Proline-containing cyclopeptides from the marine sponge Phakellia fusca.

J Nat Prod

Laboratory of Marine Drugs, Department of Pharmacy, Changzheng Hospital, Second Military Medical University, 415 Fengyang Road, Shanghai 200003, People's Republic of China.

Published: April 2010

Four new cyclopeptides, phakellistatins 15-18 (2-5), together with five known cyclopeptides, phakellistatin 13 (1), hymenistatin 1, and hymenamides G, H, and J, were isolated from the South China Sea sponge Phakellia fusca. Their structures were elucidated by HR-ESIMS, NMR, and MALDI-TOF/TOF sequence analysis. The absolute configurations of the amino acid residues of 2-5 were assigned to be l by enantioselective HPLC analysis.

Download full-text PDF

Source
http://dx.doi.org/10.1021/np9008267DOI Listing

Publication Analysis

Top Keywords

sponge phakellia
8
phakellia fusca
8
proline-containing cyclopeptides
4
cyclopeptides marine
4
marine sponge
4
fusca cyclopeptides
4
cyclopeptides phakellistatins
4
phakellistatins 15-18
4
15-18 2-5
4
2-5 cyclopeptides
4

Similar Publications

sp. nov., isolated from the marine sponge, .

Int J Syst Evol Microbiol

October 2024

Department of Biological Sciences and Biotechnology, Hannam University Jeonmin-dong, Yuseong-gu, Daejeon 34430, Republic of Korea.

A facultative anaerobic Gram-negative bacterium, designated as strain 2205BS29-5, was isolated from a marine sponge, , in Beomseom on Jeju Island, Republic of Korea, and taxonomically characterized. The cells were catalase and oxidase positive, non-motile, coccoid-rod shaped and capable of poly-β-hydroxybutyrate production. Growth was observed at 10-37 °C (optimum, 25 °C) and pH 5.

View Article and Find Full Text PDF

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.
View Article and Find Full Text PDF

Pyrrololactam alkaloids with IL-6 inhibitory activities from the sponge Phakellia fusca collected in the South China Sea.

Phytochemistry

December 2024

Research Center for Marine Drugs, Department of Pharmacy, Ren Ji Hospital, School of Medicine, State Key Laboratory of Microbial Metabolism, Shanghai Jiao Tong University, Shanghai, 200127, China. Electronic address:

Sixteen undescribed pyrrololactam alkaloids, including five 2-bromopyrrole-ε-lactam (1a, 1b, 4a, 4b and 5), two 3-bromopyrrole-ε-lactam (9 and 10), eight pyrrole-ε-lactam (2a-3 and 6a-8), and one pyrrole-δ-lactam alkaloids (11), along with three previously reported compounds (12-14) were isolated from the marine sponge Phakellia fusca collected in the South China Sea. The planar structures were determined by NMR and MS analyses, while the absolute configurations were clearly elucidated by comparing the experimental and calculated ECD spectra. Compounds 2a, 2b, 4a-7b, 10, 12 and 13 exhibited anti-inflammatory activity in inhibiting the production of inflammatory cytokines IL-6 in LPS-induced RAW264.

View Article and Find Full Text PDF

Phakellisins A-E, cyclopeptides from a marine sponge Phakellia sp. guided by LC-MS.

Bioorg Chem

October 2023

Research Center for Marine Drugs, State Key Laboratory of Oncogene and Related Genes, Department of Pharmacy, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, People's Republic of China. Electronic address:

A chemical investigation of the marine sponge Phakellia sp. from the South China Sea yielded five new cyclopeptides, phakellisins A-E (1-5). Structures of these compounds were determined by comprehensive analysis of 1D/2D NMR, HRESIMS/MS spectroscopic data and the advanced Marfey's method.

View Article and Find Full Text PDF

A new member of β-carboline alkaloids, Marinacarboline glucuronide (1), along with nine known compounds (2-10), were isolated from static liquid fermentation extracts of Actinoalloteichus cyanogriseus LHW52806 isolated from the marine sponge Phakellia fusca. Their structures were elucidated by NMR, mass spectrometry and single-crystal X-ray diffraction. All compounds exhibited neither antimicrobial activity nor cytotoxicity.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!