Identification of lipopeptide isoforms by MALDI-TOF-MS/MS based on the simultaneous purification of iturin, fengycin, and surfactin by RP-HPLC
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- 作者：Huan Yang ; Xu Li ; Xue Li ; Huimin Yu…
- 关键词：Iturin ; Fengycin ; Surfactin ; Reverse ; phase high ; performance liquid chromatography ; Phenyl isothiocyanate derivatives ; Matrix ; assisted laser desorption ionization time ; of ; flight
- 刊名：Analytical and Bioanalytical Chemistry
- 出版年：2015
- 出版时间：March 2015
- 年：2015
- 卷：407
- 期：9
- 页码：2529-2542
- 全文大小：2,021 KB
- 参考文献：1. Liu, XY, Yang, SZ, Mu, BZ (2009) Production and characterization of a C-15-surfactin-O-methyl ester by a lipopeptide producing strain Bacillus subtilis HSO121. Process Biochem 44: pp. 1144-1151 CrossRef
2. Arima, K, Kakinuma, A, Tamura, G (1968) Surfactin, a crystalline peptidelipid surfactant produced by Bacillus subtilis: isolation, characterization and its inhibition of fibrin clot formation. Biochem Biophys Res Commun 31: pp. 488-494 CrossRef
3. Chen, H, Wang, L, Su, CX, Gong, GH, Wang, P, Yu, ZL (2008) Isolation and characterization of lipopeptide antibiotics produced by Bacillus subtilis. Lett Appl Microbiol 47: pp. 180-186 CrossRef
4. Wakayama, S, Ishikawa, F, Oishi, K (1984) Mycocerein, a novel antifungal peptide antibiotic produced by Bacillus cereus. Antimicrob Agents Chemother 26: pp. 939-940 CrossRef
5. Lee, SC, Kim, SH, Park, IH, Chung, SY, Choi, YL (2007) Isolation and structural analysis of bamylocin A, novel lipopeptide from Bacillus amyloliquefaciens LP03 having antagonistic and crude oil-emulsifying activity. Arch Microbiol 188: pp. 307-312 CrossRef
6. Desai, JD, Banat, IM (1997) Microbial production of surfactants and their commercial potential. Microbiol Mol Biol Rev 61: pp. 47-64
7. Banat, IM, Makkar, RS, Cameotra, SS (2000) Potential commercial applications of microbial surfactants. Appl Microbiol Biotechnol 53: pp. 495-508 CrossRef
8. Das, P, Mukherjee, S, Sen, R (2008) Antimicrobial potential of a lipopeptide biosurfactant derived from a marine Bacillus circulans. J Appl Microbiol 104: pp. 1675-1684 CrossRef
9. Hiradate, S, Yoshida, S, Sugie, H, Yada, H, Fujii, Y (2002) Mulberry anthracnose antagonists (iturins) produced by Bacillus amyloliquefaciens RC-2. Phytochemistry 61: pp. 693-698 CrossRef
10. Yu, GY, Sinclair, JB, Hartman, GL, Bertagnolli, BL (2002) Production of iturin A by Bacillus amyloliquefaciens suppressing Rhizoctonia solani. Soil Biol Biochem 34: pp. 955-963 CrossRef
11. Vanittanakom, N, Loeffler, W, Koch, U, Jung, G (1986) Fengycin - a novel antifungal lipopeptide antibiotic produced by Bacillus subtilis F-29-3. J Antibiot 39: pp. 888-901 CrossRef
12. Villegas-Escobar, V, Ceballos, I, Mira, JJ, Argel, LE, Peralta, SO, Romero-Tabarez, M (2013) Fengycin C Produced by Bacillus subtilis EA-CB0015. J Nat Prod 76: pp. 503-509 CrossRef
13. Bonmatin, JM, Laprevote, O, Peypoux, F (2003) Diversity among microbial cyclic lipopeptides: Iturins and surfactins. Activity-structure relationships to design new bioactive agents. Comb Chem High Throughput Screen 6: pp. 541-556 CrossRef
14. Hathout, Y, Ho, YP, Ryzhov, V, Demirev, P, Fenselau, C (2000) Kurstakins: a new class of lipopeptides isolated from Bacillus thuringiensis. J Nat Prod 63: pp. 1492-1496 CrossRef
15. Peypoux, F, Pommier, MT, Marion, D, Ptak, M, Das, BC, Michel, G (1986) Revised structure of mycosubtilin, a peptidolipid antibiotic from Bacillus subtilis. J Antibiot 39: pp. 636-641 CrossRef
16. Volpon, L, Besson, F, Lancelin, JM (1999) NMR structure of active and inactive forms of the sterol-dependent antifungal antibiotic bacillomycin L. Eur J Biochem 264: pp. 200-210- 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Analytical Chemistry
Food Science
Inorganic Chemistry
Physical Chemistry
Monitoring, Environmental Analysis and Environmental Ecotoxicology- 出版者：Springer Berlin / Heidelberg
- ISSN：1618-2650
文摘
A three-stage linear gradient strategy using reverse-phase high-performance liquid chromatography (HPLC) was optimized for rapid, high-quality, and simultaneous purification of the lipopeptide isoforms of iturin, fengycin, and surfactin, which may differ in composition by only a single amino acid and/or the fatty acid residue. Matrix-assisted laser desorption ionization time-of-flight tandem mass spectrometry (MALDI-TOF-MS/MS) was applied to detect the lipopeptides harvested from each reversed-phase HPLC peak. Amino acid analysis based on phenyl isothiocyanate derivatization was further used for confirmation of the amino acid species and molar ratio in a certain HPLC fraction. By this MALDI-TOF-MS/MS coupled with amino acid analysis, it was revealed that iturin at m/z 1,043 consists of a circular Asn-Tyr-Asn-Gln-Pro-Asn-Ser peptide and C14 β-OH fatty acid. Surfactin homologs from Bacillus subtilis THY-7 at m/z 1,030, 1,044, 1,058, and 1,072 possess a circular Glu-Leu-Leu-Val-Asp-Leu-Leu peptide and the β-OH fatty acid with a different length (C13–C16). Fengycin species at m/z 1,463 and 1,477 are homologs possessing the circular peptide Glu-Orn-Tyr-Thr-Glu-Ala-Pro-Gln-Tyr-Ile linked to a C16 or C17 γ-OH fatty acid, whereas fengycin at m/z 1,505 contains a Glu-Orn-Tyr-Thr-Glu-Val-Pro-Gln-Tyr-Ile sequence with a Val instead of Ala at position 6. The method developed in this work provided an efficient approach for characterization of diverse lipopeptide isoforms from the iturin, fengycin, and surfactin families.