LC-MS/MS Based Identification of Piperine Production by Endophytic Mycosphaerella sp. PF13 from Piper nigrum

• Published in: Applied biochemistry and biotechnology Vol. 173; no. 1; pp. 30 - 35
• Main Authors: Chithra, S, Jasim, B, Anisha, C, Mathew, Jyothis, Radhakrishnan, E. K
• Format: Journal Article
• Language: English
• Published: Boston Springer-Verlag 01.05.2014; Springer US; Springer; Springer Nature B.V
• Subjects: Alkaloids - biosynthesis; Alkaloids - chemistry; Ascomycota - chemistry; Ascomycota - isolation & purification; Ascomycota - metabolism; Benzodioxoles - chemistry; Biochemistry; Biological and medical sciences; Biosynthesis; Biotechnology; Chemistry; Chemistry and Materials Science; Chromatography; Chromatography, Liquid; endophytes; Endophytes - chemistry; Endophytes - isolation & purification; Endophytes - metabolism; Fundamental and applied biological sciences. Psychology; Fungi; Ionization; ions; Liquid chromatography; Mass spectrometry; medicinal properties; Metabolites; Molecular Structure; Mycosphaerella; Piper nigrum; Piper nigrum - microbiology; Piperidines - chemistry; Polyunsaturated Alkamides - chemistry; protons; Tandem Mass Spectrometry; Liquid chromatography-tandem mass spectrometry; Endophytic fungi; Piperine; sp; Ascomycota; Mycosphaerella; Mycosphaerella sp; Piperaceae; Liquid chromatography; Identification; Fungi; Dicotyledones; Piper nigrum; Mass spectrometry MS/MS; Angiospermae; Production; Endophyte; Spermatophyta
• ISSN: 0273-2289; 1559-0291
• DOI: 10.1007/s12010-014-0832-3

Piper nigrum is very remarkable for its medicinal properties due to the presence of metabolites like piperine. Emerging understanding on the biosynthetic potential of endophytic fungi suggests the possibility to have piperine producing fungi in P. nigrum. In the current study, endophytic fungi isolated from P. nigrum were screened for the presence of piperine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). This resulted in the identification of a Mycosphaerella sp. with the ability to produce piperine extracellularly. The biosynthesis of piperine (C₁₇H₁₉NO₃) by the endophytic fungal isolate was confirmed by the presence of m/z 286.1 (M + H⁺) in the LC-MS/MS analysis using positive mode ionization. This was further supported by the presence of specific fragment ions with masses 135, 143, 171 and 201 formed due to the fragmentation of piperine present in the fungal extract.