Chinese Journal of Natural Medicines 2014, 12(2): 01480150
Chinese Journal of Natural Medicines
Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis CHEN Hui, HAO Zhi-You, WANG Xiao-Lan, ZHENG Xiao-Ke, FENG Wei-Sheng*, WANG Yan-Zhi School of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, China Available online 20 Feb. 2014
[ABSTRACT] AIM: To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring. METHODS: Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods. RESULTS: Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4O-E-D-glucopyranoside (2), (+)-medioresinol-4-O-E-D-glucopyranoside (3), pinoresinol-4, »-di-O-E-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8). CONCLUSION: Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis. [KEY WORDS] Selaginella sinensis; Chemical constituents; Sesquilignan glycoside
[CLC Number] R284.1
[Document code] A
[Article ID] 2095-6975(2014)02-0148-03 ydroamentoflavone (8) [10]. The present paper describes their isolation and structural elucidation.
Introduction Selaginella sinensis (Desv.) Spring (Selaginellaceae) is a species of the genus Selaginella P.Beauv., and is widely distributed in the north and northeast of China. It has been used as a traditional medicine for its antibacterial, antiinflammatory, and hemostatic activities, especially for the treatment of chronic tracheitis. In previous reports from this laboratory, some biflavones, sesquilignans, and secolignans were isolated from the whole plant of S. sinensis [1-3]. Further investigation has led to the isolation of a new dihydrobenzofuran sesquilignan glycoside, sinensioside A (1), together with seven known compounds, syringaresinol-4-O-E-D-glucopyranoside (2) [4], (+)-medioresinol-4-O-E-D-glucopyranoside (3) [5], pinoresinol-4, »-di-O-E-D-glucopyranoside (4) [6], quercetin (5) [7], eucomic acid (6) [8], shikimic acid (7) [9], and 2,3-dih[Received on] 18-Nov.-2012 [Research funding] This project was supported by the National Key Technologies R D Program of China (No. 2013ZX09102-022) and DoctoralScience Foundation of Henan University of Traditional Chinese Medicine (No. BSJJ2012-02) [ Corresponding author] FENG Wei-Sheng: Prof., Tel/Fax:86-3716568011, E-mail: [email protected] These authors have no conflict of interest to declare. Copyright © 2014, China Pharmaceutical University. Published by Elsevier B.V. All rights reserved
Results and Discussion Compound 1 was obtained as a white powder with the molecular formula C 35 H 42 O 13 as deduced by its positive HR-ESI-MS at m/z 693.351 7 [M + Na]+, requiring fifteen degrees of unsaturation. The UV spectrum showed an absorption maximum at 207 nm, indicating the presence of an aromatic ring. The IR spectrum showed absorption bands at 3 361, 1 608, and 1 508 cm1, revealing the presence of hydroxyl and aromatic ring groups. The 1H NMR spectrum displayed signals at G 7.29 (2H, d, J = 8.5 Hz) and G 7.07 (2H, d, J ¼' ½ #»» ^= #^^ #_ broad singlets at G 6.90 (2H) and G 6.71 (2H) for two tetrasubstituted aromatic rings, as well as two aromatic methoxy groups at G 3.84 (6H, s). The remaining 1H NMR signals indicated an n-propanol and two OCHCHCH 2 O spin systems, which were further confirmed by the 1H-1H COSY experiments. Also in the 1H NMR spectrum, the proton signals of a sugar moiety at G 3.374.89 were observed. The 13C NMR and DEPT spectra showed the presence of 35 carbons, of which 18 aromatic carbon signals at G ???'?' ^ `_ `#½# #^ oxygenated methine carbons at G 89.0 and G 88.7, three methyleneoxy carbons at G 65.0, 64.9, and G 62.2, two methine carbons at G 55.5 and G 55.4, and two methylene car-
– 148 –
CHEN Hui, et al. / Chin J Nat Med, 2014, 12(2): 148150
bons at G 35.8 and 32.9. Additionally, six carbon signals were assigned to a glucopyranosyl moiety (G 102.2, 78.1, 77.9, 74.9, 71.3, and 62.5). The 1H and 13C NMR data of the aglycone were similar to those of sinensiol A, which was reported as the first dihydrobenzofuran sesquilignan from S. sinensis [2]. Acid hydrolysis of 1 gave sinensiol A as the aglycone and glucose. The large coupling constant (J = 7.7 Hz) of the anomeric proton at G 4.89 revealed that the glucose was in the E-configuration, and the D-configuration of the moiety was established by hydrolysis and GC analysis. The glycosyl unit of 1 was shown to be attached to C-4 of the aglycone by the HMBC correlation between H-1»»»}G 4.89) of the glucopyranosyl unit and C-¾ }G 158.8) of the aglycone. Thus, the structure of 1 was determined as sinensiol A-¾-O-E-D-glucopyranoside (Fig. 1), and named sinensioside A. The full assignments of all the signals of 1 were completed by means of 1H NMR, 13C NMR, 1H-1H COSY, HSQC, and HMBC experiments (Fig. 2). The 7R and 8S and ¾R #_ ¾S configurations of the aglycone moiety were determined by analysis of the CD spectrum in a previous report [2]. To the best of our knowledge, dihydrobenzofuran sesquilignans have only been found in the genera Herpetospermum [12], Vitex [13], and Cestrum [14], and this is the second report from the family Selaginella.
recorded on a Bruker APEX II spectrometer. GC data were recorded on an Agilent 7890A instrument. Column chromatography was performed on Diaion HP-20 (Mitsubishi Chemical Corp., Tokyo, Japan), silica gel (160200 mesh, Qingdao Marine Chemical Industry, Qingdao, China), Sephadex LH-20 (Pharmacia Biotech AB, Uppsala, Sweden). TLC was conducted on self-made silica gel G (Qingdao Marine Chemical Industry, Qingdao, China) plates. All solvents used were of pure analytical grade (Beijing Chemical Factory, Beijing, China). Plant material The fresh plants of S. sinensis were collected from Xixia County, Henan province, China, in May, 2006, and identified by Prof. DONG Cheng-Ming of Henan University of Traditional Chinese Medicine. A voucher specimen (JB20060 510) is deposited in this laboratory. Extraction and isolation The fresh whole plants of S. sinensis (7.5 kg) were extracted with 70% aq. Me 2 CO twice at room temperature (each time for 3 h) to afford a residue (800 g), which was suspended in water, and extracted with ethyl ether, EtOAc, and n-BuOH, successively. The EtOAc layer (65 g) was chromatographed on silica gel, eluting with a gradient system of CHCl 3 -MeOH (70 : ? : 1) to afford fractions A-D. Compound 5 (23 mg) was obtained by column chromatography on silica gel (PEEtOAc 5 : 1) from fraction A. Compounds 2 (22 mg) and 8 (39 mg) were obtained by column chromatography on silica gel (CHCl 3 MeOH, 7 : 1) and Sephadex Table 1 1H (400 MHz) and 13C NMR (100 MHz) data for compound 1 in CD 3 OD (J in Hz).
Fig. 1
Structure of compound 1
No.
´H
´C 137.1
?»
6.90 (br s)
111.8
»
3
145.5
»
145.2
4
149.2
»
147.4
1 2
5
Fig. 2
The key HMBC ( ) and 1H-1H COSY ( correlations of 1
)
No.
´H
´C
6.71 (br s)
114.1
136.9
130.0
»
6
6.90 (br s)
115.6
»
6.71 (br s)
129.7 117.9
7
5.52 (d, J = 5.8)
88.7
»
2.63 (t, J = 7.3)
32.9
8
3.43 (m)
55.4
»
1.82 (m)
35.8
9
3.83 (m), 3.69 (m)
64.9
~»
3.57 (m)
62.2
Experimental
?»»
133.9
?»»»
4.89 (d, J = 7.7)
102.2
General experimental procedures Optical rotations were obtained using a Perkin-Elmer 341 polarimeter. UV spectra were measured with a Shimadzu UV-VIS 2201 spectrophotometer. IR spectra were measured with a Shimadzu FTIR-8201 PC spectrometer. The 1H and 13C NMR spectra were obtained on a Bruker DPX-400 spectrometer (400 MHz for 1H NMR and 100 MHz for 13C NMR) with TMS as internal reference. HR-ESI-MS were
»»
7.29 (d, J = 8.5)
127.9
»»»
3.47 (m)
74.9
»»
7.07 (d, J = 8.5)
117.8
»»»
3.42 (m)
77.9
158.8
4»»»
3.38 (m)
71.3
– 149 –
»» »»
7.07 (d, J = 8.5)
117.8
»»»
3.36 (m)
78.1
»»
7.29 (d, J = 8.5)
127.9
»»»
3.65 (m), 3.88 (m)
62.5
»»
5.57 (d, J = 5.8)
89.0 3-OMe
3.84 (s)
56.7
»»
3.43 (m)
55.5 »-OMe
3.84 (s)
56.7
CHEN Hui, et al. / Chin J Nat Med, 2014, 12(2): 148150 ~»»
3.69 (m)
[3]
65.0
LH-20 (MeOH) from fraction B. Compound 7 was obtained by column chromatography on silica gel (EtOAcEtOHH 2 O, 30 : 2 : 1) from fraction D. The n-BuOH layer (120 g) was chromatographed on Diaion HP-20, eluting with a gradient system of MeOH-H 2 O (10). The 10 MeOH fraction was then successfully subjected to Sephadex LH-20 (MeOH) to yield 6 (29 mg). The 30 MeOH fraction was chromatographed on silica gel (EtOAcEtOHH 2 O, 15 : 2 : 1) to afford 1 (13 mg), 3 (8 mg) and 4 (18 mg). Acid hydrolysis of compound 1 Compound 1 (5 mg) was dissolved in 1M aq. HCl (5 mL) and heated at 90 qC for 2 h under constant stirring. The reaction mixture was diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc layer was evaporated under pressure to give the aglycone, which was subjected to co-TLC with sinensiol A. The aqueous layer was evaporated to give a sugar residue. The absolute configuration of the glucose was determined according to a reported procedure [11]. Identification Compound 1 White amorphous powder. UV (MeOH) max (log H): 207 (4.35). IR (KBr)Q max : 3 361, 2 923, 1 608, 1 508, 1 213, 1 020 cm1. 1H and 13C NMR data, see Table 1; HR-ESI-MS m/z 693.351 7 [M + Na]+ (C 35 H 42 O 13, Calcd. 693.352 3).
[4]
[5]
[6] [7]
[8]
[9]
[10]
[11]
[12]
[13]
References [1]
[2]
Feng WS, Chen H, Zheng XK. Chemical constituents of Selaginella sinensis [J]. Chin Tradit Herb Drugs, 2008, 39 (5): 654-656. Wang YZ, Chen H, Zheng XK, Feng WS. A new sesquilignan from Selaginella sinensis (Desv.) Spring [J]. Chin Chem Lett, 2007, 18: 1224-1226.
[14]
Feng WS, Chen H, Zheng XK, et al. Two new secolignans from Selaginella sinensis (Desv.) Spring [J]. J Asian Nat Prod Res, 2009, 11 (7): 658-662. Gu HF, Chen RY, Sun YH, et al. Studies on chemical constituents in herbs of Dracocephalum moldavica Ċ [J]. China J Chin Mater Med, 2004, 30 (9): 677-679. Zhou LX, Ding Y. Studies on the constituents of Ligustrum obtusifolium Sieb. et Zucc [J]. China J Chin Mater Med, 2000, 25 (9): 541-543. Li YZ, Zhang WD, Gu ZB, et al. Lignans from Patrinia scabra [J]. Chin Tradit Herb Drugs, 2005, 36 (3): 338-340. Zhang X, Ji YQ, Li P, et al. Study on chemical constituents of Pinus massoniana leaf [J]. Nat Prod Res Dev, 2006, 18: 621-623. Luo C, Zhang WN, Yang ML. Chemical constituents of Opuntia milpa Alta Haw [J]. Nat Prod Res Dev, 2011, 23: 1038-1040. Bi YF, Zheng XK, Liu HM, et al. Studies on the chemical constituents from pine needles of Pinus massoniana Lamb [J]. Acta Pharm Sin, 2001, 36 (11): 832-835. Liu HQ, Lin RC, Ma SC, et al. Studies on chemical constituents of Selaginella stauntoniana (II) [J]. Chin Tradit Herb Drugs, 2003, 34 (4): 298-300. Chen H, Bai J, Fang ZF, et al. Indole alkaloids and quassinoids from the stems of Brucea mollis [J]. J Nat Prod, 2011, 74: 2438-2445. Kaouadji M, Favre-Bonvin J, Mariotte AM. Herpetriol and herpetetrol, new lignoids isolated from Herpetospermum caudigerum Wall [J]. Z Naturfosch, C: Biosci, 1979, 34C (12): 1129-1132. Gu Q, Zhang XM, Zhou J, et al. One new dihydrobenzofuran lignan from Vitex trifolia [J]. J Asian Nat Prod Res, 2008, 10 (6): 499-502. !»`^ ! ¥ # #, et al. Isolation and characterization of new lignans from the leaves of Cestrum parqui [J]. Nat Prod Res, 2006, 20 (3): 293-298.
Cite this article as: CHEN Hui, HAO Zhi-You, WANG Xiao-Lan, ZHENG Xiao-Ke, FENG Wei-Sheng, WANG Yan-Zhi. Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis [J]. Chinese Journal of Natural Medicines, 2014, 12(2): 148-150
– 150 –
Chinese Journal of Natural Medicines
Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis CHEN Hui, HAO Zhi-You, WANG Xiao-Lan, ZHENG Xiao-Ke, FENG Wei-Sheng*, WANG Yan-Zhi School of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, China Available online 20 Feb. 2014
[ABSTRACT] AIM: To investigate the chemical constituents of Selaginella sinensis (Desv.) Spring. METHODS: Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods. RESULTS: Eight compounds were obtained and their structures were identified as sinensioside A (1), syringaresinol-4O-E-D-glucopyranoside (2), (+)-medioresinol-4-O-E-D-glucopyranoside (3), pinoresinol-4, »-di-O-E-D-glucopyranoside (4), quercetin (5), eucomic acid (6), shikimic acid (7), and 2, 3-dihydroamentoflavone (8). CONCLUSION: Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis. [KEY WORDS] Selaginella sinensis; Chemical constituents; Sesquilignan glycoside
[CLC Number] R284.1
[Document code] A
[Article ID] 2095-6975(2014)02-0148-03 ydroamentoflavone (8) [10]. The present paper describes their isolation and structural elucidation.
Introduction Selaginella sinensis (Desv.) Spring (Selaginellaceae) is a species of the genus Selaginella P.Beauv., and is widely distributed in the north and northeast of China. It has been used as a traditional medicine for its antibacterial, antiinflammatory, and hemostatic activities, especially for the treatment of chronic tracheitis. In previous reports from this laboratory, some biflavones, sesquilignans, and secolignans were isolated from the whole plant of S. sinensis [1-3]. Further investigation has led to the isolation of a new dihydrobenzofuran sesquilignan glycoside, sinensioside A (1), together with seven known compounds, syringaresinol-4-O-E-D-glucopyranoside (2) [4], (+)-medioresinol-4-O-E-D-glucopyranoside (3) [5], pinoresinol-4, »-di-O-E-D-glucopyranoside (4) [6], quercetin (5) [7], eucomic acid (6) [8], shikimic acid (7) [9], and 2,3-dih[Received on] 18-Nov.-2012 [Research funding] This project was supported by the National Key Technologies R D Program of China (No. 2013ZX09102-022) and DoctoralScience Foundation of Henan University of Traditional Chinese Medicine (No. BSJJ2012-02) [ Corresponding author] FENG Wei-Sheng: Prof., Tel/Fax:86-3716568011, E-mail: [email protected] These authors have no conflict of interest to declare. Copyright © 2014, China Pharmaceutical University. Published by Elsevier B.V. All rights reserved
Results and Discussion Compound 1 was obtained as a white powder with the molecular formula C 35 H 42 O 13 as deduced by its positive HR-ESI-MS at m/z 693.351 7 [M + Na]+, requiring fifteen degrees of unsaturation. The UV spectrum showed an absorption maximum at 207 nm, indicating the presence of an aromatic ring. The IR spectrum showed absorption bands at 3 361, 1 608, and 1 508 cm1, revealing the presence of hydroxyl and aromatic ring groups. The 1H NMR spectrum displayed signals at G 7.29 (2H, d, J = 8.5 Hz) and G 7.07 (2H, d, J ¼' ½ #»» ^= #^^ #_ broad singlets at G 6.90 (2H) and G 6.71 (2H) for two tetrasubstituted aromatic rings, as well as two aromatic methoxy groups at G 3.84 (6H, s). The remaining 1H NMR signals indicated an n-propanol and two OCHCHCH 2 O spin systems, which were further confirmed by the 1H-1H COSY experiments. Also in the 1H NMR spectrum, the proton signals of a sugar moiety at G 3.374.89 were observed. The 13C NMR and DEPT spectra showed the presence of 35 carbons, of which 18 aromatic carbon signals at G ???'?' ^ `_ `#½# #^ oxygenated methine carbons at G 89.0 and G 88.7, three methyleneoxy carbons at G 65.0, 64.9, and G 62.2, two methine carbons at G 55.5 and G 55.4, and two methylene car-
– 148 –
CHEN Hui, et al. / Chin J Nat Med, 2014, 12(2): 148150
bons at G 35.8 and 32.9. Additionally, six carbon signals were assigned to a glucopyranosyl moiety (G 102.2, 78.1, 77.9, 74.9, 71.3, and 62.5). The 1H and 13C NMR data of the aglycone were similar to those of sinensiol A, which was reported as the first dihydrobenzofuran sesquilignan from S. sinensis [2]. Acid hydrolysis of 1 gave sinensiol A as the aglycone and glucose. The large coupling constant (J = 7.7 Hz) of the anomeric proton at G 4.89 revealed that the glucose was in the E-configuration, and the D-configuration of the moiety was established by hydrolysis and GC analysis. The glycosyl unit of 1 was shown to be attached to C-4 of the aglycone by the HMBC correlation between H-1»»»}G 4.89) of the glucopyranosyl unit and C-¾ }G 158.8) of the aglycone. Thus, the structure of 1 was determined as sinensiol A-¾-O-E-D-glucopyranoside (Fig. 1), and named sinensioside A. The full assignments of all the signals of 1 were completed by means of 1H NMR, 13C NMR, 1H-1H COSY, HSQC, and HMBC experiments (Fig. 2). The 7R and 8S and ¾R #_ ¾S configurations of the aglycone moiety were determined by analysis of the CD spectrum in a previous report [2]. To the best of our knowledge, dihydrobenzofuran sesquilignans have only been found in the genera Herpetospermum [12], Vitex [13], and Cestrum [14], and this is the second report from the family Selaginella.
recorded on a Bruker APEX II spectrometer. GC data were recorded on an Agilent 7890A instrument. Column chromatography was performed on Diaion HP-20 (Mitsubishi Chemical Corp., Tokyo, Japan), silica gel (160200 mesh, Qingdao Marine Chemical Industry, Qingdao, China), Sephadex LH-20 (Pharmacia Biotech AB, Uppsala, Sweden). TLC was conducted on self-made silica gel G (Qingdao Marine Chemical Industry, Qingdao, China) plates. All solvents used were of pure analytical grade (Beijing Chemical Factory, Beijing, China). Plant material The fresh plants of S. sinensis were collected from Xixia County, Henan province, China, in May, 2006, and identified by Prof. DONG Cheng-Ming of Henan University of Traditional Chinese Medicine. A voucher specimen (JB20060 510) is deposited in this laboratory. Extraction and isolation The fresh whole plants of S. sinensis (7.5 kg) were extracted with 70% aq. Me 2 CO twice at room temperature (each time for 3 h) to afford a residue (800 g), which was suspended in water, and extracted with ethyl ether, EtOAc, and n-BuOH, successively. The EtOAc layer (65 g) was chromatographed on silica gel, eluting with a gradient system of CHCl 3 -MeOH (70 : ? : 1) to afford fractions A-D. Compound 5 (23 mg) was obtained by column chromatography on silica gel (PEEtOAc 5 : 1) from fraction A. Compounds 2 (22 mg) and 8 (39 mg) were obtained by column chromatography on silica gel (CHCl 3 MeOH, 7 : 1) and Sephadex Table 1 1H (400 MHz) and 13C NMR (100 MHz) data for compound 1 in CD 3 OD (J in Hz).
Fig. 1
Structure of compound 1
No.
´H
´C 137.1
?»
6.90 (br s)
111.8
»
3
145.5
»
145.2
4
149.2
»
147.4
1 2
5
Fig. 2
The key HMBC ( ) and 1H-1H COSY ( correlations of 1
)
No.
´H
´C
6.71 (br s)
114.1
136.9
130.0
»
6
6.90 (br s)
115.6
»
6.71 (br s)
129.7 117.9
7
5.52 (d, J = 5.8)
88.7
»
2.63 (t, J = 7.3)
32.9
8
3.43 (m)
55.4
»
1.82 (m)
35.8
9
3.83 (m), 3.69 (m)
64.9
~»
3.57 (m)
62.2
Experimental
?»»
133.9
?»»»
4.89 (d, J = 7.7)
102.2
General experimental procedures Optical rotations were obtained using a Perkin-Elmer 341 polarimeter. UV spectra were measured with a Shimadzu UV-VIS 2201 spectrophotometer. IR spectra were measured with a Shimadzu FTIR-8201 PC spectrometer. The 1H and 13C NMR spectra were obtained on a Bruker DPX-400 spectrometer (400 MHz for 1H NMR and 100 MHz for 13C NMR) with TMS as internal reference. HR-ESI-MS were
»»
7.29 (d, J = 8.5)
127.9
»»»
3.47 (m)
74.9
»»
7.07 (d, J = 8.5)
117.8
»»»
3.42 (m)
77.9
158.8
4»»»
3.38 (m)
71.3
– 149 –
»» »»
7.07 (d, J = 8.5)
117.8
»»»
3.36 (m)
78.1
»»
7.29 (d, J = 8.5)
127.9
»»»
3.65 (m), 3.88 (m)
62.5
»»
5.57 (d, J = 5.8)
89.0 3-OMe
3.84 (s)
56.7
»»
3.43 (m)
55.5 »-OMe
3.84 (s)
56.7
CHEN Hui, et al. / Chin J Nat Med, 2014, 12(2): 148150 ~»»
3.69 (m)
[3]
65.0
LH-20 (MeOH) from fraction B. Compound 7 was obtained by column chromatography on silica gel (EtOAcEtOHH 2 O, 30 : 2 : 1) from fraction D. The n-BuOH layer (120 g) was chromatographed on Diaion HP-20, eluting with a gradient system of MeOH-H 2 O (10). The 10 MeOH fraction was then successfully subjected to Sephadex LH-20 (MeOH) to yield 6 (29 mg). The 30 MeOH fraction was chromatographed on silica gel (EtOAcEtOHH 2 O, 15 : 2 : 1) to afford 1 (13 mg), 3 (8 mg) and 4 (18 mg). Acid hydrolysis of compound 1 Compound 1 (5 mg) was dissolved in 1M aq. HCl (5 mL) and heated at 90 qC for 2 h under constant stirring. The reaction mixture was diluted with water and extracted with EtOAc (3 × 5 mL). The EtOAc layer was evaporated under pressure to give the aglycone, which was subjected to co-TLC with sinensiol A. The aqueous layer was evaporated to give a sugar residue. The absolute configuration of the glucose was determined according to a reported procedure [11]. Identification Compound 1 White amorphous powder. UV (MeOH) max (log H): 207 (4.35). IR (KBr)Q max : 3 361, 2 923, 1 608, 1 508, 1 213, 1 020 cm1. 1H and 13C NMR data, see Table 1; HR-ESI-MS m/z 693.351 7 [M + Na]+ (C 35 H 42 O 13, Calcd. 693.352 3).
[4]
[5]
[6] [7]
[8]
[9]
[10]
[11]
[12]
[13]
References [1]
[2]
Feng WS, Chen H, Zheng XK. Chemical constituents of Selaginella sinensis [J]. Chin Tradit Herb Drugs, 2008, 39 (5): 654-656. Wang YZ, Chen H, Zheng XK, Feng WS. A new sesquilignan from Selaginella sinensis (Desv.) Spring [J]. Chin Chem Lett, 2007, 18: 1224-1226.
[14]
Feng WS, Chen H, Zheng XK, et al. Two new secolignans from Selaginella sinensis (Desv.) Spring [J]. J Asian Nat Prod Res, 2009, 11 (7): 658-662. Gu HF, Chen RY, Sun YH, et al. Studies on chemical constituents in herbs of Dracocephalum moldavica Ċ [J]. China J Chin Mater Med, 2004, 30 (9): 677-679. Zhou LX, Ding Y. Studies on the constituents of Ligustrum obtusifolium Sieb. et Zucc [J]. China J Chin Mater Med, 2000, 25 (9): 541-543. Li YZ, Zhang WD, Gu ZB, et al. Lignans from Patrinia scabra [J]. Chin Tradit Herb Drugs, 2005, 36 (3): 338-340. Zhang X, Ji YQ, Li P, et al. Study on chemical constituents of Pinus massoniana leaf [J]. Nat Prod Res Dev, 2006, 18: 621-623. Luo C, Zhang WN, Yang ML. Chemical constituents of Opuntia milpa Alta Haw [J]. Nat Prod Res Dev, 2011, 23: 1038-1040. Bi YF, Zheng XK, Liu HM, et al. Studies on the chemical constituents from pine needles of Pinus massoniana Lamb [J]. Acta Pharm Sin, 2001, 36 (11): 832-835. Liu HQ, Lin RC, Ma SC, et al. Studies on chemical constituents of Selaginella stauntoniana (II) [J]. Chin Tradit Herb Drugs, 2003, 34 (4): 298-300. Chen H, Bai J, Fang ZF, et al. Indole alkaloids and quassinoids from the stems of Brucea mollis [J]. J Nat Prod, 2011, 74: 2438-2445. Kaouadji M, Favre-Bonvin J, Mariotte AM. Herpetriol and herpetetrol, new lignoids isolated from Herpetospermum caudigerum Wall [J]. Z Naturfosch, C: Biosci, 1979, 34C (12): 1129-1132. Gu Q, Zhang XM, Zhou J, et al. One new dihydrobenzofuran lignan from Vitex trifolia [J]. J Asian Nat Prod Res, 2008, 10 (6): 499-502. !»`^ ! ¥ # #, et al. Isolation and characterization of new lignans from the leaves of Cestrum parqui [J]. Nat Prod Res, 2006, 20 (3): 293-298.
Cite this article as: CHEN Hui, HAO Zhi-You, WANG Xiao-Lan, ZHENG Xiao-Ke, FENG Wei-Sheng, WANG Yan-Zhi. Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis [J]. Chinese Journal of Natural Medicines, 2014, 12(2): 148-150
– 150 –
