Citation: Weixia Ye, Kai Liu, Wei Liu, Xianbo Chen, Xuemin Ding, Haiyan Tian, Wenjun Zhang, Changsheng Zhang. Novel lipopeptides featuring unusual C–C and C–N linkages between cyclic peptides and fatty acyl chains[J]. Chinese Chemical Letters, ;2026, 37(12): 112293. doi: 10.1016/j.cclet.2025.112293 shu

Novel lipopeptides featuring unusual C–C and C–N linkages between cyclic peptides and fatty acyl chains

Weixia Ye ^{a, b} ,
Kai Liu ^a ,
Wei Liu ^a ,
Xianbo Chen ^b ,
Xuemin Ding ^{a, c} ,
Haiyan Tian ^{b, *,} ,
Wenjun Zhang ^{a, c, *,} ,
Changsheng Zhang ^{a, c, *,}

a.
State Key Laboratory of Tropical Oceanography, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
b.
Institute of Traditional Chinese Medicine and Natural Products, International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Discovery of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, Guangzhou 510632, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

thytian@jnu.edu.cn

wzhang@scsio.ac.cn

czhang@scsio.ac.cn

Received Date: 14 October 2025
Revised Date: 15 December 2025
Accepted Date: 16 December 2025
Available Online: 17 December 2025

Figures(5)

Lipounguisins (LPUs) A‒K (9‒19), eleven novel lipopeptides were isolated from the sponge-associated fungus Aspergillus sp. SCSIO 40435. LPUs represent a rare class of lipopeptides (LPs), featuring cyclic heptapeptides conjugated to diverse octadecadienoic acids (either trans Δ¹⁰, Δ¹² or trans Δ⁹, Δ¹¹) via a C‒C or C‒N bond, and showed bioactivities including anti-Gram-positive bacteria, inhibitory activity of α-glucosidase, and cytotoxicity to Huh-7 (half-maximal inhibitory concentration (IC₅₀) = 5.42 µmol/L). A radical-mediated coupling reaction between unguisins and octadecadienoic acids was proposed to account for LPU formation.
- Dracaena cochinchinensis,
- Aspergillus sp.,
- Unguisins,
- Lipounguisins A‒K,
- Inhibitory activity of α-glucosidase
1. [1]
  S. Zhang, Y. Chen, J. Zhu, et al., Nat. Prod. Rep. 40 (2023) 557–594. doi: 10.1039/D2NP00044J
2. [2]
  S.M. Sreedharan, N. Rishi, R. Singh, Microbiol. Res. 271 (2023) 127363. doi: 10.1016/j.micres.2023.127363
3. [3]
  S. Götze, P. Stallforth, Nat. Prod. Rep. 37 (2020) 29–54. doi: 10.1039/c9np00022d
4. [4]
  R. Aoki, E. Kumagawa, K. Kamata, et al., Commun. Chem. 8 (2025) 17. doi: 10.1038/s42004-024-01379-w
5. [5]
  J. Malmstrøm, J. Nat. Prod. 62 (1999) 787–789. doi: 10.1021/np980539z
6. [6]
  J. Malmstrøm, A. Ryager, U. Anthoni, et al., Phytochemistry 60 (2002) 869–872. doi: 10.1016/S0031-9422(02)00150-4
7. [7]
  S. Liu, Y. Shen, Chem. Nat. Compd. 47 (2011) 786–788. doi: 10.1007/s10600-011-0059-2
8. [8]
  W. Li, F.W. Jiao, J.Q. Wang, et al., Tetrahedron Lett. 61 (2020) 152322. doi: 10.1016/j.tetlet.2020.152322
9. [9]
  S. Neupane, M. Rodrigues de Amorim, E. Skellam, Beilstein J. Org. Chem. 20 (2024) 321–330. doi: 10.3762/bjoc.20.32
10. [10]
  W. Diao, W. Zhang, X. Zhang, et al., Mar. Drugs 23 (2025) 219. doi: 10.3390/md23050219
11. [11]
  S.H. Akone, G. Daletos, W. Lin, et al., Z. Naturforsch C 71 (2016) 15–19. doi: 10.1515/znc-2015-0137
12. [12]
  X. Wei, T.K. Chan, C.T.D. Kong, et al., J. Nat. Prod. 86 (2023) 416–422. doi: 10.1021/acs.jnatprod.2c01065
13. [13]
  A. Fu, C. Chen, Q. Li, et al., Chin. Chem. Lett. 35 (2024) 109100. doi: 10.1016/j.cclet.2023.109100
14. [14]
  H. Zhang, C.P. Li, L.L. Wang, et al., Chin. Chem. Lett. 35 (2024) 109351. doi: 10.1016/j.cclet.2023.109351
15. [15]
  W. Ye, M. Zhao, L. Wang, et al., Acta Microbiol. Sin. 62 (2022) 1819–1831.
16. [16]
  N. Matsumori, D. Kaneno, M. Murata, et al., J. Org. Chem. 64 (1999) 866–876. doi: 10.1021/jo981810k
17. [17]
  M. Alı́as, M.a.P. López, C. Cativiela, Tetrahedron 60 (2004) 885–891. doi: 10.1016/j.tet.2003.11.044
18. [18]
  J. Foote, C. Milstein, Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 10370–10374. doi: 10.1073/pnas.91.22.10370
19. [19]
  R. Radeglia, H. Poleschner, G. Haufe, Magn. Reson. Chem. 31 (1993) 1054–1056. doi: 10.1002/mrc.1260311205
20. [20]
  K. Blin, S. Shaw, A.M. Kloosterman, et al., Nucl. Acids Res. 49 (2021) W29–W35. doi: 10.1093/nar/gkab335
21. [21]
  Y.T. Huang, S.Y. Lyu, P.H. Chuang, et al., ChemBioChem 10 (2009) 2480–2487. doi: 10.1002/cbic.200900351
22. [22]
  R.E. Minto, B.J. Blacklock, Prog. Lipid Res. 47 (2008) 233–306. doi: 10.1016/j.plipres.2008.02.002
23. [23]
  J. Liu, X. Xie, S.M. Li, Angew. Chem. Int. Ed. 58 (2019) 11534–11540. doi: 10.1002/anie.201906891
24. [24]
  V.V. Shende, Y. Khatri, S.A. Newmister, et al., J. Am. Chem. Soc. 142 (2020) 17413–17424. doi: 10.1021/jacs.0c06312
25. [25]
  J.P. Kehrer, Toxicology 149 (2000) 43–50. doi: 10.1016/S0300-483X(00)00231-6
26. [26]
  C. Yang, C. Huang, C. Fang, et al., J. Org. Chem. 86 (2021) 11019–11028. doi: 10.1021/acs.joc.0c02517
27. [27]
  H. He, R.T. Williamson, B. Shen, et al., J. Am. Chem. Soc. 124 (2002) 9729–9736. doi: 10.1021/ja020257s
1. [1]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
2. [2]
  Xia Wei , Zheng-Wu Luo , Guo-Qiang Zhang , Yan-An Lin , Ze-Kun Zhang , Lin-Kun An , Xi-Xin He , Jun-Cheng Su , Cui-Xian Zhang . Sterpiperazines A and B, steroid-indole alkaloids with Tdp1 inhibitory and chemotherapy sensitizing activities from marine fungus Aspergillus sp. EGF 15-0-3. Chinese Chemical Letters, 2026, 37(2): 111048-. doi: 10.1016/j.cclet.2025.111048
3. [3]
  Hai-Ying Yu , Yu-Wei Huang , Li-Ping Lin , Ren-Xiang Tan . Unprecedented diphenyl ether hybrids and spiro-diphenyl ether with antioxidant activity from Aspergillus sp. F1-8A associated with toad venom. Chinese Chemical Letters, 2026, 37(2): 111121-. doi: 10.1016/j.cclet.2025.111121
4. [4]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
5. [5]
  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
6. [6]
  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
7. [7]
  Shuige Zhao , Pengcheng Yan , Peipei Liu , Haishan Liu , Ning Li , Peng Fu , Weiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950
8. [8]
  Xiaoyong Shu , Shizong Wang , Jianlong Wang , Qi Zhou , Yong Liu , Yongxia Sun . Treatment of high salinity wastewater by Chryseobacterium sp. coupled to ionizing irradiation technology. Chinese Chemical Letters, 2026, 37(8): 112321-. doi: 10.1016/j.cclet.2025.112321
9. [9]
  Jinwei Ren , Ruiyun Huo , Xiaoqi Sun , Guobo Guan , Ying Shi , Yangyang Han , Yongsheng Che , Ling Liu . Anti-MRSA anthrone–macrolide hybrids from the ascomycete fungus Neonectria sp.. Chinese Chemical Letters, 2026, 37(8): 111780-. doi: 10.1016/j.cclet.2025.111780
10. [10]
  Qiyao Zhang , Yuting Li , Qishun Jin , Zhengwei Liu , Hongsong Chen , Jingqi Huang , Taoyi Liu , Xiaojuan Liu , Zhenghuai Tan , Shuheng Huang , Wu Dong , Zhipei Sang . Artificial intelligence-driven development of natural multi-target derivatives with BuChE inhibitory activity for treating Alzheimer’s disease. Chinese Chemical Letters, 2026, 37(1): 110964-. doi: 10.1016/j.cclet.2025.110964
11. [11]
  Bingchuan Geng , Jiangchun Wei , Dan Hu , Xingpiao Jin , Pingping Fan , Yahui Huang , Xiaoxuan Duan , Yipin Zhao , Yonghui Zhang , Zhengxi Hu . Bioassay- and molecular network-guided discovery of PPAP derivatives from Hypericum monogynum with inhibitory activity against cardiac valve calcification. Chinese Chemical Letters, 2026, 37(9): 112069-. doi: 10.1016/j.cclet.2025.112069
12. [12]
  Zhou Li , Mengxue Yu , Shixin Chang , Zhibin Huang , Zhenmin Cheng , Weibin Zhang , Sónia A. C. Carabineiro , Zhigao Xu , Kangle Lv . Enhancing the photocatalytic activity of crystalline g-C3N4 towards NO oxidation and CO2 reduction through K+-doping and cyano defect engineering. Chinese Journal of Structural Chemistry, 2026, 45(1): 100698-100698. doi: 10.1016/j.cjsc.2025.100698
13. [13]
  Zheng-Biao Zou , Tai-Zong Wu , Chun-Lan Xie , Yuan Wang , Yan Li , Gang Zhang , Rong Chao , Lian-Zhong Luo , Li-Sheng Li , Xian-Wen Yang . neo-Dicitrinols A–C: Unprecedented PKS-NRPS hybrid citrinin dimers with ferroptosis inhibitory activity from the deep-sea-derived Penicillium citrinum W22. Chinese Chemical Letters, 2024, 35(12): 109723-. doi: 10.1016/j.cclet.2024.109723
14. [14]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
15. [15]
  Wang CHEN , Guixian WU , Yingying XIONG , Ming CHENG , Mingming ZHOU , Hui ZHANG , Zhengyun LIANG , Dejin HUANG , Minghua CHEN . Crystal structures of complexes of cyclobutanocucurbit[5]uril with Na⁺/K⁺: Coordination state in different anionic environments. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 161-169. doi: 10.11862/CJIC.20250195
16. [16]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
17. [17]
  Olga Reutova , Wenqi Jin , Congwei Xie , Junjie Li , Zhihua Yang , Xueling Hou , Shilie Pan . Topology-symmetry analysis and structure prediction in nonlinear optical AB4O6F (A = Na, K, Rb, Cs, NH4) and AAlB3O6F (A = K, Rb, Cs) polytypes. Chinese Journal of Structural Chemistry, 2026, 45(7): 100924-100924. doi: 10.1016/j.cjsc.2026.100924
18. [18]
  Kun Zou , Yihang Xiao , Jinyu Yang , Mingxuan Wu . Facile semisynthesis of histone H3 enables nucleosome probes for investigation of histone H3K79 modifications. Chinese Chemical Letters, 2024, 35(10): 109497-. doi: 10.1016/j.cclet.2024.109497
19. [19]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
20. [20]
  Junjie Duan , Dan Chen , Long Chen , Shuying Li , Ting Chen , Dong Wang . 2D hexagonal tessellations sustained by Br···Br/H contacts: From regular to semiregular to k-uniform tilings. Chinese Chemical Letters, 2025, 36(3): 110445-. doi: 10.1016/j.cclet.2024.110445

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4)
HTML views(0)

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