Login Register Cart 0
Generic placeholder image

Combinatorial Chemistry & High Throughput Screening

Editor-in-Chief

ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

The Anti-inflammatory Effects of Two Ent-kaurane Diterpenes from the Stems and Leaves of Gochnatia decora

Author(s): Yanfang Liu, Weifeng Dai, Qihui Cao and Mi Zhang*

Volume 25, Issue 11, 2022

Published on: 04 January, 2022

Page: [1907 - 1913] Pages: 7

DOI: 10.2174/1386207325666211005152100

Price: $65

Abstract

Aim & Objectives: The Gochnatia decora (Kurz) A. L. Cabrera is a rare woody plant belonging to the family of Asteraceae. The bark of this plant is used as a Chinese folk medicine to treat cough and pneumonia. However, the effective substance related to its efficacy remains unknown. This study aims to evaluate the potential anti-inflammatory activities of the chemicals isolated from this plant using a model of LPS-induced RAW264.7 cells.

Materials and Methods: Chemical constituents were isolated from the stems and leaves of G. decora by a series of chromatographic separation methods and identified by spectral analysis techniques. The model of inflammation in vitro was established by treatment of 1μM LPS on RAW264.7 cells. The influence of tested compounds on inflammatory factor production, including NO, TNF-α, IL-1β, IL-6, IL-17, was determined by ELISA. The mechanisms involved were studied by western blot analysis.

Results: Two known ent-kaurane diterpenes (1 and 2), identified as ent-17-hydroxy-15-oxokauran- 19-oic acid (1) and ent-15α-hydroxy-16-kauran-19-oic acid (2), were isolated from the stems and leaves of G. decora. The bioassay showed that both of them produced significant inhibition of LPS-induced release of NO, TNF-α, IL-1β, IL-6, IL-17, iNOS, and COX-2 expression. Western blot analysis showed that these two chemicals blocked LPS-induced phosphorylation of NF-κB.

Conclusion: Compounds 1 and 2 were obtained from the genus Gochnatia.These compounds demonstrated useful anti-inflammatory activities in the model of LPS-induced RAW264.7 cells. A potential action mechanism may be the correlation of the NF-κB pathway.

Keywords: Ent-kaurane, anti-inflammatory activity, Gochnatia decora, NF-κB pathway, Chinese folk medicine, diterpenes.

« Previous Next »
Graphical Abstract

[1]
Sun, H.D.; Li, S.H. Diterpenoid chemical; Chemical Industry Press: Beijing, 2012, pp. 224-227.
[2]
Anjaneyulu, A.S.R.; Sagar, K.S.; Rao, G.V. New cembranoid lactones from the Indian ocean soft coral Sinularia flexibilis. J. Nat. Prod., 1997, 60(1), 9-12.
[http://dx.doi.org/10.1021/np960103o]
[3]
Guilford, W.J.; Coates, R.M. Stereochemistry of casbene biosynthesis. J. Am. Chem. Soc., 1982, 104(12), 3506-3508.
[http://dx.doi.org/10.1021/ja00376a045]
[4]
Mau, C.J.; West, C.A. Cloning of casbene synthase cDNA: Evidence for conserved structural features among terpenoid cyclases in plants. Proc. Natl. Acad. Sci. USA, 1994, 91(18), 8497-8501.
[http://dx.doi.org/10.1073/pnas.91.18.8497] [PMID: 8078910]
[5]
Morikawa, T.; Xu, F.; Kashima, Y.; Matsuda, H.; Ninomiya, K.; Yoshikawa, M. Novel dolabellane-type diterpene alkaloids with lipid metabolism promoting activities from the seeds of Nigella sativa. Org. Lett., 2004, 6(6), 869-872.
[http://dx.doi.org/10.1021/ol036239c] [PMID: 15012052]
[6]
Robinson, D.R.; West, C.A. Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis L. I. Identification of diter-pene hydrocarbons formed from mevalonate. Biochemistry, 1970, 9(1), 70-79.
[http://dx.doi.org/10.1021/bi00803a010] [PMID: 5411208]
[7]
Zhang, M.; Zhao, C.; Dai, W.; He, J.; Jiao, S.; Li, B. Anti-inflammatory ent-kaurenoic acids and their glycosides from Gochnatia decora. Phytochemistry, 2017, 137, 174-181.
[http://dx.doi.org/10.1016/j.phytochem.2017.02.021] [PMID: 28236453]
[8]
Traditional Chinese Materia Medica; Shanghai Science and Technology Press: Shanghai, 1999.
[9]
Yadav, S.; Pathak, S.; Sarikhani, M.; Majumdar, S.; Ray, S.; Chandrasekar, B.S.; Adiga, V.; Sundaresan, N.R.; Nandi, D. Nitric oxide syn-thase 2 enhances the survival of mice during Salmonella typhimurium infection-induced sepsis by increasing reactive oxygen species, in-flammatory cytokines and recruitment of neutrophils to the peritoneal cavity. Free Radic. Biol. Med., 2018, 116, 73-87.
[http://dx.doi.org/10.1016/j.freeradbiomed.2017.12.032] [PMID: 29309892]
[10]
Ungurs, M.J.; Sinden, N.J.; Stockley, R.A. Progranulin is a substrate for neutrophil-elastase and proteinase-3 in the airway and its concen-tration correlates with mediators of airway inflammation in COPD. Am. J. Physiol. Lung Cell. Mol. Physiol., 2014, 306(1), L80-L87.
[http://dx.doi.org/10.1152/ajplung.00221.2013] [PMID: 24186875]
[11]
Liu, L.; Dai, W.; Xiang, C.; Chi, J.; Zhang, M. 1,10-Secoguaianolides from Artemisia austro-yunnanensis and their anti-inflammatory ef-fects. Molecules, 2018, 23(7), 1639-1652.
[http://dx.doi.org/10.3390/molecules23071639] [PMID: 29976846]
[12]
Deoliveira, A.B.; Hanson, J.R.; Takahashi, J.A. The biotransformation of ent-15-oxokaur-16-en-19-oic acid and its methyl ester by Ceph-alo sporium aphidicola. Phytochemistry, 1995, 40(2), 439-442.
[http://dx.doi.org/10.1016/0031-9422(95)00289-J]
[13]
Meccia, G.; Quintero, P.; Rojas, L.B.; Usubillaga, A.; Carmona, J. Análisis de los ácidos kaurénicos presentes en Espeletiopsis angustifolia Cuatrec. de los Andes venezolanos. Avances en Química, 2010, 5(1), 45-49.
[14]
Liu, Y.; Liu, D.; Liu, L.; Zhang, M. Cell models used in the study of anti-inflammatory activities of natural products. Nat. Prod. Res. Dev., 2020, 32, 874-881.
[15]
Chow, J.M.; Lin, H.Y.; Shen, S.C.; Wu, M.S.; Lin, C.W.; Chiu, W.T.; Lin, C.H.; Chen, Y.C. Zinc protoporphyrin inhibition of lipopolysac-charide-, lipoteichoic acid-, and peptidoglycan-induced nitric oxide production through stimulating iNOS protein ubiquitination. Toxicol. Appl. Pharmacol., 2009, 237(3), 357-365.
[http://dx.doi.org/10.1016/j.taap.2009.04.009] [PMID: 19376148]
[16]
Zhao, F.; Wang, L.; Liu, K. In vitro anti-inflammatory effects of arctigenin, a lignan from Arctium lappa L., through inhibition on iNOS pathway. J. Ethnopharmacol., 2009, 122(3), 457-462.
[http://dx.doi.org/10.1016/j.jep.2009.01.038] [PMID: 19429312]
[17]
Bonizzi, G.; Karin, M. The two NF-kappaB activation pathways and their role in innate and adaptive immunity. Trends Immunol., 2004, 25(6), 280-288.
[http://dx.doi.org/10.1016/j.it.2004.03.008] [PMID: 15145317]
[18]
Förstermann, U.; Boissel, J.P.; Kleinert, H. Expressional control of the ‘constitutive’ isoforms of nitric oxide synthase (NOS I and NOS III). FASEB J., 1998, 12(10), 773-790.
[http://dx.doi.org/10.1096/fasebj.12.10.773] [PMID: 9657518]
[19]
Sen, R.; Baltimore, D. Inducibility of kappa immunoglobulin enhancer-binding protein Nf-kappa B by a posttranslational mechanism. Cell, 1986, 47(6), 921-928.
[http://dx.doi.org/10.1016/0092-8674(86)90807-X] [PMID: 3096580]
[20]
Klayman, D.L. Qinghaosu (artemisinin): An antimalarial drug from China. Science, 1985, 228(4703), 1049-1055.
[http://dx.doi.org/10.1126/science.3887571] [PMID: 3887571]
[21]
Larsson, O.; Felton, L.M.; Perry, V.H.; Teeling, J.L. Evidence for neuroplastic changes in the brainstem following TH2 lung inflammation: A role for the central nervous system in contributing to the symptoms of asthma and investigating a potential target for therapy. Brain Behav. Immun., 2012, 26(Suppl. 1), S19.
[http://dx.doi.org/10.1016/j.bbi.2012.07.090]
[22]
David, Nd. Mauro, Mde.O.; Gonçalves, C.A.; Pesarini, J.R.; Strapasson, R.L.B.; Kassuya, C.A.L.; Stefanello, M.E.A.; Cunha-Laura, A.L.; Monreal, A.C.D.; Oliveira, R.J. Gochnatia polymorpha ssp. floccosa: Bioprospecting of an anti-inflammatory phytotherapy for use during pregnancy. J. Ethnopharmacol., 2014, 154(2), 370-379.
[http://dx.doi.org/10.1016/j.jep.2014.04.005] [PMID: 24727192]
[23]
Moreira, A.S.; Spitzer, V.; Schapoval, E.E.S.; Schenkel, E.P. Antiinflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha. Phytother. Res., 2000, 14(8), 638-640.
[http://dx.doi.org/10.1002/1099-1573(200012)14:8<638:AID-PTR681>3.0.CO;2-Q] [PMID: 11114003]

Rights & Permissions Print Cite
Article Metrics
12
1
© 2024 Bentham Science Publishers | Privacy Policy