Territrem and butyrolactone derivatives from a marine-derived fungus aspergillus terreus

Marine Drugs

Volumn 12, Issue 12, 2014, Pages 6113-6124

  Nong, Xu Hua ^a   Wang, Yi Fei ^b   Zhang, Xiao Yong ^a   Zhou, Mu Ping ^b   Xu, Xin Ya ^a   Qi, Shu Hua ^a  

^a SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

^b JINAN UNIVERSITY   (China)

Author keywords

Anti acetylcholinesterase; Anti HSV 1; Antifouling; Aspergillus terreus; Butyrolactone derivative; Territrem derivative

Indexed keywords

12A DEHYDROXYISOTERREULACTONE A; 3 HYDROXY 4 (4 HYDROXYPHENYL) 5 METHOXYCARBONYL 5 (4 HYDROXY 3 FORMYLBENZYL) 2,5 DIHYDRO 2 FURANONE; ACICLOVIR; ANTIFOULING AGENT; ANTIVIRUS AGENT; ARISUGACIN A; ARISUGACIN H; ASPERNOLIDE A; ASPERNOLIDE B; BUTYROLACTONE I; BUTYROLACTONE III; BUTYROLACTONE IV; BUTYROLACTONE V; CHOLINESTERASE INHIBITOR; HUPERZINE A; ISOBUTYROLACTONE II; ISOBUTYROLACTONE V; TERREULACTONE C; TERRITREM B; TERRITREM C; TERRITREM D; TERRITREM E; UNCLASSIFIED DRUG; ACETYLCHOLINESTERASE; LACTONE; PYRAN DERIVATIVE;

AMPHIBALANUS AMPHITRITE; ANTIVIRAL ACTIVITY; ARTICLE; ASPERGILLUS TERREUS; BIOASSAY; CHOLINESTERASE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; HERPES SIMPLEX VIRUS 1; IC50; INSECTICIDAL ACTIVITY; NONHUMAN; NUCLEOTIDE SEQUENCE; STRUCTURE ANALYSIS; ANIMAL; ASPERGILLUS; BARNACLE; CELL LINE; CHEMISTRY; CHLOROCEBUS AETHIOPS; DRUG EFFECTS; FUNGUS; LARVA; MARINE BIOLOGY; METABOLISM; MICROBIOLOGY; ORYZA; VERO CELL LINE;

ASPERGILLUS TERREUS; BALANUS AMPHITRITE; FUNGI; HUMAN HERPESVIRUS 1; THORACICA;

ACETYLCHOLINESTERASE; ANIMALS; ANTIVIRAL AGENTS; ASPERGILLUS; CELL LINE; CERCOPITHECUS AETHIOPS; CHOLINESTERASE INHIBITORS; FUNGI; LACTONES; LARVA; MARINE BIOLOGY; ORYZA; PYRANS; THORACICA; VERO CELLS;

EID: 84919797555     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12126113     Document Type: Article

References (26)

1. Viegas, C., Jr.; Bolzani, V.S.; Barreiro, E.J.; Fraga, C.A. New anti-Alzheimer drugs from biodiversity: The role of the natural acetylcholinesterase inhibitors. Mini Rev. Med. Chem. 2005, 5, 915-926.
2. Huang, X.T.; Qian, Z.M.; He, X.; Gong, Q.; Wu, K.C.; Jiang, L.R.; Lu, L.N.; Zhu, Z.J.; Zhang, H.Y.; Yung, W.H.; et al. Reducing iron in the brain: A novel pharmacologic mechanism of huperzine A in the treatment of Alzheimer's disease. Neurobiol. Aging 2014, 35, 1045-1054.
3. Fang, L.; Gou, S.H.; Fang, X.B.; Cheng, L.; Fleck, C. Current progresses of novel natural products and their derivatives/analogs as anti-Alzheimer candidates: An update. Mini Rev. Med. Chem. 2013, 13, 870-887.
4. Lee, S.S.; Peng, F.C.; Chiou, C.M.; Ling, K.H. NMR assignments of territrems A B and C and the structure of MB-2 the major metabolite of territrem B by rat liver microsomal fraction. J. Nat. Prod. 1992, 55, 251-255.
5. Otoguro, K.; Shiomi, K.; Yamaguchi, Y.; Arai, N.; Sunazuka, T.; Masuma, R.; Iwai, Y.; Omura, S. Arisugacins C and D, novel acetylcholinesterase inhibitors and their related novel metabolites produced by Penicillium sp FO-4259-11. J. Antibiot. 2000, 53, 50-57.
6. Kim, W.G.; Cho, K.M.; Lee, C.K.; Yoo, I.D. Terreulactones A, B, C, and D: Novel acetylcholinesterase inhibitors produced by Aspergillus terreus-II. Physico-chemical properties and structure determination. J. Antibiot. 2003, 56, 351-357.
7. Kuno, F.; Otoguro, K.; Shiomi, K.; Iwai, Y.; Omura, S. Arisugacins A and B, novel and selective acetylcholinesterase inhibitors from Penicillium sp. FO-4259 .1. Screening, taxonomy, fermentation, isolation and biological activity. J. Antibiot. 1996, 49, 742-747.
8. Peng, F.C. Acetylcholinesterase inhibition by territrem B derivatives J. Nat. Prod. 1995, 58, 857-862.
9. Haritakun, R.; Rachtawee, P.; Chanthaket, R.; Boonyuen, N.; Isaka, M. Butyrolactones from the fungus Aspergillus terreus BCC 4651. Chem. Pharm. Bull. 2010, 58, 1545-1548.
10. Parvatkar, R.R.; D'Souza, C.; Tripathi, A.; Naik, C.G. Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus. Phytochemistry 2009, 70, 128-132.
11. Cazar, M.E.; Schmeda-Hirschmann, G.; Astudillo, L. Antimicrobial butyrolactone I derivatives from the ecuadorian soil fungus Aspergillus terreus thorn. Var terreus. World J. Microbiol. Biotechnol. 2005, 21, 1067-1075.
12. Haroon, M.H.; Premaratne, S.R.; Choudhry, M.I.; Dharmaratne, H.R.W. A new-glucuronidase inhibiting butyrolactone from the marine endophytic fungus Aspergillus terreus . Nat. Prod. Res. 2013, 27, 1060-1066.
13. Kitagawa, M.; Okabe, T.; Ogino, H.; Matsumoto, H.; Suzukitakahashi, I.; Kokubo, T.; Higashi, H.; Saitoh, S.; Taya, Y.; Yasuda, H.; et al. Butyrolactone I, a selective inhibitor of cdk2 and cdc2 kinase. Oncogene 1993, 8, 2425-2432.
14. Shen, Y.; Zou, J.H.; Xie, D.; Ge, H.L.; Cao, X.P.; Dai, J.G. Butyrolactone and cycloheptanetrione from mangrove-associated fungus Aspergillus terreus. Chem. Pharm. Bull. 2012, 60, 1437-1441.
15. Sunazuka, T.; Handa, M.; Nagai, K.; Shirahata, T.; Harigaya, Y.; Otoguro, K.; Kuwajima, I.; Omura, S. Absolute stereochemistries and total synthesis of (+)-arisugacins A and B, potent, orally bioactive and selective inhibitors of acetylcholinesterase. Tetrahedron 2004, 60, 7845-7859.
16. Nagia, M.M.; El-Metwally, M.M.; Shaaban, M.; El-Zalabani, S.M.; Hanna, A.G. Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: Isolation and structure determination. Org. Med. Chem. Lett. 2012, 2, doi:10.1186/2191-2858-2-9.
17. Rao, K.V.; Sadhukhan, A.K.; Veerender, M.; Ravikumar, V.; Mohan, E.V.S.; Dhanvantri, S.D.; Sitaramkumar, M.; Babu, J.M.; Vyas, K.; Reddy, G.O. Butyrolactones from Aspergillus terreus . Chem. Pharm. Bull. 2000, 48, 559-562.
18. Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J.H.; Capon, R.J. Kibdelones: Novel anticancer polyketides from a rare Australian actinomycete. Chemistry 2007, 13, 1610-1619.
19. Cotelle, P.; Cotelle, N.; Teissier, E.; Vezin, H. Synthesis and antioxidant properties of a new lipophilic ascorbic acid analogue. Bioorg. Med. Chem. 2003, 11, 1087-1093.
20. Ellman, G.L.; Courtney, K.D.; Andres, V.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-90.
21. Yoo, I.D.; Cho, K.M.; Lee, C.K.; Kim, W.G. Isoterreulactone A, a novel meroterpenoid with anti-acetylcholinesterase activity produced by Aspergillus terreus . Bioorg. Med. Chem. Lett. 2005, 15, 353-356.
22. Al-Rashid, Z.F.; Hsung, R.P. (+)-Arisugacin A-Computational evidence of a dual binding site covalent inhibitor of acetylcholinesterase. Bioorg. Med. Chem. Lett. 2011, 21, 2687-2691.
23. Degen, S.J.; Mueller, K.L.; Shen, H.C.; Mulder, J.A.; Golding, G.M.; Wei, L.L.; Zificsak, C.A.; Neeno-Eckwall, A.; Hsung, R.P. Synthesis of dihydroxanthone derivatives and evaluation of their inhibitory activity against acetylcholinesterase: Unique structural analogs of tacrine based on the BCD-ring of arisugacin. Bioorg. Med. Chem. Lett. 1999, 9, 973-978.
24. Qian, P.Y.; Xu, Y.; Fusetani, N. Natural products as antifouling compounds: Recent progress and future perspectives. Biofouling 2010, 26, 223-234.
25. Nitta, K.; Shiota, H.; Naito, T.; Mimura, Y. Sensitivities to other antiviral drugs and thymidine kinase activity of aciclovir-resistant herpes simplex virus type 1. Nippon Ganka Gakkai Zasshi 1994, 98, 513-519.
26. Qi, S.H.; Xu, Y.; Gao, J.; Qian, P.Y.; Zhang, S. Antibacterial and antilarval compounds from marine bacterium Pseudomonas rhizosphaerae. Ann. Microbiol. 2009, 59, 229-233.