Citation: Yeqing Du, Ligong Yao, Xuwen Li, Yuewei Guo. Yonarolide A, an unprecedented furanobutenolide-containing norcembranoid derivative formed by photoinduced intramolecular [2+2] cycloaddition[J]. Chinese Chemical Letters, ;2023, 34(2): 107512. doi: 10.1016/j.cclet.2022.05.026 shu

Yonarolide A, an unprecedented furanobutenolide-containing norcembranoid derivative formed by photoinduced intramolecular [2+2] cycloaddition

Yeqing Du ^{a, b} ,
Ligong Yao ^b ,
Xuwen Li ^{a, b, c, *,} ,
Yuewei Guo ^{a, b, c, *,}

a.
School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China
b.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
Drug Discovery Shandong Laboratory, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China

xwli@simm.ac.cn

ywguo@simm.ac.cn

Received Date: 24 February 2022
Revised Date: 7 May 2022
Accepted Date: 11 May 2022
Available Online: 15 May 2022

Figures(6)

Eight polycyclic furanobutenolide-containing norcembrane diterpenoids featuring C19 frameworks (1–8) were rapidly recognized and isolated from the Hainan soft coral Sinularia sp. by the HSQC-based small molecule accurate recognition technology. Yonarolide A (1a), featuring an unprecedented 5/6/4/4/7 pentacyclic ring skeleton, was surprisingly obtained as a transformed product by leaving compound 1 under indoor natural light, and was further proved to be a [2 + 2] cycloaddition product of 1 by photochemical reaction. The absolute stereochemistry of 1a and the three known norcembrane diterpenoids 1, 4, and 7 were determined by using X-ray diffraction (XRD) analyses. Further, with the aid of XRD analysis, the structure of scabrolide B (2), which was previously reported of possessing 5/6/7 tricyclic skeleton, was firmly revised as 2a with the rare inelegane skeleton featured by the highly oxygenated 5/7/6 tricyclic carbocycle.
- Soft coral,
- Sinularia,
- Norcembranoid,
- Photocycloaddition,
- SMART method
1. [1]
  A.F. Ahmed, R.T. Shiue, G.H. Wang, et al., Tetrahedron 59 (2003) 7337–7344. doi: 10.1016/S0040-4020(03)01138-4
2. [2]
  C.Y. Duh, S.K. Wang, M.C. Chia, et al., Tetrahedron Lett. 40 (1999) 6033–6035. doi: 10.1016/S0040-4039(99)01194-6
3. [3]
  Y.J. Tseng, A.F. Ahmed, C.F. Dai, et al., Org. Lett. 7 (2005) 3813–3816. doi: 10.1021/ol051513j
4. [4]
  R.A. Craig, B.M. Stoltz, Chem. Rev. 117 (2017) 7878–7909. doi: 10.1021/acs.chemrev.7b00083
5. [5]
  N.P. Thao, N.H. Nam, N.X. Cuong, et al., Bioorg. Med. Chem. Lett. 23 (2013) 228–231. doi: 10.1016/j.bmcl.2012.10.129
6. [6]
  N.J. Hafeman, S.A. Loskot, C.E. Reimann, et al., J. Am. Chem. Soc. 142 (2020) 8585–8590. doi: 10.1021/jacs.0c02513
7. [7]
  Y. Li, G. Pattenden, Nat. Prod. Rep. 28 (2011) 1269–1310. doi: 10.1039/c1np00023c
8. [8]
  Y. Li, G. Pattenden, Nat. Prod. Rep. 28 (2011) 429–440. doi: 10.1039/c0np00029a
9. [9]
  C. Zhang, Y. Idelbayev, N. Roberts, et al., Sci. Rep. 7 (2017) 14243–14260. doi: 10.1038/s41598-017-13923-x
10. [10]
  W.H. Gerwick, J. Nat. Prod. 80 (2017) 2583–2588. doi: 10.1021/acs.jnatprod.7b00624
11. [11]
  R. Reher, H.W. Kim, C. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 4114–4120. doi: 10.1021/jacs.9b13786
12. [12]
  K. Iguchi, K. Kajiyama, Y. Yamada, Tetrahedron Lett. 36 (1995) 8807–8808. doi: 10.1016/0040-4039(95)01867-H
13. [13]
  W.X. Cui, M. Yang, H. Li, et al., Bioorg. Chem. 94 (2020) 103350. doi: 10.1016/j.bioorg.2019.103350
14. [14]
  J.H. Sheu, A.F. Ahmed, R.T. Shiue, et al., J. Nat. Prod. 65 (2002) 1904–1908. doi: 10.1021/np020280r
15. [15]
  A. Sato, W. Fenical, Q.T. Zheng, et al., Tetrahedron 41 (1985) 4303–4308. doi: 10.1016/S0040-4020(01)97201-1
16. [16]
  G.F. Qin, X.L. Tang, Y.T. Sun, et al., Mar. Drugs 16 (2018) 127. doi: 10.3390/md16040127
17. [17]
  M.E.F. Hegazy, T.A. Mohamed, A.I. Elshamy, et al., Molecules 21 (2016) 308. doi: 10.3390/molecules21030308
18. [18]
  Y.F. Li, S.W. Li, C. Cuadrado, et al., Chin. Chem. Lett. 32 (2021) 271–276. doi: 10.1016/j.cclet.2020.11.037
19. [19]
  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
20. [20]
  T. Kouamé, G. Bernadat, V. Turpin, et al., Org. Lett. 23 (2021) 5964–5968. doi: 10.1021/acs.orglett.1c02055
21. [21]
  R.A. Craig, R.C. Smith, J.L. Roizen, et al., J. Org. Chem. 83 (2018) 3467–3485. doi: 10.1021/acs.joc.7b02825
22. [22]
  R.A. Craig, R.C. Smith, J.L. Roizen, et al., J. Org. Chem. 84 (2019) 7722–7746. doi: 10.1021/acs.joc.9b00635
23. [23]
  A.J. Day, C.J. Sumby, J.H. George, J. Org. Chem. 85 (2020) 2103–2117. doi: 10.1021/acs.joc.9b02862
24. [24]
  J.D. Hart, L. Burchill, A.J. Day, et al., Angew. Chem. Int. Ed. 58 (2019) 2791–2794. doi: 10.1002/anie.201814089
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