Rubellawus A-D, Four New Diterpenoids Isolated from Callicarpa rubella and Their Anti-NLRP3 Inflammasome Effects.
Callicarpa rubella
NLRP3 inflammasome
anti-inflammatory activity
diterpenoids
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Dec 2020
Dec 2020
Historique:
received:
24
09
2020
accepted:
30
10
2020
pubmed:
3
11
2020
medline:
24
6
2021
entrez:
2
11
2020
Statut:
ppublish
Résumé
Four new diterpenoids, rubellawus A-D (1-4), along with three known compounds, were isolated and identified from the flowers of Callicarpa rubella. Their structures were elucidated by various spectroscopic analysis. All the compounds were screened for their anti-inflammatory activity and 14α-hydroxyisopimaric acid and isopimaric acid showed significant NLRP3 inflammasome inhibitory activity with IC
Identifiants
pubmed: 33135326
doi: 10.1002/cbdv.202000798
doi:
Substances chimiques
Diterpenes
0
Inflammasomes
0
NLR Family, Pyrin Domain-Containing 3 Protein
0
NLRP3 protein, human
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000798Subventions
Organisme : NSFC
ID : 81860615
Organisme : NSFC
ID : 21762048
Organisme : NSFC
ID : 81422046
Organisme : Yunnan Applicative and Basic Research Program
ID : 2018FY001
Organisme : Yunnan Applicative and Basic Research Program
ID : 2018FA048
Organisme : Foundation of Yunnan Educational Committee
ID : 2018JS002
Organisme : Natural Science Foundation of Yunnan University
ID : 2017YDQN03
Organisme : Program for Changjiang Scholars and Innovative Research Team in University
ID : IRT 17R94
Organisme : Yunnan University's Research Innovation Fund for Graduate Students
ID : 2019190
Organisme : Open Fund of the Guangdong Provincial Key Laboratory of Regional Immunity and Diseases, Shenzhen University School of Medicine
ID : 2019B030301009
Organisme : Project of Innovative Research Team of Yunnan Province
Organisme : Yun Ling Scholar Project to Wei-Lie Xiao
Informations de copyright
© 2020 Wiley-VHCA AG, Zurich, Switzerland.
Références
W. J. Zheng, L. G. Fu, ‘Flora of China’, Science Press, Beijing, 1982, Vol. 65, p. 63.
Z.-H. Wang, H.-J. Xu, Y.-Y. Zhai, L.-P. Yang, Q. Li, M. Huang, X.-Y. Chen, W.-K. Zhang, Y.-L. Meng, Q.-L. Zhang, C. Niu, Y.-R. Zhang, ‘Three new labdane-type diterpenoids from Callicarpa macrophylla Vahl’, Nat. Prod. Res. 2018, 33, 2904-2910.
Y. Wang, J. Lin, Q. Wang, K. Shang, D.-B. Pu, R.-H. Zhang, X.-L. Li, X.-C. Dai, X.-J. Zhang, W.-L. Xiao, ‘Clerodane diterpenoids with potential anti-inflammatory activity from the leaves and twigs of Callicarpa cathayana’, Chin. J. Nat. Med. 2019, 17, 953-962.
J. Zhang, B.-Q. Li, F. Feng, Y.-P. Tang, W.-Y. Liu, ‘Chemical constituents from Callicarpa nudiflora and their hemostatic activity’, China J. Chin. Mater. Med. 2010, 35, 3297-3301.
J. Wang, C.-X. Luo, S. Wang, J.-J. Fu, S.-C. Ma, Y.-H. Luo, ‘Hemostatic effects of butyl alcohol extracts from Callicarpa nudiflora via stimulating PI3 K/Akt activation on platelets’, Pharmacol. Clin. Chin. Mater. Med. 2016, 32, 99-102.
P.-Y. Chung, L.-Y. Chung, P. Navaratnam, ‘Potential targets by pentacyclic triterpenoids from Callicarpa farinosa against methicillin-resistant and sensitive Staphylococcus aureus’, Fitoterapia 2014, 94, 48-54.
R.-M. Pineau, S.-E. Hanson, J.-T. Lyles, C.-L. Quave, ‘Growth Inhibitory Activity of Callicarpa americana Leaf Extracts against Cutibacterium acnes’, Front. Pharmacol. 2019, 10, 1-10.
Z. Zhou, X. Wei, H. Fu, Y. Luo, ‘Chemical constituents of Callicarpa nudiflora and their anti-platelet aggregation activity’, Fitoterapia 2013, 88, 91-95.
M. Chandra, O. Prakash, R. Kumar, R. Bachheti, B. Bhushan, M. Kumar, A. Pant, ‘β-Selinene-Rich Essential Oils from the Parts of Callicarpa macrophylla and Their Antioxidant and Pharmacological Activities’, Medicine 2017, 4, 1-17.
M.-A. Ado, M. Maulidiani, I.-S. Ismail, H.-M. Ghazali, K. Shaari, F. Abas, ‘Acetylcholinesterase and α-glucosidase inhibitory compounds from Callicarpa maingayi’, Nat. Prod. Res. 2019, 1-5.
D.-T. Lam, V.-T.-T. Le, P.-M. Quan, P.-T.-H. Minh, T.-T.-T. Thuy, N.-T.-N. Anh, B.-H. Tai, P.-V. Kiem, ‘Two new terpenoids from the leaves of Callicarpa macrophylla’, Nat. Prod. Res. 2019, 1-8.
N.-H. Hung, L.-T. Huong, N.-T. Chung, N.-T.-H. Thuong, P. Satyal, N.-A. Dung, T.-A. Tai, W.-N. Setzer, ‘Callicarpa Species from Central Vietnam: Essential Oil Compositions and Mosquito Larvicidal Activities’, Plants 2020, 9, 1-32.
Y.-W. Liu, Y.-B. Cheng, C.-C. Liaw, C.-H. Chen, J.-H. Guh, T.-L. Hwang, J.-S. Tsai, W.-B. Wang, Y.-C. Shen, ‘Bioactive Diterpenes from Callicarpa longissima’, J. Nat. Prod. 2012, 75, 689-693.
Z.-H. Wang, J. Huang, C. Niu, J.-H. Wang, B. Wu, ‘Isopimarane-type diterpenoids from Callicarpa macrophylla Vahl’, Phytochem. Lett. 2017, 22, 224-228.
M.-M. Yuan, R.-J. Zhong, G. Chen, G.-P. Zhou, H.-Z. Fu, Q.-W. Yan, ‘Two new triterpenoids from Callicarpa kwangtungensis’, J. Asian Nat. Prod. Res. 2014, 17, 138-142.
H.-Z. Fu, Y.-Y. Ma, S.-C. Ma, Z.-Q. Zhou, Y.-H. Luo, ‘Two new iridoid glycosides from Callicarpa nudiflora’, J. Asian Nat. Prod. Res. 2018, 22, 264-270.
S.-X. Feng, B. Yi, M. Zhang, J. Xu, H. Lin, W.-T. Xu, ‘Iridoid glycosides from Callicarpa nudiflora Hook’, Nat. Prod. Res. 2016, 31, 181-189.
C.-Z. Lin, C.-C. Zhu, Z.-X. Zhao, X.-H. Li, T.-Q. Xiong, Y.-Y. Xia, Y. Ning, ‘Two new abietane diterpenoids from the caulis and leaves of Callicarpa kochiana’, Fitoterapia 2012, 83, 1-5.
S. Li, X. Sun, Y. Li, F. Liu, J. Ma, L. Tong, G. Su, J. Xu, Y. Ohizumi, D. Lee, Y. Guo, ‘Natural NO inhibitors from the leaves of Callicarpa kwangtungensis: Structures, activities, and interactions with iNOS’, Bioorg. Med. Chem. Lett. 2017, 27, 670-674.
J.-B. Gao, S.-J. Yang, Z.-R. Yan, X.-J. Zhang, D.-B. Pu, L.-X. Wang, X.-L. Li, R.-H. Zhang, W.-L. Xiao, ‘Isolation, Characterization, and Structure-Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors’, J. Nat. Prod. 2018, 81, 998-1006.
H.-G. Wang, F.-K. Luo, X. Lei, Y.-D. Yao, G.-C. Liao, Z.-Q. Liu, Z.-H. Jiang, H. Zhou, P. Wu, ‘3,4-seco-Labdane diterpenoids from the leaves of Callicarpa nudiflora with anti-inflammatory effects’, Chin. J. Nat. Med. 2019, 17, 707-712.
W.-P. Jones, A.-D. Kinghorn, ‘Biologically active natural products of the genus Callicarpa’, Curr. Bioact. Compd. 2008, 4, 15-32.
N. Muto, T. Tomokuni, M. Haramoto, H. Tatemoto, T. Nakanishi, Y. Inatomi, H. Murata, A. Inada, ‘Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves of Juniperus taxifolia’, Biosci. Biotechnol. Biochem. 2014, 72, 477-484.
Y.-H. Kuo, W.-C. Chen, C.-K. Lee, ‘Four New Terpenes from Pericarp of Platycladus orientalis’, Chem. Pharm. Bull. 2000, 48, 766-768.
Y. B. Ryu, H. J. Jeong, J. H. Kim, Y. M. Kim, J.-Y. Park, D. Kim, T. T. H. Naguyen, S.-J. Park, J. S. Chang, K. H. Park, ‘Biflavonoids from Torreya nucifera displaying SARS-CoV 3CLpro inhibition’, Bioorg. Med. Chem. Lett. 2010, 18, 7940-7947.
C.-G. Li, Q.-Z. Zeng, M.-Y. Chen, L.-H. Xu, C.-C. Zhang, F.-Y. Mai, C.-Y. Zeng, X.-H. He, D.-Y. Ouyang, ‘Evodiamine Augments NLRP3 Inflammasome Activation and Anti-bacterial Responses Through Inducing α-Tubulin Acetylation’, Front. Pharmacol. 2019, 10, 1-17.