New benzoxazine secondary metabolites from an arctic actinomycete

Marine Drugs

Volumn 12, Issue 5, 2014, Pages 2526-5238

  Moon, Kyuho ^a   Ahn, Chan Hong ^b   Shin, Yoonho ^a   Won, Tae Hyung ^a   Ko, Keebeom ^a   Lee, Sang Kook ^a   Oh, Ki Bong ^b   Shin, Jongheon ^a   Nam, Seung Il ^c   Oh, Dong Chan ^a  

^a Seoul National University   (South Korea)

^b Seoul National University   (South Korea)

^c Korea Polar Research Institute (KOPRI)   (South Korea)

Author keywords

Arctic; Benzoxazine; C 1027; Disaccharide; Fijiolides; Isocitrate lyase; Marine actinomycete; Secondary metabolite

Indexed keywords

ANTIBIOTIC C 1027; ARCTICOSIDE; BENZOXAZINE DERIVATIVE; C 1027 CHROMOPHORE III; C 1027 CHROMOPHORE V; FIJIOLIDE A; FIJIOLIDE B; GLUCOSE; HEXOSE; ISOCITRATE LYASE; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT;

ACID HYDROLYSIS; ARTICLE; BREAST CARCINOMA; CANDIDA ALBICANS; CARCINOMA CELL; CHEMICAL PROCEDURES; COLORECTAL CANCER; CONTROLLED STUDY; DERIVATIZATION; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENZYME INHIBITION; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; METABOLITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STREPTOMYCES; ULTRAVIOLET SPECTROSCOPY; ARCTIC; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; METABOLISM; TUMOR CELL LINE;

ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ARCTIC REGIONS; BENZOXAZINES; CANDIDA ALBICANS; CELL LINE, TUMOR; CELL PROLIFERATION; HEXOSES; HUMANS; STREPTOMYCES;

EID: 84901462532     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12052526     Document Type: Article

References (20)

1. Bérdy, J. Thoughts and facts about antibiotics: Where we are now and where we are heading. J. Antibiot. 2012, 65, 385-395.
2. Ortholand, J.-Y.; Ganesan, A. Natural products and combinatorial chemistry: Back to the future. Curr. Opin. Chem. Biol. 2004, 8, 271-280. (Pubitemid 38759402)
3. Pettit, R.K. Culturability and secondary metabolite diversity of extreme microbes: Expanding contribution of deep sea and deep-sea vent microbes to natural product discovery. Mar. Biotechnol. 2011, 13, 1-11.
4. Andrianasolo, E.H.; Haramaty, L.; Rosario-Passapera, R.; Bidle, K.; White, E.; Vetriani, C.; Falkowski, P.; Lutz, R. Ammonificins A and B, hydroxyethylamine chroman derivatives from a cultured marine hydrothermal vent bacterium, Thermovibrio ammonificans. J. Nat. Prod. 2009, 72, 1216-1219.
5. Park, H.B.; Kwon, H.C.; Lee, C.-H.; Yang, H.O. Glionitrin A, an antibiotic-antitumor metabolite derived from competitive interaction between abandoned mine microbes. J. Nat. Prod. 2009, 72, 248-252.
6. Um, S.; Kim, Y.-J.; Kwon, H.; Wen, H.; Kim, S.-H.; Kwon, H.C.; Park, S.; Shin, J.; Oh, D.-C. Sungsanpin, a lasso peptide from a deep-sea streptomycete. J. Nat. Prod. 2013, 76, 873-879.
7. Gao, X.; Lu, Y.; Xing, Y.; Ma, Y.; Lu, J.; Bao, W.; Wang, Y.; Xi, T. A novel anticancer and antifungus phenazine derivative from a marine actinomycete BM-17. Microbiol. Res. 2012, 167, 616-622.
8. Ivanova, V.; Lyutskanova, D.; Kolarova, M.; Aleksieva, K.; Raykovska, V.; Stoilova-Disheva, M. Structural elucidation of a bioactive metabolites produced by Streptomycetes avidinii SB9 strain, isolated from permafrost soil in Spitsbergen, Arctic. Biotechnol. Biotechnol. Equip. 2010, 24, 2092-2095.
9. Minami, Y.; Yoshida, K.; Azuma, R.; Saeki, M.; Otani, T. Structure of an aromatization product of C-1027 chromophore. Tetrahedron Lett. 1993, 34, 2633-2636.
10. Nam, S.-J.; Gaudencio, S.P.; Kauffman, C.A.; Jensen, P.R.; Kondratyuk, T.P.; Marler, L.E.; Pezzuto, J.M.; Fenical, W. Fijiolides A and B, inhibitors of TNF-α-induced NFκB activation, from a marine-derived sediment bacterium of the genus Nocardiopsis. J. Nat. Prod. 2010, 73, 1080-1086.
11. Pretsch, E.; Bu{combining double grave accent}hlmann, P.; Affolter, C. Structure Determination of Organic Compounds - Tables of Spectral Data; Springer: New York, NY, USA, 2000; p. 153.
12. Wahidulla, S.; Bhattacharjee, J.J. Benzoxazinoids from Acanthus illicifolius. J. Indian Inst. Sci. 2001, 81, 485-489.
13. Sakawa, K.; Yoshida, K. Isolation and characterization of non-protein chromophore and its degradation product from antibiotic C-1027. J. Antibiot. 1991, 44, 564-568.
14. Kumada, Y.; Miwa, T.; Naoi, N.; Watanabe, K.; Naganawa, H.; Takita, T.; Umezawa, H.; Nakamura, H.; Iitaka, Y. A degradation product of the chromophore of auromomycin. J. Antibiot. 1983, 36, 200-202.
15. Pretsch, E.; Bu{combining double grave accent}hlmann, P.; Affolter, C. Structure Determination of Organic Compounds - Tables of Spectral Data; Springer: New York, NY, USA, 2000; p. 176.
16. Oh, D.-C.; Williams, P.G.; Kauffman, C.A.; Jensen, P.R.; Fenical, W. Cyanosporasides A and B, chloro- and cyano-cyclopenta[a]indene glycosides from the marine actinomycete "Salinispora pacifica". Org. Lett. 2006, 8, 1021-1024. (Pubitemid 43690650)
17. Buchanan, G.O.; Williams, P.G.; Feling, R.H.; Kauffman, C.A.; Jensen, P.R.; Fenical, W. Sporolides A and B: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica. Org. Lett. 2005, 7, 2731-2734. (Pubitemid 43034250)
18. Perrin, C.L.; Rodgers, B.L.; O'Connor, J.M. Nucleophilic addition to a p-benzyne derived from an enediyne: A new mechanism for halide incorporation into biomolecules. J. Am. Chem. Soc. 2007, 129, 4795-4799. (Pubitemid 46648778)
19. Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Structure and cycloaromatization of a novel enediyne, C-1027 chromophore. Tetrahedron Lett. 1993, 34, 2637-2640.
20. Dunn, M.F.; Ramirez-Trujillo, J.A.; Hernandez-Lucas, I. Major roles of isocitrate lyase and malate synthase in bacterial and fungal pathogenesis. Microbiology 2009, 155, 3166-3175.