Citation: Shushuai Chen, Hongxin Liu, Saini Li, Yuchan Chen, Wei Ye, Haohua Li, Haibo Tan, Dongli Li, Zhaoming Liu, Weimin Zhang. Hawanoids A‒E, unprecedented diterpenoids with PAF-induced platelet aggregation inhibitory activities from the deep-sea-derived fungus Paraconiothyrium hawaiiense[J]. Chinese Chemical Letters, ;2023, 34(2): 107513. doi: 10.1016/j.cclet.2022.05.027 shu

Hawanoids A‒E, unprecedented diterpenoids with PAF-induced platelet aggregation inhibitory activities from the deep-sea-derived fungus Paraconiothyrium hawaiiense

Shushuai Chen ^{a, b, 1} ,
Hongxin Liu ^{a, 1} ,
Saini Li ^a ,
Yuchan Chen ^a ,
Wei Ye ^a ,
Haohua Li ^a ,
Haibo Tan ^c ,
Dongli Li ^b ,
Zhaoming Liu ^{a, *,} ,
Weimin Zhang ^{a, *,}

a.
State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou 510070, China
b.
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China
c.
Program for Natural Product Chemical Biology, Key Laboratory Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China

liuzm@gdim.cn

wmzhang@gdim.cn

Received Date: 18 February 2022
Revised Date: 7 May 2022
Accepted Date: 11 May 2022
Available Online: 14 May 2022

Figures(4)

Hawanoids A‒E (1‒5), five highly cyclized diterpenoids were isolated from the deep-sea-derived fungus Paraconiothyrium hawaiiense FS482. Compounds 1 and 2 possessed an unprecedented tetracyclo[6.6.2.0^2,7.0^11,15]cetane carbon skeleton while 3 and 4 possessed an unusual 11, 14-macrocyclic ether moiety in phomactin family. Their structures including the stereo-chemistry were determined through spectroscopic analysis, X-ray diffractions and computational calculations. The plausible biosynthetic pathway was proposed based on the predicted biosynthetic gene cluster. All of the isolated compounds exhibited inhibitory activities against PAF-induced platelet aggregation. The molecular docking study was carried out understand the interaction between the PAF receptor and hawanoids with different skeletons.
- Diterpenoids,
- Deep-sea-derived fungus,
- Biosynthetic pathway,
- Platelet aggregation inhibition,
- Molecular docking
1. [1]
  Y. Kuroda, K.J. Nicacio, I.A. Silva-Jr, et al., Nat. Chem. 10 (2018) 938–945. doi: 10.1038/s41557-018-0084-x
2. [2]
  J. Ciesielski, A. Frontier, Org. Prep. Proced. Int. 46 (2014) 214–251. doi: 10.1080/00304948.2014.903142
3. [3]
  J. Huang, W. Bao, S. Huang, et al., Org. Lett. 20 (2018) 7466–7469. doi: 10.1021/acs.orglett.8b03242
4. [4]
  R. Guo, H. Zhai, Li Y, Chin. Chem. Lett. 32 (2021) 1400–1402. doi: 10.1016/j.cclet.2020.09.023
5. [5]
  M. Sugano, A. Sato, Y. Iijima, et al., J. Am. Chem. Soc. 113 (1991) 5463–5464. doi: 10.1021/ja00014a053
6. [6]
  M. Sugano, A. Sato, Y. Iijima, et al., J. Org. Chem. 59 (1994) 564–569. doi: 10.1021/jo00082a012
7. [7]
  M. Sugano, A. Sato, Y. Iijima, et al., J. Antibiot. 48 (1995) 1188–1190. doi: 10.7164/antibiotics.48.1188
8. [8]
  M. Chu, I. Truumees, I. Gunnarsson, et al., J. Antibiot. 46 (1993) 554–563. doi: 10.7164/antibiotics.46.554
9. [9]
  K. Koyama, M. Ishino, K. Takatori, et al., Tetrahedron Lett. 45 (2004) 6947–6948. doi: 10.1016/j.tetlet.2004.07.071
10. [10]
  M. Ishino, N. Kiyomichi, K. Takatori, et al., Tetrahedron 66 (2010) 2594–2597. doi: 10.1016/j.tet.2010.02.040
11. [11]
  M. Ishino, K. Kinoshita, K. Takahashi, et al., Tetrahedron 68 (2012) 8572–8576. doi: 10.1016/j.tet.2012.08.013
12. [12]
  M. Ishino, H. Kamauchi, K. Takatori, et al., Tetrahedron Lett. 57 (2016) 4341–4344. doi: 10.1016/j.tetlet.2016.08.016
13. [13]
  M.R.Z. Passarini, C. Santos, N. Lima, R.G.S. Berlinck, L.D. Sette, Arch. Microbiol. 195 (2013) 99–111. doi: 10.1007/s00203-012-0854-6
14. [14]
  G. Daletos, W. Ebrahim, E. Ancheeva, et al., Curr. Med. Chem. 22 (2018) 186–207.
15. [15]
  Y.T. Wang, Y.R. Xue, C.H. Liu, Mar. Drugs 13 (2015) 4594–4616. doi: 10.3390/md13084594
16. [16]
  C.L. Xie, D. Zhang, K.Q. Guo, et al., Chin. Chem. Lett. 33 (2022) 2057–2059. doi: 10.1016/j.cclet.2021.09.073
17. [17]
  J. Xu, H. Tan, Y. Chen, et al., Chin. Chem. Lett. 30 (2019) 439–442. doi: 10.1016/j.cclet.2018.09.018
18. [18]
  C. Gui, W. Zhu, G. Chen, et al., Proteins 67 (2007) 41–52. doi: 10.1002/prot.21213
1. [1]
  Yi-Ru Bai , Qing-Chuan Duan , Dong-Jie Seng , Ying Xu , Hong-Bo Ren , Jie Zhang , Dan-Dan Shen , Li Yang , Hong-Min Liu , Shuo Yuan . A comprehensive review of small molecule drugs approved by the FDA in 2024: Advance and prospect. Chinese Chemical Letters, 2025, 36(10): 111025-. doi: 10.1016/j.cclet.2025.111025
2. [2]
  Kunya Wang , Bingyu Liu , Daojiang Yan , Jian Bai , Haibo Yu , Youcai Hu . Full biosynthetic pathway of pyrrolobenzoxazines. Chinese Chemical Letters, 2025, 36(1): 109811-. doi: 10.1016/j.cclet.2024.109811
3. [3]
  Zhi Zhou , Yu-E Lian , Yuqing Li , Hui Gao , Wei Yi . New Insights into the Molecular Mechanism Behind Clinical Tragedies of “Cephalosporin with Alcohol”. University Chemistry, 2025, 40(3): 42-51. doi: 10.12461/PKU.DXHX202403104
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Yaojun Li , Yun Li , Shenglong Liao , Yang Li , Shouchun Yin . Revolutionizing cancer therapies with organic photovoltaic non-fullerene acceptors: A deep dive into molecular engineering for advanced phototheranostics. Chinese Chemical Letters, 2025, 36(8): 110832-. doi: 10.1016/j.cclet.2025.110832
8. [8]
  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
9. [9]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
10. [10]
  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
11. [11]
  Huaran Zhang , Yuting Huang , Yingjie Tang , Dekun Kong , Yi Zou . Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type Ⅲ- polyketide pathway. Chinese Chemical Letters, 2024, 35(7): 108968-. doi: 10.1016/j.cclet.2023.108968
12. [12]
  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
13. [13]
  Xia Xu , Guiqian Yang , Zhen Zheng , Cody J. Wenthur , Jinyu Li , Gongyu Li . The sheet-to-helix transition is a potential gas-phase unfolding pathway for a multidomain protein CRM₁₉₇. Chinese Chemical Letters, 2025, 36(7): 110401-. doi: 10.1016/j.cclet.2024.110401
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Yanwei Duan , Qing Yang . Molecular targets and their application examples for interrupting chitin biosynthesis. Chinese Chemical Letters, 2025, 36(4): 109905-. doi: 10.1016/j.cclet.2024.109905
18. [18]
  Fanxin Kong , Hongzhi Wang , Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287
19. [19]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
20. [20]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1933)
HTML views(232)

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