Benzyl 2-β-Glucopyranosyloxybenzoate, a New Phenolic Acid Glycoside from Sarcandra glabra
Abstract
:1. Introduction
2. Results and Discussion
Position | δC | δH | HMBC (H to C) |
---|---|---|---|
1 | 122.6 | ||
2 | 158.8 | ||
3 | 119.0 | 7.39 (dd, 7.8, 1.8) | C-1, C-2 |
4 | 135.4 | 7.54 (m) | C-3 |
5 | 123.9 | 7.13 (m) | C-4, C-6 |
6 | 132.3 | 7.76 (dd, 8.4, 1.8) | C-7 |
7 | 168.2 | ||
1′ | 137.5 | ||
2′, 6′ | 129.4 | 7.45 (d, 7.2) | C-1′ |
3′, 5′ | 129.8 | 7.39 (m) | |
4′ | 129.5 | 7.33 (m) | |
7′ | 68.2 | 5.34 (dd, 12, 12) | C-7, C-1′ |
Glc-1 | 104.0 | 4.92 (d, 7.2) | C-2 |
2 | 75.1 | 3.52 (m) | |
3 | 77.7 | 3.48 (m) | |
4 | 71.4 | 3.40 (m) | |
5 | 78.6 | 3.46 (m) | |
6 | 62.7 | 3.71 (dd, 12.0, 6.0) | |
3.89 (dd, 12.0, 1.8) |
3. Experimental
3.1. General
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectral Data
3.5. Bioassays
4. Conclusions
Acknowledgements
- Sample Availability: Samples of the compounds 1–8 are available from the authors.
References
- Takeda, Y.; Yamashita, H.; Matsumoto, T.; Terao, H. Chloranthalactone F, a sesquiterpenoid from the leaves of Chloranthus glaber. Phytochemistry 1993, 33, 713–715. [Google Scholar] [CrossRef]
- State Pharmacopeia Committee of China. In Chinese Pharmacopoeia; Chinese Medicine Science and Technology Press: Beijing, China, 2010; Volume 1, pp. 207–208.
- Okamura, H.; Nakashima, N.; Iwagawa, T.; Nakayama, N.; Nakatani, M. The structure of two lindenane sesquiterpene glucosides from Chloranthus glaber. Chem. Lett. 1994, 67, 1541–1542. [Google Scholar]
- Okamura, H.; Iwagawa, T.; Nakatani, M. A revised structure of chloranthalactone F and chloranthalactone A photodimer. Bull. Chem. Soc. Jpn. 1995, 68, 3465–3467. [Google Scholar] [CrossRef]
- Uchida, M.; Kusano, G.; Kondo, Y.; Nozoe, S. Two new sesquiterpenoids from Chloranthus glaber Makino. Heterocycles 1978, 9, 139–144. [Google Scholar] [CrossRef]
- Shimomura, H.; Nukaga, K.; Adachi, C.; Yamamura, Y. Constituents of Chloranthus-glaber and its preparation. Shoyakugaku Zasshi 1981, 35, 217–220. [Google Scholar]
- Wang, A.Q.; Feng, S.C.; He, X.; Xu, R.S. A new sesquiterpene lactone from Sarcandra glabra. Acta Pharm. Sin. 1988, 23, 64–66. [Google Scholar]
- Tsui, W.Y.; Brown, G.D. Cycloeudesmanolides from Sarcandra glabra. Phytochemistry 1996, 43, 819–821. [Google Scholar]
- Luo, Y.M.; Liu, A.H.; Yu, B.W.; Kang, L.J.; Huang, L.Q. Studies on chemical constituents of Sarcandra glabra. Chin. Pharm. J. 2005, 40, 1296–1298. [Google Scholar]
- Luo, Y.M.; Liu, A.H.; Zhang, D.M.; Huang, L.Q. Two new triterpenoid saponins from Sarcandra glabra. J. Asian Nat. Prod. Res. 2005, 7, 829–834. [Google Scholar] [CrossRef]
- Li, Y.; Zhang, D.M.; Li, J.B.; Yu, S.S.; Li, Y.; Luo, Y.M. Hepatoprotective sesquiterpene glycosides from Sarcandra glabra. J. Nat. Prod. 2006, 69, 616–620. [Google Scholar] [CrossRef]
- Li, Y.; Zhang, D.M.; Yu, S.S.; Li, J.B.; Luo, Y.M. A novel phenylpropanoid-substituted catechin glycoside and a new dihydrochalcone from Sacandra glabra. Chin. Chem. Lett. 2006, 17, 207–210. [Google Scholar]
- Huang, M.J.; Li, Y.L.; Zeng, G.Y.; Yuan, W.M.; Tan, J.B.; Tan, G.S.; Zhou, Y.J. Chemical constituents of Sacandra glabra. Cent. S. Pharm. 2007, 5, 459–461. [Google Scholar]
- Zhu, L.P.; Li, Y.; Yang, J.Z.; Zuo, L.; Zhang, D.M. Two new sesquiterpene lactones from Sarcandra glabra. J. Asian Nat. Prod. Res. 2008, 10, 541–545. [Google Scholar] [CrossRef]
- Huang, M.J.; Zeng, G.Y.; Tan, J.B.; Li, Y.L.; Tan, G.S.; Zhou, Y.J. Studies on flavonoid glycosdies of Sarcandra glabra. China J. Chin. Mat. Med. 2008, 33, 1700–1702. [Google Scholar]
- Yuan, K.; Zhu, J.X.; Si, J.P.; Cai, H.K.; Ding, X.D.; Pan, Y.J. Studies on chemical constituents and antibacterial activity from n-butanol extract of Sarcandra glabra. China J. Chin. Mat. Med. 2008, 33, 1843–1846. [Google Scholar]
- Wang, C.; Zhu, L.P.; Yang, J.Z.; Li, C.J.; Zhang, D.M. Chemical constituents from Sarcandra glabra. China J. Chin. Mat. Med. 2010, 35, 714–717. [Google Scholar]
- He, X.F.; Yin, S.; Ji, Y.C.; Su, Z.S.; Geng, M.Y.; Yue, J.M. Sesquiterpenes and dimeric sesquiterpenoids from Sarcandra glabra. J. Nat. Prod. 2010, 73, 45–50. [Google Scholar] [CrossRef]
- Xu, X.D.; Hu, X.R.; Yuan, J.Q.; Yang, J.S. Studies on chemical constituents of Sarcandra glabra. China J. Chin. Mat. Med. 2008, 33, 900–902. [Google Scholar]
- Hu, X.R.; Yang, J.S.; Xu, X.D. Three novel sesquiterpene glycosides of Sarcandra glabra. Chem. Pharm. Bull. 2009, 57, 418–420. [Google Scholar] [CrossRef]
- Kozawa, M.; Matsuyama, Y.; Fukumoto, M.; Baba, K. Chemical studies of Coelopeurum gmelinii (D.C.) Ledeb. I. constituents of the root. Chem. Pharm. Bull. 1983, 31, 64–69. [Google Scholar] [CrossRef]
- Kuang, H.X.; Xia, Y.G.; Yang, B.Y.; Wang, Q.H.; Lü, S.W. Lignan constituents from Chloranthus japonicus Sieb. Arch. Pharm. Res. 2009, 32, 329–334. [Google Scholar] [CrossRef]
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Wu, H.; Hu, X.; Zhang, X.; Chen, S.; Yang, J.; Xu, X. Benzyl 2-β-Glucopyranosyloxybenzoate, a New Phenolic Acid Glycoside from Sarcandra glabra. Molecules 2012, 17, 5212-5218. https://doi.org/10.3390/molecules17055212
Wu H, Hu X, Zhang X, Chen S, Yang J, Xu X. Benzyl 2-β-Glucopyranosyloxybenzoate, a New Phenolic Acid Glycoside from Sarcandra glabra. Molecules. 2012; 17(5):5212-5218. https://doi.org/10.3390/molecules17055212
Chicago/Turabian StyleWu, Haifeng, Xiaoru Hu, Xiaopo Zhang, Shilin Chen, Junshan Yang, and Xudong Xu. 2012. "Benzyl 2-β-Glucopyranosyloxybenzoate, a New Phenolic Acid Glycoside from Sarcandra glabra" Molecules 17, no. 5: 5212-5218. https://doi.org/10.3390/molecules17055212