Citation: Weijia Lu, Yanqiu Zhang, Yawei Li, Shengtao Ye, Jun Luo, Lingyi Kong, Wenjun Xu. Hyperbenzones A and B, two 1,2-seco and rearranged polycyclic polyprenylated acylphloroglucinols from Hypericum beanii[J]. Chinese Chemical Letters, ;2022, 33(8): 4121-4125. doi: 10.1016/j.cclet.2021.11.011 shu

Hyperbenzones A and B, two 1,2-seco and rearranged polycyclic polyprenylated acylphloroglucinols from Hypericum beanii

Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 210009, China

wjxu@cpu.edu.cn

cpu_lykong@126.com

Received Date: 9 September 2021
Revised Date: 17 October 2021
Accepted Date: 4 November 2021
Available Online: 10 November 2021

Figures(6)

Two novel seco-polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperbenzones A (1) and B (2), were isolated from the roots of Hypericum beanii, together with one known biosynthetic congener 3. Compound 1 incorporates a 6/5/5 ring system with an unprecedented spiro[bicyclo[3.3.0]octane-3,1ʹ-cyclohexane]-2,2ʹ-dione motif. The structures of 1 and 2 were determined by a combination of high resolution electrospray ionization mass spectroscopy (HRESIMS), nuclear magnetic resonance (NMR) spectroscopic analyses, gage-independent atomic orbital (GIAO) NMR chemical shift calculation with DP4+ analyses, electronic circular dichroism (ECD) calculation, and X-ray diffraction analysis. A 1,2-seco retro-Claisen rearrangement from a bicyclo[3.3.1]nonane PPAP precursor and following chemodivergent radical cascade cyclizations are proposed as the key steps in the biosynthetic pathway to yield compounds 1 and 2. Biological investigations indicated that compounds 1 and 3 could decrease intracellular lipid accumulation in a palmitic acid-induced nonalcoholic steatohepatitis (NASH) cell model.
- seco-PPAPs,
- Hypericum beanii,
- Hyperbenzones A and B,
- NASH,
- 1,2-seco-Bicyclic derivatives
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]
  H. Bridi, G.C. Meirelles, G.L. von Poser, Phytochemistry 155 (2018) 203–232.
4. [4]
  E. Iglesias, Curr. Org. Chem. 8 (2004) 1–24. doi: 10.2174/1385272043486124
5. [5]
  N. Zhang, Z.Y. Shi, Y. Guo, et al., Org. Chem. Front. 6 (2019) 1491–1502. doi: 10.1039/c9qo00245f
6. [6]
  Y. Guo, Q.Y. Tong, N. Zhang, et al., Org. Chem. Front. 6 (2019) 817–824. doi: 10.1039/c8qo01268g
7. [7]
  R.D. Liu, Y.L. Su, J.B. Yang, A.G. Wang, Phytochemistry 142 (2017) 38–50. doi: 10.1016/j.phytochem.2017.06.011
8. [8]
  S.S. Xie, C.X. Qi, Y.L. Duan, et al., Org. Chem. Front. 7 (2020) 1349–1357. doi: 10.1039/d0qo00259c
9. [9]
  Y.L. Hu, K. Hu, L.M. Kong, et al., Org. Lett. 21 (2019) 1007–1010. doi: 10.1021/acs.orglett.8b04022
10. [10]
  H.Y. Lou, Y.N. Li, P. Yi, et al., Org. Lett. 22 (2020) 6903–6906. doi: 10.1021/acs.orglett.0c02434
11. [11]
  J.J. Zhang, X.W. Yang, X. Liu, et al., J. Nat. Prod. 78 (2015) 3075–3079. doi: 10.1021/acs.jnatprod.5b00830
12. [12]
  Z.Z. Zhang, Y.R. Zeng, Y.N. Li, et al., Org. Org. Biomol. Chem. 19 (2021) 216–219. doi: 10.1039/D0OB02072A
13. [13]
  W.J. Xu, P.F. Tang, W.J. Lu, et al., Org. Lett. 21 (2019) 8558–8562. doi: 10.1021/acs.orglett.9b03098
14. [14]
  W.X. Li, W.J. Xu, J. Luo, L. Yang, L.Y. Kong, Chin. J. Nat. Med. 19 (2021) 385–390.
15. [15]
  Y. Ishida, O. Shirota, S. Sekita, et al., Chem. Pharm. Bull. 58 (2010) 336–343. doi: 10.1248/cpb.58.336
16. [16]
  X.W. Yang, J. Yang, Y. Liao, et al., Tetrahedron Lett. 56 (2015) 5537–5540. doi: 10.1016/j.tetlet.2015.08.033
17. [17]
  G. Grogan, G.A. Roberts, D. Bougioukou, N.J. Turner, S.L. Flitsch, J. Biol. Chem. 276 (2001) 12565–12572. doi: 10.1074/jbc.M011538200
18. [18]
  Y.G. Yatluk, S.V. Chernyak, A.L. Suvorov, E.A. Khrustaleva, V.I. Abramova, Russ. J. Gen. Chem. 7 (2001) 965–967.
19. [19]
  M. Jukic, D. Sterk, Z. Casar, Curr. Org. Synth. 9 (2012) 488–512. doi: 10.2174/157017912802651438
20. [20]
  J.H. George, M.D. Hesse, J.E. Baldwin, R.M. Adlington, Org. Lett. 12 (2010) 3532–3535. doi: 10.1021/ol101380a
21. [21]
  Y. Takahashi, K. Sugimoto, H. Inui, T. Fukusato, World J. Gastroenterol 21 (2015) 3777–3785.
22. [22]
  T. Yan, N. Yan, P. Wang, et al., Acta Pharm. Sin. B 10 (2020) 3–18.
23. [23]
  Y.R. Leng, M.H. Zhang, J.G. Luo, H. Zhang, Chin. J. Nat. Med. 19 (2021) 12–27.
24. [24]
  W.J. Lu, W.J. Xu, M.H. Zhang, et al., J. Nat. Prod. 84 (2021) 1135–1148. doi: 10.1021/acs.jnatprod.0c01202
25. [25]
  X. Zhou, W.J. Xu, Y.R. Li, et al., J. Agric. Food Chem. 69 (2021) 646–654. doi: 10.1021/acs.jafc.0c05417
26. [26]
  S. Joshi-Barve, S.S. Barve, K. Amancherla, et al., Hepatology 46 (2007) 823–830. doi: 10.1002/hep.21752
27. [27]
  H. Utsunomiya, Y. Yamamoto, E. Takeshita, et al., J. Gastroenterol. 52 (2017) 940–954. doi: 10.1007/s00535-016-1298-6
28. [28]
  L. Zhao, C. Zhang, X. Luo, et al., J. Hepatol. 69 (2018) 705–717.
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