Citation: Jiwu Huang, Chuangjun Li, Jie Ma, Yingda Zang, Xingyan Sun, Xiaoguang Chen, Dongming Zhang. Psiguamers A–C, three cytotoxic meroterpenoids bearing a methylated benzoylphloroglucinol framework from Psidium guajava and total synthesis of 1 and 2[J]. Chinese Chemical Letters, ;2021, 32(5): 1721-1725. doi: 10.1016/j.cclet.2020.11.028 shu

Psiguamers A–C, three cytotoxic meroterpenoids bearing a methylated benzoylphloroglucinol framework from Psidium guajava and total synthesis of 1 and 2

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

zhangdm@imm.ac.cn

Received Date: 27 August 2020
Revised Date: 27 September 2020
Accepted Date: 12 November 2020
Available Online: 22 November 2020

Figures(4)

Three sesquiterpene-based meroterpenoids psiguamers A–C (1–3) with new skeletons were isolated from Psidium guajava leaves. Compounds (±)-1 and (±)-2 were two pairs of humulene-derived meroterpenoids bearing a rare methylated benzoylphloroglucinol unit, while 3 was an unprecedented adduct of bicyclogermacrene and methylated benzoylphloroglucinol. Their structures were determined based on comprehensive analyses of spectroscopic data, calculated electronic circular dichroism (ECD) spectra, total synthesis, and X-ray crystallographic data. The biomimetic synthesis of (±)-1 and (±)-2 was achieved. Compound (+)-1 exhibited cytotoxic activities against five human tumor cell lines (HCT-116, HepG2, BGC-823, A549, and U251), with IC₅₀ values of 2.94, 9.01, 6.45, 5.42, and 5.33 μmol/L, respectively.
- Psidium guajava,
- Methylated benzoylphloroglucinol,
- Meroterpenoids,
- Biomimetic synthesis,
- Cytotoxic activities
1. [1]
  H.Z. Fu, Y.M. Luo, C.J. Li, et al., Org. Lett. 12(2010) 656-659. doi: 10.1021/ol9024869
2. [2]
  S. Ning, Z.L. Liu, Z.C. Wang, et al., Org. Lett. 21(2019) 8700-8704. doi: 10.1021/acs.orglett.9b03299
3. [3]
  C.J. Li, J. Ma, H. Sun, et al., Org. Lett. 18(2016) 168-171. doi: 10.1021/acs.orglett.5b03117
4. [4]
  X.J. Qin, Q. Yu, H. Yan, et al., J. Agric. Food Chem. 65(2017) 4993-4999. doi: 10.1021/acs.jafc.7b01762
5. [5]
  Y.Q. Jian, X.J. Huang, D.M. Zhang, et al., Chem. Eur. J. 21(2015) 9022-9027. doi: 10.1002/chem.201500533
6. [6]
  G.H. Tang, Z. Dong, Y.Q. Guo, et al., Sci. Rep. 7(2017) 1047. doi: 10.1038/s41598-017-01028-4
7. [7]
  X.L. Yang, K.L. Hsieh, J.K. Liu, Org. Lett. 9(2007) 5135-5138. doi: 10.1021/ol702537q
8. [8]
  Y. Gao, G.T. Li, Y. Li, et al., Nat. Prod. Bioprospect. 3(2013) 14-19. doi: 10.1007/s13659-012-0102-4
9. [9]
  J. Liu, L.R. Jiang, M.F. Liu, Chem. Nat. Compd. 52(2016) 67-70. doi: 10.1007/s10600-016-1548-0
10. [10]
  H. Liu, M.Y. Feng, Q. Yu, et al., Tetrahedron 74(2018) 1540-1545. doi: 10.1016/j.tet.2018.02.020
11. [11]
  K.F. do Nascimento, F.M.F. Moreira, J.A. Santos, et al., J. Ethnopharmacol. 210(2018) 351-358. doi: 10.1016/j.jep.2017.08.030
12. [12]
  G.E. Moussa, Acta Chem. Scand. 22(1968) 3329-3330. doi: 10.3891/acta.chem.scand.22-3329
13. [13]
  T.D. de Souza, M.F. Ferreira, L. Menini, et al., Sci. Hortic. 216(2017) 38-44. doi: 10.1016/j.scienta.2016.12.026
14. [14]
  M. Shao, Y. Wang, Y.Q. Jian, et al., Org. Lett. 14(2012) 5262-5265. doi: 10.1021/ol302423b
15. [15]
  S.B. Bharate, K.K. Bhutani, S.I. Khan, et al., Biorg. Med. Chem. 14(2006) 1750-1760. doi: 10.1016/j.bmc.2005.10.027
16. [16]
  G.Y. Lv, D.J. Sun, J.W. Zhang, et al., Acta Pharm. Sin. B 7(2017) 52-58. doi: 10.1016/j.apsb.2016.06.005
1. [1]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
2. [2]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
3. [3]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
4. [4]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
5. [5]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
6. [6]
  Wei-Yu Zhou , Zi-Han Xi , Ning-Ning Du , Li Ye , Ming-Hao Jiang , Jin-Le Hao , Bin Lin , Guo-Dong Yao , Xiao-Xiao Huang , Shao-Jiang Song . Rapid discovery of two unprecedented meroterpenoids from Daphne altaica Pall. using molecular networking integrated with MolNetEnhancer and Network Annotation Propagation. Chinese Chemical Letters, 2024, 35(8): 109030-. doi: 10.1016/j.cclet.2023.109030
7. [7]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
8. [8]
  Fengjie Liu , Fansu Meng , Zhenjiang Yang , Huan Wang , Yuehong Ren , Yu Cai , Xingwang Zhang . Exosome-biomimetic nanocarriers for oral drug delivery. Chinese Chemical Letters, 2024, 35(9): 109335-. doi: 10.1016/j.cclet.2023.109335
9. [9]
  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
10. [10]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
11. [11]
  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
12. [12]
  Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
13. [13]
  Ting Li , Xinxin Zheng , Lejing Qu , Yuanyuan Ou , Sai Qiao , Xue Zhao , Yajun Zhang , Xinfeng Zhao , Qian Li . A chromatographic method for pursuing potential GPCR ligands with the capacity to characterize their intrinsic activities of regulating downstream signaling pathway. Chinese Chemical Letters, 2024, 35(10): 109792-. doi: 10.1016/j.cclet.2024.109792
14. [14]
  Yuanzheng Wang , Chen Zhang , Shuyan Han , Xiaoli Kong , Changyun Quan , Jun Wu , Wei Zhang . Cancer cell membrane camouflaged biomimetic gelatin-based nanogel for tumor inhibition. Chinese Chemical Letters, 2024, 35(11): 109578-. doi: 10.1016/j.cclet.2024.109578
15. [15]
  Wenbin Zhou , Yafei Gao , Xinyu Feng , Yanqing Zhang , Cong Yang , Lanxi He , Fenghe Zhang , Xiaoguang Li , Qing Li . Biomimetic nanoplatform integrates FRET-enhanced photodynamic therapy and chemotherapy for cascaded revitalization of the tumor immune microenvironment in OSCC. Chinese Chemical Letters, 2025, 36(1): 109763-. doi: 10.1016/j.cclet.2024.109763
16. [16]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
17. [17]
  Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
18. [18]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
19. [19]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
20. [20]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362

Get Citation

PDF

XML

Metrics

PDF Downloads(13)
Abstract views(768)
HTML views(103)

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