Dataset Information

The genetic origin of evolidine, the first cyclopeptide discovered in plants, and related orbitides

ABSTRACT:

Cyclic peptides are reported to have antibacterial, antifungal and other bioactivities. Orbitides are a class of cyclic peptide that are small, head-to-tail cyclized, composed of proteinogenic amino acids, and lack disulfide bonds; they are also known in several genera of the plant family Rutaceae. Melicope xanthoxyloides is the Australian rain forest tree of the Rutaceae family in which evolidine - the first plant cyclic peptide - was discovered. Evolidine (cyclo-SFLPVNL) has subsequently been all but forgotten in the academic literature, so to redress this we used tandem mass spectrometry and de novo transcriptomics to rediscover evolidine and decipher its biosynthetic origin from a short precursor just 48 residues in length. We also identify another six M. xanthoxyloides orbitides using the same techniques. These peptides have atypically diverse C-termini consisting of residues not recognized by either of the known proteases plants use to macrocyclize peptides, suggesting new cyclizing enzymes a wait discovery. We examined the structure of two of the novel orbitides by NMR, finding one had a definable structure, whereas the other did not. Mining RNA-seq and whole genome sequencingdata from other species of the Rutaceae familyrevealed a large and diverse family of peptides is encoded by similar sequences across the family and demonstrates how powerful de novo transcriptomics can be at accelerating the discovery of new peptide families.

INSTRUMENT(S): Liquid Chromatography MS - positive - reverse phase

SUBMITTER: Mark Fisher

PROVIDER: MTBLS1963 | MetaboLights | 2020-10-14

REPOSITORIES: MetaboLights

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Dataset's files

Source:

			Action	DRS
	MTBLS1963	Other
	FILES	Other
	a_MTBLS1963_LC-MS_positive_reverse-phase_metabolite_profiling.txt	Txt
	i_Investigation.txt	Txt
	m_MTBLS1963_LC-MS_positive_reverse-phase_metabolite_profiling_v2_maf.tsv	Tabular

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Publications

The genetic origin of evolidine, the first cyclopeptide discovered in plants, and related orbitides.

Fisher Mark F MF Payne Colton D CD Chetty Thaveshini T Crayn Darren D Berkowitz Oliver O Whelan James J Rosengren K Johan KJ Mylne Joshua S JS

The Journal of biological chemistry 20200819 42

Cyclic peptides are reported to have antibacterial, antifungal, and other bioactivities. Orbitides are a class of cyclic peptides that are small, head-to-tail cyclized, composed of proteinogenic amino acids and lack disulfide bonds; they are also known in several genera of the plant family Rutaceae. <i>Melicope xanthoxyloides</i> is the Australian rain forest tree of the Rutaceae family in which evolidine, the first plant cyclic peptide, was discovered. Evolidine (cyclo-SFLPVNL) has subsequently ...[more]

PMID: 32817170

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