Jahanyne, an Apoptosis-Inducing Lipopeptide from the Marine Cyanobacterium Lyngbya sp.

Abstract

An acetylene-containing lipopeptide, jahanyne, was isolated from the marine cyanobacterium Lyngbya sp. Its gross structure was established by spectroscopic analyses, and the absolute configuration was clarified based on a combination of chiral HPLC analyses, spectroscopic analyses, and derivatization reactions. Jahanyne significantly inhibited the growth of human cancer cells and induced apoptosis in HeLa cells.

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

“…Some of them are used in the clinic, e.g., gramicidin S and tyrocidine with bactericidal activity, while others are in clinical trials, e.g., dehydrodidemnin B, and most of them originate from natural resources. Although the literature is enriched with reports concerned with marine-derived linear proline-rich bioactive peptides [1,2,3,4,5], e.g., dolastatin 15, kurahyne B, jahanyne, cemadotin, koshikamide A 1 , etc., PRCPs from marine resources are becoming popular and attracting the attention of scientists nowadays, due to their unique structural features and a wide range of the biological properties, like cytotoxicity [6], antibacterial activity [7], antifungal activity [8], immunosuppressive activity [9], anti-inflammatory activity [10], anti-HIV activity [11], repellent (antifouling) activity [12], antitubercular activity [13] and antiviral activity [14], associated with them. PRCPs include a large and heterogeneous group of small to large-sized oligopeptides characterized by the presence of proline units often constituting peculiar sequences, which confers them a typical structure that determines the various biological functions endowed by these molecules.…”

New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

“…Jahanyne ( 25 ), isolated from Lyngbya sp. collected in Okinawa, shows significant inhibitory effects on the growth of human cancer cells in vitro, and it can induce apoptosis of HeLa cells [27]. Two novel cytotoxic peptides, named bisebromoamide ( 26 ) and norbisebromoamide ( 27 ), have been identified from the marine cyanobacterium Lyngbya sp.…”

Janadolide, a Cyclic Polyketide–Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

“…(R)-PGME amide of (S)-2-hydroxy-3,3-dimethylbutanoic acid: 1 H NMR (CD 3 Cell Growth Analysis. Cell proliferation of HeLa cells and HL60 cells was measured by the MTT assay as described previously.…”