Citation: Jiao-Zhen Zhang, Cheng-Min Zhang, Yong-Jie Wang, Pei-Lin Wu, Rui-Feng Liu, Ye Li, Ming-Zhu Zhu, Shuang-Zhi Yuan, Ze-Jun Xu, Hong-Xiang Lou. Revision of the absolute configurations of Pallavicinia diterpenoids and further discovery of their Diels−Alder cycloadducts[J]. Chinese Chemical Letters, ;2026, 37(1): 110919. doi: 10.1016/j.cclet.2025.110919 shu

Revision of the absolute configurations of Pallavicinia diterpenoids and further discovery of their Diels−Alder cycloadducts

Jiao-Zhen Zhang ^{a, 1} ,
Cheng-Min Zhang ^{a, 1} ,
Yong-Jie Wang ^{a, b} ,
Pei-Lin Wu ^a ,
Rui-Feng Liu ^a ,
Ye Li ^b ,
Ming-Zhu Zhu ^a ,
Shuang-Zhi Yuan ^a ,
Ze-Jun Xu ^a ,
Hong-Xiang Lou ^{a, *,}

a.
Department of Natural Products Chemistry, Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, Shandong University, Ji’nan 250012, China
b.
The Second Hospital, Shandong University, Ji’nan 250012, China

louhongxiang@sdu.edu.cn

Received Date: 3 November 2024
Revised Date: 31 January 2025
Accepted Date: 4 February 2025
Available Online: 6 February 2025

Figures(7)

Owing to their intricate molecular frameworks and copious chiral centers, the structural identification and configurational assignment of natural products are challenging tasks. Comprehensive spectral data analysis is crucial for the confirmation of absolute configurations. Ignoring critical parameters will lead to false structure, which may confuse the total synthesis and drug development. Herein, the configurations of seven heterogeneous Pallavicinia diterpenoids (PDs) isolated from Pallavicinia liverworts are revised using a combination of single-crystal X-ray diffraction and electronic circular dichroism (ECD) calculations. Meanwhile, identification of five unprecedented PD heterodimers PD-dimers A–E (18–22) along with eleven previously undescribed PDs (5–9, 13–17, 23) obtained by the reinvestigation of the Chinese liverwort Pallavicinia subciliata have resulted in corrections and support the revised conclusions.
- Revision,
- Absolute configurations,
- Pallavicinia diterpenoids,
- Liverwort,
- Single-crystal X-ray diffraction,
- Electronic circular dichroism calculations
1. [1]
  P.S. Grant, M.A. Brimble, Chem. Eur. J. 27 (2021) 6367–6389. doi: 10.1002/chem.202004574
2. [2]
  X.S. Peng, H.N.C. Wong, Chem. Asian. J. 1–2 (2006) 111–120. doi: 10.1002/asia.200600061
3. [3]
  J.Q. Dong, H.N.C. Wong, Angew. Chem. Int. Ed. 48 (2009) 2351–2354. doi: 10.1002/anie.200806335
4. [4]
  X.S. Xu, Z.W. Li, Y.J. Zhang, et al., Chem. Commun. 48 (2012), 8517–8519. doi: 10.1039/c2cc34310j
5. [5]
  M. Markovič, M. Ďuranová, P. Koóš, et al., Tetrahedron 69 (2013) 4185–4169. doi: 10.1016/j.tet.2013.03.100
6. [6]
  C. Ebner, E.M. Carreira, Angew. Chem. Int. Ed. 54 (2015) 11227–11230. doi: 10.1002/anie.201505126
7. [7]
  B. Huang, L. Guo, Y. Jia, Angew. Chem. Int. Ed. 54 (2015) 13599–13603. doi: 10.1002/anie.201506575
8. [8]
  L.P. Martinez, S. Umemiya, S.E. Wengryniuk, et al., J. Am. Chem. Soc. 138 (2016) 7536–7539. doi: 10.1021/jacs.6b04816
9. [9]
  X. Zhang, X. Cai, B. Huang, et al., Angew. Chem. Int. Ed. 58 (2019) 13380–13384. doi: 10.1002/anie.201907523
10. [10]
  Y. Zhang, L. Chen, Y. Jia, Angew. Chem. Int. Ed. 63 (2024) e202319127. doi: 10.1002/anie.202319127
11. [11]
  L. Chen, P. Chen, X. Zhang, et al., Chem 10 (2024) 2473–2483. doi: 10.1016/j.chempr.2024.04.003
12. [12]
  A. Almeida, L. Dong, G. Appendino, et al., Nat. Prod. Rep. 37 (2020) 1207–1228. doi: 10.1039/c9np00030e
13. [13]
  C.L. Wu, H.J. Liu, H.L. Uang, Phytochemistry 35 (1994) 822–824. doi: 10.1016/S0031-9422(00)90616-2
14. [14]
  M. Toyota, T. Saito, Y. Asakawa, Chem. Pharm. Bull. 46 (1998) 178–180. doi: 10.1248/cpb.46.178
15. [15]
  Z.J. Li, H.X. Lou, W.T. Yu, et al., Helv. Chim. Acta 88 (2005) 2637–2640. doi: 10.1002/hlca.200590204
16. [16]
  L.N. Wang, J.Z. Zhang, X. Li, et al., Org. Lett. 14 (2012) 1102–1105. doi: 10.1021/ol3000124
17. [17]
  S.G. Liu, C.Y. Zhang, J.C. Zhou, et al., Org. Chem. Front. 9 (2022) 1790–1796. doi: 10.1039/d1qo01891d
18. [18]
  C. Zhang, Y. Li, Z. Chu, et al., Chin. Chem. Lett. 35 (2024) 108206. doi: 10.1016/j.cclet.2023.108206
19. [19]
  Y. Li, X.B. Li, J.C. Zhou, et al., Phytochemistry 212 (2023) 113702. doi: 10.1016/j.phytochem.2023.113702
20. [20]
  H.J. Liu, C.L. Wu, J. Asian Nat. Prod. Res. 1 (1999) 177–182. doi: 10.1080/10286029908039862
21. [21]
  M.X. Zhou, X. Wei, A.L. Li, et al., BMC Complem. Altern. Med. 16 (2016) 360. doi: 10.1186/s12906-016-1347-y
1. [1]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
2. [2]
  Zhengyi Shi , Jie Yin , Yang Xiao , Zhangrong Hou , Fei Song , Jianping Wang , Qingyi Tong , Changxing Qi , Yonghui Zhang . Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ. Chinese Chemical Letters, 2024, 35(10): 109458-. doi: 10.1016/j.cclet.2023.109458
3. [3]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
4. [4]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
5. [5]
  Xinyi Luo , Ke Wang , Yingying Xue , Xiaobao Cao , Jianhua Zhou , Jiasi Wang . Digital PCR-free technologies for absolute quantitation of nucleic acids at single-molecule level. Chinese Chemical Letters, 2025, 36(2): 109924-. doi: 10.1016/j.cclet.2024.109924
6. [6]
  Ji-Ping Liao , Jiang Li , Wen-Jie Qin , Xiu-Mei Duan , Peng-Fei Wang , Jin-Ying Tian , Xiang Yuan , Pei-Cheng Zhang , Fei Ye , Ya-Nan Yang . Two racemic pairs of benzo bicyclo[3.3.1]/[4.2.1] nonene stilbenoid dimers from Heterosmilax yunnanensis and structural revision of syagrusin A. Chinese Chemical Letters, 2025, 36(9): 110687-. doi: 10.1016/j.cclet.2024.110687
7. [7]
  Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
8. [8]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
9. [9]
  Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
10. [10]
  Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
11. [11]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
12. [12]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
13. [13]
  Qiuting Zhang , Fan Wu , Jin Liu , Hang Su , Yanhui Zhong , Zian Lin . Facile synthesis of single-crystal 3D covalent organic frameworks as stationary phases for high-performance liquid chromatographic separation. Chinese Chemical Letters, 2025, 36(8): 110649-. doi: 10.1016/j.cclet.2024.110649
14. [14]
  Yuming Shu , Hanghang Lei , Jiangnan Huang , Qing Pan , Baichao Zhang , Yixin Xu , Ye Zhou , Guorong Hu , Yanbing Cao , Guoqiang Zou , Wentao Deng , Zhongdong Peng , Hongshuai Hou , Di Chen , Xiaobo Ji . Enabling superior performance in brick-like single-crystal LiMn₂O₄ via BaO flux. Chinese Chemical Letters, 2025, 36(9): 110345-. doi: 10.1016/j.cclet.2024.110345
15. [15]
  Yi Chen , Hua-Pan Wu , Zheng-Wei Guo , Xin-Xiong Li , Ping-Wei Cai , Shou-Tian Zheng . Construction of a diverting polyoxotungstate based on 3d-5p heterometallic cluster for high-performance single-crystal proton conduction. Chinese Chemical Letters, 2025, 36(11): 110552-. doi: 10.1016/j.cclet.2024.110552
16. [16]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
17. [17]
  Yingjie Wang , Peng Tang , Wenchao Tu , Qi Gao , Cuizhu Wang , Luying Tan , Lixin Zhao , Hongye Han , Liefeng Ma , Kouharu Otsuki , Weilie Xiao , Wenli Wang , Jinping Liu , Yong Li , Zhajun Zhan , Wei Li , Xianli Zhou , Ning Li . Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023. Chinese Chemical Letters, 2025, 36(1): 109955-. doi: 10.1016/j.cclet.2024.109955
18. [18]
  Zhiqiang Liu , Qiang Gao , Wei Shen , Meifeng Xu , Yunxin Li , Weilin Hou , Hai-Wei Shi , Yaozuo Yuan , Erwin Adams , Hian Kee Lee , Sheng Tang . Removal and fluorescence detection of antibiotics from wastewater by layered double oxides/metal-organic frameworks with different topological configurations. Chinese Chemical Letters, 2024, 35(8): 109338-. doi: 10.1016/j.cclet.2023.109338
19. [19]
  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
20. [20]
  Shiqi Peng , Yongfang Rao , Tan Li , Yufei Zhang , Jun-ji Cao , Shuncheng Lee , Yu Huang . Regulating the electronic structure of Ir single atoms by ZrO₂ nanoparticles for enhanced catalytic oxidation of formaldehyde at room temperature. Chinese Chemical Letters, 2024, 35(7): 109219-. doi: 10.1016/j.cclet.2023.109219

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(5)
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