Citation: Zong-Yi Zhang, Xin Wang, Ying Li, Yuan Gao, Yao-Yue Fan, Jian-Min Yue, Jin-Xin Zhao. Isolation of two novel terpenoid skeletons from Croton laui, an aromatic norsesterterpenoid and a highly rearranged neo-clerodane diterpenoid[J]. Chinese Chemical Letters, ;2026, 37(2): 110951. doi: 10.1016/j.cclet.2025.110951 shu

Isolation of two novel terpenoid skeletons from Croton laui, an aromatic norsesterterpenoid and a highly rearranged neo-clerodane diterpenoid

Zong-Yi Zhang ^{a, b} ,
Xin Wang ^{b, c} ,
Ying Li ^c ,
Yuan Gao ^a ,
Yao-Yue Fan ^{a, b, c} ,
Jian-Min Yue ^{a, b, c, *,} ,
Jin-Xin Zhao ^{a, b, c, *,}

a.
Ethnomedicine and Biofunctional Molecule Research Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China

jmyue@simm.ac.cn

jxzhao@simm.ac.cn

Received Date: 2 December 2024
Revised Date: 9 February 2025
Accepted Date: 11 February 2025
Available Online: 12 February 2025

Figures(10)

New-skeleton terpenoids have prompted considerable interest owing to their chemical and biological significance. A chemical study on the bark of Croton laui led to the isolation and identification of a new norsesterterpenoid, crolatinoid A (1), and two new neoclerodane diterpenoids, crolatinoids B and C (2 and 3). Structurally, compound 1 exhibits an unprecedented 12,17-cyclo20-nor phenyllabdane skeleton. Compound 2 features a novel 19(5→4)-abeo-3,5-cycloneoclerodane skeleton, which is hypothetically derived from precursor 3 through an oxa-di-π-methane rearrangement process. Furthermore, compound 1 demonstrated a significant capacity to reverse multidrug resistance in paclitaxel-resistant HCT-15 cells with a reversal fold value of 16. All three compounds displayed adipogenesis inhibition in 3T3-L1 adipocytes.
- Croton laui,
- Sesterterpenoid,
- Diterpenoid,
- Multidrug resistance reversal,
- Anti-adipogenesis
1. [1]
  Y. Cheng, D. Qin, Novel Plant Natural Product Skeletons. Discoveries from 1999 to 2021, Springer, Singapore, 2024.
2. [2]
  Z. Hu, Y. Ye, Y. Zhang, Nat. Prod. Rep. 38 (2021) 1775–1793. doi: 10.1039/d0np00069h
3. [3]
  K. Guo, Y. Liu, S.H. Li, Nat. Prod. Rep. 38 (2021) 2293–2314. doi: 10.1039/d1np00021g
4. [4]
  Z. Wang, D.R. Nelson, J. Zhang, et al., Nat. Prod. Rep. 40 (2023) 452–469. doi: 10.1039/d2np00054g
5. [5]
  Z.J. Zhan, S. Li, W. Chu, et al., Nat. Prod. Rep. 39 (2022) 2132–2174. doi: 10.1039/d2np00047d
6. [6]
  Y. Wang, P. Tang, W. Tu, et al., Chin. Chem. Lett. 36 (2025) 109955. doi: 10.1016/j.cclet.2024.109955
7. [7]
  L. Wang, B. Yang, X.P. Lin, et al., Nat. Prod. Rep. 30 (2013) 455–473. doi: 10.1039/c3np20089b
8. [8]
  J.R. Hanson, Nat. Prod. Rep. 3 (1986) 123–132. doi: 10.1039/np9860300123
9. [9]
  K. Guo, T.T. Zhou, S.H. Luo, et al., J. Med. Chem. 67 (2023) 513–528.
10. [10]
  L.L. Teng, R.F. Mu, Y.C. Liu, et al., Org. Lett. 23 (2021) 2232–2237. doi: 10.1021/acs.orglett.1c00369
11. [11]
  S.X. Jing, R. Fu, C.H. Li, et al., J. Org. Chem. 86 (2021) 11169–11176. doi: 10.1021/acs.joc.1c00374
12. [12]
  C.Y. Zheng, J.X. Zhao, C.H. Yuan, et al., Chem. Sci. 14 (2023) 13410–13418. doi: 10.1039/d3sc04238c
13. [13]
  A. Bisio, A.M. Schito, F. Pedrelli, et al., J. Nat. Prod. 83 (2020) 1027–1042. doi: 10.1021/acs.jnatprod.9b01024
14. [14]
  A. Ulubelen, G. Topcu, U. Sönmez, et al., Phytochemistry 43 (1996) 431–434. doi: 10.1016/0031-9422(96)00248-8
15. [15]
  F.M. Moghaddam, M.M. Farimani, M. Seirafi, et al., J. Nat. Prod. 73 (2010) 1601–1605. doi: 10.1021/np1002516
16. [16]
  R. Li, S.L. Morris-Natschke, K.H. Lee, Nat. Prod. Rep. 33 (2016) 1166–1226. doi: 10.1039/C5NP00137D
17. [17]
  D.W. Bi, F. Xiong, B. Cheng, et al., J. Nat. Prod. 85 (2022) 2675–2681. doi: 10.1021/acs.jnatprod.2c00568
18. [18]
  D.B. Pu, X.J. Zhang, D.-W. Bi, et al., J. Nat. Prod. 83 (2020) 2191–2199. doi: 10.1021/acs.jnatprod.0c00288
19. [19]
  M. Fan, X.J. Chen, X.D. Wu, et al., Tetrahedron Lett. 59 (2018) 3065–3068. doi: 10.1016/j.tetlet.2018.06.015
20. [20]
  Z.X. Zhang, P.Q. Wu, H.H. Li, et al., Org. Biomol. Chem. 16 (2018) 1745–1750. doi: 10.1039/c7ob02991h
21. [21]
  L.B. Zhang, H.B. Liao, H.Y. Zhu, et al., Tetrahedron 72 (2016) 8036–8041. doi: 10.1016/j.tet.2016.10.034
22. [22]
  E. Bautista, M. Fragoso-Serrano, R.A. Toscano, et al., Org. Lett. 17 (2015) 3280–3282. doi: 10.1021/acs.orglett.5b01320
23. [23]
  H.F. Dai, X.L. Zheng, F.W. Xing, et al., Records of Li Folk Medicine, China Science & Technology Press, Beijing, 2014, pp. 115–116.
24. [24]
  Z.Y. Zhang, Y. Li, J.H. Yu, et al., Phytochemistry 223 (2024) 114138. doi: 10.1016/j.phytochem.2024.114138
25. [25]
  C.P. Liu, J.B. Xu, J.X. Zhao, et al., J. Nat. Prod. 77 (2014) 1013–1020. doi: 10.1021/np500042c
26. [26]
  L. Yang, Y.B. Zhang, Z.N. Wu, et al., Chem. Lett. 45 (2016) 1235–1237. doi: 10.1246/cl.160632
27. [27]
  F. Li, D.B. Zhang, J.T. Li, et al., Nat. Prod. Res. 35 (2019) 2849–2857. doi: 10.3390/ijms20112849
28. [28]
  L. Yang, Z.N. Wu, Y.B. Zhang, et al., Nat. Prod. Res. 31 (2017) 1028–1033. doi: 10.1080/14786419.2016.1266350
29. [29]
  C. Yang, H. Chen, S. Gao, et al., Phytochem. Lett. 53 (2023) 37–41. doi: 10.1109/dsde58527.2023.00014
30. [30]
  L. Yang, Y.B. Zhang, L.F. Chen, et al., Bioorg. Med. Chem. Lett. 26 (2016) 4687–4691. doi: 10.1016/j.bmcl.2016.08.052
31. [31]
  J.S. Zhou, L. Cheng, Y. Gao, et al., Engineering 38 (2024) 144–154. doi: 10.1016/j.eng.2023.09.015
32. [32]
  C.L. Wang, Y. Dai, Q. Zhu, et al., J. Nat. Prod. 86 (2023) 1345–1359. doi: 10.1021/acs.jnatprod.3c00173
33. [33]
  J. Qi, Y. Zhang, Q. Liu, et al., Chin. J. Chem. 39 (2021) 1891–1897. doi: 10.1002/cjoc.202100117
34. [34]
  X.H. Gao, Y.Y. Fan, Q.F. Liu, et al., Org. Lett. 21 (2019) 7065–7068. doi: 10.1021/acs.orglett.9b02630
35. [35]
  T.D. Crawford, M.C. Tam, M.L. Abrams, J. Phys. Chem. A 111 (2007) 12057–12068. doi: 10.1021/jp075046u
36. [36]
  N. Berova, L.D. Bari, G. Pescitelli, Chem. Soc. Rev. 36 (2007) 914–931. doi: 10.1039/b515476f
37. [37]
  C. Diedrich, S. Grimme, J. Phys. Chem. A 107 (2003) 2524–2539. doi: 10.1021/jp0275802
38. [38]
  A. Fu, C. Chen, Q. Li, et al., Chin. Chem. Lett. 35 (2024) 109100. doi: 10.1016/j.cclet.2023.109100
39. [39]
  A. de Meijere, V. Bagutski, F. Zeuner, et al., Eur. J. Org. Chem. 2004 (2004) 3669–3678. doi: 10.1002/ejoc.200400132
40. [40]
  H.D. Flack, G. Bernardinelli, Chirality 20 (2008) 681–690. doi: 10.1002/chir.20473
41. [41]
  Z.Y. Jiang, Q. Niu, H.X. Wang, et al., Phytochemistry 226 (2024) 114206. doi: 10.1016/j.phytochem.2024.114206
42. [42]
  H.E. Zimmerman, D. Armesto, Chem. Rev. 96 (1996) 3065–3112. doi: 10.1021/cr910109c
43. [43]
  T. Chen, Z. Xiao, X. Liu, et al., Pharmacol. Res. 202 (2024) 107099. doi: 10.1016/j.phrs.2024.107099
44. [44]
  A. Kumar, V. Jaitak, Eur. J. Med. Chem. 176 (2019) 268–291. doi: 10.1504/ijef.2019.104071
45. [45]
  S. Long, E. Sousa, A. Kijjoa, et al., Molecules 21 (2016) 892. doi: 10.3390/molecules21070892
46. [46]
  C.P. Liu, C.Y. Xie, J.X. Zhao, et al., J. Am. Chem. Soc. 141 (2019) 6812–6816. doi: 10.1021/jacs.9b02259
47. [47]
  P. González-Muniesa, M.A. Mártinez-González, F.B. Hu, et al., Nat. Rev. Dis. Primers 3 (2017) 17034. doi: 10.1038/nrdp.2017.34
48. [48]
  Y.Y. Chi, J.L. Shen, J. Zhang, et al., Food Sci. Biotechnol. 25 (2016) 1147–1153. doi: 10.1007/s10068-016-0183-7
49. [49]
  Z.Y. Zhang, X.H. Gao, Y. Huang, et al., J. Nat. Prod. 87 (2024) 1441–1453. doi: 10.1021/acs.jnatprod.4c00246
50. [50]
  Q. Tan, R.Z. Fan, W. Yang, et al., Chin. Chem. Lett. 35 (2024) 109390. doi: 10.1016/j.cclet.2023.109390
51. [51]
  S.C. Chen, R. Brooks, J. Houskeeper, et al., Mol. Cell. Endocrinol. 440 (2017) 57–68. doi: 10.1016/j.mce.2016.11.011
52. [52]
  L. Ma, C. Xie, Y. Ran, et al., J. Med. Chem. 55 (2012) 9958–9972. doi: 10.1021/jm301164y
1. [1]
  Xue-Wen Wu , Bin-Bao Wang , Yu Qin , Yong-Xiang Huang , Muhammad Aurang Zeb , Bin Cheng , Xiao-Li Li , Chang-Bo Zheng , Wei-Lie Xiao . Diterpenoids with unexpected 5/6/6-fused ring system and its dimer from Strophioblachia glandulosa. Chinese Chemical Letters, 2025, 36(8): 110584-. doi: 10.1016/j.cclet.2024.110584
2. [2]
  Xiaofang Luo , Ye Wu , Xiaokun Zhang , Min Tang , Feiye Ju , Zuodong Qin , Gregory J Duns , Wei-Dong Zhang , Jiang-Jiang Qin , Xin Luan . Peptide-based strategies for overcoming multidrug-resistance in cancer therapy. Chinese Chemical Letters, 2025, 36(1): 109724-. doi: 10.1016/j.cclet.2024.109724
3. [3]
  Yun-Hong Yu , Yu Peng , Wei-Dong Z. Li . Highly fused tetracyclic diterpenoid natural products: Diverse biosynthesis and total synthesis. Chinese Chemical Letters, 2025, 36(10): 111137-. doi: 10.1016/j.cclet.2025.111137
4. [4]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
5. [5]
  Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
6. [6]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
7. [7]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
8. [8]
  Yixuan Wang , Jiexin Li , Zhihao Shang , Chengcheng Feng , Jianmin Gu , Maosheng Ye , Ran Zhao , Danna Liu , Jingxin Meng , Shutao Wang . Wettability-driven synergistic resistance of scale and oil on robust superamphiphobic coating. Chinese Chemical Letters, 2024, 35(7): 109623-. doi: 10.1016/j.cclet.2024.109623
9. [9]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
10. [10]
  Shaoqing Du , Xinyong Liu , Xueping Hu , Peng Zhan . Targeting novel sites represents an effective strategy for combating drug resistance. Chinese Chemical Letters, 2025, 36(1): 110378-. doi: 10.1016/j.cclet.2024.110378
11. [11]
  Yun Bai , Shengnan Li , Shih-Hsin Ho . How do nanomaterials influence the spread of antibiotic resistance genes in aquatic environments?. Chinese Chemical Letters, 2026, 37(1): 111183-. doi: 10.1016/j.cclet.2025.111183
12. [12]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
13. [13]
  Haiyang Peng , Zhipeng Xie , Shuiqing Lu , Da Zhang , Bin Yang , Feng Liang . Dual-functionality composites of polyaniline-coated oxidized carbon nanohorns: Efficient wave absorption and enhanced corrosion resistance. Chinese Chemical Letters, 2025, 36(6): 110818-. doi: 10.1016/j.cclet.2025.110818
14. [14]
  Chunshi He , Linqing Li , Yuanrong Sun , Xuefang Wang , Jie Ren , Jianbo Li . Enhanced durability of a novel thiol-epoxy network thermosets with excellent hygrothermal and chemical resistance. Chinese Chemical Letters, 2025, 36(6): 110905-. doi: 10.1016/j.cclet.2025.110905
15. [15]
  Hao Li , Hanzhi Lu , Linlin Hu , Xueli Zhang , Hua Shao , Fulun Li , Yanfei Shen . Dynamic surface-enhanced Raman spectroscopy-based metabolic profiling: A novel pathway to overcoming antifungal resistance. Chinese Chemical Letters, 2025, 36(7): 110342-. doi: 10.1016/j.cclet.2024.110342
16. [16]
  Daili Liu , Changxiang Yu , Liyuan Lin , Zhidong Liu , Guiqian Fang , Qingqiang Yao , Qixin Chen , Xintian Shao . Berberrubine-mediated pH indicator response enhances the efficacy of hydroxycamptothecin by reversing lysosomal drug resistance. Chinese Chemical Letters, 2025, 36(9): 110718-. doi: 10.1016/j.cclet.2024.110718
17. [17]
  Haiyang Gu , Xiang Xu . Multicolor hybrid metal halides and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(9): 100352-100352. doi: 10.1016/j.cjsc.2024.100352
18. [18]
  Yuanmao Fu , Ziang Wang , Kefan Wu , Feiyang Li , Xian Zhang , Hongyuan Cui , Xiaolin Wang , Hui Guo , Yuezhong Meng . Bio-inspired multifunctional hydrogels with adhesive, anti-bacterial, anti-icing and sensing properties. Chinese Chemical Letters, 2025, 36(7): 110479-. doi: 10.1016/j.cclet.2024.110479
19. [19]
  Yuan Xiong , Lan-Hui Qin , Bei Zhao , Lei-Zhi Xu , Yu-Fan Fan , Tian Tian , Hai-Rong Zeng , Ting Liu , Jian Huang , Jian-Ming Sun , Zhen-Hao Tian , Guang-Bo Ge . Structure-based design and development of halogenated-naphthalimides as potent hCYP1B1 inhibitors for overcoming paclitaxel resistance. Chinese Chemical Letters, 2025, 36(11): 110812-. doi: 10.1016/j.cclet.2024.110812
20. [20]
  Wenhao Yan , Shuaiya Xue , Xuerui Zhao , Wei Zhang , Jian Li . Hexagonal boron nitride based slippery liquid infused porous surface with anti-corrosion, anti-contaminant and anti-icing properties for protecting magnesium alloy. Chinese Chemical Letters, 2024, 35(4): 109224-. doi: 10.1016/j.cclet.2023.109224

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(10)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142