Citation: Ye Yansong, Jiang Nana, Yang Xianwen, Xu Gang. Polycyclic polyprenylated acylphloroglucinol with an unprecedented spirocyclic core from Hypericum patulum[J]. Chinese Chemical Letters, ;2020, 31(9): 2433-2436. doi: 10.1016/j.cclet.2020.04.028 shu

Polycyclic polyprenylated acylphloroglucinol with an unprecedented spirocyclic core from Hypericum patulum

Ye Yansong ^a,c,1 ,
Jiang Nana ^a,c,1 ,
Yang Xianwen ^b ,
Xu Gang ^a,*,

a.
State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
b.
Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Xiamen 361005, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

xugang008@mail.kib.ac.cn

Received Date: 15 March 2020
Revised Date: 14 April 2020
Accepted Date: 15 April 2020
Available Online: 22 April 2020

Figures(5)

Spirohypatone A (1), a spirocyclic PPAP (polycyclic polyprenylated acylphloroglucinol) bearing an unprecedented hexahydro-1'H-spiro [cyclohexane-1, 2'-pentalene]-2, 4, 6-trione core and a new homologue (spirohypatone B, 2) were isolated from Hypericum patulum together with two known biosynthetic precursors. Compound 1 represents the first spirocyclic PPAP possessing a 5/5/6 carbon ring system, biogenetically derived from the intermediate 3 (attack from C-3 to C-12), which was differed from normal spirocyclic PPAPs (attack from C-3 to C-11). In addition, through extensive spectroscopic analysis, an interconversion mechanism of keto-enol of 1 was postulated and confirmed by its methylated reaction. The structures and absolute configurations of 1 and 2 were determined by comprehensive spectroscopic and chemical derivatized methods and X-ray crystallography. Compounds 1, 2, and 4 were tested to exhibit cytotoxic activities against several cancer cell lines.
- Spirocyclic PPAP,
- Hypericum patulum,
- Structural elucidation,
- Derivatives,
- Cytotoxic activities
1. [1]
  R. Ciochina, R.B. Grossman, Chem. Rev. 106 (2006) 3963-3986. doi: 10.1021/cr0500582
2. [2]
  X.W. Yang, R.B. Grossman, G. Xu, Chem. Rev. 118 (2018) 3508-3558. doi: 10.1021/acs.chemrev.7b00551
3. [3]
  (a) Y.T. Duan, J. Zhang, Y.Z. Lao, et al., Tetrahedron Lett. 59 (2018) 4067-4072;
  (b) Z.N. Wu, Q.W. Niu, Y.B. Zhang, et al., RSC Adv. 9 (2019) 7961-7966;
  (c) J.J. Zhang, X.W. Yang, J.Z. Ma, et al., Nat. Prod. Bioprospect. 4 (2014) 73-79.
4. [4]
  State Administration of Traditional Chinese Medicine of the People's Republic of China, Chinese Materia Medica, Vol. 9, Shanghai Scientific and Technical Publishers, Shanghai, 1999, pp. 594-608.
5. [5]
  X. Jia, Y. Wu, C. Lei, et al., Chin. Chem. Lett. 31 (2020) 1263-1266. doi: 10.1016/j.cclet.2019.10.014
6. [6]
  (a) Y. Liao, X. Liu, J. Yang, et al., Org. Lett. 17 (2015) 1172-1175;
  (b) Y.L. Wang, Y.S. Ye, W.W. Fu, et al., Org. Lett. 21 (2019) 1534-1537;
  (c) X.W. Yang, Y.Q. Ding, J.J. Zhang, et al., Org. Lett. 16 (2014) 2434-2437.
7. [7]
  Y.S. Ye, W.Y. Li, S.Z. Du, et al., J. Med. Chem. 63 (2020) 1709-1716. doi: 10.1021/acs.jmedchem.9b02056
8. [8]
  N. Zhang, Z. Shi, Y. Guo, et al., Org. Chem. Front. 6 (2019) 1491-1502. doi: 10.1039/C9QO00245F
9. [9]
  (a) S. Abe, N. Tanaka, J. Kobayashi, J. Nat. Prod. 75 (2012) 484-488;
  (b) S. Yin, X. Chen, Z.S. Su, et al., Tetrahedron 65 (2009) 1147-1152;
  (c) W. Xin, X. Man, C. Zheng, et al., Fitoterapia 83 (2012) 1540-1547;
  (d) N. Tanaka, S. Abe, J. Kobayashi, Tetrahedron Lett. 53 (2012) 1507-1510;
  (e) H. Zhu, C. Chen, J. Liu, et al., Phytochemistry 115 (2015) 222-230.
10. [10]
  W. Hashida, N. Tanaka, Y. Kashiwada, et al., Phytochemistry 69 (2008) 2225-2230. doi: 10.1016/j.phytochem.2008.04.026
11. [11]
  L.A. Decosterd, H. Stoeckli-Evans, J.C. Chapuis, B. Sordat, K. Hostettmann, Helv. Chim. Acta 72 (1989) 1833-1845. doi: 10.1002/hlca.19890720820
12. [12]
  Y. Aramaki, K. Chiba, M. Tada, J. Chem. Soc. Perkin Trans. I 1 (1995) 683-688.
1. [1]
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2. [2]
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19. [19]
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