| ORIGINAL ARTICLES |
|
|
|
|
|
Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis |
| Shu-Ya Wei1,2, Dong-Bao Hu3, Meng-Yuan Xia2, Ji-Feng Luo2, Hui Yan2, Jing-Hua Yang1, Yun-Song Wang1, Yue-Hu Wang2 |
1 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, School of Pharmacy, Yunnan University, Kunming 650091, People's Republic of China;
2 Key Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
3 School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, People's Republic of China |
|
|
|
|
Abstract One novel spirolactone, aquilarisinolide (1), three new sesquiterpenoids, (2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one (2), (1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one (3), and (4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one (4), together with 13 known compounds (5-17) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP+), as well as inhibitory activities against BACE1. Compound 4, 5,6-dihydroxy-2-(2-phenylethyl) chromone (5), daphnauranol B (7), 6-methoxy-2-[2-(3-methyoxyphenyl) ethyl]chromone (10), isoagarotetrol (14), and 1-hydroxy-1,5-diphenylpentan-3-one (16) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001). Isoagarotetrol (14) showed a significant protective effect on MPP+-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001), while compound 4 showed a moderate activity (P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 μM.
|
| Keywords
Thymelaeaceae
Aquilaria sinensis
Sesquiterpenoids
2-(2-phenylethyl) chromones
Neuroprotective
|
| Fund:This study was supported by the National Natural Science Foundation of China (nos. 31960480, 81960629, 21662040, and 21462048) and the Joint Special Project of Local Undergraduate Universities in Yunnan Province, China (no. 2018FH001-024). |
|
Corresponding Authors:
Yun-Song Wang, Yue-Hu Wang
E-mail: wangys@ynu.edu.cn;wangyuehu@mail.kib.ac.cn
|
|
Issue Date: 27 September 2021
|
|
|
1. Editorial Board of Chinese Pharmacopoeia, Chinese Pharmacopoeia (China Medical Science Press, Beijing, 2020), Vol. 1, pp. 192–193
2. M. Gao, X. Han, Y. Sun, H. Chen, Y. Yang, Y. Liu, H. Meng, Z. Gao, Y. Xu, Z. Zhang, J. Han, RSC Adv. 9, 4113–4130 (2019)
3. A.N. Kristanti, M. Tanjung, N.S. Aminah, Mini-Rev. Org. Chem. 15, 36–55 (2018)
4. S. Wang, Z. Yu, C. Wang, C. Wu, P. Guo, J. Wei, Molecules 23, 342 (2018)
5. Q. He, D.-B. Hu, L. Zhang, M.-Y. Xia, H. Yan, X.-N. Li, J.-F. Luo, Y.-S. Wang, J.-H. Yang, Y.-H. Wang, Phytochemistry 181, 112554 (2021)
6. F.R. Chang, S.T. Huang, C.C. Liaw, M.H. Yen, T.L. Hwang, C.Y. Chen, M.F. Hou, S.S. Yuan, Y.B. Cheng, Y.C. Wu, Phytochemistry 131, 124–129 (2016)
7. S.Z. Huang, X.N. Li, Q.Y. Ma, H.F. Dai, L.C. Li, X.H. Cai, Y.Q. Liu, J. Zhou, Y.X. Zhao, Tetrahedron Lett. 55, 3693–3696 (2014)
8. S. Ahn, M. Chi Thanh, J.M. Choi, S. An, M. Lee, L. Van Thi Hong, J.J. Pyo, J. Lee, M.S. Choi, S.W. Kwon, J.H. Park, M. Noh, J. Nat. Prod. 82, 259–264 (2019)
9. T. Yagura, M. Ito, F. Kiuchi, G. Honda, Y. Shimada, Chem. Pharm. Bull. 51, 560–564 (2003)
10. K. Hashimoto, S. Nakahara, T. Inoue, Y. Sumida, M. Takahashi, Y. Masada, Chem. Pharm. Bull. 33, 5088–5091 (1985)
11. Y. Shimada, T. Tominaga, T. Konishi, S. Kiyosawa, Chem. Pharm. Bull. 30, 3791–3795 (1982)
12. K. Iwagoe, T. Konishi, S. Kiyosawa, Y. Shimada, K. Miyahara, T. Kawasaki, Chem. Pharm. Bull. 36, 2417–2422 (1988)
13. Y. Shimada, T. Konishi, S. Kiyosawa, M. Nishi, K. Miyahara, T. Kawasaki, Chem. Pharm. Bull. 34, 2766–2773 (1986)
14. T. Mukaiyama, T. Takuwa, K. Yamane, S. Imachi, Bull. Chem. Soc. Jpn. 76, 813–823 (2003)
15. B.P. Jiang, Y.M. Liu, L. Le, Z.Y. Li, J.Y. Si, X.M. Liu, Q. Chang, R.L. Pan, Cell. Physiol. Biochem. 34, 1015–1026 (2014)
16. L.L. Ji, X. Wang, J.J. Li, X.J. Zhong, B. Zhang, J. Juan, X.Y. Shang, Molecules 24, 625 (2019)
17. W. Liu, S. Kong, Q. Xie, J. Su, W. Li, H. Guo, S. Li, X. Feng, Z. Su, Y. Xu, X. Lai, Int. J. Mol. Med. 35, 739–746 (2015)
18. K.H. Lin, C.Y. Li, Y.M. Hsu, C.H. Tsai, F.J. Tsai, C.H. Tang, J.S. Yang, Z.H. Wang, M.C. Yin, Food Chem. Toxicol. 133, 110765 (2019)
19. H. Hampel, R. Vassar, B. De Strooper, J. Hardy, M. Willem, N. Singh, J. Zhou, R. Yan, E. Vanmechelen, A. De Vos, Biol. Psychiatry 89, 745–756 (2021)
20. Sigma-Aldrich, https://www.sigmaaldrich.com/content/dam/sigmaaldrich/docs/Sigma/Bulletin/cs0010bul.pdf. Accessed 8 April 2021
21. M.J. Frisch, Gaussian 09. Rev.Cl (M.J. Frisch, et al. Gaussian, Inc., Pittsburgh PA, 2009)
22. N.L. Tun, D.-B. Hu, M.-Y. Xia, D.-D. Zhang, J. Yang, T.N. Oo, Y.-H. Wang, X.-F. Yang, Nat. Prod. Bioprospect. 9, 243–249 (2019) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
