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]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
9. [9]
  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
10. [10]
  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
11. [11]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
12. [12]
  Li Lin , Song-Lin Tian , Zhen-Yu Hu , Yu Zhang , Li-Min Chang , Jia-Jun Wang , Wan-Qiang Liu , Qing-Shuang Wang , Fang Wang . Molecular crowding electrolytes for stabilizing Zn metal anode in rechargeable aqueous batteries. Chinese Chemical Letters, 2024, 35(7): 109802-. doi: 10.1016/j.cclet.2024.109802
13. [13]
  Minghao Hu , Tianci Xie , Yuqiang Hu , Longjie Li , Ting Wang , Tongbo Wu . Allosteric DNAzyme-based encoder for molecular information transfer. Chinese Chemical Letters, 2024, 35(7): 109232-. doi: 10.1016/j.cclet.2023.109232
14. [14]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
15. [15]
  Xin Lu , Haoran Sun , Xiaomeng Li , Chunrui Li , Jinfeng Wang , Dandan Zhou . C14-HSL limits the mycelial morphology of pathogen Trichosporon cells but enhances their aggregation: Mechanisms and implications. Chinese Chemical Letters, 2024, 35(6): 108936-. doi: 10.1016/j.cclet.2023.108936
16. [16]
  Chenlu Huang , Xinyu Yang , Qingyu Yu , Linhua Zhang , Dunwan Zhu . Gas-generating polymersomes-based amplified photoimmunotherapy for abscopal effect and tumor metastasis inhibition. Chinese Chemical Letters, 2024, 35(6): 109680-. doi: 10.1016/j.cclet.2024.109680
17. [17]
  Yuanyi Zhou , Ke Ma , Jinfeng Liu , Zirun Zheng , Bo Hu , Yu Meng , Zhizhong Li , Mingshan Zhu . Is reactive oxygen species the only way for cancer inhibition over single atom nanomedicine? Autophagy regulation also works. Chinese Chemical Letters, 2024, 35(6): 109056-. doi: 10.1016/j.cclet.2023.109056
18. [18]
  Qihan Lin , Jiabin Xing , Yue-Yang Liu , Gang Wu , Shi-Jia Liu , Hui Wang , Wei Zhou , Zhan-Ting Li , Dan-Wei Zhang . taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine. Chinese Chemical Letters, 2024, 35(5): 109119-. doi: 10.1016/j.cclet.2023.109119
19. [19]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
20. [20]
  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

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沈阳化工大学材料科学与工程学院沈阳 110142