Peroxisome Proliferator Activated Receptor-γ Agonistic Compounds from the Jellyfish-Derived Fungus Cladosporium oxysporum.
Cladosporium oxysporum
PPAR-γ
acyclic diterpenes
glucose uptake
lipid accumulation
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Sep 2023
Sep 2023
Historique:
received:
12
06
2023
accepted:
11
08
2023
medline:
25
9
2023
pubmed:
16
8
2023
entrez:
16
8
2023
Statut:
ppublish
Résumé
In our search for peroxisome proliferator-activated receptor (PPAR) agonists, five undescribed compounds, namely two acyclic diterpenes (1 and 2; cladopsol A and cladopsol B), two sesquiterpenes (3 and 4; cladopsol C and cladopsol D), and one C21-ecdysteroid (5; cladopsol E), and 15 known compounds were isolated from the jellyfish-derived fungus - Cladosporium oxysporum. The structures of the undescribed compounds were defined using UV, NMR, HR-ESI-MS, and electronic circular dichroism (ECD) spectroscopy and a modified Mosher's method. Luciferase reporter assay and docking analysis suggested that cladopsol B may function as a PPAR-γ partial agonist with a potential antidiabetic lead which may evade the side effects of full agonists. Moreover, cladopsol B stimulated glucose uptake in HepG2 cells with an efficacy comparable to that of rosiglitazone, but with less side effect induced by lipid accumulation in 3T3-L1 cells. Therefore, cladopsol B could serve as a molecular skeleton in a study of advanced antidiabetic lead with less side effect.
Identifiants
pubmed: 37584103
doi: 10.1002/cbdv.202300851
doi:
Substances chimiques
Peroxisome Proliferator-Activated Receptors
0
PPAR-gamma Agonists
0
Hypoglycemic Agents
0
PPAR gamma
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300851Subventions
Organisme : National Research Foundation of Korea
ID : 201901920001
Organisme : National Research Foundation of Korea
ID : NRF-2019R1A2C1010087
Organisme : National Research Foundation of Korea
ID : 2017M3A9E4078553
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
J. M. Lenhard, Recept. Channels 2001, 7, 249-258.
A. Y. Cheng, L. A. Leiter, Diabetes Obes. Metab. 2008, 10, 691-698.
I. Ahmed, K. Furlong, J. Flood, V. P. Treat, B. J. Goldstein, Am. J. Ther. 2007, 14, 49-62.
C. Janani, B. R. Kumari, Diabetes Metab. Synd. 2015, 9, 46-50.
A. K. Rines, K. Sharabi, C. D. Tavares, P. Puigserver, Nat. Rev. Drug Discovery 2016, 15, 786-804.
X. Ma, D. Wang, W. Zhao, L. Xu, Front. Endocrinol. 2018, 9, 473.
K. Schoonjans, J. Auwerx, The Lancet 2000, 355, 1008-1010.
B. L. Blazer-Yost, PPAR Res. 2010, 2010.
A. Motani, Z. Wang, J. Weiszmann, L. R. McGee, G. Lee, Q. Liu, J. Staunton, Z. Fang, H. Fuentes, M. Lindstrom, J. Mol. Biol. 2009, 386, 1301-1311.
C. Weidner, J. C. de Groot, A. Prasad, A. Freiwald, C. Quedenau, M. Kliem, A. Witzke, V. Kodelja, C.-T. Han, S. Giegold, Proc. Natl. Acad. Sci. USA 2012, 109, 7257-7262.
G. Eksi, S. Kurbanoglu, S. A. Erdem, In Recent Advances in Nat. Prod. Analysis 2020, 9, 313-345.
R. Ebel, Mar. Drugs 2010, 8, 2340-2368.
A. M. Elissawy, M. El-Shazly, S. S. Ebada, A. B. Singab, P. Proksch, Mar. Drugs 2015, 13, 1966-1992.
M. Jiang, Z. Wu, H. Guo, L. Liu, S. Chen, Mar. Drugs 2020, 18, 321.
Y. Li, W. Liu, W. Xu, X. Zeng, Z. Cheng, Q. Li, Rec. Nat. Prod. 2020, 14, 18-22.
A. Astulla, Y. Hirasawa, A. Rahman, I. Kusumawati, W. Ekasari, A. Widyawaruyanti, N. C. Zaini, H. Morita, Nat. Prod. Commun. 2011, 6, 323-326.
A. Pais, J. A. Saraiva, S. M. Rocha, A. J. Silvestre, S. A. Santos, Mar. Drugs 2019, 17, 556.
B. Ravi, D. J. Faulkner, J. Org. Chem. 1978, 43, 2127-2131.
S. Xue, P. Zhang, P. Tang, C. Wang, L. Kong, J. Luo, Fitoterapia 2020, 142, 104518.
A. Banerjee, B. Hamberger, Phytochem. Rev. 2018, 17, 81-111.
M. Figueroa, H. Raja, J. O. Falkinham III, A. F. Adcock, D. J. Kroll, M. C. Wani, C. J. Pearce, N. H. Oberlies, J. Nat. Prod. 2013, 76, 1007-1015.
A. C. Evans, A. S. Petit, S. G. Guillen, A. J. Neukirch, S. V. Hoffmann, N. C. Jones, RSC Adv. 2021, 11, 1635-1643.
V. Bermudez, F. Finol, N. Parra, M. Parra, A. Pérez, L. Penaranda, D. Vílchez, J. Rojas, N. Arráiz, M. Velasco, Am. J. Ther. 2010, 17, 274-283.
N. Behloul, G. Wu, Eur. J. Pharmacol. 2013, 698, 31-38.
M. Bazuine, P. J. van den Broek, J. A. Maassen, Biochem. Biophys. Res. Commun. 2005, 326, 511-514.
Z. C. Dang, V. Audinot, S. E. Papapoulos, J. A. Boutin, C. W. Löwik, J. Biol. Chem. 2003, 278, 962-967.
M. S. Lee, C. H. Kim, D. M. Hoang, B. Y. Kim, C. B. Sohn, M. R. Kim, J. S. Ahn, Biol. Pharm. Bull. 2009, 32, 504-508.
J. B. Bruning, M. J. Chalmers, S. Prasad, S. A. Busby, T. M. Kamenecka, Y. He, K. W. Nettles, P. R. Griffin, Structure 2007, 15, 1258-1271.
S. Garcia-Vallve, L. Guasch, S. Tomas-Hernandez, J. M. del Bas, V. Ollendorff, L. Arola, G. Pujadas, M. Mulero, J. Med. Chem. 2015, 58, 5381-5394.
A. Natali, E. Ferrannini, Diabetologia 2006, 49, 434-441.
Z. Polianskyte-Prause, T. A. Tolvanen, S. Lindfors, V. Dumont, M. Van, H. Wang, S. N. Dash, M. Berg, J. B. Naams, L. C. Hautala, The FASEB J. 2019, 33, 2858-2869.
H. i. Kim, Y. h. Ahn, Diabetes 2004, 53, S60-S65.
B. M. Spiegelman, Diabetes 1998, 47, 507-514.
J. Auwerx, Diabetologia 1999, 42, 1033-1049.
W. A. Ayer, E. R. Cruz, J. Org. Chem. 1993, 58, 7529-7534.
M. J. Cheng, B. Jayaprakasam, T. Ishikawa, H. Seki, I. L. Tsai, J. J. Wang, I. S. Chen, Helv. Chim. Acta 2002, 85, 1909-1914.
M. Ostermeier, C. Limberg, C. Herwig, B. Ziemer, In Wiley Online Library 2009.
V. Basyuk, T. Y. Gromovoi, A. Chuiko, V. Soloshonok, V. Kukhar, Dokl. Akad. Nauk SSSR 1991, 318, 905-906.
R. Laville, T. B. Nguyen, C. Moriou, S. Petek, C. Debitus, A. Al-Mourabit, Heterocycles 2015, 90, 1351-1366.
K. Nobuo, N. Koohei, N. Shoichi, Heterocycles 1989, 29, 397-402.
O. Soidinsalo, K. Wähälä, Steroids 2004, 69, 613-616.
D. d Li, Y. Wang, E. L. Kim, J. Hong, J. H. Jung, Mar. Drugs 2022, 20, 203.
N. Kulesh, N. Vasilevskaya, M. Veselova, V. Denisenko, S. Fedoreev, Chem. Nat. Compd. 2008, 44, 712-714.
M. D. Awouafack, P. Spiteller, M. Lamshöft, S. Kusari, B. Ivanova, P. Tane, M. Spiteller, J. Nat. Prod. 2011, 74, 272-278.
S. Habtemariam, P. G. Waterman, T. Hartley, Phytochemistry 1996, 43, 291-294.
X. Pang, X. Lin, J. Wang, R. Liang, Y. Q. Tian, L. Salendra, X. W. Luo, X. F. Zhou, B. Yang, Z. C. Tu, Y. H. Liu, Steroids 2018, 129, 41-46.
R. L. Baxter, K. R. Price, G. R. Fenwick, J. Nat. Prod. 1990, 53, 298-302.
K. Sasaki, N. Minowa, H. Kuzuhara, S. Nishiyama, Bioorg. Med. Chem. 2005, 13, 4900-4911.
S. Xue, P. Zhang, P. Tang, C. Wang, L. Kong, J. Luo, Fitoterapia 2020, 142, 104518.
A. Banerjee, B. Hamberger, Phytochem. Rev. 2018, 17, 81-111.