Citation: Jimei Liu, Zhenfei Wang, Jun Wu, Yaotian Han, Fei Ye, Tiantai Zhang, Haibo Yu, Zhengshun Wen, Jungui Dai. Structural diversification of phenylspirodrimane lactams by employing a biosynthetic intermediate[J]. Chinese Chemical Letters, ;2023, 34(12): 108363. doi: 10.1016/j.cclet.2023.108363 shu

Structural diversification of phenylspirodrimane lactams by employing a biosynthetic intermediate

Jimei Liu ^{a, 1} ,
Zhenfei Wang ^{b, 1} ,
Jun Wu ^{a, 1} ,
Yaotian Han ^a ,
Fei Ye ^a ,
Tiantai Zhang ^a ,
Haibo Yu ^{a, *,} ,
Zhengshun Wen ^{b, *,} ,
Jungui Dai ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, CAMS Key Laboratory of Enzyme and Biocatalysis of Natural Drugs, NHC Key Laboratory of Biosynthesis of Natural Products, and Beijing Key Laboratory of Non-Clinical Drug Metabolism and PK/PD Study, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Zhejiang Provincial Engineering Technology Research Center of Marine Biomedical Products, School of Food Science and Pharmaceutics, Zhejiang Ocean University, Zhoushan 316022, China

haiboyu@imm.ac.cn

zswenmr@163.com

jgdai@imm.ac.cn

Received Date: 15 January 2023
Revised Date: 7 March 2023
Accepted Date: 20 March 2023
Available Online: 24 March 2023

Figures(5)

Phenylspirodrimanes are a kind of meroterpenoids with structural diversity and complexity, exhibiting a wide of biological properties, especially for the lactam derivatives consisting a γ-lactam moiety and N-linked side chains. These compounds were derived from multi-step combination of enzymatic and non-enzymatic conversions of intermediates in their biosynthetic pathways. Stachbotrydial (2) with an o-phthalaldehyde unit was supposed as the high-reactivity intermediate of phenylspirodrimane lactams via nonenzymatic reaction with amines. In the present work, an effective and non-enzymatic diversification strategy was developed for the structural diversification of phenylspirodrimane lactams including monomers and dimers from 2 by feeding structurally various mono- and diamines in the fungus Stachybotrys chartarum cultures. In total, 24 phenylspirodrimane lactams (1, 3–25) including 18 new compounds were synthesized. Among them, stachybocin A (1), a bioactive phenylspirodrimane lactam dimer, was produced with the yield of 18.7 mg/g of cell dry weight. The structures of these compounds were elucidated by extensive spectroscopic data, single-crystal X-ray diffraction (Cu Kα), and calculated electronic circular dichroism (ECD) analyses. Bioassay revealed that compounds 1, 17, and 24 displayed significant inhibitory effect on the inactivated state of hNa_V 1.2 channels with IC₅₀ values of 0.22, 2.08, and 0.53 µmol/L, respectively. In addition, 1 showed potent protein tyrosine phosphatase 1B (PTP1B) inhibitory, N-methyl-D-aspartate (NMDA) receptor antagonistic, and anti-inflammatory activities.
- Phenylspirodrimane lactams,
- Stachbotrydial,
- Nonenzymatic reaction,
- hNaV 1.2 channels inhibitory activity,
- Stachybotrys chartarum
1. [1]
  R. Geris, T.J. Simpson, Nat. Prod. Rep. 26 (2009) 1063–1094. doi: 10.1039/b820413f
2. [2]
  Y. Matsuda, I. Abe, Nat. Prod. Rep. 33 (2016) 26–53. doi: 10.1039/C5NP00090D
3. [3]
  K. Ogawa, M. Nakamura, M. Hayashi, et al., J. Antibiot. 48 (1995) 1396–1400. doi: 10.7164/antibiotics.48.1396
4. [4]
  B. Wu, V. Oseker, J. Wiese, et al., Mar. Drugs 12 (2014) 1924–1938. doi: 10.3390/md12041924
5. [5]
  A. Wang, Y. Xu, Y. Gao, et al., Phytochem. Rev. 14 (2015) 623–655. doi: 10.1007/s11101-014-9365-1
6. [6]
  P. Zhang, Y. Li, C. Jia, et al., RSC Adv. 7 (2017) 49910–49916. doi: 10.1039/C7RA09859F
7. [7]
  J. Zhao, J. Feng, Z. Tan, et al., J. Nat. Prod. 80 (2017) 1819–1826. doi: 10.1021/acs.jnatprod.7b00014
8. [8]
  J. Zhao, J. Feng, Z. Tan, et al., Bioorg. Med. Chem. Lett. 28 (2018) 355–359. doi: 10.1016/j.bmcl.2017.12.039
9. [9]
  M. Zhang, J. Feng, X. Jia, et al., Chin. Chem. Lett. 30 (2019) 435–438. doi: 10.1016/j.cclet.2018.04.031
10. [10]
  J. Liu, X. Jia, J. Zhao, et al., Org. Chem. Front. 7 (2020) 531–542. doi: 10.1039/c9qo01284b
11. [11]
  M. Nakamura, Y. Ito, K. Ogawa, et al., J. Antibiot. 48 (1995) 1389–1395. doi: 10.7164/antibiotics.48.1389
12. [12]
  W.P. Deng, M. Zhong, X.C. Guo, A.S. Kende, J. Org. Chem. 68 (2003) 7422–7427. doi: 10.1021/jo030202o
13. [13]
  J. Fan, G. Liao, F. Kindinger, et al., J. Am. Chem. Soc. 141 (2019) 4225–4229. doi: 10.1021/jacs.9b00110
14. [14]
  L.M. Bouthillette, V. Aniebok, D.A. Colosimo, D. Brumley, J.B. MacMillan, Chem. Rev. 122 (2022) 14815–14841. doi: 10.1021/acs.chemrev.2c00306
15. [15]
  D.A. Colosimo, J.B. MacMillan, J. Am. Chem. Soc. 138 (2016) 2383–2388. doi: 10.1021/jacs.5b13320
16. [16]
  S. Yin, Z. Liu, J. Shen, et al., Nat. Commun. 13 (2022) 5169.
17. [17]
  R.D. Shingare, V. Aniebok, H.W. Lee, J.B. MacMillan, Org. Lett. 22 (2020) 1516–1519. doi: 10.1021/acs.orglett.0c00098
18. [18]
  P. Fu, A. Legako, S. La, J.B. MacMillan, Chem. Eur. J. 22 (2016) 3491–3495. doi: 10.1002/chem.201600024
19. [19]
  A.W. Robertson, C.F. Martinez-Farina, D.A. Smithen, et al., J. Am. Chem. Soc. 137 (2015) 3271–3275. doi: 10.1021/ja5114672
20. [20]
  Z. Lin, M. Koch, M.H. Abdel Aziz, et al., Org. Lett. 16 (2014) 4774–4777. doi: 10.1021/ol502227x
21. [21]
  T. Asai, K. Tsukada, S. Ise, et al., Nat. Chem. 7 (2015) 737–743. doi: 10.1038/nchem.2308
22. [22]
  S.M. Allin, C.C. Hodkinson, N. Taj, Synlett 8 (1996) 781–782.
23. [23]
  X. Ma, W. Zheng, K. Sun, et al., Nat. Prod. Res. 33 (2019) 386–392. doi: 10.1080/14786419.2018.1455041
24. [24]
  E. Claudia, K. Michael, T. Luigi, DE 10258650A1. 2004-06-24.
1. [1]
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2. [2]
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3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
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12. [12]
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13. [13]
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14. [14]
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15. [15]
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16. [16]
  Xuan Liu , Qing Li . Tailoring interatomic active sites for highly selective electrocatalytic biomass conversion reaction. Chinese Chemical Letters, 2025, 36(4): 110670-. doi: 10.1016/j.cclet.2024.110670
17. [17]
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18. [18]
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19. [19]
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20. [20]
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