A new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, Amycolatopsis sp.

Marine Drugs

Volumn 12, Issue 4, 2014, Pages 2326-2340

  Kwon, Yun ^a   Kim, Seong Hwan ^a   Shin, Yoonho ^a   Bae, Munhyung ^a   Kim, Byung Yong ^a   Lee, Sang Kook ^a   Oh, Ki Bong ^b   Shin, Jongheon ^a   Oh, Dong Chan ^a  

^a Seoul National University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

Amycolatopsis; Benzofuran; Cyclopiazonic acid; Rare actinomycete; Sponge

Indexed keywords

AMYCOCYCLOPIAZONIC ACID; AMYCOFURAN; AMYCOLACTAM; ANTINEOPLASTIC AGENT; BENZOFURAN DERIVATIVE; CYCLOPIAZONIC ACID; GLYCOSIDE; INDOLE ALKALOID; UNCLASSIFIED DRUG; 2 PYRROLIDONE DERIVATIVE; INDOLE DERIVATIVE;

ACTINOBACTERIA; AMYCOLATOPSIS; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; GASTRIC CANCER CELL LINE; HCT116 CELL LINE; HUMAN; HUMAN CELL; ACTINOMYCETALES; ANIMAL; CHEMISTRY; DRUG SCREENING; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; SECONDARY METABOLISM; SPONGE (PORIFERA); TUMOR CELL LINE;

ACTINOMYCETALES; ANIMALS; ANTINEOPLASTIC AGENTS; BENZOFURANS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; GLYCOSIDES; HCT116 CELLS; HUMANS; INDOLE ALKALOIDS; INDOLES; PORIFERA; PYRROLIDINONES; SECONDARY METABOLISM;

EID: 84900394773     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12042326     Document Type: Article

References (27)

1. Monster, R.; Luesch, H. Marine natural products: A new wave of drugs? Future Med. Chem. 2011, 3, 1475-1489.
2. Liu, Y. Renaissance of marine natural product drug discovery and development. J. Mar. Sci. Res. Dev. 2012, 2, e106.
3. Hentschel, U.; Piel, J.; Degnan, S.M.; Taylor, M.W. Genomic insights into the marine sponge microbiome. Nat. Rev. Microbiol. 2012, 10, 641-654.
4. Xu, Y.; Kersten, R.D.; Nam, S.-J.; Lu, L.; Al-Suwailem, A.M.; Zheng, H.; Fenical, W.; Dorrestein, P.C.; Moore, B.S.; Qian, P.-Y. Bacterial biosynthesis and maturation of the didemnin anti-cancer agents. J. Am. Chem. Soc. 2012, 134, 8625-8632.
5. Bewley, C.A.; Holland, N.D.; Faulkner, D.J. Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts. Experientia 1996, 52, 716-722.
6. Andrianasolo, E.H.; Groos, H.; Goeger, D.; Musafija-Girt, M.; McPhail, K.; Leal, R.M.; Mooberry, S.L.; Gerwick, W.H. Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteria. Org. Lett. 2005, 7, 1375-1378.
7. Piel, J.; Hui, D.; Wen, G.; Butzke, D.; Platzer, M.; Fusetani, N.; Matsunaga, S. Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei. Proc. Natl. Acad. Sci. USA 2004, 101, 16222-16227.
8. Fischbach, M.A.; Walsh, C.T. Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: logic machinery, and mechanisms. Chem. Rev. 2006, 106, 3468-3496.
9. Webster, N.S.; Taylor, M.W. Marine sponges and their microbial symbionts: Love and other relationships. Environ. Microbiol. 2012, 14, 335-346.
10. Wilson, M.C.; Mori, T.; Ruckert, C.; Uria, A.R.; Helf, M.J.; Takada, K.; Gernert, C.; Steffens, U.A.E.; Heycke, N.; Schmitt, S.; et al . An environmental bacterial taxon with a large and distinct metabolic repertoire. Nature 2014, 506, 58-62.
11. Bérdy, J. Thoughts and facts about antibiotics: Where we are now and where we are heading. J. Antibiot. 2012, 65, 385-395.
12. Vincente, J.; Stewart, A.; Song, B.; Hill, R.T.; Wright, J.L. Biodiversity of actinomycetes associated with Caribbean sponges and their potential for natural product discovery. Mar. Biotechnol. 2013, 15, 413-424.
13. Li, K.; Li, Q.-L.; Ji, N.-Y.; Liu, B.; Zhang, W.; Cao, X.-P. Deoxyuridines from the marine sponge associated actinomycete Streptomyces microflavus. Mar. Drugs 2011, 9, 690-695.
14. Wei, R.-B.; Xi, T.; Li, J.; Wang, P.; Li, F.-C.; Lin, Y.-C.; Qin, S. Lobophorin C and D, new kijanimicin derivatives from a marine sponge-associated actinomycetal strain AZS17. Mar. Drugs 2011, 9, 359-368.
15. Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds - Tables of Spectral Data ; Springer: New York, NY, USA, 2000; p. 153.
16. Berova, N.; Di Bari, L.; Pescitelli, G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem. Soc. Rev. 2007, 36 , 914-931.
17. Shi, Y.-M.; Wang, L.-Y.; Zou, X.-S.; Li, X.-N.; Shang, S.-Z.; Gao, Z.-H.; Liang, C.-Q.; Luo, H.-R.; Li, H.-L.; Xiao, W.-L.; et al . Nortriterpenoids from Schisandra chinensis and their absolute configurational assignments by electronic circular dichroism study. Tetrahedron 2014, 70, 859-868.
18. Pfefferle, W.; Anke, H.; Bross, M.; Steffan, B.; Vianden, R.; Steglich, W. Asperfuran, a novel antifungal metabolite from Aspergillus oryzae. J. Antibiot. 1990, 43, 648-654.
19. Felix, F.; Manuel, S.J.; Emilio, Q.; Riguera, R. Determining the absolute stereochemistry of secondary/secondary diols by 1H NMR: Basis and applications. J. Org. Chem. 2005, 70, 3778-3790.
20. Pabba, J.; Rempel, B.P.; Withers, S.G.; Vasella, A. Synthesis of glycaro-1,5-lactams and tetrahydrotetrazolopyridine-5-carboxylates: Inhibitors of β-D-glucuronidase and α-L -iduronidase. Helv. Chim. Acta 2006, 89, 635-666.
21. Prasad, K.R.; Pawar, A.B. Enantiospecific total synthesis of (+)-lentiginosine. ARKIVOC 2010, 6, 39-46.
22. Huang, Y.; Dalton, D.R.; Carroll, P.J. The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines. J. Org. Chem. 1997, 62, 372-376.
23. Sonoda, T.; Osada, H.; Uzawa, J.; Isono, K. Actiketal, a new member of the glutarimide antibiotics. J. Antibiot. 1991, 44, 160-163.
24. Suzuki, K.; Yahara, S.; Maehata, K.; Uyeda, M. Isoaurostatin, a novel topoisomerase inhibitor produced by Thermomonospora alba. J. Nat. Prod. 2001, 64, 204-207.
25. Simonetti, S.O.; Larghi, E.L.; Bracca, A.B.J.; Kaufman, T.S. Angular tricyclic benzofurans and related natural products of fungal origin. Isolation, biological activity and synthesis. Nat. Prod. Rep. 2013, 30, 941-969.
26. Holzapfel, C.W. Isolation and structure of cyclopiazonic acid, a toxic metabolite of Penicillium cyclopium. Tetrahedron 1968, 24, 2101-2119.
27. Liu, X.; Walsh, C.T. Characterization of cyclo-acetoacetyl-L-tryptophan dimethylallytransferase in cyclopiazonic acid biosynthesis: Substrate promiscuity and site directed mutagenesis studies. Biochemistry 2009, 48, 11032-11044.