Tersone A-G, new pyridone alkaloids from the deep-sea fungus phomopsis tersa

Marine Drugs

Volumn 17, Issue 7, 2019, Pages

  Chen, Shan Chong ^a,b   Liu, Zhao Ming ^a   Tan, Hai Bo ^c   Chen, Yu Chan ^a   Li, Sai Ni ^a   Li, Hao Hua ^a   Guo, Heng ^a   Zhu, Shuang ^b   Liu, Hong Xin ^a   Zhang, Wei Min ^a  

^a Guangdong Academy of Sciences   (China)

^b GUANGDONG PHARMACEUTICAL UNIVERSITY   (China)

^c SOUTH CHINA INSTITUTE OF BOTANY   (China)

Author keywords

Antibacterial activity; Cytotoxic activity; Diastereoisomers; Phomopsis tersa; Pyridone alkaloids

Indexed keywords

ALKALOID DERIVATIVE; PYRIDONE DERIVATIVE; TERSONE; TERSONE A; TERSONE B; TERSONE C; TERSONE D; TERSONE E; TERSONE F; TERSONE G; UNCLASSIFIED DRUG; ALKALOID; ANTIINFECTIVE AGENT;

A-549 CELL LINE; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DRUG CYTOTOXICITY; ELECTRONIC CIRCULAR DICHROISM; HEP-G2 CELL LINE; IC50; IN VITRO STUDY; MCF-7 CELL LINE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHOMOPSIS; PHOMOPSIS TERSA; PROTON NUCLEAR MAGNETIC RESONANCE; SF268 CELL LINE; STAPHYLOCOCCUS AUREUS; X RAY DIFFRACTION; AQUATIC SPECIES; CHEMISTRY; DRUG EFFECT; FUNGUS; HUMAN; MICROBIAL SENSITIVITY TEST; PROCEDURES; TUMOR CELL LINE;

A549 CELLS; ALKALOIDS; ANTI-INFECTIVE AGENTS; AQUATIC ORGANISMS; CELL LINE, TUMOR; FUNGI; HEP G2 CELLS; HUMANS; MCF-7 CELLS; MICROBIAL SENSITIVITY TESTS; PYRIDONES; STAPHYLOCOCCUS AUREUS;

EID: 85068621130     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md17070394     Document Type: Article

References (22)

1. Li, X.B.; Li, L.; Zhu, R.X.; Li, W.; Chang, W.Q.; Zhang, L.L.; Wang, X.N.; Zhao, Z.T.; Lou, H.X. Tetramic acids and pyridone alkaloids from the endolichenic fungus Tolypocladium cylindrosporum. J. Nat. Prod. 2015, 78, 2155–2160. [CrossRef]
2. Shang, Z.; Li, L.; Esposito, B.P.; Salim, A.A.; Khalil, Z.G.; Quezada, M.; Bernhardt, P.V.; Capon, R.J. New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp. Org. Biomol. Chem. 2015, 13, 7795–7802. [CrossRef]
3. Sakemi, S.; Bordner, J.; Decosta, D.L.; Dekker, K.A.; Hirai, H.; Inagaki, T.; Kim, Y.J.; Kojima, N.; Sims, J.C.; Sugie, Y. CJ-15, 696 and its analogs, new furopyridine antibiotics from the fungus Cladobotryum varium: Fermentation, isolation, structural elucidation, biotransformation and antibacterial activities. J. Antibiot. 2002, 55, 6–18. [CrossRef]
4. Breinholt, J.; Jensen, H.C.; Kjær, A.; Olsen, C.E.; Rassing, B.R.; Rosendahl, C.N.; Søtofte, I. Cladobotryal: A fungal metabolite with a novel ring system. Acta Chem. Scand. 1998, 52, 631–634. [CrossRef]
5. Xu, Y.; Wang, L.; Zhu, G.; Zuo, M.; Gong, Q.; He, W.; Li, M.; Yuan, C.; Hao, X.; Zhu, W. New phenylpyridone derivatives from the Penicillium sumatrense GZWMJZ-313, a fungal endophyte of Garcinia multiflora. Chin. Chem. Lett. 2019, 30, 431–434. [CrossRef]
6. Fukuda, T.; Yamaguchi, Y.; Masuma, R.; Tomoda, H.; Omura, S. Citridones, new potentiators of antifungal miconazole activity, produced by Penicillium sp. FKI-1938. I. taxonomy, fermentation, isolation and biological properties. J. Antibiot. 2005, 58, 309–314. [CrossRef]
7. Fukuda, T.; Sakabe, Y.; Tomoda, H.; Omura, S. Fungal citridone D having a novel phenylfuropyridine skeleton. Chem. Pharm. Bull. 2006, 54, 1659–1661. [CrossRef]
8. Fotiadou, A.D.; Zografos, A.L. Accessing the structural diversity of pyridone alkaloids: Concise total synthesis of rac-citridone A. Org. Lett. 2011, 13, 4592–4595. [CrossRef]
9. Snider, B.B.; Che, Q. Synthesis of cladobotryal, CJ16, 169, and CJ16, 170. Org. Lett. 2004, 6, 2877–2880. [CrossRef]
10. Clive, D.L.; Huang, X. Model studies and first synthesis of the antifungal and antibacterial agent cladobotryal. J. Org. Chem. 2004, 69, 1872–1879. [CrossRef]
11. Clive, D.L.; Huang, X. Studies related to furopyridinone antibiotics. Synthesis of 2-epi-CJ-16,170. Tetrahedron 2002, 58, 10243–10250. [CrossRef]
12. Moore, M.C.; Cox, R.J.; Duffin, G.R.; O’Hagan, D. Synthesis and evaluation of a putative acyl tetramic acid intermediate in tenellin biosynthesis in Beauveria bassiana. A new role for tyrosine. Tetrahedron 1998, 54, 9195–9206. [CrossRef]
13. Tomoda, H. New approaches to drug discovery for combating MRSA. Chem. Pharm. Bull. 2016, 64, 104–111. [CrossRef]
14. Miyagawa, T.; Nagai, K.; Yamada, A.; Sugihara, Y.; Fukuda, T.; Fukuda, T.; Uchida, R.; Tomoda, H.; Omura, S.; Nagamitsu, T. Total synthesis of citridone A. Org. Lett. 2011, 13, 1158–1161. [CrossRef]
15. Fukuda, T.; Shimoyama, K.; Nagamitsu, T.; Tomoda, H. Synthesis and biological activity of Citridone A and its derivatives. J. Antibiot. 2014, 67, 445–450. [CrossRef]
16. Liu, H.; Tan, H.; Chen, Y.; Guo, X.; Wang, W.; Guo, H.; Liu, Z.; Zhang, W. Cytorhizins A−D, four highly structure-combined benzophenones from the endophytic fungus Cytospora rhizophorae. Org. Lett. 2019, 21, 1063–1067. [CrossRef]
17. Liu, H.; Tan, H.; Wang, W.; Zhang, W.; Chen, Y.; Li, S.; Liu, Z.; Li, H.; Zhang, W. Cytorhizophins A and B, benzophenone-hemiterpene adducts from the endophytic fungus Cytospora rhizophorae. Org. Chem. Front. 2019, 6, 591–596. [CrossRef]
18. Xu, J.; Tan, H.; Chen, Y.; Li, S.; Huang, Z.; Guo, H.; Li, H.; Gao, X.; Liu, H.; Zhang, W. Lithocarpins A–D: Four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508. Org. Chem. Front. 2018, 5, 1792–1797. [CrossRef]
19. Chen, S.; Li, H.; Chen, Y.; Li, S.; Xu, J.; Guo, H.; Liu, Z.; Zhu, S.; Liu, H.; Zhang, W. Three new diterpenes and two new sesquiterpenoids from the endophytic fungus Trichoderma koningiopsis A729. Bioorg. Chem. 2019, 86, 368–374. [CrossRef]
20. Fukuda, T.; Tomoda, H.; Omura, S. Citridones, new potentiators of antifungal miconazole activity, produced by Penicillium sp. FKI-1938: II. structure elucidation. J. Antibiot. 2005, 58, 315–321. [CrossRef]
21. Drummond, A.J.; Waigh, R.D. Recent Research Developments in Phytochemistry; Pandalai, S.G., Ed.; Research Signpost: Thiruvananthapuram, Kerala, India, 2000; Volume 4, pp. 143–152.
22. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer. Inst. 1990, 82, 1107–1112. [CrossRef]