Aaptamines, Marine Spongean Alkaloids, As Anti-dormant Mycobacterial Substances

Overview

Journal J Nat Med

Publisher Springer

Date 2014 Jan 14

PMID 24414399

Citations 10

Authors

Masayoshi Arai

Chisu Han

Yoshi Yamano

Andi Setiawan

Motomasa Kobayashi

Affiliations

Soon will be listed here.

Abstract

A new aaptamine class alkaloid, designated 2-methoxy-3-oxoaaptamine (1), together with seven known aaptamines (2-8) were isolated from a marine sponge of Aaptos sp. as anti-mycobacterial substances against active and dormant bacilli. The chemical structure of 1 was determined on the basis of spectroscopic analysis. Compound 1 was anti-mycobacterial against Mycobacterium smegmatis in both active growing and dormancy-inducing hypoxic conditions with a minimum inhibitory concentration (MIC) of 6.25 μg/ml, and compounds 2, 5, 6, and 7 showed anti-mycobacterial activities under hypoxic condition selectively, with MIC values of 1.5-6.25 μg/ml.

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References

Pettit G, Hoffmann H, McNulty J, Higgs K, Murphy A, Molloy D . Antineoplastic agents. 380. Isolation and X-ray crystal structure determination of isoaaptamine from the Republic of Singapore Hymeniacidon sp. and conversion to the phosphate prodrug hystatin 1. J Nat Prod. 2004; 67(3):506-9. DOI: 10.1021/np0204592. View

Rustad T, Harrell M, Liao R, Sherman D . The enduring hypoxic response of Mycobacterium tuberculosis. PLoS One. 2008; 3(1):e1502. PMC: 2198943. DOI: 10.1371/journal.pone.0001502. View

Pruksakorn P, Arai M, Kotoku N, Vilcheze C, Baughn A, Moodley P . Trichoderins, novel aminolipopeptides from a marine sponge-derived Trichoderma sp., are active against dormant mycobacteria. Bioorg Med Chem Lett. 2010; 20(12):3658-63. DOI: 10.1016/j.bmcl.2010.04.100. View

Wedge D, Nagle D . A new 2D-TLC bioautography method for the discovery of novel antifungal agents To control plant pathogens. J Nat Prod. 2000; 63(8):1050-4. DOI: 10.1021/np990628r. View

Shubina L, Makarieva T, Dyshlovoy S, Fedorov S, Dmitrenok P, Stonik V . Three new aaptamines from the marine sponge Aaptos sp. and their proapoptotic properties. Nat Prod Commun. 2011; 5(12):1881-4. View

Yamano Y, Arai M, Kobayashi M . Neamphamide B, new cyclic depsipeptide, as an anti-dormant mycobacterial substance from a Japanese marine sponge of Neamphius sp. Bioorg Med Chem Lett. 2012; 22(14):4877-81. DOI: 10.1016/j.bmcl.2012.05.071. View

Dick T, Lee B . Oxygen depletion induced dormancy in Mycobacterium smegmatis. FEMS Microbiol Lett. 1998; 163(2):159-64. DOI: 10.1111/j.1574-6968.1998.tb13040.x. View

Runyoro D, Matee M, Ngassapa O, Joseph C, Mbwambo Z . Screening of Tanzanian medicinal plants for anti-Candida activity. BMC Complement Altern Med. 2006; 6:11. PMC: 1481531. DOI: 10.1186/1472-6882-6-11. View

Gul W, Hammond N, Yousaf M, Bowling J, Schinazi R, Wirtz S . Modification at the C9 position of the marine natural product isoaaptamine and the impact on HIV-1, mycobacterial, and tumor cell activity. Bioorg Med Chem. 2006; 14(24):8495-505. PMC: 4928486. DOI: 10.1016/j.bmc.2006.08.042. View

10.

Wayne L, Sohaskey C . Nonreplicating persistence of mycobacterium tuberculosis. Annu Rev Microbiol. 2001; 55:139-63. DOI: 10.1146/annurev.micro.55.1.139. View

11.

Arai M, Ishida S, Setiawan A, Kobayashi M . Haliclonacyclamines, tetracyclic alkylpiperidine alkaloids, as anti-dormant mycobacterial substances from a marine sponge of Haliclona sp. Chem Pharm Bull (Tokyo). 2009; 57(10):1136-8. DOI: 10.1248/cpb.57.1136. View

12.

Abate G, Aseffa A, Selassie A, Goshu S, Fekade B, WoldeMeskal D . Direct colorimetric assay for rapid detection of rifampin-resistant Mycobacterium tuberculosis. J Clin Microbiol. 2004; 42(2):871-3. PMC: 344497. DOI: 10.1128/JCM.42.2.871-873.2004. View

13.

Idemyor V . HIV and tuberculosis coinfection: inextricably linked liaison. J Natl Med Assoc. 2008; 99(12):1414-9. PMC: 2575925. View

14.

Aoki S, Kong D, Suna H, Sowa Y, Sakai T, Setiawan A . Aaptamine, a spongean alkaloid, activates p21 promoter in a p53-independent manner. Biochem Biophys Res Commun. 2006; 342(1):101-6. DOI: 10.1016/j.bbrc.2006.01.119. View

15.

Pham C, Hartmann R, Muller W, De Voogd N, Lai D, Proksch P . Aaptamine derivatives from the Indonesian sponge Aaptos suberitoides. J Nat Prod. 2013; 76(1):103-6. DOI: 10.1021/np300794b. View

16.

Lim A, Eleuterio M, Hutter B, Dick T . Oxygen depletion-induced dormancy in Mycobacterium bovis BCG. J Bacteriol. 1999; 181(7):2252-6. PMC: 93640. DOI: 10.1128/JB.181.7.2252-2256.1999. View

17.

Wayne L, Hayes L . An in vitro model for sequential study of shiftdown of Mycobacterium tuberculosis through two stages of nonreplicating persistence. Infect Immun. 1996; 64(6):2062-9. PMC: 174037. DOI: 10.1128/iai.64.6.2062-2069.1996. View

18.

Arai M, Sobou M, Vilcheze C, Baughn A, Hashizume H, Pruksakorn P . Halicyclamine A, a marine spongean alkaloid as a lead for anti-tuberculosis agent. Bioorg Med Chem. 2008; 16(14):6732-6. DOI: 10.1016/j.bmc.2008.05.061. View

19.

Pettit G, Hoffmann H, Herald D, Blumberg P, Hamel E, Schmidt J . Antineoplastic agents. 499. Synthesis of hystatin 2 and related 1H-benzo[de][1,6]-naphthyridinium salts from aaptamine. J Med Chem. 2004; 47(7):1775-82. DOI: 10.1021/jm030070r. View

20.

Kobayashi M, Kawazoe K, Kitagawa I . Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an okinawan marine sponge, Xestospongia sp. Chem Pharm Bull (Tokyo). 1989; 37(6):1676-8. DOI: 10.1248/cpb.37.1676. View