutical University). A voucher specimen (no. 20031112) was deposited in the Herbarium of China Pharmaceutical University, Nanjing, PR China. 2. Uses in traditional medicine The roots of L. japonicum (Chinese name ‘Hai-Jin-Sha’) are used in traditional Chinese medicine for the treatment of pneumonia, acute gastroenteritis, dysentery, and urinary tract infection [1]. 3. Previously isolated constituents Some plant growth regulators such as gibberellin A9 methyl ester, gibberellin A73 methyl ester, and phenolic acids were isolated from the spores of L. japonicum [2–7]. 4. New-isolated constituents 3,4-Dihydroxybenzoic acid 4-O-(4′-O-methyl)-β-D-glucopyranoside (1, Fig. 1) (120 mg from 5.8 kg of plant material), white needles (MeOH), mp 205–207 °C; [α]27D − 87.2° (c 0.065, MeOH); UV max (MeOH): 213 nm; IR ⁎ Corresponding author. Department of Phytochemistry, China Pharmaceutical University, Nanjing, 210009, PR China. Tel.: +86 20 85228369; fax: +86 20 85221559. E-mail address: [email protected] (W. Ye). 0367-326X/$ - see front matter © 2007 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2007.04.003
W. Ye et al. / Fitoterapia 78 (2007) 600–601
601
Fig. 1. Compound 1.
(KBr): 3291, 1705, 1601, 1455, 1303, 1240, 1105, 986, 765 cm−1; ESI-MS m/z: 331 [M + 1]+; HR-ESI-MS: m/z 331.1021. Calculated for C14H18O9 + H+: 331.1023; 1H NMR (500 MHz, CD3OD), 13C NMR (125 MHz, CD3OD) and 2D NMR (Table 1). Acknowledgments The authors thank Prof. Minjian Qin for identification of plant material. We are also grateful to Prof. Wenbin Shen for providing NMR date (Analytical Center, China Pharmaceutical University). References [1] New Medical College of Jiangsu. Dictionary of Chinese Materia Medica, vol. 2. Shanghai: Shanghai Science and Technology press; 1977. p. 1949. [2] Yamane N, Takahashi N, Takeno K, Furuya M. Planta Med 1979;147:251. [3] Yamane N, Satoh Y, Nohara K, Nakayama M, Murofushi N, Takahashi N, et al. Tetrahedron Lett 1988;29:3959. [4] Armin R, Gemmrich K. Phytochemistry 1977;16:1044. [5] Matsuda H, Yamazaki M, Naruo S, Asanuma Y, Kubo M. Biol Pharm Bull 2002;25:622. [6] Yamane H, Sato Y, Takahashi N, Takeno K, Furuya M. Agric Biol Chem 1980;44:1697. [7] Bernard V. Bull Soc Bot Fr 1976;123:219.
Table 1 H and 13C NMR data for 1 (500 and 125 MHz, CD3OD, J in Hz) a
1
δH 1 2 3 4 5 6 7 1′ 2′ 3′ 4′ 5′ 6′
7.51 (d, 2.0)
7.19 (d, 8.3) 7.49 (dd, 2.0, 8.3)
OMe a
4.88 (d, 7.6) 3.53 (dd, 7.6, 9.4) 3.60 (dd, 8.8, 9.4) 3.22 (dd, 8.8, 9.7) 3.45 (ddd, 2.1, 4.7, 9.7) 3.72 (dd, 4.7, 12.1) 3.86 (dd, 2.1, 12.1) 3.58 (s)
δC 126.8 123.3 147.9 150.6 117.3 118.4 169.6 103.1 74.9 77.4 80.6 77.5 62.1
All the signals were established by interpretation of 1D and 2D.
60.9
HMBC
NOESY
C-1, C-3, C-7
C-4, C-6 C-1, C-5, C-7
H-1′, H-5′, H-6 H-5
C-4, C-5′ C-1′, C-3′ C-2′, C-4′ C-5′, C-6′, OMe C-4′, C-6′, C-1′ C-4′, C-5′
H-3′, H-5′, H-5 H-4′ H-1′, OMe H-6′, OMe H-1′, H-6′, OMe H-4′, H-5′
C-4′
H-3′, H-4′, H-5′