Electrospray ionization mass spectra of piperazimycins A and B and γ-butyrolactones from a marine-derived Streptomyces sp

Journal of Antibiotics

Volumn 61, Issue 12, 2008, Pages 736-746

  Shaaban, Khaled A ^a   Shaaban, Mohamed ^b   Facey, Petrea ^a   Fotso, Serge ^a   Frauendorf, Holm ^a   Helmke, Elisabeth ^c   Maier, Armin ^d   Fiebig, Heinz H ^d   Laatsch, Hartmut ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c ALFRED WEGENER INSTITUTE FOR POLAR AND MARINE RESEARCH   (Germany)

^d CHARLES RIVER LABORATORIES   (United States)

Author keywords

butyrolactones; Marine derived streptomyces sp; Piperazimycins

Indexed keywords

3 INDOLECARBOXYLIC ACID; 4,10 DIHYDROXY 10 METHYL DODECAN 4 OLIDE; 4,10 DIHYDROXY 10 METHYL DODECANOIC ACID; ADENINE; ANTIBIOTIC AGENT; BUTYROLACTONE; CARBOXYLIC ACID DERIVATIVE; FERULIC ACID; GAMMA BUTYROLACTONE DERIVATIVE; GRAEFE FACTOR 1; GRAEFE FACTOR 3; PIPERAZIMYCIN A; PIPERAZIMYCIN B; STAUROSPORINE; TRYPTOPHOL; UNCLASSIFIED DRUG; VIRGINIAE BUTANOLIDE E;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; STREPTOMYCES; TANDEM MASS SPECTROMETRY; TUMOR CELL LINE;

4-BUTYROLACTONE; DEPSIPEPTIDES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREPTOMYCES; WATER MICROBIOLOGY;

STREPTOMYCES; STREPTOMYCES SP.;

EID: 60749109303     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.87     Document Type: Article

References (29)

1. Graefe U, Schlegel R, Ritzau M, Ihn W, Dornberger K, Stengel C, Fleck WF, Gutsche W, Haertl A, Paulus EF. Aurantimycins, new depsipeptide antibiotics from Streptomyces aurantiacus IMET 43917: production, isolation, structure elucidation, and biological activity. J Antibiot 48: 119-125 (1995)
2. Maehr H, Liu CM, Palleroni NJ, Smallheer J, Todaro L, Williams TH, Blount JF. Microbial products. VIII. Azinothricin, a novel hexadepsipeptide antibiotic. J Antibiot 39: 17-25 (1986)
3. Umezawa K, Nakazawa K, Uemura T, Ikeda Y, Kondo S, Naganawa H, Kinoshita N, Hashizume H, Hamada M, Takeuchi T, Ohba S. Polyoxypeptin isolated from Streptomyces: a bioactive cyclic depsipeptide containing the novel amino acid 3-hydroxy-3-methylproline. Tetrahedron Lett 39: 1389-1392 (1998)
4. Leet JE, Schroeder DR, Golik J, Matson JA, Doyle TW, Lam KS, Hill SE, Lee MS, Whitney JL, Krishnan BS. Himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus III. Structural elucidation. J Antibiot 49: 299-311 (1996)
5. Umezawa K, Ikeda Y, Uchihata Y, Naganawa H, Kondo S. Chloptosin, an apoptosis-inducing dimeric cyclohexapeptide produced by Streptomyces. J Org Chem 65: 459-163 (2000)1
6. Ogita T, Sato A, Enokita R, Suzuki K, Ishii M, Negishi T, Okazaki T, Tamaki K, Tanzawa K. Matlystatins, new inhibitors of typelV collagenases from Actinomadura atramentaria. I. Taxonomy, fermentation, isolation, and physico-chemical properties of matlystatin-group compounds. J Antibiot 45: 1723-1732 (1992)
7. Sakai Y, Yoshida T, Tsujita T, Ochiai K, Agatsuma T, Saitoh Y, Tanaka F, Akiyama T, Akinaga S, Mizukami T. GE3, a novel hexadepsipeptide antitumor antibiotic, produced by Streptomyces sp. I. Taxonomy, production, isolation, physico-chemical properties, and biological activities. J Antibiot 50: 659-664(1997)
8. Konishi M, Ohkuma H, Sakai F, Tsuno T, Koshiyama H, Naito T, Kawaguchi H. Structures of BBM-928 A, B, and C. Novel antitumor antibiotics from Actinomadura luzonensis. J Am Chem Soc 103: 1241-1243 (1981)
9. Konishi M, Ohkuma H, Sakai F, Tsuno T, Koshiyama H, Naito T, Kawaguchi H. BBM-928, a new antitumor antibiotic complex. III. Structure determination of BBM-928 A, B and C. J Antibiot 34: 148-159 (1981)
10. Morimoto K, Shimada N, Naganawa H, Takita T, Umezawa H, Kambara H. Minor congeners of antrimycin: application of secondary ion mass spectrometry (SIMS) to structure determination. J Antibiot 35: 378-380 (1982)
11. Hensens OD, Borris RP, Koupal LR, Caldwell CG, Currie SA, Haidri AA, Homnick CF, Honeycutt SS, Lindenmayer SM, Schwartz C, Weissberger B, Woodruff H, Zink D, Zitano L, Fieldhouse J, Rollins T, Springer M, Springer J. L-156,602, a C5a antagonist with a novel cyclic hexadepsipeptide structure from Streptomyces sp. MA6348: fermentation, isolation and structure determination. J Antibiot 44: 249-254 (1991)
12. Inouye Y, Take Y, Nakamura S, Nakashima H, Yamamoto N, Kawaguchi H. Screening for inhibitors of avian myeloblastosis virus reverse transcriptase and effect on the replication of AIDS virus. J Antibiot 40: 100-104 (1987)
13. Lingham RB, Hsu AHM, O'Brien JA, Sigmund JM, Sanchez M, Gagliardi MM, Heimbuch BK, Genilloud O, Martin I, Diez M, Hirsch C, Zink D, Liesch J, Koch G, Gartner S, Garrity G, Tsuo N, Salituro G. Quinoxapeptins: novel chromodepsipeptide inhibitors of HIV-1 and HIV-2 reverse transcriptase. I. The producing organism and biological activity. J Antibiot 49: 253-259 (1996)
14. Laatsch H. AntiBase 2008, A Data Base for Rapid Structural Determination of Microbial Natural Products. Wiley-VCH, Weinheim, Germany; see http://wwwuser.gwdg.de/~ucoc/laatsch/AntiBase.htm
15. + medium: 10 g malt extract, 4g yeast extract, and 4g glucose in 0.5 liters of artificial sea water and 0.5 liters of tap water was set to pH 7.8 with 2 N NaOH and sterilized for 30 minutes at 121°
16. Meksuriyen D, Cordell GA. Biosynthesis of staurosporine, 1. Proton and carbon-13 NMR assignments. J Nat Prod 51: 884-892 (1988)
17. Umezawa I, Tronquet C, Funayama S, Okada K, Komiyama K. A novel antibiotic, sohbumycin. Taxonomy, fermentation, isolation and physicochemical and biological characteristics. J Antibiot 38: 967-971 (1985)
18. Miller ED, Kauffman CA, Jensen PR, Fenical W. Piperazimycins: cytotoxic hexadepsipeptides from a marine-derived bacterium of the genus Streptomyces. J Org Chem 72: 323-330 (2007)
19. Sajid I, Shaaban KA, Frauendorf H, Hasnain S, Laatsch H. Val-Geninthiocin: Structure Elucidation and MS" Fragmentation of Thiopeptide Antibiotics Produced by Streptomyces sp. RSF18. Z Naturforsch B 63b: 1223-1230 (2008)
20. Tilvi S, Naik CG. Tandem mass spectrometry of kahalalides: identification of two new cyclic depsipeptides, kahalalide R and S from Elysia grandifolia. J Mass Spectrom 42: 70-80 (2007)
21. Kondo K, Higuchi Y, Sakuda S, Nihira T, Yamada Y. New Virginiae Butanolides from Streptomyces virgniae. J Antibiot 42: 1873-1876(1989)
22. Ohashi H, Zheng YH, Nihira T, Yamada Y. Distribution of virginiae butanolides in antibiotic-producing actinomycetes, and identification of the inducing factor from Streptomyces antibioticus as virginiae butanolide A. J Antibiot 42: 1191-1195 (1989)
23. Horinouchi S, Beppu T. In Genetics and Biochemistry of Antibiotic Production Eds., Vining LC, Stuttard C, pp. 103-119, Butterworth- Heinemann, Newton, MA (1994)
24. Ohnishi Y, Kameyama S, Onaka H, Horinouchi S. The A-factor regulatory cascade leading to streptomycin biosynthesis in Streptomyces griseus: identification of a target gene of the A-factor receptor. Mol Microbiol 34: 102-111 (1999)
25. Yamada Y, Nihira T, Sakuda S. Bio/Technology of Antibiotics, pp. 63-79, Marcel Dekker, Inc., New York (1997)
26. Yamada Y. In Microbial Signaling and Communication Eds., England R, Hobbs G, Bainton N, Roberts D, pp. 177-196, Cambridge University Press, Cambridge, United Kingdom (1999)
27. Walker JD, Colwell RR. Factors affecting enumeration and isolation of actinomycetes from Chesapeake Bay and southeastern Atlantic Ocean sediments. Mar Biol 30: 193-201 (1975)
28. Dengler WA, Schulte J, Berger DP, Mertelsmann R, Fiebig HH. Development of a propidium iodide fluorescence assay for proliferation and cytotoxicity assays. Anticancer Drugs 6: 522-532 (1995)
29. Takahashi A, Kurasawa S, Ikeda D, Okami Y, Takeuchi T. Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties. J Antibiot 32: 1556-1561 (1989)