Peptide name : Gageostatin A

Source/Organism : Bacillus subtilis

Linear/Cyclic : Linear

Chirality : Mix

Peptide length: 7

C-terminal modification: Linear

N-terminal modification : Amidation

Non-natural peptide information: None

Assay type : Sulforhodamine B (SBR) assay

Assay time : 48h

Activity : GI50 : 4.6–19.6 μg/mL

Cell line : PC-3

Cancer type : Prostate cancer

Other activity : Anti-bacterial activity; Anti-fungal activity

Amino acid composition bar chart :

Molecular mass : 813.9781 Dalton

Aliphatic index : 2.642

Instability index : -12.9

Hydrophobicity (GRAVY) : 1.7714

Isoelectric point : 4.05

Charge (pH 7) : -2.1621

Aromaticity : 0

Molar extinction coefficient (cysteine, cystine): (0, 0)

Hydrophobic/hydrophilic ratio : 2.5

hydrophobic moment : -1.874

Missing amino acid : W,T,P,I,M,K,F,N,G,C,R,H,Q,S,Y,A

Most occurring amino acid : L

Most occurring amino acid frequency : 4

Least occurring amino acid : E

Least occurring amino acid frequency : 1

Secondary structure fraction (Helix, Turn, Sheet): (0.7, 0.1, 0.7)

SMILES Notation: CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCC(=O)O)C(C)C)C(=O)O

1 : Tareq FS, et al. Gageostatins A-C, antimicrobial linear lipopeptides from a marine Bacillus subtilis. Mar Drugs. 2014; 12:871-85. doi: 10.3390/md12020871

Paper title : Gageostatins A-C, antimicrobial linear lipopeptides from a marine Bacillus subtilis.

Doi : https://doi.org/10.3390/md12020871

Abstract : Concerning the requirements of effective drug candidates to combat against high rising multidrug resistant pathogens, we isolated three new linear lipopeptides, gageostatins A-C (1-3), consisting of hepta-peptides and new 3-β-hydroxy fatty acids from the fermentation broth of a marine-derived bacterium Bacillus subtilis. Their structures were elucidated by analyzing a combination of extensive 1D, 2D NMR spectroscopic data and high resolution ESIMS data. Fatty acids, namely 3-β-hydroxy-11-methyltridecanoic and 3-β-hydroxy-9,11-dimethyltridecanoic acids were characterized in lipopeptides 1 and 2, respectively, whereas an unsaturated fatty acid (E)-7,9-dimethylundec-2-enoic acid was assigned in 3. The 3R configuration of the stereocenter of 3-β-hydroxy fatty acids in 1 and 2 was established by Mosher's MTPA method. The absolute stereochemistry of amino acid residues in 1-3 was ascertained by acid hydrolysis followed by Marfey's derivatization studies. Gageostatins 1-3 exhibited good antifungal activities with MICs values of 4-32 µg/mL when tested against pathogenic fungi (R. solani, B. cinerea and C. acutatum) and moderate antibacterial activity against bacteria (B. subtilis, S. aeureus, S. typhi and P. aeruginosa) with MICs values of 8-64 µg/mL. Futhermore, gageostatins 1-3 displayed cytotoxicity against six human cancer cell lines with GI₅₀ values of 4.6-19.6 µg/mL. It is also noteworthy that mixed compounds 1+2 displayed better antifungal and cytotoxic activities than individuals.