Jizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea

Gallegos, David A.; Saurí, Josep; Cohen, Ryan D.; Wan, Xuemei; Videau, Patrick; Vallota-Eastman, Alec O.; Shaala, Lamiaa A.; Youssef, Diaa T. A.; Williamson, R. Thomas; Martin, Gary E.; Philmus, Benjamin; Sikora, Aleksandra E.; Ishmael, Jane E.; McPhail, Kerry L.

doi:10.1021/acs.jnatprod.8b00117

i

Jizanpeptins, Cyanobacterial Protease Inhibitors from a Symploca sp. Cyanobacterium Collected in the Red Sea

2018
By Gallegos, David A. ; Saurí, Josep ; Cohen, Ryan D. ; ...

Details

Journal Title:

Journal of Natural Products
Personal Author:

Gallegos, David A. ; Saurí, Josep ; Cohen, Ryan D. ; Wan, Xuemei ; Videau, Patrick ; Vallota-Eastman, Alec O. ; Shaala, Lamiaa A. ; Youssef, Diaa T. A. ; Williamson, R. Thomas ; Martin, Gary E. ; Philmus, Benjamin ; Sikora, Aleksandra E. ; Ishmael, Jane E. ; McPhail, Kerry L.
NOAA Program & Office:

OAR (Oceanic and Atmospheric Research)
Description:

Jizanpeptins A–E (1–5) are micropeptin depsipeptides isolated from a Red Sea specimen of a Symploca sp. cyanobacterium. The planar structures of the jizanpeptins were established using NMR spectroscopy and mass spectrometry and contain 3-amino-6-hydroxy-2-piperidone (Ahp) as one of eight residues in a typical micropeptin motif, as well as a side chain terminal glyceric acid sulfate moiety. The absolute configurations of the jizanpeptins were assigned using a combination of Marfey’s methodology and chiral-phase HPLC analysis of hydrolysis products compared to commercial and synthesized standards. Jizanpeptins A–E showed specific inhibition of the serine protease trypsin (IC50 = 72 nM to 1 μM) compared to chymotrypsin (IC50 = 1.4 to >10 μM) in vitro and were not overtly cytotoxic to HeLa cervical or NCI-H460 lung cancer cell lines at micromolar concentrations.
Keywords:

Analytical Chemistry Complementary And Alternative Medicine Drug Discovery Molecular Medicine Organic Chemistry Pharmaceutical Science Pharmacology Complementary And Alternative Medicine Complementary And Alternative Medicine
Source:

Journal of Natural Products, 81(6), 1417-1425
DOI:

https://doi.org/10.1021/acs.jnatprod.8b00117
ISSN:

0163-3864 ; 1520-6025
Format:

PDF
Publisher:

American Chemical Society (ACS)
Document Type:

Journal Article
Funding:

Grant no. NA10OAR4170064
Rights Information:

Other
Compliance:

Library
Main Document Checksum:

urn:sha256:e5cac03a3c2889ab3e38577af555a43fd6a9224e1e44addc12c46cd03009c62f
Download URL:

https://repository.library.noaa.gov/view/noaa/60561/noaa_60561_DS1.pdf
File Type:

[PDF - 1.07 MB ]

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