Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(10): 109458. doi: 10.1016/j.cclet.2023.109458 shu

Unprecedented sesquiterpene-polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex Ⅴ

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

qytong@hust.edu.cn

qichangxing@hust.edu.cn

zhangyh@mails.tjmu.edu.cn

Received Date: 31 October 2023
Revised Date: 22 December 2023
Accepted Date: 22 December 2023
Available Online: 29 December 2023

Figures(4)

Monosescinol A (1), the first example of sesquiterpene–polycyclic polyprenylated acylphloroglucinol (PPAP) adduct, which represented a new subclass of PPAP-type natural products, along with two new congeners with normal spiro 6/6/5 tricyclic architecture, were isolated from Hypericum longistylum. Monosescinol A possessed an unprecedented 6/5/5/6/6 pentacyclic carbon skeleton that might be assembled from the 6/6/5 carbon skeleton, via the splitting decomposition of C-3/C-14, and the attack from the C-3 in the PPAP core to C-28 in sesquiterpene section. In addition, we have firstly confirmed that 24R configuration was existed in sec–Bu containing PPAPs by single crystal diffraction data analysis of monosescinol B (2), that might provide an enlightenment in the configurational determination of sec–Bu containing PPAPs. Significantly, further pharmacological research has found that compound 1 exhibited remarkable pharmacological effects against acute myeloid leukemia (AML) cell lines, with direct inhibition of mitochondrial complex Ⅴ and an increase in mitochondrial membrane potential, and led to an induction of oxidative stress, endogenous inflammation, and apoptosis of AML cells.
- PPAP adduct,
- Single-crystal X-ray diffraction,
- Keto-enol tautomerism,
- Plausible biosynthetic pathway,
- Cytotoxic activity
1. [1]
  F. Baron1, M. Labopin, J. Tischer, et al., J. Hematol. Oncol. 16 (2023) 10. doi: 10.1186/s13045-023-01403-x
2. [2]
  H. Jin, Y. Zhang, S.J. Yu, et al., J. Hematol. Oncol. 16 (2023) 42. doi: 10.1186/s13045-023-01437-1
3. [3]
  X.W. Yang, R.B. Grossman, G. Xu, Chem. Rev. 118 (2018) 3508–3558. doi: 10.1021/acs.chemrev.7b00551
4. [4]
  Y. Guo, F. Huang, W.G. Sun, et al., Chem. Sci. 12 (2021) 11438–11446. doi: 10.1039/D1SC03356E
5. [5]
  S. Abe, N. Tanaka, J. Kobayashi, J. Nat. Prod. 75 (2012) 484–488. doi: 10.1021/np200741x
6. [6]
  C.X. Qi, J. Bao, J.P. Wang, et al., Chem. Sci. 7 (2016) 6563–6572. doi: 10.1039/C6SC02464E
7. [7]
  S. Lin, J. Huang, H. Zeng, et al., Chin. Chem. Lett. 33 (2022) 4587–4594. doi: 10.1016/j.cclet.2022.03.064
8. [8]
  F. Li, W. Sun, S. Zhang, et al., Chin. Chem. Lett. 31 (2020) 197–201. doi: 10.1016/j.cclet.2019.04.036
9. [9]
  Y. Ye, N. Jiang, X. Yang, et al., Chin. Chem. Lett. 31 (2020) 2433–2436. doi: 10.1016/j.cclet.2020.04.028
10. [10]
  W. Lu, Y. Zhang, Y. Li, et al., Chin. Chem. Lett. 33 (2022) 4121–4125. doi: 10.1016/j.cclet.2021.11.011
11. [11]
  Z.Y. Shi, H. Hu, Y. Guo, et al., Org. Biomol. Chem. 20 (2022) 1284–1291. doi: 10.1039/D1OB02107A
12. [12]
  N. Zhang, Z.Y. Shi, Y. Guo, et al., Org. Chem. Front. 6 (2019) 1491–1502. doi: 10.1039/C9QO00245F
13. [13]
  N. Zhang, Z.Y. Shi, Q.Q. Xu, et al., Org. Lett. 22 (2020) 7926–7929. doi: 10.1021/acs.orglett.0c02853
14. [14]
  W.J. Xu, J. Luo, R.J. Li, et al., Org. Chem. Front. 4 (2017) 313–317. doi: 10.1039/C6QO00620E
1. [1]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
11. [11]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
12. [12]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
13. [13]
  Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO₃. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
14. [14]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
15. [15]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
16. [16]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
17. [17]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
18. [18]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
19. [19]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
20. [20]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(130)
HTML views(6)

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