Citation: Deli Chen, Jiawen Li, Xudong Xu, Zhaocui Sun, Yun Yang, Minghui Xu, Hanqiao Liang, Junshan Yang, Hui Meng, Guoxu Ma, Jianhe Wei. Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus[J]. Chinese Chemical Letters, ;2024, 35(10): 109451. doi: 10.1016/j.cclet.2023.109451 shu

Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus

Deli Chen ^{a, b, c, 1} ,
Jiawen Li ^{a, b, 1} ,
Xudong Xu ^{a, b} ,
Zhaocui Sun ^b ,
Yun Yang ^a ,
Minghui Xu ^a ,
Hanqiao Liang ^d ,
Junshan Yang ^b ,
Hui Meng ^{a, b, *,} ,
Guoxu Ma ^{a, b, *,} ,
Jianhe Wei ^{a, b, *,}

a.
Hainan Branch of the Institute of Medicinal Plant Development (Hainan Provincial Key Laboratory of Resources Conservation and Development of Southern Medicine), Chinese Academy of Medical Sciences & Peking Union Medical College, Haikou 570311, China
b.
Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China
c.
School of Pharmaceutical Science, Hainan Medical University, Haikou 571199, China
d.
Department of Biomedicine, Beijing City University, Beijing 100094, China

huiziqq@163.com

mgxfl8785@163.com

wjianh@263.net

Received Date: 31 October 2023
Revised Date: 20 December 2023
Accepted Date: 21 December 2023
Available Online: 28 December 2023

Figures(6)

Hidden natural products are representative of defensive strategies produced in vivo in diseased plants, a process that is induced by the plant immune system. The first transcriptome library of uninfected and pathogen infected Hibiscus tiliaceus stems was constructed by transcriptome sequencing technology, genes related to cadinene-type sesquiterpenoid biosynthesis were screened and combined with ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UPLC-QTOF-MS) analysis data, which indicated pathological tissue had potential to produce novel carbon skeletons of cadinane sesquiterpenoid dimers. Successfully, two cadinane-derived sesquiterpenoid dimers with unprecedented carbon skeletons, hibisceusanols A (1) and B (2) were isolated for the first time from the stems of H. tiliaceus induced by plant-microbial interactions. Their structures and absolute configurations were unambiguously established by spectroscopy, advanced chemistry development (ACD) and electronic circular dichroism (ECD) methods. Compounds 1 and 2 exhibited significant antitumor activity in vitro with half maximal inhibitory concentration (IC₅₀) values of 2.3–7.2 µmol/L. The anticancer effect was generated via the induction of HepG2 cell apoptosis by inhibiting the phosphatidylinositol 3-kinase (PI3K) pathway.
- Hibiscus tiliaceus,
- Cadinane-derived sesquiterpenoid,
- Anti-cancer,
- PI3K,
- Plant-microbial interactions
1. [1]
  J. Hanson, Sci. Prog. 100 (2017) 63–79. doi: 10.3184/003685017X14876775256129
2. [2]
  X.Y. Shao, S.J. Xu, X.F. Wan, et al., Chin. Chem. Lett. 34 (2023) 108349. doi: 10.1016/j.cclet.2023.108349
3. [3]
  D.J. Newman, G.M. Cragg, J. Nat. Prod. 83 (2020) 770–803. doi: 10.1021/acs.jnatprod.9b01285
4. [4]
  J.M. Winter, S. Behnken, C. Hertweck, Curr. Opin. Chem. Biol. 15 (2011) 22–31. doi: 10.1016/j.cbpa.2010.10.020
5. [5]
  F.E. Koehn, G.T. Carter, Nat. Rev. Drug Discov. 4 (2005) 206–220.
6. [6]
  A.G. Atanasov, S.B. Zotchev, V.M. Dirsch, et al., Nat. Rev. Drug Discov. 20 (2021) 200–216. doi: 10.1038/s41573-020-00114-z
7. [7]
  K. Scherlach, C. Hertweck, Nat. Commun. 12 (2021) 3864. doi: 10.1038/s41467-021-24133-5
8. [8]
  L.X. Chu, J.P. Huang, M. Muhammad, et al., Crit. Rev. Biotechnol. 40 (2020) 571–589. doi: 10.1080/07388551.2020.1751056
9. [9]
  J. Fan, H.M. Ran, P.L. Wei, et al., Angew. Chem. Int. Ed. 135 (2023) e202217212. doi: 10.1002/ange.202217212
10. [10]
  M. Klapper, A. Hübner, A. Ibrahim, et al., Science 380 (2023) 619–624. doi: 10.1126/science.adf5300
11. [11]
  M.L. Timmermans, A.C. Ross, Trends Biotechnol. 38 (2020) 7–9. doi: 10.1016/j.tibtech.2019.11.003
12. [12]
  D. Dehm, J. Krumbholz, M. Baunach, et al., ACS Chem. Biol. 14 (2019) 1271–1279. doi: 10.1021/acschembio.9b00240
13. [13]
  J. Yu, X. Tu, A.C. Huang, Nat. Prod. Rep. 39 (2022) 1393–1422. doi: 10.1039/D2NP00010E
14. [14]
  H. Zheng, X. Fu, J. Shao, et al., Trends Plant Sci. 28 (2023) 429–446. doi: 10.1016/j.tplants.2022.12.007
15. [15]
  G. Polturak, M. Dippe, M.J. Stephenson, et al., Proc. Natl. Acad. Sci. U. S. A. 119 (2022) e2123299119. doi: 10.1073/pnas.2123299119
16. [16]
  M.H. Yuan, Z.Y. Jiang, G.Z. Bi, et al., Nature 592 (2021) 105–109. doi: 10.1038/s41586-021-03316-6
17. [17]
  E. Deboever, M. Deleu, S. Mongrand, et al., Trends Plant Sci. 25 (2020) 22–34. doi: 10.1016/j.tplants.2019.09.009
18. [18]
  P.D. Sonawane, A. Jozwiak, S. Panda, et al., Curr. Opin. Plant Biol. 55 (2020) 118–128. doi: 10.1016/j.pbi.2020.03.008
19. [19]
  C. Vanzella, P. Bianchetti, S. Sbaraini, et al., BMC Complement. Altern. Med. 12 (2012) 41. doi: 10.1186/1472-6882-12-41
20. [20]
  D.L. Chen, G.X. Ma, E.L. Yang, et al., Bioorg. Chem. 127 (2022) 105982. doi: 10.1016/j.bioorg.2022.105982
21. [21]
  D.L. Chen, M.Y. Chen, Y. Hou, et al., J. Nat. Prod. 85 (2022) 127–135. doi: 10.1021/acs.jnatprod.1c00849
22. [22]
  C.B. Naman, J. Li, A. Moser, et al., Org. Lett. 17 (2015) 2988–2991. doi: 10.1021/acs.orglett.5b01284
23. [23]
  C.F. Ding, H.F. Yu, X.L. Shi, et al., Tetrahedron Lett. 68 (2021) 152949. doi: 10.1016/j.tetlet.2021.152949
24. [24]
  Y.P. Sun, L.T. Cui, Q.R. Li, et al., Chin. Chem. Lett. 33 (2022) 516–518. doi: 10.1016/j.cclet.2021.06.050
25. [25]
  X.Y. Hu, X.M. Li, S.Q. Yang, et al., Chin. Chem. Lett. 34 (2023) 107516. doi: 10.1016/j.cclet.2022.05.030
26. [26]
  I. Kubo, H. Muroi, A. Kubo, et al., Planta Med. 60 (1994) 218–221. doi: 10.1055/s-2006-959462
27. [27]
  M.A. Ferreira, T.J. King, S. Ali, et al., J. Chem. Soc. Perkin Trans. 1 (1980) 249–256.
28. [28]
  S. Ali, P. Singh, R.H. Thornson, J. Chem. Soc. Perkin Trans. 1 (1980) 257–259.
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