AI Article Synopsis
- Scientists discovered five new cycloheptapeptides, named phakefusins A-E, from the marine sponge Phakellia fusca using a probe-based molecular networking approach.
- Two of these compounds feature unique nonproteinogenic amino acids, while others have rare structural components such as methionine sulfoxide and glutamic acid ethyl ester.
- The compounds were tested for their biological activities, with compound 1 showing moderate antitumor effects and compounds 2-5 demonstrating antioxidant potential by enhancing certain protective enzyme levels.
Article Abstract
Guided by a probe-based molecular networking strategy, five undescribed cycloheptapeptides, phakefusins A-E (1-5), were isolated from the marine sponge Phakellia fusca. Compounds 1 and 2 contain the nonproteinogenic amino acid residues of dioxindolyalanine (Dioia) and β-3-oxindolylalanine (Oia), respectively. Compound 3 possesses a unique methionine sulfoxide, whereas compound 5 includes a glutamic acid ethyl ester unit. Their structures were elucidated through NMR spectroscopy, HR-MS/MS analysis, and the advanced Marfey's method. By synthesizing the (S, S/R)-Oia standard through tryptophan oxidation, we determined the configuration of this amino acid in compound 2 using the advanced Marfey's method. These cycloheptapeptides were evaluated for their antitumor, antibacterial, and antioxidant activities. Compound 1 showed moderate cytotoxicity against MCF-7 and PC9 cells, with IC values of 6.8 and 9.6 μM, respectively, while compounds 2-5 demonstrated potential antioxidant effects by upregulating HO-1, NQO1, and SOD2 levels, as well as inducing Nrf2 activation.
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| http://dx.doi.org/10.1016/j.phytochem.2024.114248 | DOI Listing |
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Discovery of cycloheptapeptides phakefusins A-E from the marine sponge Phakellia fusca based on molecular networking.
Phytochemistry
January 2025
Marine Drug Integrated Innovation Center, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai, 200127, China. Electronic address:
Article Synopsis
- Scientists discovered five new cycloheptapeptides, named phakefusins A-E, from the marine sponge Phakellia fusca using a probe-based molecular networking approach.
- Two of these compounds feature unique nonproteinogenic amino acids, while others have rare structural components such as methionine sulfoxide and glutamic acid ethyl ester.
- The compounds were tested for their biological activities, with compound 1 showing moderate antitumor effects and compounds 2-5 demonstrating antioxidant potential by enhancing certain protective enzyme levels.
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