Synthesis, Characterization and Biological Evaluation of Cyclic Peptides: Viscumamide, Yunnanin A and Evolidine.

Poojary, Boja; Belagali, S. L.

doi:10.1002/chin.200616186

Cited by 4 publications

(8 citation statements)

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“…Our results stand in contrast to the prior work (20), which found that evolidine inhibited growth of B. subtilis (strain not specified), and the fungi C. albicans and Aspergillus niger using a similar assay to ours. The same study was consistent with our finding that E. coli is unaffected by evolidine.…”

Section: Biological Activities Of M Xanthoxyloides Orbitidescontrasting

confidence: 99%

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

Fisher

Payne

Chetty

et al. 2020

Preprint

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Cyclic peptides are reported to have antibacterial, antifungal and other bioactivities. Several genera of the Rutaceae family are known to produce orbitides, which are small head-to-tail cyclic peptides composed of proteinogenic amino acids and lacking disulfide bonds. Melicope xanthoxyloides is an 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, but here we use tandem mass spectrometry to rediscover evolidine and using de novo transcriptomics we show its biosynthetic origin to be from a short precursor just 48 residues in length. In all, seven M. xanthoxyloides orbitides were found and they had atypically diverse C-termini consisting of residues not recognized by either of the known proteases plants use to macrocyclize peptides. Two of the novel orbitides were studied by nuclear magnetic resonance spectroscopy and although one had definable structure, the other did not. By mining RNA-seq and whole genome sequencing data from other species, it was apparent that a large and diverse family of peptides is encoded by sequences like these across the Rutaceae.

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Section: Biological Activities Of M Xanthoxyloides Orbitidescontrasting

confidence: 99%

“…Poojary et al (20) reported that evolidine inhibits the growth of some bacteria and fungi. We attempted to replicate these results and to extend the study to xanthoxycyclins D and F, using disc diffusion assays like those in the prior work.…”

Section: Biological Activities Of M Xanthoxyloides Orbitidesmentioning

confidence: 99%

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

Fisher

Payne

Chetty

et al. 2020

Preprint

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“…FTIR spectrophotometer, JASCO 4100 was used to record the IR spectra using KBr pellets for solids and using chloroform and NaCl cells for semisolids. Bruker AC NMR spectrometer was used to record 1 H NMR and 13 C NMR spectra with TMS as an internal standard and CDCl 3 as a solvent. JMS-DX 303 Mass spectrometer operating at 70 eV was used to record the MASS spectrum by ESIMS/MS.…”

Section: Methodsmentioning

confidence: 99%

“…The subsequent tetrapeptides were coupled using DIPC and chloroform to get a linear octapeptide (7, 7a), which were then cyclized using p-nitro phenyl ester method to develop titled compound (8, 8a). General method for preparation of Di/Tetra/linear octapeptide: [11][12][13] 10 mmol of L-Amino acid methyl ester HCl /dipeptide methyl ester/tetra peptide methyl ester was added to 20 ml CHCl 3 , followed by adding TEA (2.8 ml, 20 mmol) at 0°C and stirring for 15 min. To the above reaction mixture, 10 mmol of Boc-L-amino acid/ Boc-dipeptide/Boc-tetrapeptide, 20 ml chloroform and 10 mmol DIPC were added with stirring and the reaction was carried out for 24 hr.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of Clausenain, a Cyclic Octapeptide and its Analog for Anticancer Activity

Shinde¹,

Dhake²,

Haval³

et al. 2020

IJPER

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Keeping in mind requisite of today's era for development of new anticancer drugs, synthesis of a phenyl alanine rich cyclic octapeptide Clausenain and its analog by solution phase technique is described here. It was done through coupling a tetrapeptide BOC-Phe-Ser-Leu-Phe-OMe with another tetrapeptide BOC-Phe-Gly-Leu-Phe-OMe after proper deprotection towards carboxyl and amino terminals. The N-methyl analog of this octapeptide was prepared with N-methylated Glycine instead of Glycine as starting material. The linear peptides were then cyclized using suitable procedure. The establishment of structure for synthesized compounds was done by spectral and elemental analysis. Evaluation of synthesized compounds was done by brine shrimp lethality assay and further screening was done using a panel of 60 human tumor cell lines. The cyclic octapeptide and its analog showed good activity against cells lines of Leukemia, Non-small cell lung cancer, CNS cancer, breast cancer and renal cancer in comparison with vincristine as standard. The N-methylated analog was found to be more active than the cyclic peptide.

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“…This discrepancy was discussed as it might be as a result of subtle conformational changes of proline units during the synthesis process, which ended by diverse arrangements of proline residues in the synthetic cyclopeptides ( 37 ). In another experiment, the synthesized yunnanin A showed weak antimicrobial, anti-inflammatory, and anthelmintic activities ( 38 ). Recently, a cyclic analogue of yunnanin A was synthesized by eliminating tyrosine residue and introducing a phthalimide structure instead, inside the ring structure, through photo inducing a single electron transfer reaction (SET) ( Figure 2 ).…”

Section: Yunnaninsmentioning

confidence: 99%

Cancer Treatment by Caryophyllaceae-Type Cyclopeptides

et al. 2021

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Cancer is one of the leading diseases, which, in the most cases, ends with death and, thus, continues to be a major concern in human beings worldwide. The conventional anticancer agents used in the clinic often face resistance among many cancer diseases. Moreover, heavy financial costs preclude patients from continuing treatment. Bioactive peptides, active in several diverse areas against man’s health problems, such as infection, pain, hypertension, and so on, show the potential to be effective in cancer treatment and may offer promise as better candidates for combating cancer. Cyclopeptides, of natural or synthetic origin, have several advantages over other drug molecules with low toxicity and low immunogenicity, and they are easily amenable to several changes in their sequences. Given their many demanded homologues, they have created new hope of discovering better compounds with desired properties in the field of challenging cancer diseases. Caryophyllaceae-type cyclopeptides show several biological activities, including cancer cytotoxicity. These cyclopeptides have been discovered in several plant families but mainly are from the Caryophyllaceae family. In this review, a summary of biological activities found for these cyclopeptides is given; the focus is on the anticancer findings of these peptides. Among these cyclopeptides, information about Dianthins (including Longicalycinin A), isolated from different species of Caryophyllaceae, as well as their synthetic analogues is detailed. Finally, by comparing their structures and cytotoxic activities, finding the common figures of these kinds of cyclopeptides as well as their possible future place in the clinic for cancer treatment is put forward.

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Synthesis, Characterization and Biological Evaluation of Cyclic Peptides: Viscumamide, Yunnanin A and Evolidine.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 4 publications

References 1 publication

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

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

Total Synthesis of Clausenain, a Cyclic Octapeptide and its Analog for Anticancer Activity

Cancer Treatment by Caryophyllaceae-Type Cyclopeptides

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