New prenylated indole diketopiperazine alkaloids and polyketides from the mangrove-derived fungus Penicillium sp

Two new prenylated indole diketopiperazine alkaloids (PIDAs) penicamides A and B ( 1 and 2 ) and three new polyketides penicinones A−C ( 6 − 8 ), along with four known compounds deoxybrevianamide E ( 3 ), brevianamide V ( 4 ), 12,13-dehydroprolyl-2-(1,1-dimethylallyltryptophyl)diketopiperazine ( 5 )...

Full description

Saved in:
Bibliographic Details
Published in:Frontiers in Marine Science 2022-12, Vol.9
Main Authors: Huo, Ruiyun, Zhang, Jinxin, Niu, Shubin, Liu, Ling
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Adenocarcinoma
Alkaloids
Cell culture
Cells
Chromatography
Circular dichroism
cytotoxic activity
Cytotoxicity
Fermentation
Fungi
fungus
Hepatocellular carcinoma
mangrove rhizospheric soil
Mangroves
Melanoma
Metabolites
Natural products
Neoplasms
NMR
Nuclear magnetic resonance
Penicillium
Penicillium sp
Polyketides
secondary metabolites
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two new prenylated indole diketopiperazine alkaloids (PIDAs) penicamides A and B ( 1 and 2 ) and three new polyketides penicinones A−C ( 6 − 8 ), along with four known compounds deoxybrevianamide E ( 3 ), brevianamide V ( 4 ), 12,13-dehydroprolyl-2-(1,1-dimethylallyltryptophyl)diketopiperazine ( 5 ), and 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate ( 9 ), were isolated and identified from the culture extract of the mangrove-derived fungus Penicillium sp. Their structures were fully elucidated by analyzing spectroscopic data. The absolute configurations of these compounds were determined by the comparison of experimental and calculated electronic circular dichroism (ECD) data and Mo 2 (OAc) 4 -induced and Rh 2 (OCOCF 3 ) 4 -induced ECD experiments. Structurally, compound 1 is the first example of PIDAs featuring a 6/5/8/6/5 pentacyclic ring system with an α -hydroxy group at C-11, while compound 2 is a new analogue of PIDAs possessing the unique 3-methyleneindolin-2-ol moiety. In addition, compound 6 is a new lactone with the furo[3,4- b ]pyran-5-one moiety. Compound 6 displayed potent cytotoxicity against murine melanoma (B16) cells, human breast adenocarcinoma (MCF-7) cells, and human hepatocellular carcinoma (HepG2) cells at 50.0 µM with inhibitory ratios of 82.7%, 75.1% and 95.9%, respectively. In addition, compound 6 exhibited significantly cytotoxic activity against the HepG2 cells, with an IC 50 value of 3.87 ± 0.74 µM.
ISSN:2296-7745
2296-7745
DOI:10.3389/fmars.2022.1097594