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Chemical constituents from bulbs of Fritillaria pallidiflora Schrenk
Biochemical Systematics and Ecology 57 (2014) 198e202
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Chemical constituents from bulbs of Fritillaria pallidiflora Schrenk Wen-Long Xu, Man Liu, Dong-Lin Chen, Jian-Zhong Wang* West China School of Pharmacy, Sichuan University, 17 South Renmin Road, Chengdu 610041, PR China
a r t i c l e i n f o
a b s t r a c t
Article history: Received 21 June 2014 Accepted 23 August 2014 Available online
A new steroidal alkaloid, 5a, 14a, 17b-cevanin-6-oxo-3b, 20b, 24b-triol(1), together with ten known compounds (2e11) were isolated from the bulbs of Fritillaria pallidiflora Schrenk. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from this plant for the first time. © 2014 Elsevier Ltd. All rights reserved.
Keywords: Fritillaria pallidiflora Steroidal alkaloid Sphingolipids Flavonoids Yibeinine
1. Subject and source Fritillaria is an important traditional Chinese medicine (Xu et al., 1990a,b). Fritillaria pallidiflora Schrenk (Liliaceae) is mainly distributed in Xinjiang province of China. The bulbs of F. pallidiflora Schrenk were identified by Prof. Hong Zhang, Institute for Food and Drugs of Sichuan Province, from material collected in Changji, Xinjiang province of China, in July 2010. A voucher specimen (2010-07-10) has been deposited in the herbarium of the Department of Pharmacognosy, West China School of Pharmacy, Sichuan University, Chengdu, China. 2. Previous work Previous phytochemical investigations on F. pallidiflora led to the isolation of steroidal alkaloids (Xu et al., 1993; Jia et al., 1999; Li et al., 2002), steroidal saponins (Shen et al., 2011), a non steroidal alkaloid (Zeng and Li, 2001), phenolic glucosides, nucleoside compounds and amino acids (Shen et al., 2012). However, there are no reports in the isolation of sphingolipids and flavonoids from F. pallidiflora. 3. Present study The air-dried bulbs (150 kg) of F. pallidiflora Schrenk were extracted exhaustively with 80% EtOH (200 L 2, 3 h each time), and the solvent was combined and evaporated under reduced pressure. The residue was partitioned in H2O and extracted with 10 L Cyclohexane 2, 10 L Cyclohexane/EtOAc (1:1) 2, and 10 L EtOAc 2 to provide the extracts. The Cyclohexane
* Corresponding author. Tel.: þ86 28 85503770. E-mail address: [email protected] (J.-Z. Wang). http://dx.doi.org/10.1016/j.bse.2014.08.021 0305-1978/© 2014 Elsevier Ltd. All rights reserved.
W.-L. Xu et al. / Biochemical Systematics and Ecology 57 (2014) 198e202
199
extract (698 g) was subjected to column chromatography (CC) over silica gel eluted with a gradient of Cyclohexane/EtOAc (20:1e0:1, v/v) and EtOAc/MeOH (0:1e1:4, v/v) to afford seven fractions (Fr. 1-Fr. 7). Fr. 1 was separated on silica gel CC (PE/ EtOAc, 95:5) to get 2 (136 mg) and 6 (3067 mg). Fr. 4 was separated on silica gel CC (PE/EtOA/Diethylamine, 80:20:5e60:40:5) to yield 1 (43 mg), 3 (36 mg) and 4 (36 mg). Fr. 5 was chromatographed on silica gel CC (Cyclohexane/EtOAc, 1:1) and ODS CC (MeOH/H2O, 7:3) to yield 10 (60 mg). Fr. 6 was further purified by silica gel CC (Cycloexane/EtOAc, 1:1e1:4) to get 8 (19 mg), 9 (20 mg) and 11 (353 mg). Fr. 7 was further purified by silica gel CC (EtOAc/MeOH, 9:1) to get 5 (200 mg) and 7 (100 mg).
Fig. 1. The chemical structure of compounds 1e11 from F. pallidiflora Schrenk.
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Compounds 2e11(Fig. 1) were determined to be yubeinine (2) (Zhang et al., 1993), hupehenine (3) (Wu, 1983), peimine (4) (Li and Wu, 1986), Yibeinoside (5) (Xu et al., 1990a,b), imperialine (6) (Atta-ur-Rahman et al., 2002); imperialine-3b-DGlucoside (7) (Xu et al., 1990a,b), diosmetin (8) (Wu et al., 2012), murrayone (9) (Kumar, 1985), 1-O-b-D-glucopyranosyl(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (10) (Jung et al., 1996), a-Monopalmitin(11) (Zhang et al., 2012). Compound 1 was isolated as a white powder and gave a positive reaction to Dragendorff reagent. Its molecular formula was determined as C27H43O4N by high resolution ESIMS (m/z 446.3249, [MþH]þ). The 1H NMR spectrum of 1 showed the presence of two singlet methyl signals at d 1.09 (3H, s, H-21) and 0.75 (3H, s, H-19), one doublet methyl signals at d 1.04 (3H, d, J ¼ 6.8 Hz, H-27), and two multiplet signal centered at d 3.52 and 3.73, which may be assigned to the a-hydrogen adjacent to the b-hydroxyl group. The 13C NMR and DEPT spectrum of 1 showed the presence of total 27 carbon signals, including three methyls, ten methylenes, eleven methines and three quaternary carbons, which suggested the occurrence of an isosteroidal skeleton. Five aliphatic carbon resonated at d 72.0, 70.1, 70.2, 61.5 and 59.8 indicated the presence of oxygenated or nitrogen-linked carbons. Further HMQC, and HMBC experiments completely assigned the 1H NMR and 13C NMR spectra of 1 (Table 1). From the above data, compound 1 was strongly suggested to be a cevanine-type steroidal alkaloid with three hydroxyl groups. Comparison of NMR data of compound 1 with those of compound 6 (Atta-ur-Rahman et al., 2002) suggested that all the 13C NMR chemical shifts of two compounds were very similar except for those of the ring F. The carbon signals for C-22, C-26 and C-27 was shifted downfield to d 61.5 (Dd 2 ppm), 59.8 (Dd 2 ppm) and 10.4 (Dd 7 ppm), respectively (see Table 1), and the C-25 signal in 1 was shifted upfield dramatically to d 34.1 (Dd 7 ppm) (see Table 1). This shift change often appeared when the hydroxyl group was placed at C-24 (Pretsch et al., 2000), and it was proved by the large shift change of C-25 and C-23, finally. Thus, the structure of 1 was presumed to be 5a, 14a, 17b-cevanin-6-oxo-3b, 20b, 24b-triol. The relative configurations for ring junctions and chiral center were further confirmed through the NOESY spectrum as shown in Fig. 2. Briefly, in the NOESY spectrum the correlation between H-24a and H-25 indicated that the methyl at d 10.4 (Me-27) was b oriented. The key correlations of H-5a/H-9, Me-19a/H-22, H-13/H-17, revealed A/B trans, B/C trans, D/E cis, 3b-OH, 24b-OH, 22a-H. Therefore, compound 1 was determined as 5a, 14a, 17b-cevanin-6- oxo-3b, 20b, 24btriol. Yibeinine (1): white power; 1H NMR (CDCl3þCD3OD, 400 MHz), 13C NMR (CDCl3þCD3OD, 100 MHz) and DEPT data see Table 1, NOESY and HMBC spectral data see Fig. 2; High resolution ESIMS: 446.3249 [MþH]þ (calc. C27H44O4N, 446.3249). 4. Chemotaxonomic significance According to the previous investigations on Fritillaria species, isosteroidal alkaloids were the main constituents and 5acevanine isosteroidal alkaloids were considered to be characteristic chemical constituents of the genus Fritillaria (Zhou and Duan, 2005). In the present study, seven steroidal alkaloids (1e7), one sphingolipid (10), one flavonoid (8), one coumarin (9), and one fatty acid glyceride (11) were isolated from the dry bulbs of F. pallidiflora (Fig. 1). Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from F. pallidiflora for the first time. It is the first time that sphingolipids and flavonoids have been isolated from Fritillaria. Compound 1 is a new alkaloid, belonging to cevanine-type skeleton with a hydroxyl group at C-24. To the best of our knowledge, the cevanine-type steroidal alkaloids with a hydroxyl group at C-24 have not previously been isolated from F. pallidiflora. Table 1 1 H NMR (400 MHz) and13C NMR (100 MHz) data of compound 1 in CDCl3 and CD3OD (d, ppm; J, Hz). Positions 1 2 3 4 5 6 7 8 9 10 11 12 13 14
a
dH (J)
3.52 (1H, m)
1.78 (1H, m) 1.89 (1H, m)
dC
29.2 46.4 33.8 38.7
dH (J)
Positions
37.2 ta 30.1 t 70.1 d 29.9 t 56.2 d 211.8 s 46.6 t 39.9 d 56.5 d 38.1 s t d d d
15 16 17 18 19 20 21 22 23 24 25 26a 26b 27
2.40 (1H, dd, J ¼ 3.6, 10.4) 0.75 (3H, s)
222 2
1.09 (3H, s) 2.04 (1H, dd, J ¼ 4.8, 11.6) 3.73 5.96 1.97 2.70 2.29 1.04
(1H, m) (d, J ¼ 1.2) (1H, m) (1H, dd, J ¼ 2.4, 11.2) (1H, dd, J ¼ 2.4, 11.2) (3H, d, J ¼ 7.2)
Multiplicity was determined by DEPT experiments (s ¼ quaternary, d ¼ methine, t ¼ methylene, q ¼ methyl).
dC 22.6 19.3 41.3 58.4 12.5 72.0 22.0 61.5 27.0 27.0
t t d t q s q d t d
70.2 d 59.8 t 10.4 q
W.-L. Xu et al. / Biochemical Systematics and Ecology 57 (2014) 198e202
201
Fig. 2. Key HMBC (/) and NOSEY (O) correlations of yibeinine (1).
Compound 8 is a coumarin, while seven phenylpropionic acids have previously been isolated only from Fritillaria cirrhosa D. Don (Cao et al., 2008). The finding suggest a close phylogenetic relationship between F. pallidiflora and F. cirrhosa D. Don, but further phytochemical investigations of the genus is required to verify the chemotaxonomic significance of these compounds. Acknowledgments We are grateful to Prof. Hong Zhang for denitrification of the plant material. References Atta-ur-Rahman, Akhtar, M.N., Choudhary, M.I., Tsuda, Y., Sener, B., Khalid, A., Parvez, M., 2002. Chem. Pharm. Bull. 50, 1013. Cao, W.X., Chen, S.B., Chen, S.L., 2008. Word Sci. Technol. Modernization Tradit. Chin. Med. Materia Medica 10, 83e88. Jia, T.Y., Ding, H.B., Wang, L.S., 1999. Xibei Zhiwu Xuebao 19, 127. Jung, Jee H., Lee, Chong-Ock, Kim, Young Choong, Kang, Sam Sik, 1996. J. Nat. Prod. 59, 319e322.
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Kumar, Vijaya, 1985. Chem. Sri Lanka 2, 22e24. Li, Q.H., Wu, Z.H., 1986. Acta Pharm. Sin. 21, 767e771. Li, P., Zeng, L.J., Li, S.L., Lin, G., 2002. Phytochem. Anal. 13, 158. Pretsch, E., Btihlmann, P., Afrolter, C., 2000. Structure Determination of Organic Compounds-tables of Spectral Data. Springer, Berlin. Shen, S., Chen, C.J., Bu, R., Lu, G., Li, G.Y., Tan, Y., Li, X., Wang, J.H., 2011. J. Asian Nat. Prod. Res. 13, 1014. Shen, S., Li, G.Y., Huang, J., Tan, Y., Chen, C.J., Ren, B., Lu, G., Zhang, C., Li, X., Wang, J.H., 2012. BioChem. Syst. Ecol. 45, 183e187. Wu, J.Z., 1983. Chin. Traditional Herb. Drugs 13, 3e6, 15. Wu, D., Chen, G.Y., Han, C.R., Liu, W.J., Yang, H.Z., 2012. Chin. Tradit. Herb. Drugs 43, 1068e1070. Xu, D.M., Zhuang, Z.S., Yang, X.W., Huang, E.X., Li, C.S., 1990a. Acta Pharm. Sin. 25, 795e797. Xu, D.M., Huang, E.X., Wang, S.Q., Wen, X.G., Wu, X.Y., 1990b. Acta Bot. Sin. 32, 789e793. Xu, Y.J., Xu, D.M., Cui, D.B., Huang, E.X., Jin, X.Q., Liu, S.Y., Yan, M.M., 1993. Acta Pharm. Sin. 28, 192. Zeng, L.J., Li, P., 2001. Chin. Tradit. Herb. Drugs 32, 579e581. Zhang, J.X., Lao, A.N., Xu, R.S., 1993. Act. Bot. Sin. 35, 963e967. Zhang, F., Tan, J.J., Cheng, X.R., Jin, H.Z., Zhang, W.D., 2012. Nat. Prod. Res. Dev. 24, 427e431, 449. Zhou, R.H., Duan, J.A., 2005. Plant Chemotaxonomy. Shanghai Science and Technology Press, Shanghai, pp. 1110e1129.
Contents lists available at ScienceDirect
Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco
Chemical constituents from bulbs of Fritillaria pallidiflora Schrenk Wen-Long Xu, Man Liu, Dong-Lin Chen, Jian-Zhong Wang* West China School of Pharmacy, Sichuan University, 17 South Renmin Road, Chengdu 610041, PR China
a r t i c l e i n f o
a b s t r a c t
Article history: Received 21 June 2014 Accepted 23 August 2014 Available online
A new steroidal alkaloid, 5a, 14a, 17b-cevanin-6-oxo-3b, 20b, 24b-triol(1), together with ten known compounds (2e11) were isolated from the bulbs of Fritillaria pallidiflora Schrenk. Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from this plant for the first time. © 2014 Elsevier Ltd. All rights reserved.
Keywords: Fritillaria pallidiflora Steroidal alkaloid Sphingolipids Flavonoids Yibeinine
1. Subject and source Fritillaria is an important traditional Chinese medicine (Xu et al., 1990a,b). Fritillaria pallidiflora Schrenk (Liliaceae) is mainly distributed in Xinjiang province of China. The bulbs of F. pallidiflora Schrenk were identified by Prof. Hong Zhang, Institute for Food and Drugs of Sichuan Province, from material collected in Changji, Xinjiang province of China, in July 2010. A voucher specimen (2010-07-10) has been deposited in the herbarium of the Department of Pharmacognosy, West China School of Pharmacy, Sichuan University, Chengdu, China. 2. Previous work Previous phytochemical investigations on F. pallidiflora led to the isolation of steroidal alkaloids (Xu et al., 1993; Jia et al., 1999; Li et al., 2002), steroidal saponins (Shen et al., 2011), a non steroidal alkaloid (Zeng and Li, 2001), phenolic glucosides, nucleoside compounds and amino acids (Shen et al., 2012). However, there are no reports in the isolation of sphingolipids and flavonoids from F. pallidiflora. 3. Present study The air-dried bulbs (150 kg) of F. pallidiflora Schrenk were extracted exhaustively with 80% EtOH (200 L 2, 3 h each time), and the solvent was combined and evaporated under reduced pressure. The residue was partitioned in H2O and extracted with 10 L Cyclohexane 2, 10 L Cyclohexane/EtOAc (1:1) 2, and 10 L EtOAc 2 to provide the extracts. The Cyclohexane
* Corresponding author. Tel.: þ86 28 85503770. E-mail address: [email protected] (J.-Z. Wang). http://dx.doi.org/10.1016/j.bse.2014.08.021 0305-1978/© 2014 Elsevier Ltd. All rights reserved.
W.-L. Xu et al. / Biochemical Systematics and Ecology 57 (2014) 198e202
199
extract (698 g) was subjected to column chromatography (CC) over silica gel eluted with a gradient of Cyclohexane/EtOAc (20:1e0:1, v/v) and EtOAc/MeOH (0:1e1:4, v/v) to afford seven fractions (Fr. 1-Fr. 7). Fr. 1 was separated on silica gel CC (PE/ EtOAc, 95:5) to get 2 (136 mg) and 6 (3067 mg). Fr. 4 was separated on silica gel CC (PE/EtOA/Diethylamine, 80:20:5e60:40:5) to yield 1 (43 mg), 3 (36 mg) and 4 (36 mg). Fr. 5 was chromatographed on silica gel CC (Cyclohexane/EtOAc, 1:1) and ODS CC (MeOH/H2O, 7:3) to yield 10 (60 mg). Fr. 6 was further purified by silica gel CC (Cycloexane/EtOAc, 1:1e1:4) to get 8 (19 mg), 9 (20 mg) and 11 (353 mg). Fr. 7 was further purified by silica gel CC (EtOAc/MeOH, 9:1) to get 5 (200 mg) and 7 (100 mg).
Fig. 1. The chemical structure of compounds 1e11 from F. pallidiflora Schrenk.
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Compounds 2e11(Fig. 1) were determined to be yubeinine (2) (Zhang et al., 1993), hupehenine (3) (Wu, 1983), peimine (4) (Li and Wu, 1986), Yibeinoside (5) (Xu et al., 1990a,b), imperialine (6) (Atta-ur-Rahman et al., 2002); imperialine-3b-DGlucoside (7) (Xu et al., 1990a,b), diosmetin (8) (Wu et al., 2012), murrayone (9) (Kumar, 1985), 1-O-b-D-glucopyranosyl(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (10) (Jung et al., 1996), a-Monopalmitin(11) (Zhang et al., 2012). Compound 1 was isolated as a white powder and gave a positive reaction to Dragendorff reagent. Its molecular formula was determined as C27H43O4N by high resolution ESIMS (m/z 446.3249, [MþH]þ). The 1H NMR spectrum of 1 showed the presence of two singlet methyl signals at d 1.09 (3H, s, H-21) and 0.75 (3H, s, H-19), one doublet methyl signals at d 1.04 (3H, d, J ¼ 6.8 Hz, H-27), and two multiplet signal centered at d 3.52 and 3.73, which may be assigned to the a-hydrogen adjacent to the b-hydroxyl group. The 13C NMR and DEPT spectrum of 1 showed the presence of total 27 carbon signals, including three methyls, ten methylenes, eleven methines and three quaternary carbons, which suggested the occurrence of an isosteroidal skeleton. Five aliphatic carbon resonated at d 72.0, 70.1, 70.2, 61.5 and 59.8 indicated the presence of oxygenated or nitrogen-linked carbons. Further HMQC, and HMBC experiments completely assigned the 1H NMR and 13C NMR spectra of 1 (Table 1). From the above data, compound 1 was strongly suggested to be a cevanine-type steroidal alkaloid with three hydroxyl groups. Comparison of NMR data of compound 1 with those of compound 6 (Atta-ur-Rahman et al., 2002) suggested that all the 13C NMR chemical shifts of two compounds were very similar except for those of the ring F. The carbon signals for C-22, C-26 and C-27 was shifted downfield to d 61.5 (Dd 2 ppm), 59.8 (Dd 2 ppm) and 10.4 (Dd 7 ppm), respectively (see Table 1), and the C-25 signal in 1 was shifted upfield dramatically to d 34.1 (Dd 7 ppm) (see Table 1). This shift change often appeared when the hydroxyl group was placed at C-24 (Pretsch et al., 2000), and it was proved by the large shift change of C-25 and C-23, finally. Thus, the structure of 1 was presumed to be 5a, 14a, 17b-cevanin-6-oxo-3b, 20b, 24b-triol. The relative configurations for ring junctions and chiral center were further confirmed through the NOESY spectrum as shown in Fig. 2. Briefly, in the NOESY spectrum the correlation between H-24a and H-25 indicated that the methyl at d 10.4 (Me-27) was b oriented. The key correlations of H-5a/H-9, Me-19a/H-22, H-13/H-17, revealed A/B trans, B/C trans, D/E cis, 3b-OH, 24b-OH, 22a-H. Therefore, compound 1 was determined as 5a, 14a, 17b-cevanin-6- oxo-3b, 20b, 24btriol. Yibeinine (1): white power; 1H NMR (CDCl3þCD3OD, 400 MHz), 13C NMR (CDCl3þCD3OD, 100 MHz) and DEPT data see Table 1, NOESY and HMBC spectral data see Fig. 2; High resolution ESIMS: 446.3249 [MþH]þ (calc. C27H44O4N, 446.3249). 4. Chemotaxonomic significance According to the previous investigations on Fritillaria species, isosteroidal alkaloids were the main constituents and 5acevanine isosteroidal alkaloids were considered to be characteristic chemical constituents of the genus Fritillaria (Zhou and Duan, 2005). In the present study, seven steroidal alkaloids (1e7), one sphingolipid (10), one flavonoid (8), one coumarin (9), and one fatty acid glyceride (11) were isolated from the dry bulbs of F. pallidiflora (Fig. 1). Compounds 8, 9, 10 were obtained from the genus Fritillaria for the first time; Compounds 2, 3, 4 and 11 are isolated from F. pallidiflora for the first time. It is the first time that sphingolipids and flavonoids have been isolated from Fritillaria. Compound 1 is a new alkaloid, belonging to cevanine-type skeleton with a hydroxyl group at C-24. To the best of our knowledge, the cevanine-type steroidal alkaloids with a hydroxyl group at C-24 have not previously been isolated from F. pallidiflora. Table 1 1 H NMR (400 MHz) and13C NMR (100 MHz) data of compound 1 in CDCl3 and CD3OD (d, ppm; J, Hz). Positions 1 2 3 4 5 6 7 8 9 10 11 12 13 14
a
dH (J)
3.52 (1H, m)
1.78 (1H, m) 1.89 (1H, m)
dC
29.2 46.4 33.8 38.7
dH (J)
Positions
37.2 ta 30.1 t 70.1 d 29.9 t 56.2 d 211.8 s 46.6 t 39.9 d 56.5 d 38.1 s t d d d
15 16 17 18 19 20 21 22 23 24 25 26a 26b 27
2.40 (1H, dd, J ¼ 3.6, 10.4) 0.75 (3H, s)
222 2
1.09 (3H, s) 2.04 (1H, dd, J ¼ 4.8, 11.6) 3.73 5.96 1.97 2.70 2.29 1.04
(1H, m) (d, J ¼ 1.2) (1H, m) (1H, dd, J ¼ 2.4, 11.2) (1H, dd, J ¼ 2.4, 11.2) (3H, d, J ¼ 7.2)
Multiplicity was determined by DEPT experiments (s ¼ quaternary, d ¼ methine, t ¼ methylene, q ¼ methyl).
dC 22.6 19.3 41.3 58.4 12.5 72.0 22.0 61.5 27.0 27.0
t t d t q s q d t d
70.2 d 59.8 t 10.4 q
W.-L. Xu et al. / Biochemical Systematics and Ecology 57 (2014) 198e202
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Fig. 2. Key HMBC (/) and NOSEY (O) correlations of yibeinine (1).
Compound 8 is a coumarin, while seven phenylpropionic acids have previously been isolated only from Fritillaria cirrhosa D. Don (Cao et al., 2008). The finding suggest a close phylogenetic relationship between F. pallidiflora and F. cirrhosa D. Don, but further phytochemical investigations of the genus is required to verify the chemotaxonomic significance of these compounds. Acknowledgments We are grateful to Prof. Hong Zhang for denitrification of the plant material. References Atta-ur-Rahman, Akhtar, M.N., Choudhary, M.I., Tsuda, Y., Sener, B., Khalid, A., Parvez, M., 2002. Chem. Pharm. Bull. 50, 1013. Cao, W.X., Chen, S.B., Chen, S.L., 2008. Word Sci. Technol. Modernization Tradit. Chin. Med. Materia Medica 10, 83e88. Jia, T.Y., Ding, H.B., Wang, L.S., 1999. Xibei Zhiwu Xuebao 19, 127. Jung, Jee H., Lee, Chong-Ock, Kim, Young Choong, Kang, Sam Sik, 1996. J. Nat. Prod. 59, 319e322.
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Kumar, Vijaya, 1985. Chem. Sri Lanka 2, 22e24. Li, Q.H., Wu, Z.H., 1986. Acta Pharm. Sin. 21, 767e771. Li, P., Zeng, L.J., Li, S.L., Lin, G., 2002. Phytochem. Anal. 13, 158. Pretsch, E., Btihlmann, P., Afrolter, C., 2000. Structure Determination of Organic Compounds-tables of Spectral Data. Springer, Berlin. Shen, S., Chen, C.J., Bu, R., Lu, G., Li, G.Y., Tan, Y., Li, X., Wang, J.H., 2011. J. Asian Nat. Prod. Res. 13, 1014. Shen, S., Li, G.Y., Huang, J., Tan, Y., Chen, C.J., Ren, B., Lu, G., Zhang, C., Li, X., Wang, J.H., 2012. BioChem. Syst. Ecol. 45, 183e187. Wu, J.Z., 1983. Chin. Traditional Herb. Drugs 13, 3e6, 15. Wu, D., Chen, G.Y., Han, C.R., Liu, W.J., Yang, H.Z., 2012. Chin. Tradit. Herb. Drugs 43, 1068e1070. Xu, D.M., Zhuang, Z.S., Yang, X.W., Huang, E.X., Li, C.S., 1990a. Acta Pharm. Sin. 25, 795e797. Xu, D.M., Huang, E.X., Wang, S.Q., Wen, X.G., Wu, X.Y., 1990b. Acta Bot. Sin. 32, 789e793. Xu, Y.J., Xu, D.M., Cui, D.B., Huang, E.X., Jin, X.Q., Liu, S.Y., Yan, M.M., 1993. Acta Pharm. Sin. 28, 192. Zeng, L.J., Li, P., 2001. Chin. Tradit. Herb. Drugs 32, 579e581. Zhang, J.X., Lao, A.N., Xu, R.S., 1993. Act. Bot. Sin. 35, 963e967. Zhang, F., Tan, J.J., Cheng, X.R., Jin, H.Z., Zhang, W.D., 2012. Nat. Prod. Res. Dev. 24, 427e431, 449. Zhou, R.H., Duan, J.A., 2005. Plant Chemotaxonomy. Shanghai Science and Technology Press, Shanghai, pp. 1110e1129.