Citation: Yunshao Xu, Tian Zhang, Lu Feng, Zheling Feng, Qingwen Zhang, Yang Ye, Lishe Gan, Ligen Lin. Biscaesalmins A and B from Caesalpinia minax, highly oxidized dimeric cassane diterpenoids as interleukin-1β inhibitors[J]. Chinese Chemical Letters, ;2021, 32(4): 1475-1479. doi: 10.1016/j.cclet.2020.09.048 shu

Biscaesalmins A and B from Caesalpinia minax, highly oxidized dimeric cassane diterpenoids as interleukin-1β inhibitors

Yunshao Xu ^{a, 1} ,
Tian Zhang ^{a, 1} ,
Lu Feng ^b ,
Zheling Feng ^a ,
Qingwen Zhang ^a ,
Yang Ye ^{b, c} ,
Lishe Gan ^{d, *,} ,
Ligen Lin ^{a, *,}

a.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Avenida da Universidade, Taipa, Macau 999078, China
b.
State Key Laboratory of Drug Research, & Natural Products Chemistry Department, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
School of Life Science and Technology, Shanghai Tech University, Shanghai 201203, China
d.
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, China

ganlishe@126.com

ligenl@um.edu.mo

Received Date: 17 July 2020
Revised Date: 1 September 2020
Accepted Date: 25 September 2020
Available Online: 28 September 2020

Figures(4)

To search naturally occurring interleukin-1β (IL-1β) inhibitors, biscaesalmins A (1) and B (2), two highly oxidized dimeric cassane diterpenoids with a newly formed alicyclic skeleton, have been isolated from the traditional Chinese medicine Kushilian (Caesalpinia minax). Their full structures were determined by comprehensive spectroscopic analysis and quantum chemical TD-DFT (time-dependent density functional theory) calculation. Biosynthetically, 1 and 2 were formed via an intermolecular [4+2] Diels-Alder cycloaddition of two monomers, affording an additional six-membered carbon ring linkage. Compounds 1 and 2 inhibited nitric oxide production on lipopolysaccharide-stimulated THP-1 macrophages, with IC₅₀ values being at 1.20±0.23 and 2.30±0.15 μmol/L, respectively. Furthermore, compound 1 inhibited NLRP3 (NOD-, LRR- and pyrin domain-containing protein 3) inflammasome-mediated IL-1β production and blocked the migration of macrophages towards adipocyte conditioned medium. Biscaesalmins A and B might be candidates for treating inflammation-related metabolic diseases.
- Caesalpinia minax,
- IL-1β,
- Dimeric cassane diterpenoids,
- NLRP3,
- TD-DFT
1. [1]
  J.E. Sims, D.E. Smith, Nat. Rev. Immunol. 10(2010) 89-102.
2. [2]
  D. Gao, M. Madi, C. Ding, et al., Am. J. Physiol. Endocrinol. Metab. 307(2014) E289-E304. doi: 10.1152/ajpendo.00430.2013
3. [3]
  L.G. Lin, C.O.L. Ung, Z.L. Feng, L. Huang, H. Hu, Planta Med. 82(2016) 1309-1328. doi: 10.1055/s-0042-114573
4. [4]
  X.H. Huang, L.X. Tao, C.Q. Ke, et al., Org. Lett. 19(2017) 556-559. doi: 10.1021/acs.orglett.6b03597
5. [5]
  W.H. Jing, X.X. Zhang, H.X. Zhou, et al., Fitoterapia 134(2019) 226-249. doi: 10.1016/j.fitote.2019.02.023
6. [6]
  H. Bao, L.L. Zhang, Q.Y. Liu, et al., Molecules 21(2016) 791. doi: 10.3390/molecules21060791
7. [7]
  Z.F. Wu, H. Bao, F.Y. Zhou, et al., Chin. Chem. Lett. 28(2017) 1711-1715. doi: 10.1016/j.cclet.2017.04.023
8. [8]
  P. Tane, K.E. Bergquist, M. Tene, et al., Tetrahedron 51(1995) 11595-11600. doi: 10.1016/0040-4020(95)00720-S
9. [9]
  Nanjing University of Traditional Chinese Medicine, Dictionary of Chinese Traditional Medicine, Vol. 1, Shanghai People's Publishing House, Shanghai, 2005, pp. 1766.
10. [10]
  G.X. Ma, J.Q. Yuan, H.F. Wu, et al., J. Nat. Prod. 76(2013) 1025-1031. doi: 10.1021/np300918q
11. [11]
  J.L. Zhang, Z.H. Chen, J. Xu, et al., RSC Adv. 5(2015) 76567-76574. doi: 10.1039/C5RA14221K
12. [12]
  M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision A. 1, Gaussian Inc., Wallingford CT, 2009.
13. [13]
  S.R. Laplante, P.J. Edwards, L.D. Fader, A. Jakalian, O. Hucke, ChemMedChem 6(2011) 505-513. doi: 10.1002/cmdc.201000485
14. [14]
  R.W. Jiang, P.P. But, S.C. Ma, T.C.W. Mak, Phytochemistry 57(2001) 517-521. doi: 10.1016/S0031-9422(01)00134-0
15. [15]
  R.W. Jiang, S.C. Ma, P.P. But, T.C.W. Mak, J. Nat. Prod. 64(2001) 1266-1272. doi: 10.1021/np010174+
16. [16]
  S.K. Kalauni, S. Awale, Y. Tezuka, et al., J. Nat. Prod. 67(2004) 1859-1863. doi: 10.1021/np049742m
17. [17]
  C.N. Lemeng, S.M. DeYong, J.L. Bodzin, A.R. Saltiel, Diabetes 56(2007) 16-23. doi: 10.2337/db06-1076
18. [18]
  D. Li, T. Zhang, J.J. Lu, C. Peng, L.G. Lin, Crit. Rev. Food Sci. Nutr. (2020), doi: http://dx.doi.org/10.1080/10408398.2020.1768044. doi: 10.1080/10408398.2020.1768044
19. [19]
  T. Liu, L.Y. Zhang, D.H. Joo, S.C. Sun, Signal Transduct. Target. Ther. 2(2017) e17023. doi: 10.1038/sigtrans.2017.23
20. [20]
  D. Li, Q.Y. Liu, W. Sun, et al., Br. J. Pharmacol. 175(2018) 1590-1606. doi: 10.1111/bph.14162
1. [1]
  Ling-Hao Zhao , Hai-Wei Yan , Jian-Shuang Jiang , Xu Zhang , Xiang Yuan , Ya-Nan Yang , Pei-Cheng Zhang . Effective assignment of positional isomers in dimeric shikonin and its analogs by ¹H NMR spectroscopy. Chinese Chemical Letters, 2024, 35(5): 108863-. doi: 10.1016/j.cclet.2023.108863
2. [2]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
3. [3]
  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
4. [4]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
5. [5]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
6. [6]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
7. [7]
  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
8. [8]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
9. [9]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
10. [10]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
11. [11]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
12. [12]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
13. [13]
  Boyuan Hu , Jian Zhang , Yulin Yang , Yayu Dong , Jiaqi Wang , Wei Wang , Kaifeng Lin , Debin Xia . Dual-functional POM@IL complex modulate hole transport layer properties and interfacial charge dynamics for highly efficient and stable perovskite solar cells. Chinese Chemical Letters, 2024, 35(7): 108933-. doi: 10.1016/j.cclet.2023.108933
14. [14]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
15. [15]
  Tao Ban , Xi-Yang Yu , Hai-Kuo Tian , Zheng-Qing Huang , Chun-Ran Chang . One-step conversion of methane and formaldehyde to ethanol over SA-FLP dual-active-site catalysts: A DFT study. Chinese Chemical Letters, 2024, 35(4): 108549-. doi: 10.1016/j.cclet.2023.108549
16. [16]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
17. [17]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
18. [18]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
19. [19]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
20. [20]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(625)
HTML views(113)

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