A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv.
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental
3.1. General Procedures
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectral Data
3.5. PTP1B Activity Assay [25]
4. Conclusions
Acknowledgments
References
- Jiangsu New Medical College, Dictionary of Traditional Chinese Medicine; Shanghai Science and Technique Publishing House: Shanghai, China, 1986; p. 1031.
- Guan, S.Y.; Su, W.W. Advances in the study of chemical constituents and pharmacology of Eucommia ulmoides Oliver. J. Chin. Med. Mater. 2003, 26, 124–129. [Google Scholar]
- Ji, Z.P.; Su, Y.P. Study on antimicrobial activities of extracts from Eucommia ulmoides Oliv. leaves. Chem. Ind. For. Prod. 2008, 28, 63–66. [Google Scholar]
- Deyama, T. The constituents of Eucommia ulmoides Oliv. I. Isolation of (+)-medioresinol di-O-β-D-glucopyranoside. Chem. Pharm. Bull. 1983, 31, 2993–2997. [Google Scholar] [CrossRef]
- Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. The constituents of Eucommia ulmoides Oliv. II. Isolation and structures of three new lignan glycosides. Chem. Pharm. Bull. 1985, 33, 3651–3657. [Google Scholar] [CrossRef]
- Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. The constituents of Eucommia ulmoides Oliv. III. Isolation and structure of a new lignan glycoside. Chem. Pharm. Bull. 1986, 34, 523–527. [Google Scholar] [CrossRef]
- Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. The constituents of Eucommia ulmoides Oliv. VI. Isolation of new sesquilignan and neolignan glycosides. Chem. Pharm. Bull. 1987, 35, 1803–1807. [Google Scholar] [CrossRef]
- Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. The constituents of Eucommia ulmoides Oliv. V. Isolation of dihydroxydehydrodiconiferyl alcohol isomers and phenolic compounds. Chem. Pharm. Bull. 1987, 35, 1785–1783. [Google Scholar] [CrossRef]
- Deyama, T.; Ikawa, T.; Kitagawa, S.; Nishibe, S. The constituents of Eucommia ulmoides Oliv. IV. Isolation of a new sesquilignan glycoside and iridoids. Chem. Pharm. Bull. 1986, 34, 4933–4938. [Google Scholar] [CrossRef]
- Yao, L.N.; Su, Y.F.; Yin, Z.Y.; Qin, N.; Li, T.X.; Si, C.L.; Liu, E.W.; Gao, X.M. A new phenolic glucoside and flavonoids from the bark of Eucommia ulmoides Oliv. Holzforschung 2010, 64, 571–575. [Google Scholar] [CrossRef]
- Takamura, C.; Hirata, T.; Yamaguchi, Y.; Ono, M.; Miyashita, H.; Ikeda, T.; Nohara, T. Studies on the chemical constituents of green leaves of Eucommia ulmoides Oliv. J. Nat. Med. 2007, 61, 220–221. [Google Scholar] [CrossRef]
- Cheng, J.; Zhao, Y.Y.; Cui, Y.X.; Cheng, T.M. Studies on flavonoids from leave of Eucommia ulmoides Oliv. China. J. Chin. Mater. Med. 2000, 25, 284–286. [Google Scholar]
- Hua, H.M.; Yin, H.Q.; Li, B.Q.; Hu, B.; Pei, Y.H. A new monoterpene from the bark of Eucommia ulmoides. J. Asian Nat. Prod. Res. 2002, 4, 201–204. [Google Scholar] [CrossRef] [PubMed]
- Tanaka, C.; Takamura, T.; Nakazawa, Y.; Nohara, T. A new triterpenoid from the leaves of Eucommia ulmoides Oliv. Chem. Pharm. Bull. 1997, 45, 1379–1380. [Google Scholar] [CrossRef]
- Xiang, W.; Song, Q.S.; Zhang, H.J.; Li, R.T.; Na, Z.; Sun, H.D. Adenanthusone, a new ursanetype nortriterpenoid from Isodon adenanthus. Helv. Chim. Acta 2004, 87, 2842–2847. [Google Scholar] [CrossRef]
- Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; et al. Gaussian 09; Revision B. 01, Gaussian, Inc.: Wallingford, CT, USA, 2009. [Google Scholar]
- Berova, N.; Bari, D.L.; Pescitelli, G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem. Soc. Rev. 2007, 36, 914–931. [Google Scholar] [CrossRef] [PubMed]
- Taniguchi, S.; Imayoshi, Y.; Kobayashi, E.; Takamatsu, Y.; Ito, H.; Hatano, T.; Sakagami, H.; Tokuda, H.; Nishino, H.; Sugita, D.; et al. Production of bioactive triterpenes by Eriobotrya japonicacalli. Phytochemistry 2002, 59, 315–323. [Google Scholar] [CrossRef]
- Ballesta-Acosta, M.C.; Pascual-Villalobos, M.J.; Rodriguez, B. A new 24-nor-oleanane triterpenoid from Salvia carduacea. J. Nat. Prod. 2002, 65, 1513–1515. [Google Scholar] [CrossRef] [PubMed]
- Li, Y.S.; Wang, Z.T.; Zhang, M.; Luo, S.D.; Chen, J.J. Study on identification of terpenes from Ligulria Kanaitzensis. Chin. Pharm. J. 2002, 37, 12–14. [Google Scholar]
- Gaspar, M.E.M.; Dasneves, H.J.C. Steroidal constituents from mature wheat straw. Phytochemistry 1993, 34, 523–527. [Google Scholar] [CrossRef]
- Nakamura, S.; Zhang, Y.; Pongpiriyadacha, Y.; Wang, T.; Matsuda, H.; Yoshikawa, M. Megastigmane glycosides from the leaves of Salacia chinensis. Heterocycles 2008, 75, 131–143. [Google Scholar]
- Matsuda, N.; Isawa, K.; Kikuchi, M. Studies on the constituents of Lonicera species. Part II. Megastigmane glycosides from Lonicera gracilipes var. glandulosa. Phytochemistry 1997, 45, 777–779. [Google Scholar] [CrossRef]
- Ito, H.; Kobayashi, E.; Li, S.H.; Hatano, T.; Sugita, D.; Kubo, N.; Shimura, S.; Itoh, Y.; Yoshida, T. Megastigmane glycosides and an acylate driterpenoid from Eriobotrya japonica. J. Nat. Prod. 2001, 64, 737–740. [Google Scholar] [CrossRef] [PubMed]
- Ma, Y.M.; Liu, Q.; Li, J.; Tian, J.Y.; Zhang, X.L.; Xiao, Z.Y.; Ye, F. PTP1B inhibitor improves both insulin resistance and lipidabnormalities in vivo and in vitro. Mol. Cell Biochem. 2011, 357, 65–72. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds 1–11 are available from the authors. |
Position | 1H | 13C |
---|---|---|
1 | 6.47 s | 123.22 |
2 | 144.88 | |
2-OH | 6.23 s | |
3 | 181.44 | |
4 | 127.34 | |
5 | 163.62 | |
6 | 2.50 (td, 13.5, 4.5) 2.80 (brd, 13.5) | 24.10 |
7 | 1.39 m 1.26 m | 31.93 |
8 | 41.68 | |
9 | 1.75 (brs) | 47.72 |
10 | 41.91 | |
11 | 3.38 (dd, 4.0, 2.0) | 54.71 |
12 | 3.08 (d, 4.0) | 56.60 |
12 | ||
13 | 88.67 | |
14 | 41.68 | |
15 | 1.11(dd,14.0,5.5) 1.74 m | 27.20 |
16 | 2.13 (td, 13.5, 5.5) 1.37 m | 22.68 |
17 | 45.10 | |
18 | 1.79 m | 60.46 |
19 | 0.97 m | 40.20 |
20 | 1.67m | 37.50 |
21 | 1.60 m1.25 m | 30.49 |
22 | 1.81 m 1.53 (td, 13.5, 4.5) | 31.32 |
23 | 2.01 s | 10.89 |
25 | 1.40 s | 22.44 |
26 | 1.33 s | 19.13 |
27 | 0.97 s | 16.21 |
28 | 178.83 | |
29 | 1.18 (d, 6.5) | 17.16 |
30 | 0.98 (d, 5.5) | 19.46 |
Comp. | Inhibition (%) at 10 μM |
---|---|
1 | 4.8 |
2 | 3.0 |
3 | 81.3 |
4 | 79.8 |
5 | 28.3 |
6 | 43.5 |
8 | 13.4 |
9 | 28.6 |
10 | 17.8 |
CCCFO6240 a | 108.5 |
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Li, C.; Li, L.; Wang, C.; Yang, J.; Ye, F.; Tian, J.; Si, Y.; Zhang, D. A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv. Molecules 2012, 17, 13960-13968. https://doi.org/10.3390/molecules171213960
Li C, Li L, Wang C, Yang J, Ye F, Tian J, Si Y, Zhang D. A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv. Molecules. 2012; 17(12):13960-13968. https://doi.org/10.3390/molecules171213960
Chicago/Turabian StyleLi, Chuangjun, Li Li, Chao Wang, Jingzhi Yang, Fei Ye, Jinying Tian, Yikang Si, and Dongming Zhang. 2012. "A New Ursane-Type Nor-Triterpenoid from the Leaves of Eucommia ulmoides Oliv." Molecules 17, no. 12: 13960-13968. https://doi.org/10.3390/molecules171213960